{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T03:27:59Z","timestamp":1788406079678,"version":"build-2803163510"},"reference-count":282,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2026,2,24]],"date-time":"2026-02-24T00:00:00Z","timestamp":1771891200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["25-14-00162"],"award-info":[{"award-number":["25-14-00162"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>Phytochemicals, including flavonoids, stilbenoids, alkaloids, terpenoids, and structurally related synthetic small molecules, exhibit a broad spectrum of beneficial pharmacological effects. These effects stem not only from interactions with specific protein targets but also from their capacity to modify the physical properties of biological membranes. A key membrane property influenced by these plant-derived compounds is the electrical potential drop at the membrane\u2013water interface, which plays a crucial role in numerous cellular processes. Changes in membrane potential impact the function of embedded proteins and ion channels, thereby modulating cell signaling, transport, and pharmacological responses. This review compiles data on how diverse plant and synthetic small molecules alter membrane physical characteristics, particularly the dipole component of the boundary potential in lipid bilayers primarily composed of phosphatidylcholine, a predominant membrane lipid in mammals and fungi. In-depth analysis of structure\u2013activity relationships in this context elucidates how various structural modifications affect the compounds\u2019 ability to shift membrane electrical potential. Understanding these relationships can pinpoint molecular features that drive membrane interactions and facilitate the discovery and design of more potent dipole-modifying agents with therapeutic potential.<\/jats:p>","DOI":"10.3390\/biom16030342","type":"journal-article","created":{"date-parts":[[2026,2,24]],"date-time":"2026-02-24T15:05:27Z","timestamp":1771945527000},"page":"342","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Alteration of Lipid Bilayer Electrical Potential by Phytochemicals and Synthetic Analogs: Implications for Cellular Function"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2429-2007","authenticated-orcid":false,"given":"Svetlana S.","family":"Efimova","sequence":"first","affiliation":[{"name":"Institute of Cytology of Russian Academy of Science, Tikhoretsky Ave. 4, St. Petersburg 194064, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6922-1627","authenticated-orcid":false,"given":"Quan Minh","family":"Pham","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Vietnamese Academic of Science and Technology (ICH, VAST), 18 Hoang Quoc Viet, Hanoi 113000, Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huong Thi Thu","family":"Trinh","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Vietnamese Academic of Science and Technology (ICH, VAST), 18 Hoang Quoc Viet, Hanoi 113000, Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Long Quoc","family":"Pham","sequence":"additional","affiliation":[{"name":"Laboratory of Biophysics, Institute for Advanced Study in Technology, Ton Duc Thang University, 19 Nguyen Huu Tho Street, Ho Chi Minh City 700000, Vietnam"},{"name":"Faculty of Pharmacy, Ton Duc Thang University, 19 Nguyen Huu Tho Street, Ho Chi Minh City 700000, Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga S.","family":"Ostroumova","sequence":"additional","affiliation":[{"name":"Institute of Cytology of Russian Academy of Science, Tikhoretsky Ave. 4, St. Petersburg 194064, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,2,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1146\/annurev.bb.15.060186.001115","article-title":"Electrostatic interactions in membranes and proteins","volume":"15","author":"Honig","year":"1986","journal-title":"Annu. Rev. Biophys. Biophys. Chem."},{"key":"ref_2","unstructured":"Hille, B. (2001). Ion Channels of Excitable Membranes, Sinauer. [3rd ed.]."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"336","DOI":"10.1016\/j.pbiomolbio.2006.10.001","article-title":"Quantitative techniques for steady-state calculation and dynamic integrated modelling of membrane potential and intracellular ion concentrations","volume":"94","author":"Fraser","year":"2007","journal-title":"Prog. Biophys. Mol. Biol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1007\/s00249-010-0641-8","article-title":"Ion fluxes, transmembrane potential, and osmotic stabilization: A new dynamic electrophysiological model for eukaryotic cells","volume":"40","author":"Poignard","year":"2011","journal-title":"Eur. Biophys. J."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1093\/jb\/mvg052","article-title":"Biosynthetic regulation and intracellular transport of phosphatidylserine in mammalian cells","volume":"133","author":"Kuge","year":"2003","journal-title":"J. Biochem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"407","DOI":"10.1146\/annurev.biophys.093008.131234","article-title":"The distribution and function of phosphatidylserine in cellular membranes","volume":"39","author":"Leventis","year":"2010","journal-title":"Annu. Rev. Biophys."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"781","DOI":"10.1016\/j.nut.2014.10.014","article-title":"Phosphatidylserine and the human brain","volume":"31","author":"Glade","year":"2015","journal-title":"Nutrition"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"956","DOI":"10.1016\/j.fgb.2009.09.001","article-title":"Cryptococcus neoformans cryoultramicrotomy and vesicle fractionation reveals an intimate association between membrane lipids and glucuronoxylomannan","volume":"46","author":"Oliveira","year":"2009","journal-title":"Fungal Genet. Biol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/j.plipres.2013.02.002","article-title":"Bacterial lipids: Metabolism and membrane homeostasis","volume":"52","author":"Parsons","year":"2013","journal-title":"Prog. Lipid. Res."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1093\/femsre\/fuv008","article-title":"Bacterial membrane lipids: Diversity in structures and pathways","volume":"40","author":"Sohlenkamp","year":"2016","journal-title":"FEMS Microbiol. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"102315","DOI":"10.1016\/j.mib.2023.102315","article-title":"Bacterial lipid biophysics and membrane organization","volume":"74","author":"Belin","year":"2023","journal-title":"Curr. Opin. Microbiol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"160","DOI":"10.3390\/v3020160","article-title":"Flavivirus cell entry and membrane fusion","volume":"3","author":"Smit","year":"2011","journal-title":"Viruses"},{"key":"ref_13","first-page":"102","article-title":"Effects of lipids on mitochondrial functions","volume":"1862","author":"Doan","year":"2017","journal-title":"Biochim. Biophys. Acta. Mol. Cell Biol. Lipids."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1016\/S0006-3495(93)81051-8","article-title":"Internal electrostatic potentials in bilayers: Measuring and controlling dipole potentials in lipid vesicles","volume":"65","author":"Franklin","year":"1993","journal-title":"Biophys. J."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2134","DOI":"10.1104\/pp.108.127464","article-title":"Cell membrane surface potential (psi0) plays a dominant role in the phytotoxicity of copper and arsenate","volume":"148","author":"Wang","year":"2008","journal-title":"Plant Physiol."},{"key":"ref_16","first-page":"654","article-title":"Sur la constitution de la charge electrique a la surface d\u2019un electrolyte","volume":"149","author":"Gouy","year":"1910","journal-title":"Compt. Rend."},{"key":"ref_17","first-page":"508","article-title":"The theory of the electrolytic double-layer","volume":"30","author":"Stern","year":"1924","journal-title":"Z. Elektrochem. Angew. Phys. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"505","DOI":"10.1104\/pp.118.2.505","article-title":"Computation of surface electrical potentials of plant cell membranes. Correspondence To published zeta potentials from diverse plant sources","volume":"118","author":"Kinraide","year":"1998","journal-title":"Plant Physiol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1016\/j.jcis.2006.12.075","article-title":"International union of pure and applied chemistry, physical and biophysical chemistry division IUPAC technical report. Measurement and interpretation of electrokinetic phenomena","volume":"309","author":"Delgado","year":"2007","journal-title":"J. Colloid Interface Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"102778","DOI":"10.1016\/j.cis.2022.102778","article-title":"A review of zeta potential measurements using electroacoustics","volume":"309","author":"Waters","year":"2022","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_21","first-page":"4439","article-title":"High-concentration zeta potential measurements using light-scattering techniques","volume":"368","author":"Kaszuba","year":"2010","journal-title":"Philos. Trans A Math. Phys. Eng. Sci."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Ermakov, Y.A. (2023). Electric fields at the lipid membrane interface. Membranes, 13.","DOI":"10.3390\/membranes13110883"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1016\/S0006-3495(86)83663-3","article-title":"Hydrophobic ion interactions with membranes. Thermodynamic analysis of tetraphenylphosphonium binding to vesicles","volume":"49","author":"Flewelling","year":"1986","journal-title":"Biophys. J."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1016\/S0006-3495(86)83664-5","article-title":"The membrane dipole potential in a total membrane potential model. Applications to hydrophobic ion interactions with membranes","volume":"49","author":"Flewelling","year":"1986","journal-title":"Biophys. J."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1399","DOI":"10.1016\/S0006-3495(98)77852-X","article-title":"The adsorption of phloretin to lipid monolayers and bilayers cannot be explained by langmuir adsorption isotherms alone","volume":"74","author":"Cseh","year":"1998","journal-title":"Biophys. J."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/S0009-3084(02)00013-0","article-title":"Origin of membrane dipole potential: Contribution of the phospholipid fatty acid chains","volume":"117","author":"Peterson","year":"2002","journal-title":"Chem. Phys. Lipids."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1722","DOI":"10.1529\/biophysj.104.044529","article-title":"The 4,5-double bond of ceramide regulates its dipole potential, elastic properties, and packing behavior","volume":"87","author":"Brockman","year":"2004","journal-title":"Biophys. J."