Amino acids as raw material for biocompatible surfactants

Industrial and Engineering Chemistry Research

Volumn 50, Issue 9, 2011, Pages 4805-4817

  Pinazo, Aurora ^a   Pons, Ramon ^a   Pérez, Lourdes ^a   Infante, Maria Rosa ^a  

^a INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID-BASED SURFACTANTS; BIOCOMPATIBLE SURFACTANTS; CHEMICAL PRODUCTS; COSMETIC INDUSTRY; GEMINI SURFACTANT; RENEWABLE RAW MATERIALS; SINGLE CHAINS;

AMINO ACIDS;

SURFACE ACTIVE AGENTS;

EID: 79955537181     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie1014348     Document Type: Review

References (97)

1. Utagawa, T. Production of arginine by fermentation J. Nutr. 2004, 134, 28545
2. Lee, CH-H. The role of biotechnology in modern food production J. Food Sci. 2004, 69, 92
3. Williams, M. A. Extraction of lipids from natural sources. In Lipid Technologies and Applications; Gunstone, F. D.; Padley, F. B., Eds., Marcel Dekker, Inc.: New York, 1997; pp 113 - 135.
4. Bondi, S. Lipoproteid and the analyis of degenerative adiposis lipoepetides, their meaning, synthesis and characterestics (laurylglycin and laurylalanin) Z. Biochem. 1909, 17, 543
5. Xia, J; Nnanna, I. An overview of the basis, technology, and surface phenomena of protein-based surfactants. In Protein-Based Surfactants; Nnanna, I. A.; Xia, J., Eds.; Marcel Dekker: New York, 2001.
6. Biobased Surfactants and Detergents: Synthesis, Properties, and Applications; Hayes, D. G.; Kitamoto, D.; Solaiman, D.; Ashby, R. D., Eds.; AOCS Press: Urbana, IL, 2009.
7. Pérez, N.; Pérez, L.; Infante, M. R.; Garcia, M. T. Biological properties of arginine-based glycerolipid cationic surfactants Green Chem. 2005, 7, 540
8. Moran, C.; Clapes, P.; Comelles, F.; Garcia, M. T.; Perez, L.; Vinardell, M. P.; Mitjans, M.; Infante, M. R. Chemical structure/property relationship in single-chain arginine surfactants Langmuir 2001, 17, 5071
9. Perez, L.; Garcia, M. T.; Ribosa, I.; Vinardell, M. P.; Manresa, A.; Infante, M. R. Biological properties of arginine-based gemini cationic surfactants Environ. Toxicol. Chem. 2002, 6, 1279
10. Vinardell, M. P.; Molinero, J.; Parra, J. L.; Infante, M. R. Comparative ocular test of lipopeptidic surfactants Int. J. Cosmet. Sci. 1990, 12, 13
11. Mitjans, M.; Martinez, V.; Clapes, P.; Perez, L.; Infante, M. R.; Vinardell, M. P. Low potential ocular irritation of arginine-based gemini surfactants and their mixtures with nonionic and zwitterionic surfactants Pharm. Res. 2003, 20, 1693
12. Benavides, T.; Martinez, V.; Mitjans, M.; Infante, M. R.; Moran, C.; Clapes, P.; Clothier, R.; Vinardell, M. P. Assessment of the potential irritation and photoirritation of novel amino acid-based surfactants by in vitro methods as alternative to the animal tests Toxicology 2004, 1-3, 87
13. Vinardell, M. P.; Benavides, T.; Mitjans, M.; Infante, M. R.; Clapes, P.; Clothier, R. Comparative evaluation of cytotoxicity and phototoxicity of mono and diacylglycerol amino acid-based surfactants Food Chem. Toxicol. 2008, 46, 3837
14. Infante, M. R.; Molinero, J.; Seguer, J.; Vinardell, M. P. Synthesis, Physicochemical Properties, and Applications. In Protein-Based Surfactants; Nnanna, I. A.; Xia, J., Eds; Marcel Dekker: New York, 2001; pp 147.
