Arginine as a promising amino acid for functionalized nanosystems: Innovations, challenges, and future directions
Source abstract
Abstract
Abstract The amino acid arginine has been identified as a promising building block for the construction of functionalized nanosystems due to its unique chemical properties. Arginine-based peptides and polymers have been widely used in targeted drug delivery, gene therapy, and cancer therapy, as they can target specific cells and organs, thus increasing the efficiency and specificity of drug delivery. In addition, arginine-based nanosystems have shown potential in other applications such as imaging, regenerative medicine, environmental remediation, biosensing, gene editing, water treatment, and food safety. The synthetic methods for arginine-based nanosystems have been improved over the years, and new characterization techniques have been developed to properly evaluate the performance and properties of arginine-based nanosystems. However, several challenges need to be overcome to fully realize the potential of arginine-based nanosystems. These include scale-up and industrial production, biocompatibility and toxicity, and in vivo evaluation. In addition, the safety and toxicity of arginine-based nanosystems need to be carefully evaluated. This review covers recent progress in the field of arginine-based nanosystems, highlighting the advantages and limitations of arginine-based nanosystems as well as the current challenges and future perspectives in the field. It is an important source of information for researchers, scientists, and engineers working in the field of functionalized nanosystems, and it highlights the potential of arginine-based nanosystems in various applications and the challenges that need to be overcome to fully realize their potential.
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Research context
OpenAlex topics: RNA Interference and Gene Delivery · Biopolymer Synthesis and Applications · Antimicrobial agents and applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Ophthalmology, the Second Hospital of Jilin University , Changchun , 130000 , China
Department of General Practice and Family Medicine, the Second Hospital of Jilin University , Changchun , 130000 , China
References (100+)
Show source-provided references
1. Puri A, Loomis K, Smith B, Lee J-H, Yavlovich A, Heldman E, et al. Lipid-based nanoparticles as pharmaceutical drug carriers: from concepts to clinic. Crit Reviews™ Ther Drug Carr Syst. 2009;26(6):523–80.10.1615/CritRevTherDrugCarrierSyst.v26.i6.10 ↗
2. Wang S, Zhao Y, Zhang Z, Zhang Y, Li L. Recent advances in amino acid-metal coordinated nanomaterials for biomedical applications. Chin J Chem Eng. 2021;38:30–42.10.1016/j.cjche.2021.03.013 ↗
3. Zhou Y, Han S, Liang Z, Zhao M, Liu G, Wu J. Progress in arginine-based gene delivery systems. J Mater Chem B. 2020;8(26):5564–77.10.1039/D0TB00498G ↗
4. Zhang RX, Wong HL, Xue HY, Eoh JY, Wu XY. Nanomedicine of synergistic drug combinations for cancer therapy–Strategies and perspectives. J Controlled Rel. 2016;240:489–503.10.1016/j.jconrel.2016.06.012 ↗
5. Dreaden EC, El-Sayed IH, El-Sayed MA. Structure–Activity relationships for Tumor-targeting gold nanoparticles. In handbook of nanobiomedical research: Fundamentals, applications and recent developments: Volume 1. Materials for nanomedicine. USA: World Scientific; 2014. p. 519–63.10.1142/9789814520652_0014 ↗
6. Peng F, Zhang W, Qiu F. Self-assembling peptides in current nanomedicine: versatile nanomaterials for drug delivery. Curr Med Chem. 2020;27(29):4855–81.10.2174/0929867326666190712154021 ↗
7. Kuei B, Gomez ED. Chain conformations and phase behavior of conjugated polymers. Soft Matter. 2017;13(1):49–67.10.1039/C6SM00979D ↗
