{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T17:54:32Z","timestamp":1790186072006,"version":"4.1.0"},"reference-count":83,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2024,6,19]],"date-time":"2024-06-19T00:00:00Z","timestamp":1718755200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2024,6,19]],"date-time":"2024-06-19T00:00:00Z","timestamp":1718755200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"name":"National Science Centre, Poland within the OPUS 16 program","award":["2018\/31\/B\/NZ9\/03878"],"award-info":[{"award-number":["2018\/31\/B\/NZ9\/03878"]}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Sci Rep"],"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Newly synthesized gemini quaternary ammonium salts (QAS) with different counterions (bromide, hydrogen chloride, methylcarbonate, acetate, lactate), chain lengths (C12, C14, C16) and methylene linker (3xCH\n                    <jats:sub>2<\/jats:sub>\n                    ) were tested. Dihydrochlorides and dibromides with 12 carbon atoms in hydrophobic chains were characterized by the highest biological activity against planktonic forms of yeast and yeast-like fungi. The tested gemini surfactants also inhibited the production of filaments by\n                    <jats:italic>C. albicans<\/jats:italic>\n                    . Moreover, they reduced the adhesion of\n                    <jats:italic>C. albicans<\/jats:italic>\n                    cells to the surfaces of stainless steel, silicone and glass, and slightly to polystyrene. In particular, the gemini compounds with 16-carbon alkyl chains were most effective against biofilms. It was also found that the tested surfactants were not cytotoxic to yeast cells. Moreover, dimethylcarbonate (2xC\n                    <jats:sub>12<\/jats:sub>\n                    MeCO\n                    <jats:sub>3<\/jats:sub>\n                    G\n                    <jats:sub>3<\/jats:sub>\n                    ) did not cause hemolysis of sheep erythrocytes. Dihydrochlorides, dilactate and diacetate showed no mutagenic potential.\n                  <\/jats:p>","DOI":"10.1038\/s41598-024-64859-y","type":"journal-article","created":{"date-parts":[[2024,6,19]],"date-time":"2024-06-19T00:01:50Z","timestamp":1718755310000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Anti-adhesive, anti-biofilm and fungicidal action of newly synthesized gemini quaternary ammonium salts"],"prefix":"10.1038","volume":"14","author":[{"given":"Edyta","family":"Mazurkiewicz","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u0141ukasz","family":"Lamch","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazimiera A.","family":"Wilk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ewa","family":"Ob\u0142\u0105k","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2024,6,19]]},"reference":[{"key":"64859_CR1","doi-asserted-by":"publisher","first-page":"1731","DOI":"10.3390\/en12091731","volume":"12","author":"SM Shakil Hussain","year":"2019","unstructured":"Shakil Hussain, S. M., Kamal, M. S. & Murtaza, M. Synthesis of novel ethoxylated quaternary ammonium gemini surfactants for enhanced oil recovery application. Energies 12, 1731. https:\/\/doi.org\/10.3390\/en12091731 (2019).","journal-title":"Energies"},{"key":"64859_CR2","doi-asserted-by":"publisher","DOI":"10.1002\/9781118228920","volume-title":"Surfactants and Interfacial Phenomena","author":"MJ Rosen","year":"2012","unstructured":"Rosen, M. J. & Kunjappu, J. T. Surfactants and Interfacial Phenomena 4th edn. (Wiley, 2012).","edition":"4"},{"key":"64859_CR3","doi-asserted-by":"publisher","first-page":"35","DOI":"10.1016\/j.cis.2017.07.032","volume":"248","author":"R Sharma","year":"2017","unstructured":"Sharma, R., Kamal, A., Abdinejad, M., Mahajan, R. K. & Kraatz, H. B. Advances in the synthesis, molecular architectures and potential applications of gemini surfactants. Adv. Coll. Interface. Sci. 248, 35\u201368. https:\/\/doi.org\/10.1016\/j.cis.2017.07.032 (2017).","journal-title":"Adv. Coll. Interface. Sci."},{"key":"64859_CR4","doi-asserted-by":"publisher","DOI":"10.1201\/9780203913093","volume-title":"Gemini Surfactants","author":"R Zana","year":"2003","unstructured":"Zana, R. & Xia, J. Gemini Surfactants (CRC Press, 2003). https:\/\/doi.org\/10.1201\/9780203913093."},{"key":"64859_CR5","doi-asserted-by":"publisher","first-page":"2","DOI":"10.1007\/s11743-015-1776-5","volume":"19","author":"MS Kamal","year":"2016","unstructured":"Kamal, M. S. A review of gemini surfactants: Potential application in enhanced oil recovery. J. Surfactants Deterg. 19, 2. https:\/\/doi.org\/10.1007\/s11743-015-1776-5 (2016).","journal-title":"J. Surfactants Deterg."},{"key":"64859_CR6","doi-asserted-by":"publisher","first-page":"1425","DOI":"10.1039\/C8MD00249E","volume":"9","author":"M Damen","year":"2018","unstructured":"Damen, M. et al. Transfection by cationic gemini lipids and surfactants. Med. Chem. Commun. 