15. Takehara, M. Properties and applications of amino-acid based surfactants Colloids Surf. 1989, 38, 149
16. Boyat, C.; Rolland-Fulcrand, V.; Roumestant, M-L; Viallefont, Ph; Martinez, J. Chemo-enzymatic synthesis of new nonionic surfactants from unprotected carbohydrates Prep. Biochem. Biotechnol. 2000, 30, 281
17. Zhang, X. M.; Adachi, S.; Watanabe, Y.; Matsuno, R. Lipase-catalyzed synthesis of O -lauroyl L -serinamide and O -lauroyl L -threoninamide Food Res. Int. 2005, 38, 297
18. Gerova, M.; Rodrigues, F.; Lamere, J. F.; Dobrev, A; Fery-Forgues, S Self-assembly properties of some chiral N -palmitoyl amino acid surfactants in aqueous solution J. Colloid Interface Sci. 2008, 319, 526
19. Vijay, R.; Angayarkanny, S.; Bhasker, G. Amphiphilic dodecyl ester derivatives from aromatic amino acids: Significance of chemical architecture in interfacial adsorption characteristics Colloids Surf. A 2008, 317, 643
20. Roy, S.; Dey, J. Self-organization properties and microstructures of sodium N -(11-acrylamidoundecanoyl)- L -valinate and-L -threoninate in water Bull. Chem. Soc. Jpn. 2006, 79, 59
21. Das, D.; Dasgupta, A.; Roy, S.; Mitra, R. N.; Debnath, S.; Das, P. K. Water gelation of an amino acid-based amphiphile Chem.-Eur. J. 2006, 12, 5068
22. Varka, E. M.; Heli, M. G.; Coutouli-Argyropoulou, E.; Pegiadou, S. A. Synthesis and characterization of nonconventional surfactants of aromatic amino acid-glycerol ethers: effect of the amino acid moiety on the orientation and surface properties of these soap-type amphiphiles Chem.-Eur. J. 2006, 12, 8305
23. Ohta, A; K. Toda, K; Morimoto, Y.; Asakawa, T.; Miyagishi, S. Effect of the side chain of N -acyl amino, acid surfactants on micelle formation: An isothermal titration calorimetry study Colloids Surf. A 2008, 317, 316
24. Capone, S; Walde, P.; Seebach, D.; Ishikawa, T.; Caputo, R. pH-sensitive vesicles containing a lipidic beta-amino acid with two hydrophobic chains Chem. Biodiversity 2008, 5, 16
25. Infante, M. R.; Moses, V. Synthesis and surface activity properties of hydrophobic/hydrophilic peptides Int. J. Pep. Prot. Res. 1994, 43, 173
26. Epand, R. F.; Infante, M. R.; Flanagan, T. D.; Epand, R. Properties of lipoaminoacids incorporated into membrane Biophys. Biochim. Acta 1998, 1373, 67
27. Pinazo, A.; Infante, M. R.; Izquierdo, P.; Solans, C. Synthesis of arginine-based surfactants in highly concentrated W/O emulsions J. Chem Soc., Perkin Trans. 2 2000, 1535
28. Clapés, P.; Morán, M. C.; Infante, M. R. Papain catalized synthesis of arginine based cationic surfactants Biotechnol. Bioeng. 1999, 63, 333
29. Vinardell, M. P.; Molinero, J.; Parra, J. L.; Infante, M. R. Comparative ocular test of lipopeptidic surfactants Int. J. Cosmet. Sci. 1990, 12, 1
30. Moran, C.; Clapés, P.; Comelles, F.; García, M. T.; Perez, L.; Vinardell, P.; Infante, M. R. Chemical structure/properties relationship in single-chain arginine surfactants Langmuir 2001, 17, 5071