8. Sim S, Figueiras A, Veiga F. Modular hydrogels for drug delivery. Portugal: Scientific Research; 2012.
9. Lim SB, Banerjee A, Önyüksel H. Improvement of drug safety by the use of lipid-based nanocarriers. J Controlled Rel. 2012;163(1):34–45.10.1016/j.jconrel.2012.06.002 ↗
10. Liu BR, Li J-F, Lu S-W, Lee H-J, Huang Y-W, Shannon KB, et al. Cellular internalization of quantum dots noncovalently conjugated with arginine-rich cell-penetrating peptides. J Nanosci Nanotechnol. 2010;10(10):6534–43.10.1166/jnn.2010.2637 ↗
11. Gao Y, Xu Z, Chen S, Gu W, Chen L. and Li YJIjopArginine-chitosan/DNA self-assemble nanoparticles for gene delivery: In vitro characteristics and transfection efficiency. Int J Pharmaceutics. 2008;359(1–2):241–6.10.1016/j.ijpharm.2008.03.037 ↗
12. Hsan N, Dutta PK, Kumar S, Koh J. Arginine containing chitosan-graphene oxide aerogels for highly efficient carbon capture and fixation. J CO2 Util. 2022;59:101958.10.1016/j.jcou.2022.101958 ↗
13. Zhu K, Li J, Lai H, Yang C, Guo C, Wang C. Reprogramming fibroblasts to pluripotency using arginine-terminated polyamidoamine nanoparticles based non-viral gene delivery system. Int J Nanomed. 2014;9:5837.10.2147/IJN.S73961 ↗
14. Bryan MC, Dunn PJ, Entwistle D, Gallou F, Koenig SG, Hayler JD, et al. Key Green Chemistry research areas from a pharmaceutical manufacturers’ perspective revisited. Green Chem. 2018;20(22):5082–103.10.1039/C8GC01276H ↗
15. Zern BJ, Chu H, Osunkoya AO, Gao J, Wang Y. A biocompatible arginine‐based polycation. Adv Funct Mater. 2011;21(3):434–40.10.1002/adfm.201000969 ↗
16. Xu G, Liu X, Liu P, Pranantyo D, Neoh KG, Kang ET. Arginine-based polymer brush coatings with hydrolysis-triggered switchable functionalities from antimicrobial (Cationic) to antifouling (Zwitterionic). Langmuir. 2017;33(27):6925–36.10.1021/acs.langmuir.7b01000 ↗
17. Sandle T, Vijayakumar R, Saleh Al Aboody M, Saravanakumar S. In vitro fungicidal activity of biocides against pharmaceutical environmental fungal isolates. J Appl Microbiology. 2014;117(5):1267–73.10.1111/jam.12628 ↗
18. Market PE. Pharmaceutical Excipients Market by Product (Organic (Oleochemicals, Carbohydrates) Inorganic (Calcium Carbonate), Functionality (Fillers, Binders, Lubricants, Diluents), Formulation (Oral, Parenteral), Application (Stablizers) & Region - Global Forecast to 2028. USA: Markets and Markets; 2023.
19. Salih N, Salimon J. A review on eco-friendly green biolubricants from renewable and sustainable plant oil sources. Biointerface Res Appl Chem. 2021;11(5):13303–27.10.33263/BRIAC115.1330313327 ↗
20. Patel DV, Patel MN, Dholakia MS, Suhagia BN. Green synthesis and properties of arginine derived complexes for assorted drug delivery systems: A review. Sustain Chem Pharm. 2021;21:100441.10.1016/j.scp.2021.100441 ↗
21. Rahman KM. Food and high value products from microalgae: market opportunities and challenges. Microalgae biotechnology for food, health and high value products. Singapore: Springer; 2020. p. 3–27.10.1007/978-981-15-0169-2_1 ↗
22. Silveira BM, Barcelos MC, Vespermann KA, Pelissari FM, Molina G. An overview of biotechnological processes in the food industry. Bioprocessing for biomolecules production. Wiley; 2019. p. 1–19.10.1002/9781119434436.ch1 ↗