9, 1425. https:\/\/doi.org\/10.1039\/C8MD00249E (2018).","journal-title":"Med. Chem. Commun."},{"key":"64859_CR7","doi-asserted-by":"publisher","first-page":"115342","DOI":"10.1016\/j.molliq.2021.115342","volume":"326","author":"EA Badr","year":"2021","unstructured":"Badr, E. A. et al. Synthesis of Schiff base-based cationic Gemini surfactants and evaluation of their effect on in-situ AgNPs preparation: Structure, catalytic, and biological activity study. J. Mol. Liquid 326, 115342. https:\/\/doi.org\/10.1016\/j.molliq.2021.115342 (2021).","journal-title":"J. Mol. Liquid"},{"key":"64859_CR8","doi-asserted-by":"publisher","first-page":"205","DOI":"10.1016\/S0001-8686(01)00069-0","volume":"97","author":"R Zana","year":"2002","unstructured":"Zana, R. Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: A review. Adv. Colloid Interface Sci. 97, 205\u2013253. https:\/\/doi.org\/10.1016\/S0001-8686(01)00069-0 (2002).","journal-title":"Adv. Colloid Interface Sci."},{"key":"64859_CR9","doi-asserted-by":"publisher","first-page":"182","DOI":"10.1006\/jcis.2001.7921","volume":"246","author":"R Zana","year":"2002","unstructured":"Zana, R. Alkanediyl-\u03b1;\u03c9-bis(dimethylalkylammonium bromide) surfactants: 10. Behavior in aqueous solution at concentrations below the critical micellization concentration: An electrical conductivity study. J. Colloid Interface Sci. 246, 182\u2013190. https:\/\/doi.org\/10.1006\/jcis.2001.7921 (2002).","journal-title":"J. Colloid Interface Sci."},{"key":"64859_CR10","doi-asserted-by":"publisher","DOI":"10.1201\/9780203911730","volume-title":"Novel Surfactants","author":"R Zana","year":"2003","unstructured":"Zana, R. & Alami, E. O. Novel Surfactants (CRC Press, 2003). https:\/\/doi.org\/10.1201\/9780203911730."},{"key":"64859_CR11","doi-asserted-by":"publisher","first-page":"3171","DOI":"10.1021\/la702619a","volume":"24","author":"J Wegrzy\u0144ska","year":"2008","unstructured":"Wegrzy\u0144ska, J., Para, G., Chlebicki, J., Warszy\u0144ski, P. & Wilk, K. A. Adsorption of multiple ammonium salts at the air\/solution interface. Langmuir 24, 3171\u20133180. https:\/\/doi.org\/10.1021\/la702619a (2008).","journal-title":"Langmuir"},{"key":"64859_CR12","doi-asserted-by":"publisher","first-page":"625","DOI":"10.1007\/s00253-018-9523-2","volume":"103","author":"E Ob\u0142\u0105k","year":"2019","unstructured":"Ob\u0142\u0105k, E., Piecuch, A., Rewak-Soroczy\u0144ska, J. & Paluch, E. Activity of gemini quaternary ammonium salts against microorganisms. Appl. Microbiol. Biotechnol. 103, 625\u2013632. https:\/\/doi.org\/10.1007\/s00253-018-9523-2 (2019).","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"64859_CR13","doi-asserted-by":"publisher","first-page":"112579","DOI":"10.1016\/j.molliq.2020.112579","volume":"302","author":"ZH Asadov","year":"2020","unstructured":"Asadov, Z. H. et al. Aggregation and antimicrobial properties of gemini surfactants with mono- and di-(2-hydroxypropyl)ammonium head-groups: Effect of the spacer length and computational studies. J. Mol. Liquid 302, 112579. https:\/\/doi.org\/10.1016\/j.molliq.2020.112579 (2020).","journal-title":"J. Mol. Liquid"},{"key":"64859_CR14","doi-asserted-by":"publisher","first-page":"8","DOI":"10.1016\/j.molliq.2017.06.049","volume":"242","author":"Y Bao","year":"2017","unstructured":"Bao, Y., Guo, J., Ma, J., Li, M. & Li, X. Physicochemical and antimicrobial activities of cationic gemini surfactants with polyether siloxane linked group. J. Mol. Liquid 242, 8\u201315. https:\/\/doi.org\/10.1016\/j.molliq.2017.06.049 (2017).","journal-title":"J. Mol. Liquid"},{"key":"64859_CR15","doi-asserted-by":"publisher","first-page":"1348","DOI":"10.3390\/molecules25061348","volume":"25","author":"A Labena","year":"2020","unstructured":"Labena, A., Hegazy, M. A., Sami, R. M. & Hozzein, W. N. Multiple applications of a novel cationic gemini surfactant: Anti-microbial, anti-biofilm, biocide, salinity corrosion inhibitor, and biofilm dispersion (Part II). Molecules 25, 1348. https:\/\/doi.org\/10.3390\/molecules25061348 (2020).","journal-title":"Molecules"},{"key":"64859_CR16","doi-asserted-by":"publisher","first-page":"22","DOI":"10.1007\/s11274-020-02978-0","volume":"37","author":"E Ob\u0142\u0105k","year":"2021","unstructured":"Ob\u0142\u0105k, E., Futoma-Ko\u0142och, B. & Wieczy\u0144ska, A. Biological activity of quaternary ammonium salts and resistance of microorganisms to these compounds. World J. Microbiol. Biotechnol. 37, 22. https:\/\/doi.org\/10.1007\/s11274-020-02978-0 (2021).","journal-title":"World J. Microbiol. Biotechnol."