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1213","DOI":"10.1016\/S0006-3495(92)81931-8","article-title":"Membrane dipole potentials, hydration forces, and the ordering of water at membrane surfaces","volume":"61","author":"Gawrisch","year":"1992","journal-title":"Biophys. J."},{"key":"ref_29","first-page":"452","article-title":"Permeability of bimolecular phospholipid membranes for fat-soluble ions","volume":"14","author":"Liberman","year":"1969","journal-title":"Biofizika"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1016\/0005-2736(72)90178-2","article-title":"Ion transfer across lipid membranes in the presence of gramicidin A. I. Studies of the unit conductance channel","volume":"274","author":"Hladky","year":"1972","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1007\/BF01870551","article-title":"Transport mechanism of hydrophobic ions through lipid bilayer membranes","volume":"5","author":"Ketterer","year":"1971","journal-title":"J. Membr. Biol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1016\/0005-2736(78)90397-8","article-title":"Influence of sterols on ion transport through lipid bilayer membranes","volume":"506","author":"Benz","year":"1978","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1016\/S0005-2736(97)00075-8","article-title":"Effect of lipid structure on the dipole potential of phosphatidylcholine bilayers","volume":"1327","author":"Clarke","year":"1997","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1007\/978-3-030-04278-3_6","article-title":"Effect of Cholesterol on the Dipole Potential of Lipid Membranes","volume":"1115","author":"Clarke","year":"2019","journal-title":"Adv. Exp. Med. Biol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"7818","DOI":"10.1021\/acs.jpcb.9b06570","article-title":"Effects of Ether Linkage on Membrane Dipole Potential and Cholesterol Flip-Flop Motion in Lipid Bilayer Membranes","volume":"123","author":"Shen","year":"2019","journal-title":"J. Phys. Chem. B"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1007\/s00249-008-0392-y","article-title":"Effect of headgroup on the dipole potential of phospholipid vesicles","volume":"39","author":"Clarke","year":"2009","journal-title":"Eur. Biophys. J."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"9648","DOI":"10.1063\/1.1806791","article-title":"Comparative molecular dynamics study of ether- and ester-linked phospholipid bilayers","volume":"121","author":"Shinoda","year":"2004","journal-title":"J. Chem. Phys."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/0009-3084(94)90174-0","article-title":"Dipole potential of lipid membranes","volume":"73","author":"Brockman","year":"1994","journal-title":"Chem. Phys. Lipids"},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Cardoso, R.M.S., Lairion, F., Disalvo, E.A., Loura, L.M.S., and Moreno, M.J. (2024). Dipole Potential of Monolayers with Biologically Relevant Lipid Compositions. Molecules, 29.","DOI":"10.20944\/preprints202410.0151.v1"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1016\/S0001-8686(00)00061-0","article-title":"The dipole potential of phospholipid membranes and methods for its detection","volume":"89\u201390","author":"Clarke","year":"2001","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4415","DOI":"10.1021\/acs.jpcb.2c02476","article-title":"Membrane Dipole Potential: An Emerging Approach to Explore Membrane Organization and Function","volume":"126","author":"Sarkar","year":"2022","journal-title":"J. Phys. Chem. B"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4536","DOI":"10.1021\/bi00437a003","article-title":"Dual-wavelength ratiometric fluorescence measurements of membrane potential","volume":"28","author":"Montana","year":"1989","journal-title":"Biochem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.chemphyslip.2009.05.002","article-title":"Nanoscopic description of biomembrane electrostatics: Results of molecular dynamics simulations and fluorescence probing","volume":"160","author":"Demchenko","year":"2009","journal-title":"Chem. Phys. Lipids"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"11219","DOI":"10.1073\/pnas.1934603100","article-title":"Ultrasensitive two-color fluorescence probes for dipole potential in phospholipid membranes","volume":"100","author":"Klymchenko","year":"2003","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1016\/j.bbamem.2005.03.015","article-title":"Two-color fluorescent probes for imaging the dipole potential of cell plasma membranes","volume":"1712","author":"Shynkar","year":"2005","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"4160","DOI":"10.1021\/jp1111372","article-title":"Di-8-ANEPPS emission spectra in phospholipid\/cholesterol membranes: A theoretical study","volume":"115","author":"Robinson","year":"2011","journal-title":"J. Phys. Chem. B"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1016\/S0006-3495(98)77765-3","article-title":"Membrane electric properties by combined patch clamp and fluorescence ratio imaging in single neurons","volume":"74","author":"Zhang","year":"1998","journal-title":"Biophys. J."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1250","DOI":"10.1016\/j.bbamem.2012.12.019","article-title":"The effect of oxidative stress on the membrane dipole potential of human red blood cells","volume":"1828","author":"Jewell","year":"2013","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1016\/j.bbamem.2012.11.022","article-title":"Differential effect of sterols on dipole potential in hippocampal membranes: Implications for receptor function","volume":"1828","author":"Singh","year":"2013","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2890","DOI":"10.1021\/acschemneuro.0c00499","article-title":"Cell cycle dependent modulation of membrane dipole potential and neurotransmitter receptor activity: Role of membrane cholesterol","volume":"11","author":"Sarkar","year":"2020","journal-title":"ACS Chem. Neurosci."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"749","DOI":"10.1085\/jgp.67.6.749","article-title":"Effect of phloretin on the permeability of thin lipid membranes","volume":"67","author":"Andersen","year":"1976","journal-title":"J. Gen. Physiol."},{"key":"ref_52","first-page":"424","article-title":"Measurement of potential jumps during the adsorption of phloretin and phloricin on the surface of lipid membranes using the intramembrane field compensation method","volume":"29","author":"Sokolov","year":"1984","journal-title":"Biophysics"},{"key":"ref_53","first-page":"846","article-title":"Boundary potentials on a bilayer membrane in the presence of rimantadine. Analysis of three measurement methods","volume":"3","author":"Simonova","year":"1986","journal-title":"Biochem. Moscow Suppl. Ser. A"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"9399","DOI":"10.1021\/acs.jpcb.8b06726","article-title":"Molecular Dynamics Simulations of Ether- and Ester-Linked Phospholipid Bilayers: A Comparative Study of Water Models","volume":"122","author":"Shen","year":"2018","journal-title":"J Phys Chem B"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"4585","DOI":"10.1021\/acs.jpclett.6b02123","article-title":"What Can We Learn about Cholesterol\u2019s Transmembrane Distribution Based on Cholesterol-Induced Changes in Membrane Dipole Potential?","volume":"7","author":"Falkovich","year":"2016","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1529\/biophysj.107.104208","article-title":"Effect of local anesthetic lidocaine on electrostatic properties of a lipid bilayer","volume":"94","author":"Lyubartsev","year":"2008","journal-title":"Biophys. J."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"12850","DOI":"10.1039\/D1CP01238J","article-title":"Extension of the CAVS model to the simulation of helical peptides in a membrane environment","volume":"23","author":"Shen","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"18080","DOI":"10.1021\/acsomega.0c01633","article-title":"Interfacial Water Structure at Zwitterionic Membrane\/Water Interface: The Importance of Interactions between Water and Lipid Carbonyl Groups","volume":"5","author":"Shen","year":"2020","journal-title":"ACS Omega"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.bpc.2011.10.002","article-title":"Influence of the membrane dipole potential on peptide binding to lipid bilayers","volume":"161","author":"Zhan","year":"2012","journal-title":"Biophys. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"104386","DOI":"10.1016\/j.jmbbm.2021.104386","article-title":"Mechanical properties of ester- and ether-DPhPC bilayers: A molecular dynamics study","volume":"117","author":"Rasouli","year":"2021","journal-title":"J. Mech. Behav. Biomed. Mater."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"8081","DOI":"10.1021\/acs.langmuir.4c04779","article-title":"Membrane Binding of Hydrophobic Ions: Application of New Kinetic Techniques","volume":"41","author":"Baumgart","year":"2025","journal-title":"Langmuir"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1007\/BF01875422","article-title":"The gramicidin A channel: A review of its permeability characteristics with special reference to the single-file aspect of transport","volume":"59","author":"Finkelstein","year":"1981","journal-title":"J. Membr. Biol."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"721","DOI":"10.1007\/s00232-014-9697-1","article-title":"Measurement of dipole potential in bilayer lipid membranes by dielectric spectroscopy","volume":"247","author":"Hidaka","year":"2014","journal-title":"J. Membr. Biol."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"18528","DOI":"10.1073\/pnas.0608714103","article-title":"Using cryo-EM to measure the dipole potential of a lipid mem brane","volume":"103","author":"Wang","year":"2006","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_65","first-page":"100090","article-title":"Optimization of cryo-electron microscopy for quantitative analysis of lipid bilayers","volume":"3","author":"Heberle","year":"2022","journal-title":"Biophys. Rep."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"5193","DOI":"10.1529\/biophysj.108.136507","article-title":"Probing the lipid membrane dipole potential by atomic force microscopy","volume":"95","author":"Yang","year":"2008","journal-title":"Biophys. J."