Concentration and pH-dependent aggregation behavior of an l-histidine based amphiphile in aqueous solution

Chemistry and Physics of Lipids

Volumn 163, Issue 6, 2010, Pages 561-568

  Ghosh, Arjun ^a   Shrivastava, Saurabh ^a   Dey, Joykrishna ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Electron microscopy; Fluorescence; Nanotubes; Surface activity; Vesicles

Indexed keywords

AMPHOPHILE; CHOLESTEROL; HISTIDINE; N (2 HYDROXYDODECYL) LEVO HISTIDINE; NANOTUBE; SURFACTANT; UNCLASSIFIED DRUG; FLUORESCENT DYE; N-(2-HYDROXYDODECYL)HISTIDINE; WATER;

ARTICLE; PH MEASUREMENT; PRIORITY JOURNAL; TRANSMISSION ELECTRON MICROSCOPY; ANALOGS AND DERIVATIVES; CHEMISTRY; PH; PHASE TRANSITION; SURFACE TENSION; TEMPERATURE;

CHOLESTEROL; FLUORESCENT DYES; HISTIDINE; HYDROGEN-ION CONCENTRATION; NANOTUBES; PHASE TRANSITION; SURFACE TENSION; SURFACE-ACTIVE AGENTS; TEMPERATURE; WATER;

EID: 77954195446     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2010.04.003     Document Type: Article

References (37)