},{"key":"64859_CR17","doi-asserted-by":"publisher","first-page":"14446","DOI":"10.1021\/jp8027935","volume":"112","author":"RS Dias","year":"2008","unstructured":"Dias, R. S. et al. Interaction between DNA and cationic surfactants: Effect of DNA conformation and surfactant headgroup. J. Phys. Chem. B 112, 14446\u201314452. https:\/\/doi.org\/10.1021\/jp8027935 (2008).","journal-title":"J. Phys. Chem. B"},{"key":"64859_CR18","doi-asserted-by":"publisher","first-page":"11703","DOI":"10.1021\/la901641f","volume":"25","author":"A Bhadani","year":"2009","unstructured":"Bhadani, A. & Singh, S. Novel gemini pyridinium surfactants: Synthesis and study of their surface activity, DNA binding, and cytotoxicity. Langmuir 25, 11703\u201311712. https:\/\/doi.org\/10.1021\/la901641f (2009).","journal-title":"Langmuir"},{"key":"64859_CR19","doi-asserted-by":"publisher","first-page":"314","DOI":"10.1016\/j.jcis.2021.02.019","volume":"591","author":"F Peng","year":"2021","unstructured":"Peng, F. et al. Facile design of gemini surfactant-like peptide for hydrophobic drug delivery and antimicrobial activity. J. Colloid Interface Sci. 591, 314\u2013325. https:\/\/doi.org\/10.1016\/j.jcis.2021.02.019 (2021).","journal-title":"J. Colloid Interface Sci."},{"key":"64859_CR20","doi-asserted-by":"publisher","first-page":"289","DOI":"10.2217\/nnm.15.203","volume":"11","author":"T Ahmed","year":"2016","unstructured":"Ahmed, T., Kamel, A. O. & Wettig, S. D. Interactions between DNA and Gemini surfactant: Impact on gene therapy: Part I. Nanomedicine 11, 289. https:\/\/doi.org\/10.2217\/nnm.15.203 (2016).","journal-title":"Nanomedicine"},{"key":"64859_CR21","doi-asserted-by":"publisher","first-page":"403","DOI":"10.2217\/nnm.15.204","volume":"11","author":"T Ahmed","year":"2016","unstructured":"Ahmed, T., Kamel, A. O. & Wettig, S. D. Interactions between DNA and gemini surfactant: Impact on gene therapy: Part II. Nanomedicine 11, 403. https:\/\/doi.org\/10.2217\/nnm.15.204 (2016).","journal-title":"Nanomedicine"},{"key":"64859_CR22","doi-asserted-by":"publisher","first-page":"83","DOI":"10.1016\/j.colsurfb.2015.04.042","volume":"131","author":"Z Pietralik","year":"2015","unstructured":"Pietralik, Z., Kumita, J. R., Dobson, C. M. & Kozak, M. The influence of novel gemini surfactants containing cycloalkyl side-chains on the structural phases of DNA in solution. Colloids Surfaces B Biointerfaces 131, 83\u201392. https:\/\/doi.org\/10.1016\/j.colsurfb.2015.04.042 (2015).","journal-title":"Colloids Surfaces B Biointerfaces"},{"key":"64859_CR23","doi-asserted-by":"publisher","first-page":"1037","DOI":"10.1039\/C8NR06442C","volume":"11","author":"S Taheri-Araghi","year":"2019","unstructured":"Taheri-Araghi, S., Chen, D. W., Kohandel, M., Sivaloganathan, S. & Foldvari, M. Tuning optimum transfection of gemini surfactant-phospholipid-DNA nanoparticles by validated theoretical modeling. Nanoscale 11, 1037\u20131046. https:\/\/doi.org\/10.1039\/C8NR06442C (2019).","journal-title":"Nanoscale"},{"key":"64859_CR24","doi-asserted-by":"publisher","first-page":"34","DOI":"10.1016\/j.jcis.2020.09.077","volume":"584","author":"C Costa","year":"2021","unstructured":"Costa, C. et al. Effective cytocompatible nanovectors based on serine-derived gemini surfactants and monoolein for small interfering RNA delivery. Colloids Surfaces B Biointerfaces 584, 34\u201344. https:\/\/doi.org\/10.1016\/j.jcis.2020.09.077 (2021).","journal-title":"Colloids Surfaces B Biointerfaces"},{"key":"64859_CR25","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1016\/j.cocis.2007.05.006","volume":"12","author":"A Tehrani-Bagha","year":"2007","unstructured":"Tehrani-Bagha, A. & Holmberg, K. Cleavable surfactants. Curr Opin. Colloid Interface Sci. 12, 81\u201391. https:\/\/doi.org\/10.1016\/j.cocis.2007.05.006 (2007).","journal-title":"Curr Opin. Colloid Interface Sci."},{"key":"64859_CR26","doi-asserted-by":"publisher","first-page":"3823","DOI":"10.1021\/jm049106l","volume":"48","author":"J Haldar","year":"2005","unstructured":"Haldar, J., Kondaiah, P. & Bhattacharya, S. Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles Incorporation of multiple head groups leads to impressive antibacterial activity. J. Med. Chem. 48, 3823\u20133831. https:\/\/doi.org\/10.1021\/jm049106l (2005).","journal-title":"J. Med. Chem."},{"key":"64859_CR27","doi-asserted-by":"publisher","unstructured":"Overkempe, C. et al. Esterquats. In Novel Surfactants: Preparation, Applications, and Biodegradability, second ed. (ed. Holmberg, K.) 347\u2013384 (Marcel Dekker, 2003). https:\/\/doi.org\/10.1201\/9780203911730.","DOI":"10.1201\/9780203911730"},{"key":"64859_CR28","doi-asserted-by":"publisher","first-page":"57","DOI":"10.1007\/12_2008_162","volume":"218","author":"D Lundberg","year":"2008","unstructured":"Lundberg, D., Stjerndahl, M. & Holmberg, K. Surfactants containing hydrolyzable bonds. Adv. Polymer Sci. 218, 57. https:\/\/doi.org\/10.1007\/12_2008_162 (2008).","journal-title":"Adv. Polymer Sci."