},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Szabo, M., Cs Szabo, B., Kurtan, K., Varga, Z., Panyi, G., Nagy, P., Zakany, F., and Kovacs, T. (2025). Look Beyond Plasma Membrane Biophysics: Revealing Considerable Variability of the Dipole Potential Between Plasma and Organelle Membranes of Living Cells. Int. J. Mol. Sci., 26.","DOI":"10.3390\/ijms26030889"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"1561","DOI":"10.1016\/j.bpj.2012.03.004","article-title":"Differential effect of cholesterol and its biosynthetic precursors on membrane dipole potential","volume":"102","author":"Haldar","year":"2012","journal-title":"Biophys. J."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/S0006-3495(80)85053-3","article-title":"Effects of the dipolar form of phloretin on potassium conductance in squid giant axons","volume":"31","author":"Strichartz","year":"1980","journal-title":"Biophys. J."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1393","DOI":"10.1152\/physrev.00036.2011","article-title":"hERG K+ Channels: Structure, Function, and Clinical Significance","volume":"92","author":"Vandenberg","year":"2012","journal-title":"Physiol. Rev."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/j.bbamem.2016.11.005","article-title":"Contributions of the membrane dipole potential to the function of voltage-gated cation channels and modulation by small molecule potentiators","volume":"1859","author":"Pearlstein","year":"2017","journal-title":"Biochim. Biophys. Acta Biomembr."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.bpc.2008.02.018","article-title":"Influence of membrane potentials upon reversible protonation of acidic residues from the OmpF eyelet","volume":"135","author":"Asandei","year":"2008","journal-title":"Biophys. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1142\/S0219635212500094","article-title":"A quantum-mechanical description of ion motion within the confining potentials of voltage-gated ion channels","volume":"11","author":"Summhammer","year":"2012","journal-title":"J. Integr. Neurosci."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"2795","DOI":"10.1016\/j.bbamem.2013.03.002","article-title":"Role of terminal dipole charges in aggregation of \u03b1-helix pair in the voltage gated K(+) channel","volume":"1828","author":"Adhya","year":"2013","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1529\/biophysj.104.049411","article-title":"State-dependent changes in the electrostatic potential in the pore of a GluR channel","volume":"88","author":"Sobolevsky","year":"2005","journal-title":"Biophys. J."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"912","DOI":"10.1529\/biophysj.103.038448","article-title":"Determinants of gating polarity of a connexin 32 hemichannel","volume":"87","author":"Oh","year":"2004","journal-title":"Biophys. J."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1080\/07391102.2007.10507148","article-title":"Towards a mechanism of function of the viral ion channel Vpu from HIV-1","volume":"24","author":"Mehnert","year":"2007","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_78","doi-asserted-by":"crossref","unstructured":"Knyazev, D.G., Kuttner, R., Bondar, A.N., Zimmerman, M., Siligan, C., and Pohl, P. (2020). Voltage Sensing in Bacterial Protein Translocation. Biomolecules, 10.","DOI":"10.3390\/biom10010078"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1085\/jgp.200509378","article-title":"A single P-loop glutamate point mutation to either lysine or arginine switches the cation-anion selectivity of the CNGA2 channel","volume":"127","author":"Qu","year":"2006","journal-title":"J. Gen. Physiol."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"493","DOI":"10.1016\/j.jmb.2004.08.036","article-title":"Structural determinants of proton blockage in aquaporins","volume":"343","author":"Chakrabarti","year":"2004","journal-title":"J. Mol. Biol."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"850","DOI":"10.1016\/S0006-3495(97)78117-7","article-title":"Effect of the dipole potential of a bilayer lipid membrane on gramicidin channel dissociation kinetics","volume":"73","author":"Rokitskaya","year":"1997","journal-title":"Biophys. J."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"2830","DOI":"10.1016\/S0006-3495(98)77726-4","article-title":"Noncontact dipole effects on channel permeation. I. Experiments with (5F-indole)Trp13 gramicidin A channels","volume":"75","author":"Busath","year":"1998","journal-title":"Biophys. J."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"2987","DOI":"10.1021\/la800206v","article-title":"Altering the activity of syringomycin E via the membrane dipole potential","volume":"24","author":"Ostroumova","year":"2008","journal-title":"Langmuir"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1016\/S0006-3495(02)75448-9","article-title":"Membrane dipole potential modulates proton conductance through gramicidin channel: Movement of negative ionic defects inside the channel","volume":"82","author":"Rokitskaya","year":"2002","journal-title":"Biophys. J."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/S1567-5394(03)00041-0","article-title":"Effective gating charge of ion channels induced by toxin syringomycin E in lipid bilayers","volume":"60","author":"Schagina","year":"2003","journal-title":"Bioelectrochemistry"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"8452","DOI":"10.1021\/la0613777","article-title":"Phlorizin- and 6-ketocholestanol-mediated antagonistic modulation of alamethicin activity in phospholipid planar membranes","volume":"22","author":"Luchian","year":"2006","journal-title":"Langmuir"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.colsurfb.2008.08.006","article-title":"Ion selectivity, transport properties and dynamics of amphotericin B channels studied over a wide range of acidity changes","volume":"67","author":"Asandei","year":"2008","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"809","DOI":"10.1016\/j.bbagen.2009.04.002","article-title":"The RH 421 styryl dye induced, pore model-dependent modulation of antimicrobial peptides activity in reconstituted planar membranes","volume":"1790","author":"Apetrei","year":"2009","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"15092","DOI":"10.1021\/la102691y","article-title":"Surfactin activity depends on the membrane dipole potential","volume":"26","author":"Ostroumova","year":"2010","journal-title":"Langmuir"},{"key":"ref_90","doi-asserted-by":"crossref","unstructured":"Mereuta, L., Asandei, A., and Luchian, T. (2011). Meet me on the other side: Trans-bilayer modulation of a model voltage-gated ion channel activity by membrane electrostatics asymmetry. PLoS ONE, 6.","DOI":"10.1371\/journal.pone.0025276"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"7884","DOI":"10.1021\/la501549v","article-title":"Channel-forming activity of cecropins in lipid bilayers: Effect of agents modifying the membrane dipole potential","volume":"30","author":"Efimova","year":"2014","journal-title":"Langmuir"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"781","DOI":"10.1007\/s00232-016-9926-x","article-title":"Local Anesthetics Affect Gramicidin A Channels via Membrane Electrostatic Potentials","volume":"249","author":"Efimova","year":"2016","journal-title":"J. Membr. Biol."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1007\/s00232-018-0031-1","article-title":"Ion channels induced by antimicrobial agents in model lipid membranes are modulated by plant polyphenols through surrounding lipid media","volume":"251","author":"Efimova","year":"2018","journal-title":"J. Membr. Biol."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1016\/j.bbamem.2017.12.010","article-title":"Lipid-mediated regulation of pore-forming activity of syringomycin E by thyroid hormones and xanthene dyes","volume":"1860","author":"Efimova","year":"2018","journal-title":"Biochim. Biophys. Acta Biomembr."},{"key":"ref_95","doi-asserted-by":"crossref","unstructured":"Zakharova, A.A., Efimova, S.S., and Ostroumova, O.S. (2022). Lipid Microenvironment Modulates the Pore-Forming Ability of Polymyxin B. Antibiotics, 11.","DOI":"10.3390\/antibiotics11101445"},{"key":"ref_96","doi-asserted-by":"crossref","unstructured":"Chernyshova, D.N., Tyulin, A.A., Ostroumova, O.S., and Efimova, S.S. (2022). Discovery of the Potentiator of the Pore-Forming Ability of Lantibiotic Nisin: Perspectives for Anticancer Therapy. Membranes, 12.","DOI":"10.3390\/membranes12111166"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"35850","DOI":"10.1038\/srep35850","article-title":"The Dipole Potential Modifies the Clustering and Ligand Binding Affinity of ErbB Proteins and Their Signaling Efficiency","volume":"6","author":"Batta","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"R663","DOI":"10.1152\/ajpregu.00434.2004","article-title":"Electric field strength of membrane lipids from vertebrate species: Membrane lipid composition and Na+-K+-ATPase molecular activity","volume":"288","author":"Turner","year":"2005","journal-title":"Am. J. Physiol. Regul. Integr. Comp. Physiol."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"1352","DOI":"10.1016\/j.bpj.2014.05.054","article-title":"Identification of electric-field-dependent steps in the Na(+), K(+)-pump cycle","volume":"107","author":"Mares","year":"2014","journal-title":"Biophys. J."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1016\/j.bpc.2005.09.007","article-title":"Influence of N-dodecyl-N,N-dimethylamine N-oxide on the activity of sarcoplasmic reticulum Ca(2+)-transporting ATPase reconstituted into diacylphosphatidylcholine vesicles: Efects of bilayer physical parameters","volume":"119","author":"Kucerka","year":"2006","journal-title":"Biophys. Chem."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"14282","DOI":"10.1038\/srep14282","article-title":"Hofmeister effect of anions on calcium translocation by sarcoplasmic reticulum Ca(2+)-ATPase","volume":"5","author":"Moncelli","year":"2015","journal-title":"Sci. Rep."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"1513","DOI":"10.1016\/j.bpj.2015.08.022","article-title":"Dipole-Potential-Mediated Effects on Ion Pump Kinetics","volume":"109","author":"Clarke","year":"2015","journal-title":"Biophys. J."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"930\u2212939","DOI":"10.1016\/S0022-2275(20)32128-3","article-title":"Modulation of phospholipase A2 by electrostatic fields and dipole potential of glycosphingolipids in monolayers","volume":"40","author":"Maggio","year":"1999","journal-title":"J. Lipid Res."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"4144","DOI":"10.1016\/S0006-3495(03)75139-X","article-title":"Activation of phospholipase C increases intramembrane electric fields in N1E-115 neuroblastoma cells","volume":"84","author":"Xu","year":"2003","journal-title":"Biophys. J."