23. Wang Z, Zhu H, Wang X, Yang F, Yang XJN. One-pot green synthesis of biocompatible arginine-stabilized magnetic nanoparticles. Nanotechnology. 2009;20(46):465606.10.1088/0957-4484/20/46/465606 ↗
24. Pang X, Wu J, Chu C-C, Chen X. Development of an arginine-based cationic hydrogel platform: synthesis, characterization and biomedical applications. Acta Biomater. 2014;10(7):3098–107.10.1016/j.actbio.2014.04.002 ↗
25. Hoseinpour Najar M, Minaiyan M, Taheri A. Preparation and in vivo evaluation of a novel gel-based wound dressing using arginine–alginate surface-modified chitosan nanofibers. J Biomater Appl. 2018;32(6):689–701.10.1177/0885328217739562 ↗
26. Iacob A-T, Drăgan M, Ghețu N, Pieptu D, Vasile C, Buron F, et al. Preparation, characterization and wound healing effects of new membranes based on chitosan, hyaluronic acid and arginine derivatives. Polymers. 2018;10(6):607.10.3390/polym10060607 ↗
27. Sarker SR, Aoshima Y, Hokama R, Inoue T, Sou K, Takeoka S. Arginine-based cationic liposomes for efficient in vitro plasmid DNA delivery with low cytotoxicity. Int J Nanomed. 2013;8:1361–75.10.2147/IJN.S38903 ↗
28. Benavides T, Mitjans M, Martı́nez V, Clapés P, Infante MR, Clothier R, et al. Assessment of primary eye and skin irritants by in vitro cytotoxicity and phototoxicity models: an in vitro approach of new arginine-based surfactant-induced irritation. Toxicology. 2004;197(3):229–37.10.1016/j.tox.2004.01.011 ↗
29. Qin L, Gao H. The application of nitric oxide delivery in nanoparticle-based tumor targeting drug delivery and treatment. Asian J Pharm Sci. 2019;14(4):380–90.10.1016/j.ajps.2018.10.005 ↗
30. Mudakavi RJ, Vanamali S, Chakravortty D, Raichur AM. Development of arginine based nanocarriers for targeting and treatment of intracellular Salmonella. RSC Adv. 2017;7(12):7022–32.10.1039/C6RA27868J ↗
31. Fan Y, Liu Y, Wu Y, Dai F, Yuan M, Wang F, et al. Natural polysaccharides based self-assembled nanoparticles for biomedical applications–A review. Int J Biol Macromolecules. 2021;192:1240–55.10.1016/j.ijbiomac.2021.10.074 ↗
32. Ma Y, Mou Q, Sun M, Yu C, Li J, Huang X, et al. Cancer theranostic nanoparticles self-assembled from amphiphilic small molecules with equilibrium shift-induced renal clearance. Theranostics. 2016;6(10):1703.10.7150/thno.15647 ↗
33. Li T, Takeoka S. Smart liposomes for drug delivery, in Smart nanoparticles for biomedicine. Netherland: Elsevier; 2018. p. 31–47.10.1016/B978-0-12-814156-4.00003-3 ↗
34. Durante WJ. Role of arginase in vessel wall remodeling. Front Immunol. 2013;4:111.10.3389/fimmu.2013.00111 ↗
35. Shi HP, Most D, Efron DT, Witte MB, Barbul A. Supplemental L‐arginine enhances wound healing in diabetic rats. Wound Repair Regeneration. 2003;11(3):198–203.10.1046/j.1524-475X.2003.11308.x ↗
36. Patel D, Patel M, Soni T, Suhagia B. Topical arginine solid lipid nanoparticles: Development and characterization by QbD approach. J Drug Delivery Sci Technol. 2021;61:102329.10.1016/j.jddst.2021.102329 ↗
37. Seifter E, Rettura G, Barbul A, Levenson SJS. Arginine: an essential amino acid for injured rats. Surgery. 1978;84(2):224–30.
38. Soneja A, Drews M, Malinski T. Role of nitric oxide, nitroxidative and oxidative stress in wound healing. Pharmacol Rep. 2005;57:108.
39. Takano S, Kobayashi T, Miyoshi T, Takehara M. Arginine derivatives and cosmetic compositions containing the same, US Pat., 5100655, 1992.