},{"key":"64859_CR29","doi-asserted-by":"publisher","first-page":"235","DOI":"10.1016\/S0304-4175(00)00013-7","volume":"1508","author":"MJ Scott","year":"2000","unstructured":"Scott, M. J. & Jones, M. N. The biodegradation of surfactants in the environment. Biochim. Biophys. Acta BBA Biomembranes 1508, 235\u2013251. https:\/\/doi.org\/10.1016\/S0304-4175(00)00013-7 (2000).","journal-title":"Biochim. Biophys. Acta BBA Biomembranes"},{"key":"64859_CR30","doi-asserted-by":"publisher","first-page":"124","DOI":"10.1016\/j.cocis.2020.01.002","volume":"45","author":"A Bhadani","year":"2020","unstructured":"Bhadani, A. et al. Current perspective of sustainable surfactants based on renewable building blocks. Curr. Opin. Colloid Interface Sci. 45, 124\u2013135. https:\/\/doi.org\/10.1016\/j.cocis.2020.01.002 (2020).","journal-title":"Curr. Opin. Colloid Interface Sci."},{"key":"64859_CR31","doi-asserted-by":"publisher","first-page":"73","DOI":"10.1016\/0927-7757(95)03093-S","volume":"98","author":"A Soko\u0142owski","year":"1995","unstructured":"Soko\u0142owski, A., Bieniecki, A., Wilk, K. A. & Burczyk, B. Surface activity and micelle formation of chemodegradable cationic surfactants containing the 1,3-dioxolane moiety. Colloids Surfaces A: Physicochem. Eng. Aspects 98, 73\u201382. https:\/\/doi.org\/10.1016\/0927-7757(95)03093-S (1995).","journal-title":"Colloids Surfaces A: Physicochem. Eng. Aspects"},{"key":"64859_CR32","doi-asserted-by":"publisher","first-page":"444","DOI":"10.1016\/j.jcis.2007.03.044","volume":"312","author":"AR Tehrani-Bagha","year":"2007","unstructured":"Tehrani-Bagha, A. R., Oskarsson, H., van Ginkel, C. G. & Holmberg, K. Cationic ester-containing gemini surfactants: Chemical hydrolysis and biodegradation. J. Colloid Interface Sci. 312, 444\u2013452. https:\/\/doi.org\/10.1016\/j.jcis.2007.03.044 (2007).","journal-title":"J. Colloid Interface Sci."},{"key":"64859_CR33","doi-asserted-by":"publisher","first-page":"11434","DOI":"10.1021\/la700430u","volume":"23","author":"D Lundberg","year":"2007","unstructured":"Lundberg, D., Unga, J., Galloway, A. L. & Menger, F. M. Studies on an ester-modified cationic amphiphile in aqueous systems: Behavior of binary solutions and ternary mixtures with conventional surfactants. Langmuir 23, 11434\u201311442. https:\/\/doi.org\/10.1021\/la700430u (2007).","journal-title":"Langmuir"},{"key":"64859_CR34","doi-asserted-by":"publisher","unstructured":"Stjerndahl, M., Lundberg D. & Holmberg K. Esterquats. In Novel Surfactants: Preparation, Applications, and Biodegradability (CRC Press, 2003). https:\/\/doi.org\/10.1201\/9780203911730.","DOI":"10.1201\/9780203911730"},{"key":"64859_CR35","doi-asserted-by":"publisher","first-page":"269","DOI":"10.5650\/jos.56.269","volume":"56","author":"S Mishra","year":"2007","unstructured":"Mishra, S. & Tyagi, V. K. Esterquats: the novel class of cationic fabric softeners. J. Oleo Sci. 56, 269\u2013276. https:\/\/doi.org\/10.5650\/jos.56.269 (2007).","journal-title":"J. Oleo Sci."},{"key":"64859_CR36","doi-asserted-by":"publisher","first-page":"1633","DOI":"10.1016\/j.jiec.2013.08.010","volume":"20","author":"I Aiad","year":"2014","unstructured":"Aiad, I., El-Sukkary, M. M., Soliman, E. A., El-Awady, M. Y. & Shaban, S. M. Characterization, surface properties and biological activity of new prepared cationic surfactants. J. Ind. Eng. Chem. 20, 1633\u20131640. https:\/\/doi.org\/10.1016\/j.jiec.2013.08.010 (2014).","journal-title":"J. Ind. Eng. Chem."},{"key":"64859_CR37","doi-asserted-by":"publisher","first-page":"2048","DOI":"10.3390\/molecules22122048","volume":"22","author":"T Padrtova","year":"2017","unstructured":"Padrtova, T. et al. Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts. Molecules 22, 2048. https:\/\/doi.org\/10.3390\/molecules22122048 (2017).","journal-title":"Molecules"},{"key":"64859_CR38","doi-asserted-by":"publisher","first-page":"1464","DOI":"10.3390\/molecules24081464","volume":"24","author":"UC Okeke","year":"2019","unstructured":"Okeke, U. C., Snyder, C. R. & Frukhtbeyn, S. A. Synthesis, purification and characterization of polymerizable multifunctional quaternary ammonium compounds. Molecules 24, 1464. https:\/\/doi.org\/10.3390\/molecules24081464 (2019).","journal-title":"Molecules"},{"key":"64859_CR39","first-page":"197","volume":"111","author":"T Padrtov\u00e1","year":"2017","unstructured":"Padrtov\u00e1, T., Marvanova, P. & Mokr\u00fd, P. Quaternary ammonium salts synthesis and use. Chem. Listy 111, 197\u2013205 (2017).","journal-title":"Chem. Listy"},{"key":"64859_CR40","doi-asserted-by":"publisher","first-page":"80","DOI":"10.1177\/0040517510363193","volume":"2010","author":"B Simoncic","year":"2010","unstructured":"Simoncic, B. & Tomsic, B. Structures of novel antimicrobial agents for textiles\u2014a review. Textile Res. J. 2010, 80. https:\/\/doi.org\/10.1177\/0040517510363193 (2010).","journal-title":"Textile Res. J."