{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,31]],"date-time":"2026-01-31T09:27:29Z","timestamp":1769851649455,"version":"3.49.0"},"reference-count":103,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2019,11,21]],"date-time":"2019-11-21T00:00:00Z","timestamp":1574294400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Catalysts"],"abstract":"<jats:p>Biosurfactant compounds have been studied in many applications, including biomedical, food, cosmetic, agriculture, and bioremediation areas, mainly due to their low toxicity, high biodegradability, and multifunctionality. Among biosurfactants, the lipoplexes of lipoaminoacids play a key role in medical and pharmaceutical fields. Lipoaminoacids (LAAs) are amino acid-based surfactants that are obtained from the condensation reaction of natural origin amino acids with fatty acids or fatty acid derivatives. LAA can be produced by biocatalysis as an alternative to chemical synthesis and thus become very attractive from both the biomedical and the environmental perspectives. Gemini LAAs, which are made of two hydrophobic chains and two amino acid head groups per molecule and linked by a spacer at the level of the amino acid residues, are promising candidates as both drug and gene delivery and protein disassembly agents. Gemini LAA usually show lower critical micelle concentration, interact more efficiently with proteins, and are better solubilising agents for hydrophobic drugs when compared to their monomeric counterparts due to their dimeric structure. A clinically relevant human gene therapy vector must overcome or avoid detect and silence foreign or misplaced DNA whilst delivering sustained levels of therapeutic gene product. Many non-viral DNA vectors trigger these defence mechanisms, being subsequently destroyed or rendered silent. The development of safe and persistently expressing DNA vectors is a crucial prerequisite for a successful clinical application, and it one of the main strategic tasks of non-viral gene therapy research.<\/jats:p>","DOI":"10.3390\/catal9120977","type":"journal-article","created":{"date-parts":[[2019,11,22]],"date-time":"2019-11-22T02:49:27Z","timestamp":1574390967000},"page":"977","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Lipoaminoacids Enzyme-Based Production and Application as Gene Delivery Vectors"],"prefix":"10.3390","volume":"9","author":[{"given":"Maria","family":"Ribeiro","sequence":"first","affiliation":[{"name":"Faculty of Pharmacy, Universidade Lisboa, Av. Gama Pinto, 1649-003 Lisboa, Portugal"},{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade Lisboa, Av. Gama Pinto, 1649-003 Lisboa, Portugal"}]},{"given":"Patricia","family":"Carvalho","sequence":"additional","affiliation":[{"name":"Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, 1649-028 Lisbon, Portugal"}]},{"given":"Tiago","family":"Martins","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Universidade Lisboa, Av. Gama Pinto, 1649-003 Lisboa, Portugal"}]},{"given":"C\u00e9lia","family":"Faustino","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Universidade Lisboa, Av. Gama Pinto, 1649-003 Lisboa, Portugal"},{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade Lisboa, Av. Gama Pinto, 1649-003 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2019,11,21]]},"reference":[{"key":"ref_1","first-page":"58","article-title":"Biosurfactants in Pharmaceutical Industry (A Mini-Review)","volume":"1","year":"2011","journal-title":"Am. J. Drug Discov. Dev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1093\/jac\/dkl024","article-title":"Biosurfactants: Potential applications in medicine","volume":"57","author":"Rodrigues","year":"2006","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Zakharova, L., Pashirova, T., Doktorovova, S., Fernandes, A., Sanchez-Lopez, E., Silva, A., and Souto, S. (2019). Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications. Int. J. Mol. Sci., 20.","DOI":"10.3390\/ijms20225534"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3754","DOI":"10.1021\/acsnano.8b07858","article-title":"Lipid-Based DNA Therapeutics: Hallmarks of Non-Viral Gene Delivery","volume":"13","author":"Buck","year":"2019","journal-title":"ACS Nano"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.cis.2017.12.006","article-title":"A review on cationic lipids with different linkers for gene delivery","volume":"253","author":"Zhi","year":"2018","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Grijalvo, S., Puras, G., Z\u00e1rate, J., Sainz-Ramos, M., Qtaish, N.A.L., L\u00f3pez, T., Mashal, M., Attia, N., D\u00edaz, D., and Pons, R. (2019). Cationic Niosomes as Non-Viral Vehicles for Nucleic Acids: Challenges and Opportunities in Gene Delivery. Pharmaceutics, 11.","DOI":"10.3390\/pharmaceutics11020050"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/j.ejps.2010.03.019","article-title":"Gene delivery by lipoplexes and polyplexes","volume":"40","author":"Ilarduya","year":"2010","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"9","DOI":"10.2174\/156652308783688491","article-title":"Gemini surfactants: A new family of building blocks for non-viral gene delivery systems","volume":"8","author":"Wettig","year":"2008","journal-title":"Curr. Gene Ther."