31. Hawkins, D. R.; Rocabayera, X.; Ruckman, S.; Segret, R.; Shaw, D. Metabolism and pharmacokinetics of ethyl N -alpha-lauroyl- L -arginate hydrochloride in human volunteers Food Chem. Toxicol. 2009, 47, 2711
32. Pérez, L.; Pinazo, A.; García, M. T.; Lozano, M.; Manresa, A.; Angelet, M.; Vinardell, M. P.; Mitjans, M.; Pons, R.; Infante, M. R. Cationic surfactants from lysine: Synthesis, micellization and biological evaluation Eur. J. Med. Chem. 2009, 44, 1884
33. Moran, C.; Pinazo, A.; Clapes, P.; Perez, L.; Vinardell, M. P.; Infante, M. R. "Green" amino acid-based surfactants Green Chem. 2004, 6, 233
34. Infante, M. R.; Molinero, J.; Erra, P.; Juliá, M. R.; García Dominguez, J. J. A comparative study on surface active and antimicrobial properties of some N -lauroyl-dibasic amino acid derivatives Fette Seifen Anstr. 1985, 8, 309
35. Infante, M. R.; Pinazo, A.; Seguer, J. Nonconventional surfactants from amino acids and glycolipids: Structure, preparation and properties Colloids Surf. A 1997, 123, 49
36. Rosen, M. J. Surfactants and Interfacial Phenomena, 3 rd ed.; Wiley-Interscience: Hoboken, NJ, 2004; pp 62 - 64.
37. Solans, C.; Infante, M. R.; Azemar, N.; Warnheim, T. Phase behaviour of cationic lipoaminoacid surfactant systems Prog. Colloid Polym. Sci. 1989, 79, 70
38. Solans, C.; Pés, M. A.; Azemar, N.; Infante, M. R. Lipoaminoacid surfactants: Phase behaviour of long N -acyl arginine methyl esters Progr. Coll. Polym. Sci. 1990, 81, 144
39. Infante, M. R.; Pérez, L.; Pinazo, A.; Clapes, P.; Morán, M. C.; Angelet, M.; García, M. T.; Vinardell, M. P. Amino acid-based surfactantes C. R. Chim. 2004, 7, 583
40. Pes, M. A. Estudio del comportamiento fásico de sistemas con tensioactivos derivados de amino acidos y caracterización estructural de las diversas fases isotropas y anisotropas (Phase behavior study of systems with surfactants derived from amino acids and structural characterization of various isotropic and anisotropic phases). Ph.D. Thesis, Barcelona University, Barcelona, Spain, 1993.
41. Gerova, M.; Rodrigues, F.; Lamere, J. F.; Dobrev, A.; Fery-Forgues, S. Self-assembly properties of some chiral N -palmitoyl amino acid surfactants in aqueous solution J. Colloid Interface Sci. 2008, 319, 526
42. Lee, S.; Kim, E.; Seo, M. L.; Do, Y.; Lee, Y.-A.; Lee, S. S.; Jung, J. H.; Kogiso, M.; Shimizu, T. Self-assembled helical ribbon and tubes of alanine-based amphiphiles induced by two different formation mechanisms Tetrahedron 2008, 64, 1301
43. Fördedal, H.; Sjöblolm, S.; Infante, M. R. Lipoaminoacid association in the system Na-lauroyl- l -arginine methyl ester/1-pentanol/water as studied by dielectric spectroscopy Colloids Surf. A 1993, 79, 81
44. McGrath, K. M. Phase behavior of dodecyltrimethylammonium bromide/water mixtures Langmuir 1995, 11, 1835
45. Laughlin, R. G. Aqueous phase science of cationic surfactant salts. In Cationic Surfactants: Physical Chemistry; Rubingh, D. N.; Holland, P. M., Eds.; Marcel Dekker Inc.: New York, 1991; Vol. 2, pp 1 - 40.