},{"key":"64859_CR41","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1038\/s41598-022-24760-y","volume":"12","author":"N Kula","year":"2022","unstructured":"Kula, N., Lamch, \u0141, Futoma-Ko\u0142och, B., Wilk, K. A. & Ob\u0142\u0105k, E. The effectiveness of newly synthesized quaternary ammonium salts differing in chain length and type of counterion against priority human pathogens. Sci. Rep. 12, 1\u201318. https:\/\/doi.org\/10.1038\/s41598-022-24760-y (2022).","journal-title":"Sci. Rep."},{"key":"64859_CR42","doi-asserted-by":"publisher","first-page":"239","DOI":"10.1006\/fstl.2001.0759","volume":"34","author":"E Trauth","year":"2001","unstructured":"Trauth, E., Lema\u00eetre, J. P., Rojas, C., Divi\u00e8s, C. & Cachon, R. Resistance of immobilized lactic acid bacteria to the inhibitory effect of quaternary ammonium sanitizers. LWT Food Sci. Technol. 34, 239\u2013243. https:\/\/doi.org\/10.1006\/fstl.2001.0759 (2001).","journal-title":"LWT Food Sci. Technol."},{"key":"64859_CR43","doi-asserted-by":"publisher","first-page":"682","DOI":"10.1111\/jam.13204","volume":"121","author":"A Piecuch","year":"2016","unstructured":"Piecuch, A., Lamch, P. E., Ob\u0142\u0105k, E. & Wilk, K. A. Biofilm prevention by dicephalic cationic surfactants and their interactions with DNA. J. Appl. Microbiol. 121, 682\u2013692. https:\/\/doi.org\/10.1111\/jam.13204 (2016).","journal-title":"J. Appl. Microbiol."},{"key":"64859_CR44","doi-asserted-by":"publisher","first-page":"6793","DOI":"10.3390\/ijms22136793","volume":"22","author":"AN Vereshchagin","year":"2021","unstructured":"Vereshchagin, A. N., Frolov, N. A., Egorova, K. S., Seitkalieva, M. M. & Ananikov, V. P. Quaternary ammonium compounds (Qacs) and ionic liquids (ils) as biocides: From simple antiseptics to tunable antimicrobials. Int. J. Mol. Sci. 22, 6793. https:\/\/doi.org\/10.3390\/ijms22136793 (2021).","journal-title":"Int. J. Mol. Sci."},{"key":"64859_CR45","doi-asserted-by":"publisher","first-page":"1103","DOI":"10.1016\/j.chemosphere.2012.05.090","volume":"89","author":"M Pietka-Ottlik","year":"2012","unstructured":"Pietka-Ottlik, M., Frackowiak, R., Maliszewska, I., Ko\u0142wzan, B. & Wilk, K. A. Ecotoxicity and biodegradability of antielectrostatic dicephalic cationic surfactants. Chemosphere 89, 1103\u20131111. https:\/\/doi.org\/10.1016\/j.chemosphere.2012.05.090 (2012).","journal-title":"Chemosphere"},{"key":"64859_CR46","doi-asserted-by":"publisher","first-page":"630","DOI":"10.1016\/j.micres.2013.06.001","volume":"168","author":"E Ob\u0142ak","year":"2013","unstructured":"Ob\u0142ak, E., Piecuch, A., Krasowska, A. & \u0141uczy\u0144ski, J. Antifungal activity of gemini quaternary ammonium salts. Microbiol. Res. 168, 630\u2013638. https:\/\/doi.org\/10.1016\/j.micres.2013.06.001 (2013).","journal-title":"Microbiol. Res."},{"key":"64859_CR47","doi-asserted-by":"publisher","first-page":"4380","DOI":"10.3390\/molecules24234380","volume":"24","author":"M Pis\u00e1r\u010dik","year":"2019","unstructured":"Pis\u00e1r\u010dik, M. et al. The synthesis, self-assembled structures, and microbicidal activity of cationic gemini surfactants with branched tridecyl chains. Molecules 24, 4380. https:\/\/doi.org\/10.3390\/molecules24234380 (2019).","journal-title":"Molecules"},{"key":"64859_CR48","doi-asserted-by":"publisher","first-page":"639","DOI":"10.1248\/cpb.54.639","volume":"54","author":"A Shirai","year":"2006","unstructured":"Shirai, A. et al. Synthesis and biological properties of gemini quaternary ammonium compounds, 5,5\u2032-[2,2\u2032-(\u03b1, \u03c9-polymethylnedicarbonyldioxy) diethyl]bis-(3-alkyl-4-methylthiazolium iodide) and 5,5\u2032-[2,2\u2032-(p- phenylenedicarbonyldioxy)diethyl]bis(3-alkyl-4-methylthiazolium bromide). Chem. Pharmaceut. Bull. (Tokyo) 54, 639\u2013645. https:\/\/doi.org\/10.1248\/cpb.54.639 (2006).","journal-title":"Chem. Pharmaceut. Bull. (Tokyo)"},{"key":"64859_CR49","doi-asserted-by":"publisher","unstructured":"Fisher, J. Cleaning procedures in the factory. Types of Disinfectant. In Encyclopedia of Food Sciences and Nutrition. (2003). https:\/\/doi.org\/10.1016\/b0-12-227055-x\/00249-2.","DOI":"10.1016\/b0-12-227055-x\/00249-2"},{"key":"64859_CR50","doi-asserted-by":"publisher","unstructured":"Sandle, T. Disinfectants. In Encyclopedia of Infection and Immunity 630\u2013639 (Elsevier, 2022). https:\/\/doi.org\/10.1016\/B978-0-12-818731-9.00206-8.","DOI":"10.1016\/B978-0-12-818731-9.00206-8"},{"key":"64859_CR51","doi-asserted-by":"publisher","first-page":"381","DOI":"10.5650\/jos.55.381","volume":"55","author":"D Shukla","year":"2006","unstructured":"Shukla, D. & Tyagi, V. K. Cationic gemini surfactants: A review. J. Oleo Sci. 55, 381\u2013390. https:\/\/doi.org\/10.5650\/jos.55.381 (2006).","journal-title":"J. Oleo Sci."