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"299","DOI":"10.2174\/156720111795256200","article-title":"Amino acid-substituted gemini surfactant-based nanoparticles as safety and versatile gene delivery agents","volume":"8","author":"Singh","year":"2011","journal-title":"Curr. Drug Deliv."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1186\/1477-3155-10-7","article-title":"Evaluation of cellular uptake and intracellular trafficking as determining factors of gene expression for amino acid-substituted gemini surfactant-based DNA nanoparticles","volume":"10","author":"Singh","year":"2012","journal-title":"J. Nanobiotechnol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1016\/S0001-8686(01)00069-0","article-title":"Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: A review","volume":"97","author":"Zana","year":"2002","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"11703","DOI":"10.1021\/la901641f","article-title":"Novel gemini pyridinium surfactants: Synthesis and study of their surface activity, DNA binding, and cytotoxicity","volume":"25","author":"Bhadani","year":"2009","journal-title":"Langmuir"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"4805","DOI":"10.1021\/ie1014348","article-title":"Amino Acids as raw material for biocompatible surfactants","volume":"50","author":"Pinazo","year":"2011","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/j.colsurfa.2012.08.060","article-title":"DNA compaction and multi-molecular DNA condensation induced by cationic imidazolium gemini surfactants","volume":"41","author":"Zhou","year":"2012","journal-title":"Colloids Surf. A."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/j.cis.2014.10.013","article-title":"Amino acid-based surfactants\u2013do they deserve more attention?","volume":"222","author":"Bordes","year":"2015","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"134","DOI":"10.1016\/j.cis.2013.10.020","article-title":"Gemini surfactants from natural amino acids","volume":"205","author":"Pinazo","year":"2014","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3700","DOI":"10.1039\/C9SM00399A","article-title":"Temperature-responsive self-assembled nanostructures from lysine-based surfactants with high chain length asymmetry: From tubules and helical ribbons to micelles and vesicles","volume":"15","author":"Oliveira","year":"2019","journal-title":"Soft Matter"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Huang, Z., Zhao, D.M., Deng, X., Zhang, J., Zhang, Y.M., and Yu, X.Q. (2018). Functionalized asymmetric bola-type amphiphiles for efficient gene and drug delivery. Nanomaterials, 8.","DOI":"10.3390\/nano8020115"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"394","DOI":"10.1016\/j.colsurfa.2016.12.042","article-title":"Concentration dependent morphological transition of nanostructured self-assembly towards hydrogelation seeding from micellar aggregates through stereochemically optimized H-bonding network of amino acid derived cationic amphiphiles","volume":"516","author":"Haldar","year":"2017","journal-title":"Colloids Surf. A"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1007\/s11743-016-1895-7","article-title":"Investigation of the physicochemical and biological properties of proline-based surfactants in single and mixed surfactant systems","volume":"20","author":"Joondan","year":"2017","journal-title":"J. Surfactants Deterg."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1016\/j.bmcl.2015.10.086","article-title":"Synthesis and biological evaluation of novel lipoamino acid derivatives","volume":"26","author":"Kaki","year":"2016","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"5198","DOI":"10.1016\/j.bmcl.2016.09.063","article-title":"Synthesis and biological evaluation of ricinoleic acid-based lipoamino acid derivatives","volume":"26","author":"Mohini","year":"2016","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1016\/j.micres.2014.02.010","article-title":"A study of the antibacterial activity of L-phenylalanine and L-tyrosine esters in relation to their CMCs and their interactions with1,2-dipalmitoyl-sn-glycero-3-phosphocholine, DPPC as model membrane","volume":"169","author":"Joondan","year":"2014","journal-title":"Microbiol. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"312","DOI":"10.1016\/j.ijpharm.2011.11.030","article-title":"Drug solubilization and in vitro toxicity evaluation of lipoamino acid surfactants","volume":"423","author":"Tsapis","year":"2012","journal-title":"Int. J. Pharm."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1016\/j.ijpharm.2017.06.083","article-title":"Pharmaceutical versatility of cationic niosomes derived from amino acid-based surfactants: Skin penetration behavior and controlled drug release","volume":"529","author":"Muzzalupo","year":"2017","journal-title":"Int. J. Pharm."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"426","DOI":"10.1016\/j.colsurfa.2014.11.039","article-title":"Solubilization power of an amino acid-based gemini surfactant towards the hydrophobic drug amphotericin B","volume":"480","author":"Faustino","year":"2015","journal-title":"Colloids Surf. A."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.ijpharm.2015.11.034","article-title":"Lipoamino acid-based micelles as promising delivery vehicles for monomeric amphotericin B","volume":"497","author":"Serafim","year":"2016","journal-title":"Int. J. Pharm."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1016\/j.colsurfa.2017.04.017","article-title":"Monocatenary histidine-based surfactants: Role of the alkyl chain length in antimicrobial activity and their selectivity over red blood cells","volume":"532","author":"Bustelo","year":"2017","journal-title":"Colloids Surf. A"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"186","DOI":"10.1208\/s12249-019-1396-x","article-title":"Design and toxicity evaluation of novel fatty acid-amino acid-based biocompatible surfactants","volume":"20","author":"Katiyar","year":"2019","journal-title":"AAPS Pharm. Sci. Tech."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.crci.2017.11.005","article-title":"Synthesis, chemistry, physicochemical properties and industrial applications of amino acid surfactants: A review","volume":"21","author":"Mishra","year":"2018","journal-title":"Comptes Rendus Chim."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1499","DOI":"10.1039\/C1CS15217C","article-title":"Derivation and synthesis of renewable surfactants","volume":"41","author":"Foley","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6491","DOI":"10.1039\/c3cs00004d","article-title":"Immobilised enzymes in biorenewables production","volume":"42","author":"Franssen","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/j.molcatb.2008.08.013","article-title":"Screening of plant peptidases for the synthesis of arginine-based surfactants","volume":"57","author":"Morcelle","year":"2009","journal-title":"J. Mol. Catal. B"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Faustino, C., Martins, T., Duarte, N., and Ribeiro, M.H. (2019). Self-assembly of lipoaminoacids-DNA based on thermodynamic and aggregation properties. J. Surfactants Deterg., Submitted.","DOI":"10.1002\/jsde.12391"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1016\/j.biotechadv.2007.06.001","article-title":"Lipases in lipophilization reactions","volume":"25","author":"Villeneuve","year":"2007","journal-title":"Biotechnol. Adv."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1016\/j.cej.2014.10.004","article-title":"Valorization of tannery wastes: Lipoamino acid surfactant mixtures from the protein fraction of process wastewater","volume":"262","author":"Bautista","year":"2015","journal-title":"Chem. Eng. J."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1007\/s00253-007-0932-x","article-title":"Biomass in the manufacture of industrial products\u2013the use of proteins and amino acids","volume":"75","author":"Scott","year":"2007","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_38","first-page":"308","article-title":"Production of protease from rice mill wastes by Aspergillus niger in solid state fermentation","volume":"5","author":"Paranthaman","year":"2009","journal-title":"World J. Agric. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.molcatb.2009.09.003","article-title":"Technical methods to improve yield, activity and stability in the development of microbial lipases","volume":"62","author":"Shu","year":"2010","journal-title":"J. Mol. Catal. B"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1016\/j.procbio.2012.01.011","article-title":"Lipase promiscuity and its biochemical applications","volume":"47","author":"Kapoor","year":"2012","journal-title":"Process Biochem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"777","DOI":"10.1002\/biot.200600059","article-title":"Novel biocatalysts for white biotechnology","volume":"1","author":"Drepper","year":"2006","journal-title":"Biotechnol. J."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"390","DOI":"10.1016\/S0958-1669(02)00341-5","article-title":"Lipases for biotechnology","volume":"13","author":"Jaeger","year":"2002","journal-title":"Curr. Opin. Biotechnol."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Brockman, H.L. (2004). Lipases Encyclopedia of Biological Chemistry, Elsevier.","DOI":"10.1016\/B0-12-443710-9\/00359-8"},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Polaina, J., and MacCabe, A. (2007). Lipases: Molecular Structure and Function. Industrial Enzymes, Springer.","DOI":"10.1007\/1-4020-5377-0"},{"key":"ref_45","first-page":"1","article-title":"Bacterial Protease Enzyme: Safe and Good Alternative for Industrial and Commercial Use","volume":"3","author":"Hamza","year":"2017","journal-title":"Int. J. Chem. Biomol. Sci."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1007\/s12257-009-3079-z","article-title":"Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis","volume":"15","author":"Gorke","year":"2010","journal-title":"Biotechnol. Bioprocess Eng."},{"key":"ref_47","first-page":"243","article-title":"Choline-based deep eutectic solvents for enzymatic preparation of biodiesel from soybean oil","volume":"85","author":"Zhao","year":"2012","journal-title":"J. Mol. Catal. B"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1039\/B400293H","article-title":"\u201cGreen\u201d amino acid-based surfactants","volume":"6","author":"Pinazo","year":"2004","journal-title":"Green Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1080\/10242420290004947","article-title":"Amino Acid-based Surfactants: Enzymatic Synthesis, Properties and Potential Applications","volume":"20","author":"Clapes","year":"2002","journal-title":"J. Biocatal. Biotransform."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1002\/ejlt.200390062","article-title":"Industrial lipase immobilization","volume":"105","author":"Christensen","year":"2003","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.molcatb.2016.04.006","article-title":"Improving enantioselectivity of lipase from Candida rugosa by carrier bound and carrier-free immobilization","volume":"130","year":"2016","journal-title":"J. Mol. Catal. B Enzym."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.molcatb.2008.12.001","article-title":"Magnetic nanoparticles supported ionic liquids for lipase immobilization: Enzyme activity in catalyzing esterification","volume":"58","author":"Jiang","year":"2009","journal-title":"J. Mol. Catal. B"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1451","DOI":"10.1016\/j.enzmictec.2007.01.018","article-title":"Improvement of enzyme activity, stability and selectivity via immobilization techniques","volume":"40","author":"Mateo","year":"2007","journal-title":"Enzym. Microb. Technol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1016\/j.foodchem.2017.06.105","article-title":"Selective and eco-friendly synthesis of lipoaminoacid-based surfactants for food, using immobilized lipase and protease biocatalysts","volume":"239","author":"Bernal","year":"2018","journal-title":"Food Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1465","DOI":"10.1007\/s00726-015-1979-0","article-title":"Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants","volume":"47","author":"Fait","year":"2015","journal-title":"Amino Acids"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Ribeiro, M., Martins, T.S., and Faustino, C. (2018, January 9\u201312). Enzymatic development of lipoaminoacids towards nanostructured gene delivery systems. Proceedings of the European Symposium on Biochemical Engineering Sciences, Lisbon, Portugal. Book of Abstracts ESBES 2018.","DOI":"10.3390\/catal9120977"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"977","DOI":"10.1021\/jp807396k","article-title":"New urea-based surfactants derived from \u03b1, \u03c9-amino acids","volume":"113","author":"Faustino","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2508","DOI":"10.1021\/bm9004723","article-title":"Gemini surfactant-protein interactions: Effect of pH, temperature and surfactant stereochemistry","volume":"10","author":"Faustino","year":"2009","journal-title":"Biomacromolecules"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1443","DOI":"10.1093\/nar\/gkm1146","article-title":"Interaction of cationic surfactants with DNA: A single-molecule study","volume":"36","author":"Husale","year":"2008","journal-title":"Nucleic Acids Res."