40. Pinheiro L, Faustino C. Amino acid-based surfactants for biomedical applications. Appl Charact Surfactants. 2017;6:111–33.10.5772/67977 ↗
41. Kharissova OV, Kharisov BI, Oliva González CM, Méndez YP, López I. Greener synthesis of chemical compounds and materials. R Soc Open Sci. 2019;6(11):191378.10.1098/rsos.191378 ↗
42. Corsetti G, Pasini E, Scarabelli TM, Romano C, Singh A, Scarabelli CC, et al. Importance of energy, dietary protein sources, and amino acid composition in the regulation of metabolism: An indissoluble dynamic combination for life. Nutrients. 2024;16(15):2417.10.3390/nu16152417 ↗
43. Turek M, Różycka-Sokołowska E, Koprowski M, Marciniak B, Bałczewski P. Can pharmaceutical excipients threaten the aquatic environment? A risk assessment based on the Microtox® biotest. Molecules. 2023;28(18):6590.10.3390/molecules28186590 ↗
44. Thakur S, Singh A, Sharma R, Aurora R, Jain SK. Biosurfactants as a novel additive in pharmaceutical formulations: current trends and future implications. Curr Drug Metab. 2020;21(11):885–901.10.2174/1389200221666201008143238 ↗
45. Santos DKF, Rufino RD, Luna JM, Santos VA, Sarubbo LA. Biosurfactants: multifunctional biomolecules of the 21st century. Int J Mol Sci. 2016;17(3):401.10.3390/ijms17030401 ↗
46. De S, Malik S, Ghosh A, Saha R, Saha B. A review on natural surfactants. RSC Adv. 2015;5(81):65757–67.10.1039/C5RA11101C ↗
47. Holmberg K. Nat surfactantsCurr OpColloid Interface Sci. 2001;6(2):148–59.10.1016/S1359-0294(01)00074-7 ↗
48. Morán MC, Pinazo A, Pérez L, Clapés P, Angelet M, García MT, et al. “Green” amino acid-based surfactants. Green Chem. 2004;6(5):233–40.10.1039/B400293H ↗
49. Chandra N, Tyagi VK. Synthesis, properties, and applications of amino acids based surfactants: a review. J Dispers Sci Technol. 2013;34(6):800–8.10.1080/01932691.2012.695967 ↗
50. Widmer U. A convenient preparation of t-butyl esters. Synthesis. 1983;1983(2):135–6.10.1055/s-1983-30253 ↗
51. Li J, Sha YJM. A convenient synthesis of amino acid methyl esters. Molecules. 2008;13(5):1111–9.10.3390/molecules13051111 ↗
52. Chen B-C, Skoumbourdis AP, Guo P, Bednarz MS, Kocy OR, Sundeen JE, et al. A facile method for the transformation of N-(tert-butoxycarbonyl) α-amino acids to N-unprotected α-amino methyl esters. J Org Chem. 1999;64(25):9294–6.10.1021/jo990311w ↗
53. Pérez L, Torres JL, Manresa A, Solans C. Synthesis, aggregation, and biological properties of a new class of gemini cationic amphiphilic compounds from arginine, bis (Args). Langmuir. 1996;12(22):5296–301.10.1021/la960301f ↗
54. Piera E, Infante MR, Clapés P. Chemo‐enzymatic synthesis of arginine‐based gemini surfactants. Biotechnol Bioeng. 2000;70(3):323–31.10.1002/1097-0290(20001105)70:3<323::AID-BIT9>3.0.CO;2-N ↗
55. Pérez L, Pinazo A, Rosen MJ. Surface activity properties at equilibrium of novel gemini cationic amphiphilic compounds from arginine, Bis (Args). Langmuir. 1998;14(9):2307–15.10.1021/la971135u ↗
56. Morán C, Infante MR, Clapés P. Synthesis of glycero amino acid-based surfactants. Part 1. Enzymatic preparation of rac-1-O-(N α-acetyl-l-aminoacyl) glycerol derivatives. J Chem Soc Perkin Trans 1. 2001;(17):2063–70.10.1039/b103132p ↗