},{"key":"64859_CR52","doi-asserted-by":"publisher","first-page":"111156","DOI":"10.1016\/j.molliq.2019.111156","volume":"289","author":"A Pinazo","year":"2019","unstructured":"Pinazo, A. et al. Gemini histidine based surfactants: Characterization; surface properties and biological activity. J. Mol. Liquid 289, 111156. https:\/\/doi.org\/10.1016\/j.molliq.2019.111156 (2019).","journal-title":"J. Mol. Liquid"},{"key":"64859_CR53","first-page":"161","volume":"64","author":"T Piskorska","year":"2010","unstructured":"Piskorska, T. & Ob\u0142\u0105k, E. Gemini surfactants as gene carriers. Post\u0119py Higieny i Medycyny Do\u015bwiadczalnej 64, 161\u2013166 (2010).","journal-title":"Post\u0119py Higieny i Medycyny Do\u015bwiadczalnej"},{"key":"64859_CR54","doi-asserted-by":"publisher","first-page":"98","DOI":"10.1080\/14756366.2017.1396456","volume":"33","author":"X Xie","year":"2018","unstructured":"Xie, X. et al. Synthesis, physiochemical property and antimicrobial activity of novel quaternary ammonium salts. J. Enzyme Inhibit. Med. Chem. 33, 98\u2013105. https:\/\/doi.org\/10.1080\/14756366.2017.1396456 (2018).","journal-title":"J. Enzyme Inhibit. Med. Chem."},{"key":"64859_CR55","doi-asserted-by":"publisher","first-page":"588","DOI":"10.1016\/j.mib.2006.10.003","volume":"9","author":"JR Blankenship","year":"2006","unstructured":"Blankenship, J. R. & Mitchell, A. P. How to build a biofilm: A fungal perspective. Curr. Opin. Microbiol. 9, 588\u2013594. https:\/\/doi.org\/10.1016\/j.mib.2006.10.003 (2006).","journal-title":"Curr. Opin. Microbiol."},{"key":"64859_CR56","doi-asserted-by":"publisher","first-page":"801","DOI":"10.1111\/j.1439-0507.2011.02028.x","volume":"54","author":"C Messier","year":"2011","unstructured":"Messier, C. & Grenier, D. Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. Mycoses 54, 801\u2013806. https:\/\/doi.org\/10.1111\/j.1439-0507.2011.02028.x (2011).","journal-title":"Mycoses"},{"key":"64859_CR57","doi-asserted-by":"publisher","first-page":"212","DOI":"10.1111\/lam.13195","volume":"69","author":"J Rewak-Soroczy\u0144ska","year":"2019","unstructured":"Rewak-Soroczy\u0144ska, J., Paluch, E., Siebert, A., Sza\u0142kiewicz, K. & Ob\u0142\u0105k, E. Biological activity of glycine and alanine derivatives of quaternary ammonium salts (QASs) against micro-organisms. Lett. Appl. Microbiol. 69, 212\u2013220. https:\/\/doi.org\/10.1111\/lam.13195 (2019).","journal-title":"Lett. Appl. Microbiol."},{"key":"64859_CR58","doi-asserted-by":"publisher","first-page":"527","DOI":"10.5650\/jos.ess14195","volume":"64","author":"E Ob\u0142\u0105k","year":"2015","unstructured":"Ob\u0142\u0105k, E., Piecuch, A., Dworniczek, E. & Olejniczak, T. The influence of biodegradable gemini surfactants, N, N\u2019-bis(1-decyloxy-1-oxopronan-2-yl)-N, N, N\u2019, N\u2019- tetramethylpropane-1,3-diammonium dibromide and N, N\u2019-bis(1-dodecyloxy-1-oxopronan-2-yl)-N, N, N\u2019, N\u2019-tetramethylethane-1,2-diammonium dibromide, on fungal biofilm and adhesion. J. Oleo Sci. 64, 527\u2013537. https:\/\/doi.org\/10.5650\/jos.ess14195 (2015).","journal-title":"J. Oleo Sci."},{"key":"64859_CR59","doi-asserted-by":"publisher","first-page":"97","DOI":"10.1007\/s00253-018-9467-6","volume":"103","author":"ME Fait","year":"2019","unstructured":"Fait, M. E., Bakas, L., Garrote, G. L., Morcelle, S. R. & Saparrat, M. C. N. Cationic surfactants as antifungal agents. Appl. Microbiol. Biotechnol. 103, 97\u2013112. https:\/\/doi.org\/10.1007\/s00253-018-9467-6 (2019).","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"64859_CR60","doi-asserted-by":"publisher","first-page":"1528","DOI":"10.1021\/acs.biomac.8b00183","volume":"19","author":"A Zywicka","year":"2018","unstructured":"Zywicka, A., Fija\u0142kowski, K., Junka, A. F., Grzesiak, J. & El Fray, M. Modification of bacterial cellulose with quaternary ammonium compounds based on fatty acids and amino acids and the effect on antimicrobial activity. Biomacromolecules 19, 1528\u20131538. https:\/\/doi.org\/10.1021\/acs.biomac.8b00183 (2018).","journal-title":"Biomacromolecules"},{"key":"64859_CR61","doi-asserted-by":"publisher","first-page":"651","DOI":"10.1016\/j.colsurfb.2010.10.027","volume":"82","author":"J Song","year":"2011","unstructured":"Song, J., Kong, H. & Jang, J. Bacterial adhesion inhibition of the quaternary ammonium functionalized silica nanoparticles. Colloids Surfaces B Biointerfaces 82, 651\u2013656. https:\/\/doi.org\/10.1016\/j.colsurfb.2010.10.027 (2011).","journal-title":"Colloids Surfaces B Biointerfaces"},{"key":"64859_CR62","doi-asserted-by":"publisher","first-page":"143","DOI":"10.1016\/j.colsurfb.2006.02.004","volume":"48","author":"CI Pereni","year":"2006","unstructured":"Pereni, C. I., Zhao, Q., Liu, Y. & Abel, E. Surface free energy effect on bacterial retention. Colloids .Surfaces B Biointerfaces 48, 143\u2013147. https:\/\/doi.org\/10.1016\/j.colsurfb.2006.02.004 (2006).","journal-title":"Colloids .Surfaces B Biointerfaces"},{"key":"64859_CR63","doi-asserted-by":"publisher","first-page":"367","DOI":"10.1016\/j.msec.2014.10.079","volume":"47","author":"A Labena","year":"2015","unstructured":"Labena, A., Hegazy, M. A., Horn, H. & M\u00fcller, E. The biocidal effect of a novel synthesized gemini surfactant on environmental sulfidogenic bacteria: Planktonic cells and biofilms. Mater. Sci. Eng. C 47, 367\u2013375. https:\/\/doi.org\/10.1016\/j.msec.2014.10.079 (2015).","journal-title":"Mater. Sci. Eng. C"},{"key":"64859_CR64","doi-asserted-by":"publisher","first-page":"2107","DOI":"10.4315\/0362-028X.JFP-11-220","volume":"74","author":"G Gozzelino","year":"2011","unstructured":"Gozzelino, G., Tobar, D. E. R., Chaitiemwong, N., Hazeleger, W. & Beumer, R. Antibacterial activity of reactive quaternary ammonium compounds in solution and in nonleachable coatings. J. Food Protect. 