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"2434","DOI":"10.1016\/S0006-3495(98)77951-2","article-title":"Intramembrane molecular dipoles affect the membrane insertion and folding of a model amphiphilic peptide","volume":"74","author":"Cladera","year":"1998","journal-title":"Biophys. J."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"1000","DOI":"10.1016\/S0006-291X(88)80973-2","article-title":"Inhibition of Na,K-ATPase and sodium pump by anticancer ether lipids and protein kinase C inhibitors ET-18-OCH3 and BM 41.440","volume":"157","author":"Oishi","year":"1988","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"7748","DOI":"10.1039\/C5SM00876J","article-title":"Clostridium perfringens\u03b1-toxin interaction with red cells and model membranes","volume":"11","author":"Jewell","year":"2015","journal-title":"Soft. Matter."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"1681","DOI":"10.1194\/jlr.M077339","article-title":"The dipole potential correlates with lipid raft markers in the plasma membrane of living cells","volume":"58","author":"Batta","year":"2017","journal-title":"J. Lipid Res."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1007\/s00249-015-1101-2","article-title":"Two types of syringomycin E channels in sphingomyelin-containing bilayers","volume":"45","author":"Efimova","year":"2016","journal-title":"Eur. Biophys. J."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1007\/978-1-0716-0814-2_16","article-title":"Characterization of the Effect of Sphingolipid Accumulation on Membrane Compactness, Dipole Potential, and Mobility of Membrane Components","volume":"2187","author":"Batta","year":"2021","journal-title":"Methods Mol. Biol."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"1543","DOI":"10.1194\/jlr.M059519","article-title":"\u03b1-Tocopherols modify the membrane dipole potential leading to modulation of ligand binding by P-glycoprotein","volume":"56","author":"Davis","year":"2015","journal-title":"J. Lipid Res."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"1349","DOI":"10.1002\/prot.26508","article-title":"Structure and elasticity of healthy and Alzheimer\u2019s disease cell membranes revealed by molecular dynamics simulations","volume":"93","author":"Mai","year":"2025","journal-title":"Proteins"},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.chemphyslip.2017.10.001","article-title":"Solubilization of the serotonin1A receptor monitored utilizing membrane dipole potential","volume":"209","author":"Sarkar","year":"2017","journal-title":"Chem. Phys. Lipids"},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"29951","DOI":"10.1074\/jbc.274.42.29951","article-title":"Characterization of the sequence of interactions of the fusion domain of the simian immunodeficiency virus with membranes. Role of the membrane dipole potential","volume":"274","author":"Cladera","year":"1999","journal-title":"J. Biol. Chem."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"15768","DOI":"10.1021\/bi060622i","article-title":"Effect of cholesterol on the interaction of the HIV GP41 fusion peptide with model membranes. Importance of the membrane dipole potential","volume":"45","author":"Cladera","year":"2006","journal-title":"Biochemistry"},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1016\/j.bbamem.2018.02.001","article-title":"Effect of 25-hydroxycholesterol in viral membrane fusion: Insights on HIV inhibition","volume":"1860","author":"Gomes","year":"2018","journal-title":"Biochim. Biophys. Acta Biomembr."},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"38457","DOI":"10.1074\/jbc.M103269200","article-title":"Effects of the membrane dipole potential on the interaction of saquinavir with phospholipid membranes and plasma membrane receptors of Caco-2 cells","volume":"276","author":"Asawakarn","year":"2001","journal-title":"J. Biol. Chem."},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"270","DOI":"10.1016\/j.bbrc.2010.11.013","article-title":"The role of blood cell membrane lipids on the mode of action of HIV-1 fusion inhibitor sifuvirtide","volume":"403","author":"Matos","year":"2010","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_119","doi-asserted-by":"crossref","unstructured":"Matos, P.M., Castanho, M.A., and Santos, N.C. (2010). HIV-1 fusion inhibitor peptides enfuvirtide and T-1249 interact with erythrocyte and lymphocyte membranes. PLoS ONE, 5.","DOI":"10.1371\/journal.pone.0009830"},{"key":"ref_120","doi-asserted-by":"crossref","unstructured":"Hollmann, A., Matos, P.M., Augusto, M.T., Castanho, M.A., and Santos, N.C. (2013). Conjugation of cholesterol to HIV-1 fusion inhibitor C34 increases peptide-membrane interactions potentiating its action. PLoS ONE, 8.","DOI":"10.1371\/journal.pone.0060302"},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"2765","DOI":"10.1016\/j.bbamem.2008.07.021","article-title":"Membrane insertion of the three main membranotropic sequences from SARS-CoV S2 glycoprotein","volume":"1778","author":"Kinnunen","year":"2008","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"16962","DOI":"10.1039\/D5CP01030F","article-title":"Binding of SARS-CoV-2 fusion peptides to hybrid phospholipid bilayers: Exploring the influence of ether-linked phospholipids","volume":"27","author":"Shen","year":"2025","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1124\/mol.104.000075","article-title":"Dipole potential and head-group spacing are determinants for the membrane partitioning of pregnanolone","volume":"66","author":"Alakoskela","year":"2004","journal-title":"Mol. Pharmacol."},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"5180","DOI":"10.1039\/C7CP07243K","article-title":"The interfacial electrostatic potential modulates the insertion of cell-penetrating peptides into lipid bilayers","volume":"20","author":"Via","year":"2018","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_125","doi-asserted-by":"crossref","first-page":"3667","DOI":"10.1111\/bph.15509","article-title":"Statin-boosted cellular uptake and endosomal escape of penetratin due to reduced membrane dipole potential","volume":"178","author":"Batta","year":"2021","journal-title":"Br. J. Pharmacol."},{"key":"ref_126","doi-asserted-by":"crossref","first-page":"3102","DOI":"10.1021\/acs.langmuir.7b04038","article-title":"Negative Dipole Potentials and Carboxylic Polar Head Groups Foster the Insertion of Cell-Penetrating Peptides into Lipid Monolayers","volume":"34","author":"Via","year":"2018","journal-title":"Langmuir"},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"1018","DOI":"10.1002\/jps.10344","article-title":"Influence of molecular dipoles on human skin permeability: Use of 6-ketocholestanol to enhance the transdermal delivery of bacitracin","volume":"92","author":"Cladera","year":"2003","journal-title":"J. Pharm. Sci."},{"key":"ref_128","doi-asserted-by":"crossref","first-page":"41346","DOI":"10.1038\/srep41346","article-title":"Lipid-II Independent Antimicrobial Mechanism of Nisin Depends On Its Crowding And Degree Of Oligomerization","volume":"7","author":"Prince","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_129","doi-asserted-by":"crossref","first-page":"1174","DOI":"10.1093\/jac\/dkaa560","article-title":"Polyalanine peptide variations may have different mechanisms of action against multidrug-resistant bacterial pathogens","volume":"76","author":"Silveira","year":"2021","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_130","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1042\/bj3210691","article-title":"Partition of the organochlorine insecticide lindane into the human sperm surface induces membrane depolarization and Ca2+ influx","volume":"321","author":"Silvestroni","year":"1997","journal-title":"Biochem. J."},{"key":"ref_131","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1016\/S0006-3495(79)85175-9","article-title":"Effect of the anesthetics benzyl alcohol and chloroform on bilayers made from monolayers","volume":"28","author":"Reyes","year":"1979","journal-title":"Biophys. J."},{"key":"ref_132","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1016\/S0378-4274(98)00217-3","article-title":"Dipole potentials and spontaneous curvature: Membrane properties that could mediate anesthesia","volume":"100\u2013101","author":"Cafiso","year":"1998","journal-title":"Toxicol. Lett."},{"key":"ref_133","doi-asserted-by":"crossref","first-page":"1962","DOI":"10.1194\/jlr.M073932","article-title":"Assessing anesthetic activity through modulation of the membrane dipole potential","volume":"58","author":"Davis","year":"2017","journal-title":"J. Lipid Res."},{"key":"ref_134","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1007\/s00249-016-1164-8","article-title":"Study of procaine and tetracaine in the lipid bilayer using molecular dynamics simulation","volume":"46","author":"Jalili","year":"2017","journal-title":"Eur. Biophys. J."},{"key":"ref_135","doi-asserted-by":"crossref","first-page":"5536","DOI":"10.1021\/bi00016a027","article-title":"Anesthetics reduce the magnitude of the membrane dipole potential. Measurements in lipid vesicles using voltage-sensitive spin probes","volume":"34","author":"Qin","year":"1995","journal-title":"Biochemistry"},{"key":"ref_136","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1007\/s00232-022-00240-2","article-title":"Effect of Local Anesthetics on Dipole Potential of Different Phase Membranes: A Fluorescence Study","volume":"255","author":"Shrivastava","year":"2022","journal-title":"J. Membr. Biol."},{"key":"ref_137","doi-asserted-by":"crossref","first-page":"113394","DOI":"10.1016\/j.colsurfb.2023.113394","article-title":"Novel customized age-dependent corneal membranes and interactions with biodegradable nanoparticles loaded with dexibuprofen","volume":"228","author":"Esteruelas","year":"2023","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_138","doi-asserted-by":"crossref","first-page":"106986","DOI":"10.1016\/j.ejps.2024.106986","article-title":"Membrane interaction studies of isoniazid derivatives active against drug-resistant tuberculosis","volume":"205","author":"Terreiro","year":"2025","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_139","doi-asserted-by":"crossref","first-page":"184350","DOI":"10.1016\/j.bbamem.2024.184350","article-title":"Ergosterol promotes aggregation of natamycin in the yeast plasma membrane","volume":"1866","author":"Szomek","year":"2024","journal-title":"Biochim. Biophys. Acta Biomembr."