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1016\/j.jcis.2011.03.034","article-title":"Micellization of cationic gemini surfactant and its interaction with DNA in dilute brine","volume":"358","author":"He","year":"2011","journal-title":"J. Colloid Interface Sci."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"14446","DOI":"10.1021\/jp8027935","article-title":"Interaction between DNA and cationic surfactants: Effect of DNA conformation and surfactant headgroup","volume":"112","author":"Dias","year":"2008","journal-title":"J. Phys. Chem. B"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1016\/S1567-5394(02)00130-5","article-title":"Structural and thermodynamic features of complexes formed by DNA and synthetic polynucleotides with dodecylamine and dodecyltrimethylammonium bromide","volume":"58","author":"Petrov","year":"2002","journal-title":"Bioelectrochemistry"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3735","DOI":"10.1021\/la052161s","article-title":"Molecular mechanism and thermodynamics study of plasmid DNA and cationic surfactants interactions","volume":"22","author":"Zhu","year":"2006","journal-title":"Langmuir"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"472","DOI":"10.1016\/j.jcis.2010.08.007","article-title":"Dimeric and monomeric surfactants derived from sulfur-containing amino acids","volume":"351","author":"Faustino","year":"2010","journal-title":"J. Colloid Interface Sci."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"493","DOI":"10.1016\/j.jcis.2011.04.016","article-title":"Mixed micelle formation between amino acid-based surfactants and phospholipids","volume":"359","author":"Faustino","year":"2011","journal-title":"J. Colloid Interface Sci."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1021\/acs.jpcb.7b11954","article-title":"Cationic gemini surfactant-plasmid deoxyribonucleic acid condensates as a single amphiphilic entity","volume":"122","author":"Shortall","year":"2018","journal-title":"J. Phys. Chem. B"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1016\/j.colsurfa.2014.12.022","article-title":"Amino acid-based cationic gemini surfactant-protein interactions","volume":"480","author":"Branco","year":"2015","journal-title":"Colloids Surf. A"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1016\/S0927-7757(03)00334-0","article-title":"DNA-cationic amphiphile interactions","volume":"228","author":"Miguel","year":"2003","journal-title":"Colloids Surf. A"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"7331","DOI":"10.1021\/ja0124055","article-title":"Thermodynamics of cationic lipid binding to DNA and DNA condensation: Roles of electrostatics and hydrophobicity","volume":"124","author":"Matulis","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1016\/j.bpc.2008.09.014","article-title":"Biophysical characterization of complexation of DNA with oppositely charged Gemini surfactant 12-3-12","volume":"138","author":"Zhao","year":"2008","journal-title":"Biophys. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"722","DOI":"10.1080\/01932691.2012.685850","article-title":"Polymer-surfactant interactions and the effect of tail size variation on micellization process of cationic ATAB surfactants in aqueous medium","volume":"34","author":"Ansari","year":"2013","journal-title":"J. Disper. Sci. Technol."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1016\/S0301-4622(02)00107-2","article-title":"Studies on surfactant\u2013biopolymer interaction. I. Microcalorimetric investigation on the interaction of cetyltrimetylammonium bromide (CTAB) and sodium dodecylsulfate (SDS) with gelatin (Gn), lysozyme (Lz) and deoxyribonucleic acid (DNA)","volume":"98","author":"Chaterjee","year":"2002","journal-title":"Biophys. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"30795","DOI":"10.1039\/C6RA00640J","article-title":"Interaction of cationic gemini surfactant tetramethylene-1,4-bis(dimethyltetradecylammonium bromide) with anionic polyelectrolyte sodium carboxymethyl cellulose, with two different molar masses, in aqueous and aquo-organic (isopropanol) media","volume":"6","author":"Das","year":"2016","journal-title":"RSC Adv."