46. Kunieda, H.; Nakamura, K.; Infante, M R.; Solans, C. Reversed vesicles from biocompatible surfactants Adv. Mater. 1992, 4, 291
47. Infante, M. R.; Contijoch, A.; Erra, P. Laboratorios Miret, S.A., Spain. Synthesis of cationic surfactants by condensation of fatty acids with esterified diamino acids, and their use as antimicrobial agents. USA 5 780 658, 1998; EPO 0 749 960, 2001;CA 2 185 165, 2001.
48. Rosa, M.; Infante, M. R.; Miguel, M. G.; Lindman, B. Spontaneous Formation of Vesicles and Dispersed Cubic and Hexagonal Particles in Amino Acid-Based Catanionic Surfactant systems Langmuir 2006, 22, 5588
49. Rosa, M.; Morán, M. C.; Miguel, M. G.; Lindman, B. The association of DNA and stable catanionic amino acid-based vesicles Colloids Surf. A 2007, 301, 361
50. Rosa, M.; Penacho, N.; Simões, S.; Lima, M. C. P.; Lindman, B.; Miguel, M. G. DNA pre-condensation with an amino acid-based cationic amphiphile. A viable approach for liposome-based gene delivery Mol. Membr. Biol. 2008, 25, 23
51. Moran, M. C.; Miguel, M. G.; Lindman, B.; Infante, M. R.; Pons, R. Novel biocompatible DNA gel particles Langmuir 2010, 26, 10606
52. Zana, R.; Xia, J.. Gemini Surfactants: Synthesis, Interfacial and Solution-Phase Behavior, and Applications; Surfactant Science Series; Marcel Dekker: New York, 2004.
53. Roy, S.; Das, P. K. Antibacterial hydrogegels of amino acid-based cationic amphiphiles Biotechnol. Bioeng. 2008, 4, 756
54. Robb, I. D. Specialist Surfactants; Blackie Academic and Professional: London, 1997.
55. Pinazo, A.; Diz, M.; Solans, C.; Erra, P.; Infante, M. R. Synthesis and properties of cationic surfactants containing a disulphide bond J. Am. Oil Chem. Soc. 1993, 70, 37
56. Infante, M. R.; Pinazo, A.; Diz, M.; Gomez, N.; Erra, P. Treatments of new surfactants on keratinic fibres. Proceedings of 17th I.F.S.C.C. Int. Congress, Yokohama, Japan, October, 1992.
57. Diz, M.; Pinazo, A.; Erra, P.; Infante, M. R. Synthesis, surface active properties and antimicrobial activity of new bisquaternary ammonium compounds J. Chem. Soc., Perkin Trans. 2 1994, 2, 1871
58. Pinazo, A.; Infante, R. M.; Chang, C. H.; Franses, E. I. Surface tension properties of aqueous solutions of disulfur betaine derivatives Colloids Surf. 1994, 87, 117
59. Chang, C. H.; Franses, E. I. Modified Langmuir-Hinshelwood kinetics for dynamic adsorption of surfactants at the air/water interface Colloids Surf. 1992, 69, 189
60. Pinazo, A.; Chang, C. H.; Franses, E. I. Dynamic surface-tension behavior of aqueous-solutions of N -dodecyl- N, N -dimethyl aminobetaine chlorhydrate Collois Polym. Sci. 1994, 272, 447
61. Chang, C. H.; Wang, N.-H. L.; Franses, E. I. Adsorption dynamics of single and binary surfactants at the air/water interface Colloids Surf. 1992, 62, 321
62. Holmberg, K. Novel Surfactants; Surfactant Science Series, Vol. 74; Marcel Dekker, Inc.: New York, 1998.
63. Boething, R. S. Environmental Aspects of Cationic Surfactants. In Cationirc Surfactants: Analytical and Biological Evaluation; Cross, J.; Singer, E. J., Eds.; Marcel Dekker: New York, 1994; pp 95 - 130.