},{"key":"ref_140","doi-asserted-by":"crossref","unstructured":"Starosta, R., Santos, T.C., Dinis de Sousa, A.F., Santos, M.S., Corvo, M.L., Tomaz, A.I., and de Almeida, R.F.M. (2023). Assessing the role of membrane lipids in the action of ruthenium(III) anticancer compounds. Front. Mol. Biosci., 9.","DOI":"10.3389\/fmolb.2022.1059116"},{"key":"ref_141","doi-asserted-by":"crossref","first-page":"1362","DOI":"10.1016\/j.bbamem.2017.04.026","article-title":"Interaction of procyanidin B3 with membrane lipids - Fluorescence, DSC and FTIR studies","volume":"1859","author":"Jurkiewicz","year":"2017","journal-title":"Biochim. Biophys. Acta Biomembr."},{"key":"ref_142","doi-asserted-by":"crossref","first-page":"2553","DOI":"10.1016\/j.bbamem.2009.10.007","article-title":"Interaction of nicotinamide and picolinamide with phosphatidylcholine and phosphatidylethanolamine membranes: A combined approach using dipole potential measurements and quantum chemical calculations","volume":"1788","author":"Borba","year":"2009","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_143","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/S0005-2736(98)00098-4","article-title":"Changes of the membrane potential profile induced by verapamil and propranolol","volume":"1373","author":"Pohl","year":"1998","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_144","doi-asserted-by":"crossref","first-page":"450","DOI":"10.1016\/j.bbamem.2006.11.022","article-title":"Effect of arbutin on the dipole potential and area per lipid of ester and ether phosphatidylcholine and phosphatidyl ethanolamine monolayers","volume":"1768","author":"Lairion","year":"2007","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_145","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.chemphyslip.2016.09.001","article-title":"Micellar dipolar rearrangement is sensitive to hydrophobic chain length: Implication for structural switchover of piroxicam","volume":"200","author":"Sethy","year":"2016","journal-title":"Chem. Phys. Lipids"},{"key":"ref_146","doi-asserted-by":"crossref","first-page":"604","DOI":"10.1038\/s41598-025-30210-2","article-title":"The structure-dependent effects of newly synthesised cationic gemini surfactants against yeast cells","volume":"9","author":"Mazurkiewicz","year":"2025","journal-title":"Sci. Rep."},{"key":"ref_147","first-page":"753","article-title":"Characterization of mixed monolayers of phosphatidylcholine and a dicationic gemini surfactant SS-1 with a langmuir balance: Effects of DNA","volume":"89","author":"Matti","year":"2001","journal-title":"Biophys. J."},{"key":"ref_148","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/j.csbj.2024.04.022","article-title":"Unlocking the specificity of antimicrobial peptide interactions for membrane-targeted therapies","volume":"25","author":"Calvelo","year":"2024","journal-title":"Comput. Struct. Biotechnol. J."},{"key":"ref_149","doi-asserted-by":"crossref","first-page":"9908","DOI":"10.1021\/la301653s","article-title":"Effect of dipole modifiers on the magnitude of the dipole potential of sterol-containing bilayers","volume":"28","author":"Efimova","year":"2012","journal-title":"Langmuir"},{"key":"ref_150","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1016\/S0005-2736(96)00185-X","article-title":"Permeation of phloretin across bilayer lipid membranes monitored by dipole potential and microelectrode measurements","volume":"1323","author":"Pohl","year":"1997","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_151","doi-asserted-by":"crossref","unstructured":"Efimova, S.S., Zakharova, A.A., and Ostroumova, O.S. (2020). Alkaloids Modulate the Functioning of Ion Channels Produced by Antimicrobial Agents via an Influence on the Lipid Host. Front. Cell Dev. Biol., 8.","DOI":"10.3389\/fcell.2020.00537"},{"key":"ref_152","doi-asserted-by":"crossref","unstructured":"Efimova, S.S., and Ostroumova, O.S. (2021). Is the Membrane Lipid Matrix a Key Target for Action of Pharmacologically Active Plant Saponins?. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22063167"},{"key":"ref_153","doi-asserted-by":"crossref","first-page":"114269","DOI":"10.1016\/j.colsurfb.2024.114269","article-title":"The effects of plant flavones on the membrane boundary potential and lipid packing stress","volume":"245","author":"Martynyuk","year":"2025","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_154","doi-asserted-by":"crossref","first-page":"9482","DOI":"10.1021\/acs.jpcb.4c04469","article-title":"The Membrane Dipole Potential and the Roles of Interfacial Water and Lipid Hydrocarbon Chains","volume":"128","author":"Lev","year":"2024","journal-title":"J. Phys. Chem. B"},{"key":"ref_155","doi-asserted-by":"crossref","unstructured":"Galassi, V.V., and Wilke, N. (2021). On the Coupling between Mechanical Properties and Electrostatics in Biological Membranes. Membranes, 11.","DOI":"10.3390\/membranes11070478"},{"key":"ref_156","doi-asserted-by":"crossref","first-page":"2608","DOI":"10.1016\/j.bbamem.2011.06.010","article-title":"Effect of membrane tension on the electric field and dipole potential of lipid bilayer membrane","volume":"1808","author":"Warshaviak","year":"2011","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_157","doi-asserted-by":"crossref","first-page":"1800","DOI":"10.1016\/j.bpj.2016.03.012","article-title":"Polyunsaturated lipids regulate membrane domain stability by tuning membrane order","volume":"110","author":"Levental","year":"2016","journal-title":"Biophys. J."},{"key":"ref_158","doi-asserted-by":"crossref","first-page":"foaa045","DOI":"10.1093\/femsyr\/foaa045","article-title":"A detailed lipidomic study of human pathogenic fungi Candida auris","volume":"20","author":"Shahi","year":"2020","journal-title":"FEMS Yeast Res."},{"key":"ref_159","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/j.crfs.2021.03.011","article-title":"Extraction of phenolic compounds: A review","volume":"4","author":"Alara","year":"2021","journal-title":"Curr. Res. Food Sci."},{"key":"ref_160","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.3390\/nu2121231","article-title":"Chemistry and biochemistry of dietary polyphenols","volume":"2","author":"Tsao","year":"2010","journal-title":"Nutrients"},{"key":"ref_161","doi-asserted-by":"crossref","first-page":"184","DOI":"10.3390\/ddc3010011","article-title":"Plant-Derived Natural Products: A Source for Drug Discovery and Development","volume":"3","author":"Chaachouay","year":"2024","journal-title":"Drugs Drug Candidates"},{"key":"ref_162","doi-asserted-by":"crossref","unstructured":"Thomford, N.E., Senthebane, D.A., Rowe, A., Munro, D., Seele, P., Maroyi, A., and Dzobo, K. (2018). Natural Products for Drug Discovery in the 21st Century: Innovations for Novel Drug Discovery. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19061578"},{"key":"ref_163","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1038\/s41573-020-00114-z","article-title":"International Natural Product Sciences Taskforce; Supuran CT. Natural products in drug discovery: Advances and opportunities","volume":"20","author":"Atanasov","year":"2021","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_164","doi-asserted-by":"crossref","first-page":"2253","DOI":"10.1038\/s41598-024-52781-2","article-title":"Recent insights into catechins-rich Assam tea extract for photoaging and senescent ageing","volume":"14","author":"Kanlayavattanakul","year":"2024","journal-title":"Sci. Rep."},{"key":"ref_165","doi-asserted-by":"crossref","unstructured":"Wu, J., Bai, Q., Chen, J., Yang, Z., and Zhu, X. (2024). Systemic Analyses of Anti-Cell-Senescence Active Compounds in Camellia Sect. Chrysantha Chang and Their Mechanisms. Plants, 13.","DOI":"10.3390\/plants13152139"},{"key":"ref_166","doi-asserted-by":"crossref","first-page":"5812401","DOI":"10.1155\/2017\/5812401","article-title":"Effects of Polyphenol Intake on Metabolic Syndrome: Current Evidences from Human Trials","volume":"2017","author":"Badimon","year":"2017","journal-title":"Oxid. Med. Cell Longev."},{"key":"ref_167","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1159\/000105477","article-title":"Pomegranate polyphenols and resveratrol protect the neonatal brain against hypoxic-ischemic injury","volume":"29","author":"West","year":"2007","journal-title":"Dev. Neurosci."},{"key":"ref_168","first-page":"79","article-title":"Polyphenols and cancer cell growth","volume":"159","author":"Kampa","year":"2007","journal-title":"Rev. Physiol. Biochem. Pharmacol."},{"key":"ref_169","doi-asserted-by":"crossref","first-page":"111082","DOI":"10.1016\/j.cbi.2024.111082","article-title":"The influence of the chlorine atom on the biological activity of 2\u2032-hydroxychalcone in relation to the lipid phase of biological membranes\u2014Anticancer and antimicrobial activity","volume":"398","author":"Matczak","year":"2024","journal-title":"Chem. Biol. Interact."},{"key":"ref_170","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/j.freeradbiomed.2017.12.002","article-title":"Differential targeting of membrane lipid domains by caffeic acid and its ester derivatives","volume":"115","author":"Filipe","year":"2018","journal-title":"Free Radic. Biol. Med."},{"key":"ref_171","doi-asserted-by":"crossref","first-page":"184443","DOI":"10.1016\/j.bbamem.2025.184443","article-title":"Complexes of star-shaped block copolymers of poly(2-alkyl-2-oxazine)s and curcumin can affect lipid bilayers mimicking biomembranes","volume":"1867","author":"Efimova","year":"2025","journal-title":"Biochim. Biophys. Acta Biomembr."},{"key":"ref_172","doi-asserted-by":"crossref","first-page":"596","DOI":"10.1016\/S0006-291X(02)00905-1","article-title":"Solubility of amphiphiles in membranes: Influence of phase properties and amphiphile head group","volume":"296","author":"Estronca","year":"2002","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_173","doi-asserted-by":"crossref","first-page":"602","DOI":"10.1134\/S1990519X24700524","article-title":"Membrane dipole potential: Modification methods and consequences for ion channels incorporation in the membrane","volume":"18","author":"Efimova","year":"2024","journal-title":"Cell Tissue Biol."},{"key":"ref_174","doi-asserted-by":"crossref","first-page":"356","DOI":"10.1038\/s42003-020-1089-8","article-title":"The ubiquitous flavonoid quercetin is an atypical KCNQ potassium channel activator","volume":"3","author":"Redford","year":"2020","journal-title":"Commun. Biol."},{"key":"ref_175","doi-asserted-by":"crossref","first-page":"174030","DOI":"10.1016\/j.ejphar.2021.174030","article-title":"Flavonoids and hERG channels: Friends or foes?","volume":"899","author":"Saponara","year":"2021","journal-title":"Eur. J. Pharmacol."