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1939","DOI":"10.1039\/c0cp01196g","article-title":"Aggregation behavior of gemini surfactants and their interaction with macromolecules in aqueous solution","volume":"13","author":"Han","year":"2011","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"290","DOI":"10.1006\/jcis.2002.8477","article-title":"Compaction of DNA by gemini surfactants: Effects of surfactant architecture","volume":"252","author":"Karlsson","year":"2002","journal-title":"J. Colloid Interface Sci."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"759","DOI":"10.1016\/j.jcis.2004.10.055","article-title":"Microcalorimetric study on the interaction of dissymmetric gemini surfactants with DNA","volume":"284","author":"Jiang","year":"2005","journal-title":"J. Colloid Interface Sci."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1016\/j.jconrel.2005.06.014","article-title":"Cationic lipid saturation influences intracelular delivery of encapsulated nucleic acids","volume":"107","author":"Heyes","year":"2005","journal-title":"J. Control. Release"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"5702","DOI":"10.1039\/C4SM00881B","article-title":"Structure-delivery relationships of lysine-based gemini surfactants and their lipoplexes","volume":"10","author":"Damen","year":"2014","journal-title":"Soft Matter"},{"key":"ref_79","doi-asserted-by":"crossref","unstructured":"Pi-Boleda, B., Bouzas, M., Gaztelumendi, N., Illa, O., Nogu\u00e9s, C., Branchadell, V., Pons, R., and Ortu\u00f1o, R.M. (2019). Chiral pH-sensitive cyclobutane \u03b2-amino acid-based cationic amphiphiles: Possible candidates for use in gene therapy. J. Mol. Liq., 111856. in press.","DOI":"10.1016\/j.molliq.2019.111856"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1616","DOI":"10.1039\/b618579g","article-title":"Investigation of complexes formed by interaction of cationic gemini surfactants with deoxyribonucleic acid","volume":"9","author":"Wang","year":"2007","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1016\/j.colsurfb.2014.03.040","article-title":"Conformational changes of DNA in the presence of 12-s-12 gemini surfactants (s = 2 and 10). Role of the spacer\u2019s length in the interaction surfactant-polynucleotide","volume":"118","year":"2014","journal-title":"Colloids Surf. B"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1016\/j.colsurfb.2016.04.028","article-title":"Binding of 12-s-12 dimeric surfactants to calf thymus DNA: Evaluation of the spacer length influence","volume":"144","author":"Bernal","year":"2016","journal-title":"Colloids Surf. B"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"15385","DOI":"10.1021\/jp0488057","article-title":"Micellization of cationic gemini surfactants with various counterions and their interaction with DNA in aqueous solution","volume":"108","author":"Jiang","year":"2004","journal-title":"J. Phys. Chem. B"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"8502","DOI":"10.1021\/jp068571m","article-title":"Effect of headgroup on DNA-cationic surfactant interactions","volume":"111","author":"Dasgupta","year":"2007","journal-title":"J. Phys. Chem. B"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.jcis.2006.07.084","article-title":"DNA encapsulation by biocompatible catanionic vesicles","volume":"312","author":"Rosa","year":"2007","journal-title":"J. Colloid Interface Sci."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1016\/j.colsurfa.2006.12.082","article-title":"The association of DNA and stable catanionic amino acid-based vesicles","volume":"301","author":"Rosa","year":"2007","journal-title":"Colloids Surf. A"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1080\/09687680701499451","article-title":"DNA pre-condensation with an amino acid-based cationic amphiphile. A viable approach for liposome-based gene delivery","volume":"25","author":"Rosa","year":"2008","journal-title":"Mol. Membr. Biol."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"5831","DOI":"10.1021\/jp301069t","article-title":"Kinetic studies of amino acid-based surfactant binding to DNA","volume":"116","author":"Santhiya","year":"2012","journal-title":"J. Phys. Chem. B"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"346","DOI":"10.1016\/j.colsurfb.2015.07.076","article-title":"Reversibility of the interactions between a novel surfactant derived from lysine and biomolecules","volume":"135","author":"Robina","year":"2015","journal-title":"Colloids Surf. B"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"13770","DOI":"10.1021\/la901546t","article-title":"Role of linker groups between hydrophilic and hydrophobic moieties of