57. Morán C, Infante MR, Clapés P. Synthesis of glycero amino acid-based surfactants. Part 2. 1 Lipase-catalysed synthesis of 1-O-lauroyl-rac-glycero-3-O-(N α-acetyl-L-amino acid) and 1, 2-di-O-lauroyl-rac-glycero-3-O-(N α-acetyl-l-amino acid) derivatives. J Chem Soc Perkin Trans 1. 2002;(8):1124–34.10.1039/b200577h ↗
58. Pérez N, Pérez L, Infante MR, García MT. Biological properties of arginine-based glycerolipidic cationic surfactants. Green Chem. 2005;7(7):540–6.10.1039/b419204d ↗
59. Pérez L, Infante MR, Pons R, Morán C, Vinardell P, Mitjans M, et al. A synthetic alternative to natural lecithins with antimicrobial properties. Colloids Surf B: Biointerfaces. 2004;35(3–4):235–42.10.1016/j.colsurfb.2004.03.014 ↗
60. Perez L, Pinazo A, García MT, del Carmen Moran M. Monoglyceride surfactants from arginine: synthesis and biological properties. N J Chem. 2004;28(11):1326–34.10.1039/B405733C ↗
61. Tripathy DB, Mishra A, Clark J, Farmer T. Synthesis, chemistry, physicochemical properties and industrial applications of amino acid surfactants: A review. Comptes Rendus Chimie. 2018;21(2):112–30.10.1016/j.crci.2017.11.005 ↗
62. da Silva ER, Walter MNM, Reza M, Castelletto V, Ruokolainen J, Connon CJ, et al. Self-assembled arginine-capped peptide bolaamphiphile nanosheets for cell culture and controlled wettability surfaces. Biomacromolecules. 2015;16(10):3180–90.10.1021/acs.biomac.5b00820 ↗
63. Edwards-Gayle CJ, Castelletto V, Hamley IW, Barrett G, Greco F, Hermida-Merino D, et al. Self-assembly, antimicrobial activity, and membrane interactions of arginine-capped peptide bola-amphiphiles. ACS Appl Bio Mater. 2019;2(5):2208–18.10.1021/acsabm.9b00172 ↗
64. Pinazo A, Manresa M, Marques A, Bustelo M, Espuny M, Pérez L, et al. Amino acid–based surfactants: New antimicrobial agents. Adv Colloid Interface Sci. 2016;228:17–39.10.1016/j.cis.2015.11.007 ↗
65. Görbitz CH. Hydrophobic dipeptides: the final piece in the puzzle. Struct Sci. 2018;74(3):311–8.10.1107/S2052520618007151 ↗
66. Sharma P, Vaiwala R, Parthasarathi S, Patil N, Verma A, Waskar M, et al. Interactions of surfactants with the bacterial cell wall and inner membrane: Revealing the link between aggregation and antimicrobial activity. Langmuir. 2022;38(50):15714–28.10.1021/acs.langmuir.2c02520 ↗
67. Saini SM, Sagar TK, Dwivedi Y, Chandrashekharappa S. Brief overview of surfactants, properties, classification, passivation, and role in chemistry. Surfactant based electrochemical sensors and biosensors. Elsevier; 2024. p. 3–20.10.1016/B978-0-443-15493-5.00018-X ↗
68. Sarkar R, Pal A, Rakshit A, Saha B. Properties and applications of amphoteric surfactant: A concise review. J Surfactants Deterg. 2021;24(5):709–30.10.1002/jsde.12542 ↗
69. Shaban SM, Kang J, Kim D-H. Surfactants: Recent advances and their applications. Compos Commun. 2020;22:100537.10.1016/j.coco.2020.100537 ↗
70. Ghosh S, Ray A, Pramanik N. Self-assembly of surfactants: An overview on general aspects of amphiphiles. Biophys Chem. 2020;265:106429.10.1016/j.bpc.2020.106429 ↗
71. Ahmadi M, Chen Z. Insight into the interfacial behavior of surfactants and asphaltenes: molecular dynamics simulation study. Energy Fuels. 2020;34(11):13536–51.10.1021/acs.energyfuels.0c01596 ↗