},{"key":"ref_176","doi-asserted-by":"crossref","first-page":"142","DOI":"10.1111\/nyas.13361","article-title":"Actions of quercetin, a flavonoid, on ion transporters: Its physiological roles","volume":"1398","author":"Marunaka","year":"2017","journal-title":"Ann. N Y Acad Sci."},{"key":"ref_177","doi-asserted-by":"crossref","unstructured":"Richter-Laskowska, M., Trybek, P., Delfino, D.V., and Wawrzkiewicz-Ja\u0142owiecka, A. (2023). Flavonoids as Modulators of Potassium Channels. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24021311"},{"key":"ref_178","doi-asserted-by":"crossref","unstructured":"Kicinska, A., Kampa, R.P., Daniluk, J., Sek, A., Jarmuszkiewicz, W., Szewczyk, A., and Bednarczyk, P. (2020). Regulation of the Mitochondrial BKCa Channel by the Citrus Flavonoid Naringenin as a Potential Means of Preventing Cell Damage. Molecules, 25.","DOI":"10.3390\/molecules25133010"},{"key":"ref_179","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/0304-3940(94)90736-6","article-title":"Activating effect of the flavonoid phloretin on Ca(2+)-activated K+ channels in myelinated nerve fibers of Xenopus laevis [corrected]","volume":"165","author":"Koh","year":"1994","journal-title":"Neurosci. Lett."},{"key":"ref_180","doi-asserted-by":"crossref","first-page":"e46","DOI":"10.1111\/j.1755-5922.2010.00212.x","article-title":"Cardiovascular ion channels as a molecular target of flavonoids","volume":"28","author":"Scholz","year":"2010","journal-title":"Cardiovasc. Ther."},{"key":"ref_181","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1038\/sj.bjp.0706897","article-title":"Inhibition of cardiac voltage-gated sodium channels by grape polyphenols","volume":"149","author":"Wallace","year":"2006","journal-title":"Br. J. Pharmacol."},{"key":"ref_182","doi-asserted-by":"crossref","first-page":"607","DOI":"10.1165\/rcmb.2009-0281OC","article-title":"Activation of the cystic fibrosis transmembrane conductance regulator by the flavonoid quercetin: Potential use as a biomarker of \u0394F508 cystic fibrosis transmembrane conductance regulator rescue","volume":"43","author":"Pyle","year":"2010","journal-title":"Am. J. Respir. Cell Mol. Biol."},{"key":"ref_183","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/S0014-2999(03)01309-8","article-title":"Flavonoid modulation of ionic currents mediated by GABA(A) and GABA(C) receptors","volume":"461","author":"Goutman","year":"2003","journal-title":"Eur. J. Pharmacol."},{"key":"ref_184","doi-asserted-by":"crossref","unstructured":"Zahra, M., Abrahamse, H., and George, B.P. (2024). Flavonoids: Antioxidant Powerhouses and Their Role in Nanomedicine. Antioxidants, 13.","DOI":"10.3390\/antiox13080922"},{"key":"ref_185","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1111\/j.1745-7254.2006.00238.x","article-title":"Flavonoid-membrane interactions: Possible consequences for biological effects of some polyphenolic compounds","volume":"27","author":"Hendrich","year":"2006","journal-title":"Acta Pharmacol. Sin."},{"key":"ref_186","doi-asserted-by":"crossref","unstructured":"M\u0119czarska, K., Cyboran-Miko\u0142ajczyk, S., Solarska-\u015aciuk, K., Oszmia\u0144ski, J., Siejak, K., and Bonarska-Kujawa, D. (2025). Protective Effect of Field Horsetail Polyphenolic Extract on Erythrocytes and Their Membranes. Int. J. Mol. Sci., 26.","DOI":"10.3390\/ijms26073213"},{"key":"ref_187","doi-asserted-by":"crossref","unstructured":"Ka\u017amierczak, T., Cyboran-Miko\u0142ajczyk, S., Trochanowska-Pauk, N., Walski, T., Nowicka, P., and Bonarska-Kujawa, D. (2025). Insights on the Mechanisms of the Protective Action of Naringenin, Naringin and Naringin Dihydrochalcone on Blood Cells in Terms of Their Potential Anti-Atherosclerotic Activity. Molecules, 30.","DOI":"10.3390\/molecules30030547"},{"key":"ref_188","doi-asserted-by":"crossref","first-page":"695","DOI":"10.1099\/0022-1317-81-3-695","article-title":"The effects of interferon on the expression of human papillomavirus oncogenes","volume":"81","author":"Kim","year":"2000","journal-title":"J. Gen. Virol."},{"key":"ref_189","first-page":"367","article-title":"Studies of the liver function in experimental burns. Iv. The radioiodine rose bengal (rirb) test in the burned rabbit","volume":"127","author":"Stenberg","year":"1964","journal-title":"Acta Chir. Scand."},{"key":"ref_190","first-page":"801","article-title":"Iodine-containing hormones\u2014Dipole modifiers of phospholipid membranes","volume":"29","author":"Tsymbulskaya","year":"1984","journal-title":"Biophysics"},{"key":"ref_191","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1038\/nrendo.2015.205","article-title":"Nongenomic actions of thyroid hormone","volume":"12","author":"Davis","year":"2016","journal-title":"Nat. Rev. Endocrinol."},{"key":"ref_192","doi-asserted-by":"crossref","first-page":"4744","DOI":"10.1210\/endo.137.11.8895342","article-title":"Acute effects of thyroid hormone on inward rectifier potassium channel currents in guinea pig ventricular myocytes","volume":"137","author":"Sakaguchi","year":"1996","journal-title":"Endocrinology"},{"key":"ref_193","doi-asserted-by":"crossref","unstructured":"Lin, H.Y., Davis, F.B., Luidens, M.K., Mousa, S.A., Cao, J.H., Zhou, M., and Davis, P.J. (2011). Molecular basis for certain neuroprotective effects of thyroid hormone. Front. Mol. Neurosci., 4.","DOI":"10.3389\/fnmol.2011.00029"},{"key":"ref_194","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1007\/s00232-002-1058-9","article-title":"Thyroid hormones affect the membrane dipolar organization. Is it a general event in their non-genomic action?","volume":"191","author":"Isse","year":"2003","journal-title":"J. Membr. Biol."},{"key":"ref_195","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1111\/j.1751-1097.2012.01080.x","article-title":"Xanthene dyes induce membrane permeabilization of bacteria and erythrocytes by photoinactivation","volume":"88","author":"Kato","year":"2012","journal-title":"Photochem. Photobiol."},{"key":"ref_196","first-page":"24","article-title":"Triterpenoid saponins: A review on biosynthesis, applications and mechanism of their action","volume":"7","author":"Netala","year":"2015","journal-title":"Int. J. Pharm. Pharm. Sci."},{"key":"ref_197","first-page":"27","article-title":"In vitro and in vivo anticancer activity of steroid saponins of paris polyphylla var","volume":"31","author":"Yan","year":"2009","journal-title":"Yunnanensis Exp. Oncol."},{"key":"ref_198","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1016\/0005-2760(72)90190-7","article-title":"Interaction of leucerne saponins with steroids","volume":"270","author":"Gestetner","year":"1972","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_199","doi-asserted-by":"crossref","first-page":"1252","DOI":"10.1126\/science.adf3727","article-title":"Elucidation of the pathway for biosynthesis of saponin adjuvants from the soapbark tree","volume":"379","author":"Reed","year":"2023","journal-title":"Science"},{"key":"ref_200","doi-asserted-by":"crossref","first-page":"eadn7187","DOI":"10.1126\/sciadv.adn7187","article-title":"Saponin nanoparticle adjuvants incorporating Toll-like receptor agonists drive distinct immune signatures and potent vaccine responses","volume":"10","author":"Ou","year":"2024","journal-title":"Sci. Adv."},{"key":"ref_201","doi-asserted-by":"crossref","first-page":"2189885","DOI":"10.1080\/21645515.2023.2189885","article-title":"The Matrix-M\u2122 adjuvant: A critical component of vaccines for the 21st century","volume":"19","author":"Stertman","year":"2023","journal-title":"Hum. Vaccin. Immunother."},{"key":"ref_202","doi-asserted-by":"crossref","first-page":"24948","DOI":"10.1038\/s41598-024-76155-w","article-title":"Glycyrrhizin ameliorates colorectal cancer progression by regulating NHEJ pathway through inhibiting HMGB1-induced DNA damage response","volume":"14","author":"Han","year":"2024","journal-title":"Sci. Rep."},{"key":"ref_203","first-page":"3697","article-title":"Saikosaponins Targeting Programmed Cell Death as Anticancer Agents: Mechanisms and Future Perspectives","volume":"18","author":"Xiao","year":"2024","journal-title":"Drug Des. Devel. Ther."},{"key":"ref_204","doi-asserted-by":"crossref","first-page":"117049","DOI":"10.1016\/j.biopha.2024.117049","article-title":"Ginsenosides in cancer: Proliferation, metastasis, and drug resistance","volume":"177","author":"Yang","year":"2024","journal-title":"Biomed. Pharmacother."},{"key":"ref_205","doi-asserted-by":"crossref","first-page":"4325","DOI":"10.1080\/10408398.2021.2000933","article-title":"Comprehensive review on signaling pathways of dietary saponins in cancer cells suppression","volume":"63","author":"Zhou","year":"2023","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_206","doi-asserted-by":"crossref","first-page":"703","DOI":"10.1016\/j.fitote.2010.06.004","article-title":"Chemical study and medical application of saponins as anti-cancer agents","volume":"81","author":"Man","year":"2010","journal-title":"Fitoterapia"},{"key":"ref_207","doi-asserted-by":"crossref","first-page":"3347","DOI":"10.1039\/D2NJ05388H","article-title":"One-pot synthesis of quaternary pyridinium salts of lupane triterpenoids and their antimicrobial properties","volume":"47","author":"Shakurova","year":"2023","journal-title":"New J. Chem."},{"key":"ref_208","doi-asserted-by":"crossref","first-page":"1286","DOI":"10.1111\/j.1471-4159.2009.06545.x","article-title":"Cholesterol modulates ion channels via down-regulation of phosphatidylinositol 4,5-bisphosphate","volume":"112","author":"Chun","year":"2010","journal-title":"J. Neurochem."},{"key":"ref_209","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1007\/978-3-031-21547-6_8","article-title":"Cholesterol and PIP2 Modulation of BKCa Channels","volume":"1422","author":"Vaithianathan","year":"2023","journal-title":"Adv. Exp. Med. Biol."},{"key":"ref_210","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/j.ejphar.2010.11.017","article-title":"Ginsenoside-Rd, a purified component from panax notoginseng saponins, prevents atherosclerosis in apoE knockout mice","volume":"652","author":"Li","year":"2011","journal-title":"Eur. J. Pharmacol."},{"key":"ref_211","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1007\/s11696-024-03802-x","article-title":"Estimation of total flavonoids, phenols, alkaloids, tannins and in vitro antioxidant activity of Costus pictus D. Don. ex. Lindl. and Dodonaea viscosa (L.) Jacq. leaf extracts","volume":"79","author":"Prakash","year":"2025","journal-title":"Chem. Pap."