1. E. Abel, S.L. De Wall, W.B. De Edwards, S. Lalitha, D.F. Couvey, and G.W. Gokel Formation of stable vesicles from N-or 3-alkylindoles: possible evidence for tryptophan as a membrane anchor in proteins J. Org. Chem. 65 2000 5901 5909
2. I. Bertini, and A. Scozzafava H. Sigel, Metal Ions in Biological Systems vol. 12 1981 Marcel Dekker New York 31 74
3. D.T. Bong, T.D. Clark, J.R. Granja, and M.R. Ghadiri Self-assembling organic nanotubes Angew. Chem. Int. Ed. Engl. 40 2001 988 1011
4. R. Bonomo, E. Conte, G. Impellizzeri, G. Pappalardo, R. Purrello, and E. Rizzarelli Copper(II) complexes with cyclo(l-aspartyl-l-aspartyl) and cyclo(l-glutamyl-l-glutamyl) derivatives and their antioxidant properties J. Chem. Soc. Dalton Trans. 1996 3093 3099
5. M. Casolaro, M. Chelli, M. Ginanneschi, F. Laschi, L. Messori, M. Muniz-Miranda, A.M. Papini, T. Kowalik-Jankowska, and H. Kozlowsky Spectroscopic and potentiometric study of the SOD mimic system copper(II)/acetyl-l- histidylglycyl-l-histidylglycine J. Inorg. Biochem. 89 2002 181 190
6. M. Félix, and A.A. Goñi Spectroscopic techniques in the study of membrane solubilization, reconstitution and permeabilization by detergents Biochim. Biophys. Acta 1508 2000 51 68
7. S. Fernandez-Lopez, H.S. Kim, E.C. Choi, M. Delgado, J.R. Granja, A. Khasanov, K. Kraehenbuehl, G. Long, D.A. Weinberger, K.M. Wilcoxen, and M.R. Gghadiri Antibacterial agents based on the cyclic d,l-α-peptide architecture Nature (Lond.) 41 2001 452 455
8. A. Ghosh, and J. Dey Physicochemical characterization and tube-like structure formation of a novel amino acid-based zwitterionic amphiphile N-(2-hydroxydodecyl)-l-valine in water J. Phys. Chem. B 112 2008 6629 6635
9. A. Ghosh, and J. Dey Effect of hydrogen bonding on the physicochemical properties and bilayer self-assembly formation of N-(2-hydroxydodecyl)-l-alanine in aqueous solution Langmuir 24 2008 6018 6026
10. F. Han, X. He, J. Huang, Z. Li, Y. Wang, and H. Fu Surface properties and aggregates in the mixed systems of bolaamphiphiles and their oppositely charged conventional surfactants J. Phys. Chem. B. 108 2004 5256 5262
11. H. Hidaka, M. Murata, and T. Onai Helical aggregates of chiral N-(2-hydroxydodecyl) amino acids Chem. Commun. 1984 562 564
12. J.-B. Huang, M. Mao, and B.-Y. Zhu The surface physico-chemical properties of surfactants in ethanol-water mixtures Colloids Surf. A 155 1999 339 345
13. Y. Ihara, R. Hosako, M. Nango, and N. Kurok Efficient synthesis of estriol 16-glucuronide via 2,4,16 α-tribromoestrone Chem. Commun. 1981 383 384
14. J.N. Israelachvili Intermolecular and Surface Forces 1985 Academic Press London
15. D. Khatua, and J. Dey Fluorescence, circular dichroism, light scattering, and microscopic characterization of vesicles of the sodium salts of three N-acyl peptides J. Phys. Chem. B 111 2007 124 127
16. T. Kowalik-Jankowska, M. Jasionowski, and L. Lankiewicz Copper(II) complexation by pituitary adenylate cyclase activating polypeptide fragments J. Inorg. Biochem. 76 1999 63 70
17. V.V. Kumar, C. Pichon, M. Refregiers, B. Guerin, P. Midoux, and A. Chaudhuri Single histidine residue in head-group region is sufficient to impart remarkable gene transfection properties to cationic lipids: evidence for histidine-mediated membrane fusion at acidic pH Gene Therapy 10 2003 1206 1215
18. T. Lu, F. Han, Z. Li, J. Huang, and H. Fu Transitions of organized assemblies in mixed systems of cationic bolaamphiphile and anionic conventional surfactants Langmuir 22 2006 2045 2049
19. A. Mohanty, T. Patra, and J. Dey Salt-induced vesicle to micelle transition in aqueous solution of sodium N-(4-octyloxybenzoyl)-l-valinate J. Phys. Chem. B 111 2007 7155 7159
20. H. Murase, A. Nagao, and J. Terao Antioxidant and emulsifying activity of N-(long-chain-acyl)histidine and N-(long-chain-acyl)carnosine J. Agric. Food Chem. 41 1993 1601 1604
21. R.R. Nayak, S. Roy, and J. Dey Characterization of polymeric vesicles of poly(sodium 11-acrylamidoundecanoate) in water Colloid Polym. Sci. 285 2006 219 224
22. N.A. Nemkovich, W. Baumann, Y.V. Kruchenok, H. Reis, and A.N. Rubinov Dipole moments of phenylnaphthylamine fluorescence probes and study of dielectric interactions in human erythrocyte ghosts J. Fluoresc. 7 1997 363 370
23. K. Ohkubo, K. Sugahara, H. Ohta, K. Tokuda, and R. Ueoka The stereoselective deacylation of long-chain amino acid esters by comicelles of N-acyl-l-histidine and various cationic surfactants Bull. Chem. Soc. Jpn. 54 1981 576 580
24. A. Ohta, R. Danev, K. Nagayama, T. Mita, T. Asakwa, and S. Miyagishi Transition from nanotubes to micelles with increasing concentration in dilute aqueous solution of potassium N-acyl phenylalaninate Langmuir 22 2006 8472 8477
25. K.G. Ragunath, and S. Bhattacharya Formation of gel and fibrous microstructures by 1-alkyne amphiphiles bearing l-serine headgroup in organic solvents Chem. Phys. Lipids 77 1995 13 23
26. M.J. Rosen Surfactants and Interfacial Phenomena 4th ed. 2004 Wiley-Interscience New York
27. S. Roy, A. Mohanty, and J. Dey Microviscosity of bilayer membranes of some N-acyl amino acid surfactants determined by fluorescence probe method Chem. Phys. Lett. 414 2005 23 27
28. S. Roy, R.R. Nayak, and J. Dey Stable vesicle formation through intra-and inter-chain aggregation of poly[sodium N-(11-acryl-amidoundecanoyl)-l-valinate] in aqueous solution Colloids Surf. A: Physicochem. Eng. Aspects 290 2006 62 69
29. T. Saitoh, S. Matsushima, and M. Hiraide Flotation of polycyclic aromatic hydrocarbons coprecipitated with aluminum hydroxide containing sodium dodecyl sulfate and magnesium Colloids Surf. A: Physicochem. Eng. Aspects 299 2007 88 92
30. M. Shinitzky Physical Methods on Biological Membranes and their Model Systems 1984 Plenum Publishing Corp. New York 237 pp.
31. α-acyl-l-histidine Chem. Phys. Lipids 14 1975 1 14
32. V. Sylvain, S. Santoso, H. Gong, N. Watson, and S. Zhang Molecular self-assembly of surfactant-like peptides to form nanotubes and nanovesicles Proc. Natl. Acad. Sci. U.S.A. 99 2002 5355 5360
33. M.M. Velázquez, F. Ortega, F. Monroy, R.G. Rubio, S. Pegiadou, L. Pérez, and M.R. Infante Langmuir monolayers of zwitterionic surfactant hexadecyl 1-N-l-tryptophan glycerol ether J. Colloid Interface Sci. 283 2005 144 152
34. L. Wang, S. Jacobi, J. Sun, M. Overs, H. Fuchs, H.J. Schaefer, X. Zhang, J. Shen, and L. Chi Anisotropic aggregation and phase transition in Langmuir monolayers of methyl/ethyl esters of 2,3-dihydroxy fatty acids J. Colloid Interface Sci. 285 2005 814 820
35. N. Watanabe, T. Nakajima, and H. Touhara Graphite Fluorides 1988 Elsevier Amsterdam
36. Y. Yan, J. Huang, Z. Li, F. Han, and J. Ma Aggregates transition depending on the concentration in the cationic bolaamphiphile/SDS mixed systems Langmuir 19 2003 972 974
37. R. Zana, M. In, and H. Lévy Alkanediyl-α,ω- bis(dimethylalkylammonium bromide). 7. Fluorescence probing studies of micelle micropolarity and microviscosity Langmuir 13 1997 5552 5557