72. Cao T, Borkovec M, Trefalt G. Heteroaggregation and homoaggregation of latex particles in the presence of alkyl sulfate surfactants. Colloids Interfaces. 2020;4(4):52.10.3390/colloids4040052 ↗
73. Pinazo A, Diz M, Solans C, Pés M, Erra P, Infante MR. Synthesis and properties of cationic surfactants containing a disulfide bond. J Am Oil Chem Soc. 1993;70(1):37–42.10.1007/BF02545364 ↗
74. Weihs D, Danino D, Pinazo-Gassol A, Perez L, Franses EI, Talmon YJC, et al. Self-aggregation in dimeric arginine-based cationic surfactants solutions. Colloids Surf A: Physicochem Eng Asp. 2005;255(1–3):73–8.10.1016/j.colsurfa.2004.11.035 ↗
75. Pérez L, Pinazo A, Infante MR, Pons R. Investigation of the micellization process of single and gemini surfactants from arginine by SAXS, NMR self-diffusion, and light scattering. J Phys Chem B. 2007;111(39):11379–87.10.1021/jp071121p ↗
76. Jansson M, Stilbs P. Organic counterion binding to micelles. Effects of counterion structure on micellar aggregation and counterion binding and location. J Phys Chem. 1987;91(1):113–6.10.1021/j100285a026 ↗
77. Pinazo A, Pérez L, del Carmen Morán M, Pons R. Arginine-based surfactants: synthesis, aggregation properties, and applications. In Biobased Surfactants. Barcelona, Spain: Elsevier; 2019. p. 413–45.10.1016/B978-0-12-812705-6.00013-7 ↗
78. Kunieda H, Nakamura K, Infante MR, Solans C. Reversed vesicles from biocornpatible surfactants. Adv Mater. 1992;4(4):291–3.10.1002/adma.19920040411 ↗
79. Suresh Babu VV. Ultrasound accelerated synthesis of proteinogenic and Î ± , Î ± -dialkylamino acid ester salts. Indian J Chem Sect B: Org Chem, Including Med Chemistry. 2006;45(8):1942–4.
80. Pinazo A, Wen X, Pérez L, Infante M-R, Franses EI. Aggregation behavior in water of monomeric and gemini cationic surfactants derived from arginine. Langmuir. 1999;15(9):3134–42.10.1021/la981295l ↗
81. Pinazo A, Pérez L, Infante MR, Franses EI. Relation of foam stability to solution and surface properties of gemini cationic surfactants derived from arginine. Colloids Surf A: Physicochem Eng Asp. 2001;189(1–3):225–35.10.1016/S0927-7757(01)00595-7 ↗
82. Behjatmanesh-Ardakani R, Farsad M. On the difference between self-assembling process of monomeric and dimeric surfactants with the same head to tail ratio: a lattice Monte Carlo simulation. J Chem. 2013;2013(1):525948.10.1155/2013/525948 ↗
83. Danino D, Talmon Y, Zana R. Alkanediyl-. alpha.,. omega.-bis (dimethylalkylammonium bromide) surfactants (dimeric surfactants). 5. aggregation and microstructure in aqueous solutions. Langmuir. 1995;11(5):1448–56.10.1021/la00005a008 ↗
84. Pérez L, Garcia MT, Ribosa I, Vinardell MP, Manresa A, Infante MR, et al. Biological properties of arginine‐based gemini cationic surfactants. Environ Toxicol Chem. 2002;21(6):1279–85.10.1002/etc.5620210624 ↗
85. Mitjans M, Martínez V, Clapés P, Pérez L, Infante MR, Vinardell MP. Low potential ocular irritation of arginine-based gemini surfactants and their mixtures with nonionic and zwitterionic surfactants. Pharm Res. 2003;20:1697–701.10.1023/A:1026164123938 ↗