74, 2107\u20132112. https:\/\/doi.org\/10.4315\/0362-028X.JFP-11-220 (2011).","journal-title":"J. Food Protect."},{"key":"64859_CR65","doi-asserted-by":"publisher","first-page":"85","DOI":"10.3389\/fmicb.2020.545419","volume":"11","author":"C McGoverin","year":"2020","unstructured":"McGoverin, C., Robertson, J., Jonmohamadi, Y., Swift, S. & Vanholsbeeck, F. Species dependence of SYTO 9 staining of bacteria. Front. Microbiol. 11, 85. https:\/\/doi.org\/10.3389\/fmicb.2020.545419 (2020).","journal-title":"Front. Microbiol."},{"key":"64859_CR66","doi-asserted-by":"publisher","first-page":"6483","DOI":"10.1038\/s41598-019-42906-3","volume":"9","author":"M Rosenberg","year":"2019","unstructured":"Rosenberg, M., Azevedo, N. F. & Ivask, A. Propidium iodide staining underestimates viability of adherent bacterial cells. Sci. Rep. 9, 6483. https:\/\/doi.org\/10.1038\/s41598-019-42906-3 (2019).","journal-title":"Sci. Rep."},{"key":"64859_CR67","doi-asserted-by":"publisher","first-page":"4668","DOI":"10.3390\/ijms20194668","volume":"20","author":"CY Lee","year":"2019","unstructured":"Lee, C. Y., Chen, Y. T., Lee, B. S. & Chang, C. C. Suppressing antibacterial resistance: Chemical binding of monolayer quaternary ammonium salts to polymethyl methacrylate in an aqueous solution and its clinical efficacy. Int. J. Mol. Sci. 20, 4668. https:\/\/doi.org\/10.3390\/ijms20194668 (2019).","journal-title":"Int. J. Mol. Sci."},{"key":"64859_CR68","doi-asserted-by":"publisher","first-page":"2513","DOI":"10.1007\/s10096-012-1634-6","volume":"31","author":"M Cu\u00e9llar-Cruz","year":"2012","unstructured":"Cu\u00e9llar-Cruz, M. et al. The effect of biomaterials and antifungals on biofilm formation by Candida species: A review. Eur. J. Clin. Microbiol. Infect. Dis. 31, 2513\u20132527. https:\/\/doi.org\/10.1007\/s10096-012-1634-6 (2012).","journal-title":"Eur. J. Clin. Microbiol. Infect. Dis."},{"key":"64859_CR69","doi-asserted-by":"publisher","first-page":"12161","DOI":"10.1021\/acs.langmuir.5b01430","volume":"31","author":"S Zhang","year":"2015","unstructured":"Zhang, S. et al. Antibacterial activity, in vitro cytotoxicity, and cell cycle arrest of gemini quaternary ammonium surfactants. Langmuir 31, 12161\u201312169. https:\/\/doi.org\/10.1021\/acs.langmuir.5b01430 (2015).","journal-title":"Langmuir"},{"key":"64859_CR70","doi-asserted-by":"publisher","first-page":"120750","DOI":"10.1016\/j.molliq.2022.120750","volume":"368","author":"FMS Costa","year":"2022","unstructured":"Costa, F. M. S., Saraiva, M. L. M. F. S. & Passos, M. L. C. Ionic liquids and organic salts with antimicrobial activity as a strategy against resistant microorganisms. J. Mol. Liquids 368, 120750. https:\/\/doi.org\/10.1016\/j.molliq.2022.120750 (2022).","journal-title":"J. Mol. Liquids"},{"key":"64859_CR71","doi-asserted-by":"publisher","first-page":"220","DOI":"10.1016\/j.molliq.2018.08.134","volume":"271","author":"T Gundolf","year":"2018","unstructured":"Gundolf, T., Rauch, B., Kalb, R., Rossmanith, P. & Mester, P. Influence of bacterial lipopolysaccharide modifications on the efficacy of antimicrobial ionic liquids. J. Mol. Liquids 271, 220\u2013227. https:\/\/doi.org\/10.1016\/j.molliq.2018.08.134 (2018).","journal-title":"J. Mol. Liquids"},{"key":"64859_CR72","doi-asserted-by":"publisher","first-page":"8896","DOI":"10.1038\/s41598-021-88244-1","volume":"11","author":"E Paluch","year":"2021","unstructured":"Paluch, E., Szperlik, J., Lamch, \u0141, Wilk, K. A. & Ob\u0142\u0105k, E. Biofilm eradication and antifungal mechanism of action against Candida albicans of cationic dicephalic surfactants with a labile linker. Sci. Rep. 11, 8896. https:\/\/doi.org\/10.1038\/s41598-021-88244-1 (2021).","journal-title":"Sci. Rep."