cationic surfactants on oligonucleotide-surfactant interactions","volume":"25","author":"Santhiya","year":"2009","journal-title":"Langmuir"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"1852","DOI":"10.1021\/bm8000765","article-title":"Effect of the headgroup geometry of amino acid-based cationic surfactants on interaction with plasmid DNA","volume":"9","author":"Jadhav","year":"2008","journal-title":"Biomacromolecules"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"1148","DOI":"10.1016\/j.bbamem.2009.02.014","article-title":"Plasmid DNA-encapsulating liposomes: Effect of a spacer between the cationic headgroup and hydrophobic moieties of the lipids on gene expression efficiency","volume":"1788","author":"Obata","year":"2009","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.nano.2009.04.005","article-title":"Evaluation of cationic liposomes composed of an amino acid-based lipid for neuronal transfection","volume":"6","author":"Obata","year":"2010","journal-title":"Nanomedicine"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1016\/j.ejpb.2014.12.013","article-title":"New serine-derived gemini surfactants as gene delivery systems","volume":"89","author":"Cardoso","year":"2015","journal-title":"Eur. J. Pharm. Biopharm."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"364","DOI":"10.1016\/j.ijpharm.2011.10.044","article-title":"Evaluation of the influence of ionization states and spacers in the thermotropic phase behavior of amino acid-based cationic lipids and the transfection efficiency of their assemblies","volume":"422","author":"Sarker","year":"2012","journal-title":"Int. J. Pharm."},{"key":"ref_96","doi-asserted-by":"crossref","unstructured":"Najjar, R. (2017). Amino Acid-Based Surfactants for Biomedical Applications. Application and Characterization of Surfactants, IntechOpen.","DOI":"10.5772\/65591"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1016\/j.ejpb.2010.04.007","article-title":"Enhanced gene expression in epithelial cells transfected with amino acid-substituted gemini nanoparticles","volume":"75","author":"Yang","year":"2010","journal-title":"Eur. J. Pharm. Biopharm."},{"key":"ref_98","doi-asserted-by":"crossref","unstructured":"Mart\u00ednez-Negro, M., Blanco-Fern\u00e1ndez, L., Tentori, P.M., P\u00e9rez, L., Pinazo, A., Tros de Ilarduya, C., Aicart, E., and Junquera, E. (2018). A gemini cationic lipid with histidine residues as a novel lipid-based gene nanocarrier: A biophysical and biochemical study. Nanomaterials, 8.","DOI":"10.3390\/nano8121061"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"111156","DOI":"10.1016\/j.molliq.2019.111156","article-title":"Gemini histidine based surfactants: Characterization; surface properties and biological activity","volume":"289","author":"Pinazo","year":"2019","journal-title":"J. Mol. Liq."},{"key":"ref_100","first-page":"125","article-title":"Reducible amino acid based cationic lipids as highly efficient and serum-tolerant gene vectors","volume":"81","author":"Zheng","year":"2016","journal-title":"Chem. Plus Chem."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"4692","DOI":"10.1016\/j.bmcl.2016.08.050","article-title":"Lipoic acid functionalized amino acids cationic lipids as gene vectors","volume":"26","author":"Su","year":"2016","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"1809","DOI":"10.1021\/acs.molpharmaceut.5b00967","article-title":"Specially-made lipid-based assemblies for improving transmembrane gene delivery: Comparison of basic amino acid residue rich periphery","volume":"13","author":"Jiang","year":"2016","journal-title":"Mol. Pharm."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"4781","DOI":"10.1016\/j.bmcl.2017.10.001","article-title":"Arginine-rich cross-linking peptides with different SV40 nuclear localization signal content as vectors for intranuclear DNA delivery","volume":"27","author":"Bogacheva","year":"2017","journal-title":"Bioorg. Med. Chem. Lett."}],"container-title":["Catalysts"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4344\/9\/12\/977\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:36:26Z","timestamp":1760189786000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4344\/9\/12\/977"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11,21]]},"references-count":103,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2019,12]]}},"alternative-id":["catal9120977"],"URL":"https:\/\/doi.org\/10.3390\/catal9120977","relation":{},"ISSN":["2073-4344"],"issn-type":[{"value":"2073-4344","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,11,21]]}}}