},{"key":"ref_212","doi-asserted-by":"crossref","unstructured":"Tsuchiya, H. (2017). Anesthetic Agents of Plant Origin: A Review of Phytochemicals with Anesthetic Activity. Molecules, 22.","DOI":"10.3390\/molecules22081369"},{"key":"ref_213","first-page":"401","article-title":"Natural alkaloids: Basic aspects, biological roles, and future perspectives","volume":"12","author":"Qiu","year":"2014","journal-title":"Chin. J. Nat. Med."},{"key":"ref_214","doi-asserted-by":"crossref","unstructured":"Salimova, E.V., Mozgovoj, O.S., Efimova, S.S., Ostroumova, O.S., and Parfenova, L.V. (2023). 3-Amino-substituted analogues of fusidic acid as membrane-active antibacterial compounds. Membranes, 13.","DOI":"10.3390\/membranes13030309"},{"key":"ref_215","doi-asserted-by":"crossref","first-page":"680","DOI":"10.1124\/mol.105.013573","article-title":"Capsaicin regulates voltage-dependent sodium channels by altering lipid bilayer elasticity","volume":"68","author":"Lundbaek","year":"2005","journal-title":"Mol. Pharmacol."},{"key":"ref_216","doi-asserted-by":"crossref","first-page":"1788","DOI":"10.1021\/cb500086e","article-title":"Phytochemicals perturb membranes and promiscuously alter protein function","volume":"9","author":"Thakur","year":"2014","journal-title":"ACS Chem. Biol."},{"key":"ref_217","doi-asserted-by":"crossref","first-page":"1321","DOI":"10.1016\/j.bpj.2018.01.028","article-title":"Modulation of DEG\/ENaCs by Amphiphiles Suggests Sensitivity to Membrane Alterations","volume":"114","author":"Schmidt","year":"2018","journal-title":"Biophys. J."},{"key":"ref_218","doi-asserted-by":"crossref","first-page":"13118","DOI":"10.1021\/bi060734+","article-title":"GABA(A) receptor function is regulated by lipid bilayer elasticity","volume":"45","author":"Werge","year":"2006","journal-title":"Biochemistry"},{"key":"ref_219","doi-asserted-by":"crossref","first-page":"1145","DOI":"10.1016\/j.pharep.2017.05.018","article-title":"Phytochemicals genistein and capsaicin modulate Kv2.1 channel gating","volume":"69","year":"2017","journal-title":"Pharmacol. Rep."},{"key":"ref_220","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1085\/jgp.69.4.497","article-title":"Local anesthetics: Hydrophilic and hydrophobic pathways for the drug-receptor reaction","volume":"69","author":"Hille","year":"1977","journal-title":"J. Gen. Physiol."},{"key":"ref_221","doi-asserted-by":"crossref","first-page":"1724","DOI":"10.1126\/science.8085162","article-title":"Molecular determinants of state-dependent block of Na+ channels by local anesthetics","volume":"265","author":"Ragsdale","year":"1994","journal-title":"Science"},{"key":"ref_222","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/S0006-3495(99)77192-4","article-title":"State-dependent cocaine block of sodium channel isoforms, chimeras, and channels coexpressed with the beta1 subunit","volume":"76","author":"Wright","year":"1999","journal-title":"Biophys. J."},{"key":"ref_223","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1074\/jbc.M006992200","article-title":"Molecular determinants of voltage-dependent gating and binding of pore-blocking drugs in transmembrane segment IIIS6 of the Na(+) channel alpha subunit","volume":"276","author":"Brown","year":"2001","journal-title":"J. Biol. Chem."},{"key":"ref_224","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/0005-2736(81)90017-1","article-title":"Correlation of general anesthetic potency with solubility in membranes","volume":"649","author":"Janoff","year":"1981","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_225","doi-asserted-by":"crossref","first-page":"887","DOI":"10.1007\/s12264-018-0239-1","article-title":"Regulatory Effect of General Anesthetics on Activity of Potassium Channels","volume":"34","author":"Li","year":"2018","journal-title":"Neurosci. Bull."},{"key":"ref_226","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/j.jmgm.2014.08.001","article-title":"The interaction of local anesthetics with lipid membranes","volume":"53","year":"2014","journal-title":"J. Mol. Graph. Model."},{"key":"ref_227","doi-asserted-by":"crossref","first-page":"111527","DOI":"10.1016\/j.mce.2021.111527","article-title":"Phosphodiesterase (PDE) 5 inhibitors sildenafil, tadalafil and vardenafil impact cAMP-specific PDE8 isoforms-linked second messengers and steroid production in a mouse Leydig tumor cell line","volume":"542","author":"Limoncella","year":"2022","journal-title":"Mol. Cell Endocrinol."},{"key":"ref_228","doi-asserted-by":"crossref","first-page":"1921","DOI":"10.1016\/j.jacc.2011.09.086","article-title":"Role of cGMP Signaling and Phosphodiesterase-5 inhibitors in Cardioprotection","volume":"59","author":"Kukreja","year":"2012","journal-title":"J. Am. Coll. Cardiol."},{"key":"ref_229","doi-asserted-by":"crossref","unstructured":"Zakharova, A.A., Efimova, S.S., and Ostroumova, O.S. (2021). Phosphodiesterase Type 5 Inhibitors Greatly Affect Physicochemical Properties of Model Lipid Membranes. Membranes, 11.","DOI":"10.3390\/membranes11110893"},{"key":"ref_230","doi-asserted-by":"crossref","unstructured":"Pu\u0219ca\u0219u, C., Zanfirescu, A., Negre\u0219, S., and \u0218eremet, O.C. (2023). Exploring the Multifaceted Potential of Sildenafil in Medicine. Medicina, 59.","DOI":"10.3390\/medicina59122190"},{"key":"ref_231","doi-asserted-by":"crossref","unstructured":"Malykhina, A.I., Efimova, S.S., and Ostroumova, O.S. (2025). Membrane-Mediated Action of Phosphodiesterase 5 Inhibitors. Pharmaceutics, 17.","DOI":"10.3390\/pharmaceutics17050563"},{"key":"ref_232","doi-asserted-by":"crossref","first-page":"230183","DOI":"10.1183\/16000617.0183-2023","article-title":"The nitric oxide-soluble guanylate cyclase-cGMP pathway in pulmonary hypertension: From PDE5 to soluble guanylate cyclase","volume":"33","author":"Benza","year":"2024","journal-title":"Eur. Respir. Rev."},{"key":"ref_233","doi-asserted-by":"crossref","unstructured":"Waring, D.H., and Hallas, G. (1990). Classification of dyes by chemical structure. The Chemistry and Application of Dyes, Plenum Press.","DOI":"10.1007\/978-1-4684-7715-3"},{"key":"ref_234","doi-asserted-by":"crossref","first-page":"5749","DOI":"10.1021\/bi00342a010","article-title":"Spectra, membrane binding, and potentiometric responses of new charge shift probes","volume":"24","author":"Fluhler","year":"1985","journal-title":"Biochemistry"},{"key":"ref_235","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1016\/S0006-3495(82)84520-7","article-title":"Improved fluorescent probes for the measurement of rapid changes in membrane potential","volume":"39","author":"Grinvald","year":"1982","journal-title":"Biophys. J."},{"key":"ref_236","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1016\/S0006-3495(81)84854-0","article-title":"Charge-shift probes of membrane potential: A probable electrochromic mechanism for p-aminostyrylpyridinium probes on a hemispherical lipid bilayer","volume":"34","author":"Loew","year":"1981","journal-title":"Biophys. J."},{"key":"ref_237","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1146\/annurev.bb.08.060179.000403","article-title":"Dye indicators of membrane potential","volume":"8","author":"Waggoner","year":"1979","journal-title":"Annu. Rev. Biophys. Bioeng."},{"key":"ref_238","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1016\/B978-0-12-407761-4.00016-6","article-title":"Ratio imaging: Practical considerations for measuring intracellular Ca2+ and pH in living cells","volume":"114","author":"Silver","year":"2013","journal-title":"Methods Cell Biol."},{"key":"ref_239","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1016\/0005-2736(95)00197-2","article-title":"Fluorescent styryl dyes of the RH series affect a potential drop on the membrane\/solution boundary","volume":"1278","author":"Malkov","year":"1996","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_240","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/S1567-5394(01)00167-0","article-title":"Estimation of electrochrome dyes position in the bilayer through the 2nd harmonic of capacitive current","volume":"55","author":"Passechnik","year":"2002","journal-title":"Bioelectrochemistry"},{"key":"ref_241","doi-asserted-by":"crossref","first-page":"16806","DOI":"10.1021\/bi00051a031","article-title":"Fluorescent styryl dyes as probes for Na,K-ATPase reaction mechanism: Significance of the charge of the hydrophilic moiety of RH dyes","volume":"34","author":"Fedosova","year":"1995","journal-title":"Biochemistry"},{"key":"ref_242","doi-asserted-by":"crossref","first-page":"6304","DOI":"10.1002\/ejoc.201801159","article-title":"Synthesis of chromone-containing allylmorpholines through a Morita-Baylis-Hillman-type reaction","volume":"2018","author":"Chernov","year":"2018","journal-title":"Eur. J. Org. Chem."},{"key":"ref_243","doi-asserted-by":"crossref","first-page":"8934","DOI":"10.1021\/acs.jmedchem.8b01148","article-title":"Lowering lipophilicity by adding carbon: One-carbon bridges of morpholines and piperazines","volume":"61","author":"Degorce","year":"2018","journal-title":"J. Med. Chem."},{"key":"ref_244","doi-asserted-by":"crossref","unstructured":"Efimova, S.S., Martynyuk, V.A., Zakharova, A.A., Yudintceva, N.M., Chernov, N.M., Yakovlev, I.P., and Ostroumova, O.S. (2022). Chromone-Containing Allylmorpholines Influence Ion Channels in Lipid Membranes via Dipole Potential and Packing Stress. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms231911554"},{"key":"ref_245","doi-asserted-by":"crossref","first-page":"138438","DOI":"10.1016\/j.molstruc.2024.138438","article-title":"A review on recent progress in synthesis and biological activities of thiadiazole and its derivatives","volume":"1312","author":"Ahmad","year":"2024","journal-title":"J. Mol. Struct."},{"key":"ref_246","doi-asserted-by":"crossref","first-page":"3489","DOI":"10.1007\/s00253-022-11969-0","article-title":"Biological activity of oxadiazole and thiadiazole derivatives","volume":"106","author":"Atmaram","year":"2022","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_247","doi-asserted-by":"crossref","unstructured":"Kalogirou, A.S., Oh, H.J., and Asquith, C.R.M. (2023). The Synthesis and Biological Applications of the 1,2,3-Dithiazole Scaffold. Molecules, 28.","DOI":"10.3390\/molecules28073193"},{"key":"ref_248","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/S1473-3099(13)70328-1","article-title":"New antituberculosis drugs, regimens, and adjunct therapies: Needs, advances, and future prospects","volume":"14","author":"Zumla","year":"2014","journal-title":"Lancet Infect Dis."