86. Castillo JA, Clapés P, Infante MR, Comas J, Manresa A. Comparative study of the antimicrobial activity of bis (Nα-caproyl-L-arginine)-1, 3-propanediamine dihydrochloride and chlorhexidine dihydrochloride against Staphylococcus aureus and Escherichia coli. J Antimicrob Chemother. 2006;57(4):691–8.10.1093/jac/dkl012 ↗
87. Tavano L, Infante MR, Riya MA, Pinazo A, Vinardell MP, Mitjans M, et al. Role of aggregate size in the hemolytic and antimicrobial activity of colloidal solutions based on single and gemini surfactants from arginine. Soft Matter. 2013;9(1):306–19.10.1039/C2SM26670A ↗
88. Rosen MJ, Zhu ZH. Synergism in binary mixtures of surfactants. 7. Synergism in foaming and its relation to other types of synergism. J Am Oil Chem Soc. 1988;65(4):663–8.10.1007/BF02540698 ↗
89. Yamanaka T, Ogihara N, Ohhori T, Hayashi H, Muramatsu T. Surface chemical properties of homologs and analogs of lysophosphatidylcholine and lysophosphatidylethanolamine in water. Chem Phys Lipids. 1997;90(1–2):97–107.10.1016/S0009-3084(97)00088-1 ↗
90. Pinazo A, Lozano N, Pérez L, Morán MC, Infante MR, Pons R. Arginine diacyl-glycerolipid conjugates as multifunctional biocompatible surfactants. C R Chim. 2011;14(7–8):726–35.10.1016/j.crci.2010.10.004 ↗
91. Tausk RJM, Karmiggelt J, Oudshoorn C, Overbeek JT. Physical chemical studies of short-chain lecithin homologues. I.: Influence of the chain length of the fatty acid ester and of electrolytes on the critical micelle concentration. 1974;1(3):175–83.10.1016/0301-4622(74)80004-9 ↗
92. Walter A, Kuehl G, Barnes K, VanderWaerdt G. The vesicle-to-micelle transition of phosphatidylcholine vesicles induced by nonionic detergents: effects of sodium chloride, sucrose and urea. Biochim Biophys Acta (BBA)-Biomembr. 2000;1508(1–2):20–33.10.1016/S0304-4157(00)00005-8 ↗
93. Lozano N, Pinazo A, Pérez L, Pons R. Dynamic properties of cationic diacyl-glycerol-arginine-based surfactant/phospholipid mixtures at the air/water interface. Langmuir. 2010;26(4):2559–66.10.1021/la902850j ↗
94. Mello LR, Aguiar RB, Yamada RY, Moraes JZ, Hamley IW, Alves WA, et al. Amphipathic design dictates self-assembly, cytotoxicity and cell uptake of arginine-rich surfactant-like peptides. J Mater Chem B. 2020;8(12):2495–507.10.1039/C9TB02219H ↗
95. Castelletto V, Barnes RH, Karatzas K-A, Edwards-Gayle CJ, Greco F, Hamley IW, et al. Restructuring of lipid membranes by an arginine-capped peptide bolaamphiphile. 2018;35(5):1302–11.10.1021/acs.langmuir.8b01014 ↗
96. Xia J. Protein-based surfactants: synthesis: physicochemical properties, and applications. Boca Raton: CRC Press; 2001.
97. Lee OR, Kim SJ, Kim HJ, Hong JK, Ryu SB, Lee SH, et al. Phospholipase A2 is required for PIN-FORMED protein trafficking to the plasma membrane in the Arabidopsis root. Plant Cell. 2010;22(6):1812–25.10.1105/tpc.110.074211 ↗
98. Pinazo A, Pons R, Pérez L, Infante MR. Amino acids as raw material for biocompatible surfactants. Ind Eng Chem Res. 2011;50(9):4805–17.10.1021/ie1014348 ↗
99. Desale K, Kuche K, Jain S. Cell-penetrating peptides (CPPs): An overview of applications for improving the potential of nanotherapeutics. Biomaterials. Science. 2021;9(4):1153–88.10.1039/D0BM01755H ↗
100. Ruseska I, Zimmer A. Internalization mechanisms of cell-penetrating peptides. Beilstein J Nanotechnol. 2020;11(1):101–23.10.3762/bjnano.11.10 ↗