64. Perez, L.; Torres, J. L.; Manresa, A.; Infante, R. I. Synthesis, aggregation, and biological properties of a new class of gemini cationic amphiphilic compounds from arginine, bis(Args) Langmuir 1996, 12, 5296
65. Piera, E.; Infante, M. R.; Clapés, P. Chemo-enzymatic synthesis of Arg-based gemini surfactants Biotechnol. Bioeng. 2000, 70, 323
66. Pinazo, A.; Wen, X.; Pérez, L.; Infante, M. R.; Franses, E. I. Aggregation behavior in water of monomeric and gemini cationic surfactants derived from arginine Langmuir 1999, 15, 3134
67. Alami, E.; Beinert, P.; Marie, P.; Zana, R. Alkanediyl- bis(dimethylalkylammonium bromide) surfactants. 3. Behavior at the air-water interface Langmuir 1993, 9, 1465
68. Kamrath, R. F.; Franses, E. I. Mass-action model of mixed micellization J. Phys. Chem. 1984, 88, 1642
69. Shanks, P. C.; Franses, E. I. Estimation of micellization parameters of aqueous sodium dodecyl sulfate from conductivity data J. Phys. Chem. 1992, 96, 1794
70. Pinazo, A.; Perez, L.; Infante, M. R.; Pons, R. Unconventional vesicle-to-ribbon transition behaviour of diacyl glycerol amino-acid-based surfactants in extremely diluted systems induced by pH-concentration effects Phys. Chem. Chem. Phys. 2004, 6, 1475
71. Perez, L.; Pinazo, A.; Rosen, M. J.; Infante, M. R. Surface activity properties at equilibrium of novel gemini cationic amphiphilic compounds from arginine, bis(Args) Langmuir 1998, 14, 2307
72. Pinazo, A.; Perez, L.; Infante, M. R.; Franses, E. I. Relation of foam stability to solution and surface properties of gemini cationic surfactants derived from arginine Colloids Surf. A 2001, 189, 225
73. Pérez, L.; Pinazo, A.; Infante, M. R.; 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, 11379
74. Stilbs, P. Fourier transform pulsed-gradient spin-echo studies of molecular diffusion Prog. Nucl. Magn. Reson. Spectrosc. 1987, 19, 1
75. Cocquyt, J.; Olsson, U.; Olofsson, G.; Van der Meeren, P. Temperature quenched DODAB dispersions: Fluid and solid state coexistence and complex formation with oppositely charged surfactant Langmuir 2004, 20, 3906
76. Danino, D.; Talmon, Y.; Zana., R. Alkanediyl-α, -bis(dimethylalkylammonium bromide) surfactants (dimeric surfactants). 5. Aggregation and microstructure in aqueous-solutions Langmuir 1995, 11, 1448
77. Weihs, D.; Danino, D.; Pinazo, A.; Pérez, L.; Franses, E. I.; Talmon, Y. Self-aggregation in dimeric arginine-based cationic surfactants solutions Colloids. Surf. A 2005, 255, 73
78. Pons, R.; Morán, M. C.; Infante, M. R.; Pinazo, A.; Pérez, L. Lysine-Based Surfactants. In Colloids in Biotechnology; Fanun, M., Ed., CRC Press: Boca Raton, FL, 2010; Vol. 152, pp 125 - 138.