},{"key":"ref_249","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1016\/j.bbrc.2022.08.001","article-title":"Dithiadiazole derivative 3-(4-nitrophenyl)-5-phenyl-3H-1,2,3,4-dithiadiazole-2-oxide\u2014Novel modulator of store-operated calcium entry","volume":"626","author":"Grekhnev","year":"2022","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_250","doi-asserted-by":"crossref","first-page":"149333","DOI":"10.1016\/j.bbrc.2023.149333","article-title":"1,2,3,4-dithiadiazole derivatives as a novel class of calcium signaling modulators","volume":"691","author":"Novikova","year":"2024","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_251","doi-asserted-by":"crossref","unstructured":"Zakharova, A.A., Efimova, S.S., Yuskovets, V.N., Yakovlev, I.P., Sarkisyan, Z.M., and Ostroumova, O.S. (2020). 1,3-Thiazine, 1,2,3,4-Dithiadiazole, and Thiohydrazide Derivatives Affect Lipid Bilayer Properties and Ion-Permeable Pores Induced by Antifungals. Front. Cell Dev. Biol., 8.","DOI":"10.3389\/fcell.2020.00535"},{"key":"ref_252","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1007\/s10517-025-06475-y","article-title":"1,2,3,4-Dithiadiazole Derivative 3-(4-Nitrophenyl)-5-Phenyl-3H-1,2,3,4-Dithiadiazole-2-Oxide Affects Both STIM1- and STIM2-Dependent Store-Operated Calcium Channels","volume":"179","author":"Grekhnev","year":"2025","journal-title":"Bull. Exp. Biol. Med."},{"key":"ref_253","doi-asserted-by":"crossref","unstructured":"Zlodeeva, P.D., Shekunov, E.V., Ostroumova, O.S., and Efimova, S.S. (2023). The degree of hydroxylation of phenolic rings determines the ability of flavonoids and stilbenes to inhibit calcium-mediated membrane fusion. Nutrients, 15.","DOI":"10.3390\/nu15051121"},{"key":"ref_254","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1134\/S1990519X23010030","article-title":"The specific effect of grapefruit seeds, sea buckthorn leaves and chaga extracts on the properties of model lipid membranes","volume":"17","author":"Efimova","year":"2023","journal-title":"Cell Tissue Biol."},{"key":"ref_255","doi-asserted-by":"crossref","unstructured":"Efimova, S.S., Malykhina, A.I., and Ostroumova, O.S. (2023). Triggering the amphotericin B pore-forming activity by phytochemicals. Membranes, 13.","DOI":"10.3390\/membranes13070670"},{"key":"ref_256","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1007\/BF01870299","article-title":"Effect of small molecules on the dipalmitoyl lecithin liposomal bilayer: III. Phase transition in lipid bilayer","volume":"34","author":"Jain","year":"1977","journal-title":"J. Membr. Biol."},{"key":"ref_257","doi-asserted-by":"crossref","first-page":"374","DOI":"10.1134\/S1990519X25600140","article-title":"Assessing the Influence of Xanthene Dyes on the Physical Properties of Lipid Membranes Using a Molecular Dynamics Simulation","volume":"19","author":"Malykhina","year":"2025","journal-title":"Cell Tissue Biol."},{"key":"ref_258","first-page":"648","article-title":"Potential inhibitory activities of phytoconstituents in Salvia miltiorrhiza against coronary heart disease drug targets using docking and ADMET studies","volume":"62","author":"Duong","year":"2024","journal-title":"Vietnam. J. Sci. Technol."},{"key":"ref_259","doi-asserted-by":"crossref","first-page":"113104","DOI":"10.1016\/j.jep.2020.113104","article-title":"Ameliorative effect of Boesenbergin A, a chalcone isolated from Boesenbergia rotunda (Fingerroot) on oxidative stress and inflammation in ethanol-induced gastric ulcer in vivo","volume":"261","author":"Mohan","year":"2020","journal-title":"J. Ethnopharmacol."},{"key":"ref_260","doi-asserted-by":"crossref","first-page":"1211","DOI":"10.1007\/s12272-014-0334-4","article-title":"Protective effects of 2\u2032,4\u2032-dihydroxy-6\u2032-methoxy-3\u2032,5\u2032-dimethylchalcone against hydrogen peroxide-induced oxidative stress in hepatic L02 cell","volume":"37","author":"Lu","year":"2014","journal-title":"Arch. Pharm. Res."},{"key":"ref_261","doi-asserted-by":"crossref","first-page":"336","DOI":"10.3109\/08923973.2013.770521","article-title":"Toxicity, analgesic and anti-inflammatory activities of tectorigenin","volume":"35","author":"Ha","year":"2013","journal-title":"Immunopharmacol. Immunotoxicol."},{"key":"ref_262","doi-asserted-by":"crossref","first-page":"4888","DOI":"10.1080\/07391102.2023.2223664","article-title":"Acetylcholinesterase inhibitory activities of some flavonoids from the root bark of Pinus krempfii Lecomte: In vitro and in silico study","volume":"42","author":"Cuong","year":"2024","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_263","doi-asserted-by":"crossref","first-page":"100312","DOI":"10.1016\/j.kjs.2024.100312","article-title":"Identification of natural curcumins as potential dual inhibitors of PTP1B and \u03b1-glucosidase through experimental and computational study","volume":"52","author":"Nguyen","year":"2025","journal-title":"Kuwait J. Sci."},{"key":"ref_264","doi-asserted-by":"crossref","first-page":"287","DOI":"10.15625\/2525-2518\/57\/3\/13119","article-title":"Flavonoids isolated from the flowers of Camellia chrysantha","volume":"57","author":"Van","year":"2019","journal-title":"Vietnam. J. Sci. Technol."},{"key":"ref_265","doi-asserted-by":"crossref","first-page":"214","DOI":"10.15625\/0866-708X\/54\/2\/6741","article-title":"Flavonoids and triterpenoids from Callistemon citrinus and their inhibitory effect on no production in LPS-stimulated RAW264. 7 macrophages","volume":"54","author":"Cuong","year":"2016","journal-title":"Vietnam. J. Sci. Technol."},{"key":"ref_266","first-page":"1934578X2095324","article-title":"Identification of Cytotoxic Constituents from the Whole Plant of Isodon ternifolius","volume":"15","author":"Pham","year":"2020","journal-title":"Nat. Prod. Commun."},{"key":"ref_267","first-page":"1","article-title":"Acontribution to study chemical constituents of Desmodium gangeticum of Viet Nam","volume":"57","author":"Phuong","year":"2019","journal-title":"Vietnam. J. Sci. Technol."},{"key":"ref_268","first-page":"652","article-title":"PTP1B inhibitory flavonols from Orthosiphon stamineus Benth","volume":"55","author":"Hung","year":"2017","journal-title":"Vietnam. J. Chem."},{"key":"ref_269","first-page":"699","article-title":"Isoflavonoids from Desmodium heterophyllum Aerial Parts","volume":"13","author":"Ha","year":"2018","journal-title":"Nat. Prod. Commun."},{"key":"ref_270","doi-asserted-by":"crossref","first-page":"108613","DOI":"10.1016\/j.carres.2022.108613","article-title":"Steroid glycosides isolated from Paris polyphylla var. chinensis aerial parts and paris saponin II induces G1\/S-phase MCF-7 cell cycle arrest","volume":"519","author":"Duyen","year":"2022","journal-title":"Carbohydr. Res."},{"key":"ref_271","doi-asserted-by":"crossref","first-page":"1417","DOI":"10.1248\/cpb.59.1417","article-title":"Oleanolic triterpene saponins from the roots of Panax bipinnatifidus","volume":"59","author":"Nguyen","year":"2011","journal-title":"Chem. Pharm. Bull."},{"key":"ref_272","doi-asserted-by":"crossref","first-page":"1926","DOI":"10.1007\/s12272-015-0591-x","article-title":"Chemical components from the leaves of Ardisia insularis and their cytotoxic activity","volume":"38","author":"Van","year":"2015","journal-title":"Arch. Pharm. Res."},{"key":"ref_273","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1007\/s11030-021-10206-6","article-title":"Antioxidative and \u03b1-glucosidase inhibitory constituents of Polyscias guilfoylei: Experimental and computational assessments","volume":"26","author":"Anh","year":"2022","journal-title":"Mol. Divers."},{"key":"ref_274","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1016\/j.jare.2024.11.016","article-title":"Kaempferol regulating macrophage foaming and atherosclerosis through Piezo1-mediated MAPK\/NF-\u03baB and Nrf2\/HO-1 signaling pathway","volume":"75","author":"Chu","year":"2025","journal-title":"J. Adv. Res."},{"key":"ref_275","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1007\/BF01870680","article-title":"Effect of 3-phenylindole on lipophilic ion and carrier-mediated ion transport across bilayer lipid membranes","volume":"71","author":"Sinha","year":"1983","journal-title":"J. Membr. Biol."},{"key":"ref_276","doi-asserted-by":"crossref","first-page":"243","DOI":"10.3109\/09687688409150281","article-title":"Changes in interfacial potentials induced by carbonylcyanide phenylhydrazone uncouplers: Possible role in inhibition of mitochondrial oxygen consumption and other transport processes","volume":"5","author":"Reyes","year":"1984","journal-title":"Membr. Biochem."},{"key":"ref_277","doi-asserted-by":"crossref","first-page":"2452","DOI":"10.1016\/S0006-3495(00)76789-0","article-title":"Effect of trehalose and sucrose on the hydration and dipole potential of lipid bilayers","volume":"78","author":"Luzardo","year":"2000","journal-title":"Biophys. J."},{"key":"ref_278","doi-asserted-by":"crossref","first-page":"5946","DOI":"10.1021\/jp101007b","article-title":"Role of guanidyl moiety in the insertion of arginine and Nalpha-benzoyl-L-argininate ethyl ester chloride in lipid membranes","volume":"114","author":"Fonseca","year":"2010","journal-title":"J. Phys. Chem. B"},{"key":"ref_279","doi-asserted-by":"crossref","unstructured":"Bord\u00f3n, A., Rodr\u00edguez, S.A., Chaves, D.S.A., Cutr\u00f3, A.C., and Hollmann, A. (2025). Antimicrobial Action of Essential Oil of Tagetes minuta: Role of the Bacterial Membrane in the Mechanism of Action. Antibiotics, 14.","DOI":"10.3390\/antibiotics14070632"},{"key":"ref_280","doi-asserted-by":"crossref","first-page":"2656","DOI":"10.1016\/j.bbamem.2014.06.019","article-title":"Antiradical activity of gallic acid included in lipid interphases","volume":"1838","author":"Salcedo","year":"2014","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_281","doi-asserted-by":"crossref","first-page":"2380","DOI":"10.1021\/acs.jpcb.4c07578","article-title":"Spectrally resolved single-molecule orientation imaging reveals a direct correspondence between the polarity and microviscosity experienced by nile red in supported lipid bilayer membranes","volume":"129","author":"Sarkar","year":"2025","journal-title":"J. Phys. Chem. B"},{"key":"ref_282","doi-asserted-by":"crossref","first-page":"4812","DOI":"10.1021\/acs.jpcb.6b03439","article-title":"Quantifying the relationship between curvature and electric potential in lipid bilayers","volume":"120","author":"Bruhn","year":"2016","journal-title":"J. Phys. Chem. 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