},{"key":"64859_CR73","doi-asserted-by":"publisher","first-page":"26965","DOI":"10.1371\/journal.pone.0026965","volume":"6","author":"JAS Almeida","year":"2011","unstructured":"Almeida, J. A. S., Faneca, H., Carvalho, R. A., Marques, E. F. & Pais, A. A. C. C. Dicationic alkylammonium bromide gemini surfactants membrane perturbation and skin irritation. PLOS One 6, 26965. https:\/\/doi.org\/10.1371\/journal.pone.0026965 (2011).","journal-title":"PLOS One"},{"key":"64859_CR74","doi-asserted-by":"publisher","first-page":"670","DOI":"10.1016\/j.msec.2016.12.122","volume":"73","author":"J Li","year":"2017","unstructured":"Li, J. & Guo, Y. Basic evaluation of typical nanoporous silica nanoparticles in being drug carrier: Structure, wettability and hemolysis. Mater. Sci. Eng. C 73, 670\u2013673. https:\/\/doi.org\/10.1016\/j.msec.2016.12.122 (2017).","journal-title":"Mater. Sci. Eng. C"},{"key":"64859_CR75","doi-asserted-by":"publisher","first-page":"1010","DOI":"10.1002\/jps.2600540712","volume":"54","author":"DE Cadwallader","year":"1965","unstructured":"Cadwallader, D. E. & Ansel, H. C. Hemolysis of erythrocytes by antibacterial preservatives II. Quaternary ammonium salts. J. Pharmaceut. Sci. 54, 1010\u20131012. https:\/\/doi.org\/10.1002\/jps.2600540712 (1965).","journal-title":"J. Pharmaceut. Sci."},{"key":"64859_CR76","doi-asserted-by":"publisher","first-page":"1163","DOI":"10.1016\/S0040-4020(01)86681-3","volume":"46","author":"JS Bradshaw","year":"1990","unstructured":"Bradshaw, J. S., Krakowiak, K. E., An, H. & Izatt, R. M. The synthesis of new diaza-N-pivot lariat 15-crown-5 and 18-crown-6 macrocycles. Tetrahedron 46, 1163\u20131170. https:\/\/doi.org\/10.1016\/S0040-4020(01)86681-3 (1990).","journal-title":"Tetrahedron"},{"key":"64859_CR77","unstructured":"Clinical, L. S. I. Reference method for broth dilution antifungal suscetibility testing of yeasts-4th ed. CLSI standard M27 (2017)."},{"key":"64859_CR78","doi-asserted-by":"publisher","first-page":"162","DOI":"10.1016\/j.colsurfb.2014.12.018","volume":"126","author":"LQ Pang","year":"2015","unstructured":"Pang, L. Q., Zhong, L. J., Zhou, H. F., Wu, X. E. & Chen, X. D. Grafting of ionic liquids on stainless steel surface for antibacterial application. Colloids Surfaces B Biointerfaces 126, 162\u2013168. https:\/\/doi.org\/10.1016\/j.colsurfb.2014.12.018 (2015).","journal-title":"Colloids Surfaces B Biointerfaces"},{"key":"64859_CR79","unstructured":"Pierce, B. The thermo Scientific alamarBlue Cell Viability Assay Reagent. US Patent 6,403,378 0747 (2012)."},{"key":"64859_CR80","doi-asserted-by":"publisher","first-page":"190","DOI":"10.1111\/1574-6968.12331","volume":"350","author":"E Ob\u0142ak","year":"2014","unstructured":"Ob\u0142ak, E., Piecuch, A., Guz-Regner, K. & Dworniczek, E. Antibacterial activity of gemini quaternary ammonium salts. FEMS Microbiol. Lett. 350, 190\u2013198. https:\/\/doi.org\/10.1111\/1574-6968.12331 (2014).","journal-title":"FEMS Microbiol. Lett."},{"key":"64859_CR81","doi-asserted-by":"publisher","first-page":"220","DOI":"10.1016\/j.jcis.2019.09.100","volume":"558","author":"\u0141 Lamch","year":"2020","unstructured":"Lamch, \u0141 et al. New mild amphoteric sulfohydroxybetaine-type surfactants containing different labile spacers: Synthesis, surface properties and performance. J. Colloid Interface Sci. 558, 220\u2013229. https:\/\/doi.org\/10.1016\/j.jcis.2019.09.100 (2020).","journal-title":"J. Colloid Interface Sci."},{"key":"64859_CR82","doi-asserted-by":"publisher","first-page":"37","DOI":"10.1002\/jsde.12681","volume":"27","author":"\u0141 Lamch","year":"2024","unstructured":"Lamch, \u0141, Witek, K., Oszcz\u0119da, W. & Wilk, K. A. Synthesis, surface activity and performance in \u201cgreen\u201d shampoo formulations of new carboxybetaine-type surfactants. J. Surfact. Detergents 27, 37\u201348. https:\/\/doi.org\/10.1002\/jsde.12681 (2024).","journal-title":"J. Surfact. Detergents"},{"key":"64859_CR83","doi-asserted-by":"publisher","first-page":"347","DOI":"10.1016\/0165-1161(75)90046-1","volume":"31","author":"BN Ames","year":"1975","unstructured":"Ames, B. N., McCann, J. & Yamasaki, E. Methods for detecting carcinogens and mutagens with the Salmonella\/mammalian microsome mutagenicity test. Mutat. Res. 31, 347\u2013364. https:\/\/doi.org\/10.1016\/0165-1161(75)90046-1 (1975).","journal-title":"Mutat. Res."}],"container-title":["Scientific Reports"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-64859-y.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-64859-y","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-64859-y.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,6,22]],"date-time":"2024-06-22T04:03:35Z","timestamp":1719029015000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-64859-y"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,19]]},"references-count":83,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["64859"],"URL":"https:\/\/doi.org\/10.1038\/s41598-024-64859-y","relation":{},"ISSN":["2045-2322"],"issn-type":[{"value":"2045-2322","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,19]]},"assertion":[{"value":"13 February 2024","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"13 June 2024","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"19 June 2024","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"The authors declare no competing interests.","order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"14110"}}