79. Seguer, J.; Infante, M. R.; Allouch, M.; Vinardell, P.; Mansuy, L.; Selve, C. Synthesis and evaluation of nonionic amphiphilic compounds from amino-acids-molecular mimics of lecithins New J. Chem. 1994, 18, 765
80. Seguer, J.; Selve, C.; Infante, M. R. New nonionic surfactants from lysine and their performance J. Disp. Sci. Technol. 1994, 15, 591
81. Seguer, J.; Selve, C.; Allouch, M.; Infante, M. R. Nonionic amphiphilic compounds from lysine as molecular mimics of lecithins J. Am. Oil Chem. Soc. 1996, 73, 79
82. Pinazo, A.; Pérez, L.; Lozano, M.; Angelet, M.; Infante, M. R.; Vinardell, M. P.; Pons, R. Aggregation properties of diacyl lysine surfactant compounds: Hydrophobic chain length and counterion effect J. Phys. Chem. B 2008, 112, 8578
83. Tausk, R J M. 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 Biophys. Chem. 1974, 1, 175
84. Pinazo, A.; Seguer, J.; Infante, M. R.; Park, S. Y.; Franses, E. I. Surface properties of aqueous systems of new nonionic double-chain surfactants and their mixtures with dilauroylphosphatidylcholine Colloids Surf. A 1997, 126, 49
85. Brito, R. O.; Marques, E. F.; Gomes, P.; Araújo, M. J.; Pons, R. Structure/property relationships for the tharmotropic behavior of lysine-based amphiphiles: From hexagonal to smetic phases J. Phys. Chem. B 2008, 112, 14877
86. Marques, E. F.; Brito, R. O.; Silased, S. G.; Rodriguez-Borges, J. E.; do Vale, M. L.; Gomez, S. P.; Araújo, M. J.; Söderman, O. Spontaneous vesicle formation in catanionic mixtures of amino-acid-based surfactants: Chain length symmetry effects Langmuir 2008, 24, 11009
87. Pinazo, A.; Angelet, M.; Pons, R.; Lozano, M.; Infante, M. R.; Perez, L. Lysine-bisglycidol conjugates as novel lysine cationic surfactants Langmuir 2009, 25, 7803
88. Perez, L.; Pinazo, A.; Vinardell, P.; Clapés, P.; Angelet, M.; Infante, M. R. Synthesis and biological properties of dicationic arginine-diglycerides New J. Chem. 2002, 26, 1221
89. Pérez, L.; Infante, M. R.; Angelet, M.; Clapés, P.; Pinazo, A. Glycerolipid arginine-based surfactants: synthesis and surface active properties Prog. Colloid Polym. Sci. 2004, 123, 210
90. Pérez, L.; Infante, M. R.; Pons, R.; Morán, C.; Vinardell; Mitjans, M.; Pinazo, A. A synthetic alternative to natural lecithins with antimicrobial properties Colloids Surf. 2004, 35, 235
91. Perez, L.; Pinazo, A.; García, M. T.; Morán, M. C.; Infante, M. R. Monoglyceride surfactants from arginine: synthesis and biological properties New J. Chem. 2004, 28, 1326
92. 13C NMR study of the effect of headgroup size, chain length, and concentration on fatty acid pK, at a nonionic micellar interface J. Phys. Chem. 2003, 107, 1001
93. Lozano, N.; Pinazo, A.; La Mesa, C.; Pérez, L.; Andreozzi, P.; Pons, R. Catanionic vesicles formed with arginine-based surfactants and 1,2-dipalmitoyl-glycero-phosphate monosodium salt J. Phys. Chem. B 2009, 113, 6321
94. Albalat, R.; Claret, J.; Ignés-Mullol, J.; Sagues, F.; Morán, C.; Pérez, L.; Clapés, P.; Pinazo, A. Langmuir monolayers of diacyl glycerol amino acid surfactants. Effect of the substitution pattern of the glycerol backbone Langmuir 2003, 19, 10878
95. Lozano, N.; Pérez, L.; Pons, R.; Luque-Ortega, J. R.; Fernández-Reyes, M.; Rivas, L.; Pinazo, A. Interaction studies of diacyl glycerol arginine-based surfactants with DPPC and DMPC monolayers, relation with antimicrobial activity Colloids Surf. A 2008, 319, 196
96. Lozano, N.; Pinazo, A.; Pérez, L.; Pons, R. dynamic properties of cationic diacyl-glycerol-arginine- based surfactants/phospholipid mixtures at the air/water interface Langmuir 2010, 26, 2559
97. Lozano, N.; Pinazo, A.; Pons, R.; Pérez, L.; Franses, E. I. Surface tension and adsorption behavior of mixtures of diacyl glycerol arginine-based surfactants with DPPC and DMPC phospholipids Colloids Surf. B 2009, 74, 67