Effect of peptide architecture on the self-assembly properties of tripeptide based anionic surfactants issued from two different peptide sequences: Ala-Ala-Val and Ala-Pro-Val in aqueous media (pH 7.4)

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 414, Issue , 2012, Pages 422-432

  Maji, Sudipta Kumar ^a   Haldar, Saubhik ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

Hydrophobic effect; Peptide amphiphile; Self assembly; Sheet

Indexed keywords

AGGREGATES; AMINO ACIDS; ANIONIC SURFACTANTS; HYDROPHOBICITY; MICELLES; PEPTIDES;

AGGREGATION NUMBERS; AQUEOUS MEDIA; ARCHITECTURAL CHANGES; CMC VALUES; DRIVING FORCES; ELONGATED MICELLES; FLUORESCENCE LIFETIMES; FLUORIMETRY; H-BONDING INTERACTION; H-BONDING NETWORKS; HYDROPHOBIC EFFECT; INTERMOLECULAR H-BONDING; MICELLAR AGGREGATES; MICELLAR GROWTH; MOLECULAR AGGREGATION; PEPTIDE AMPHIPHILES; PEPTIDE SEQUENCES; PHYSICOCHEMICAL PROPERTY; PROLINE RESIDUES; RANDOM COIL; SELF ASSEMBLY PROCESS; TENSIOMETRY; TRIPEPTIDE;

SELF ASSEMBLY;

EID: 84868338164     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2012.07.017     Document Type: Article

References (65)

1. Versluis F., Marsden H.R., Kros A. Power struggles in peptide-amphiphile nanostructures. Chem. Soc. Rev. 2010, 39:3434.
2. Löwik D.W.P.M., van Hest J.C.M. Peptide based amphiphiles. Chem. Soc. Rev. 2004, 33:234.
3. Cavalli S., Kros A. Scope and applications of amphiphilic alkyl- and lipopeptides. Adv. Mater. 2008, 20:627.
4. Cui H.G., Webber M.J., Stupp S.I. Self-assembly of peptide amphiphiles: from molecules to nanostructures to biomaterials. Biopolymers 2010, 94:1.
5. Hamley I.W. Self-assembly of amphiphilic peptides. Soft Matter 2011, 7:4122.
6. Zhang S.G. Fabrication of novel biomaterials through molecular self-assembly. Nat. Biotechnol. 2003, 21:1171.
7. Santoso S., Hwang W., Hartman H., Zhang S.G. Self-assembly of surfactant-like peptides with variable glycine tails to form nanotubes and nanovesicles. Nano Lett. 2002, 2:687.
8. Cui H., Muraoka T., Cheetham A.G., Stupp S.I. Self-assembly of giant peptide nanobelts. Nano Lett. 2009, 9:945.
9. Castelletto V., Hamley I.W., Perez J., Abezgauz L., Danino D. Fibrillar superstructure from extended nanotapes formed by a collagen-stimulating peptide. Chem. Commun. 2010, 46:9185.
10. Hartgerink J.D., Beniash E., Stupp S.I. Self-assembly and mineralization of peptide-amphiphile nanofibers. Science 2001, 294:1684.
11. Zhang S.G., Holmes T., Lockshin C., Rich A. Spontaneous assembly of a self-complementary oligopeptide to form a stable macroscopic membrane. Proc. Natl. Acad. Sci. U.S.A. 1993, 90:3334.
12. Fields G.B., Lauer J.L., Dori Y., Forns P., Yu Y.C., Tirrell M. Protein-like molecular architecture: biomaterial applications for inducing cellular receptor binding and signal transduction. Biopolymers 1998, 47:143.
13. Murakami Y., Nakano A., Yoshimatsu A., Uchitomi K., Matsuda Y. Characterization of molecular aggregates of peptide amphiphiles and kinetics of dynamic processes performed by single-walled vesicles. J. Am. Chem. Soc. 1984, 106:3613.
14. Neumann R., Ringsdorf H. Peptide liposomes from amphiphilic amino acids. J. Am. Chem. Soc. 1986, 108:487.
15. Rosen M.J. Surfactants and Interfacial Phenomena 2004, Wiley-Interscience, New York. 4th ed.
16. Laughlin R.G. The Aqueous Phase Behavior of Surfactants 1994, Academic Press, London, UK.
17. Evans D.F., Myers D. Surfaces, Interfaces and Colloids: Principles and Applications 1991, VCH, New York.
18. Paramonov S.E., Jun H.-W., Hartgerink J.D. Self-assembly of peptide-amphiphile nanofibers: the roles of hydrogen bonding and amphiphilic packing. J. Am. Chem. Soc. 2006, 128:7291. and reference therein.
19. Chen C.-L., Zhang P., Rosi N.L. A new peptide-based method for the design and synthesis of nanoparticle superstructures: construction of highly ordered gold nanoparticle double helices. J. Am. Chem. Soc. 2008, 130:13555.
20. Ke D., Zhan C., Li A.D.Q., Yao J. Morphological transformation between nanofibers and vesicles in a controllable bipyridine-tripeptide self-assembly. Angew. Chem. Int. Ed. 2011, 50:3715.
21. Castelletto V., Hamley I.W., Adamcik J., Mezzenga R., Gummel J. Modulating self-assembly of a nanotape-forming peptide amphiphile with an oppositely charged surfactant. Soft Matter 2012, 8:217.
22. Bordes R., Tropsch J., Holmberg K. Role of an amide bond for self-assembly of surfactants. Langmuir 2010, 26(5):3077.
23. Akhter M.S., Alawi S.M. The effect of organic additives on critical micelle concentration of non-aqueous micellar solutions. Colloids Surf. A 2000, 175:311.
24. Ohta A., Toda K., Morimoto Y., Asakawa T., Miyagishi S. Effect of the side chain ofN-acyl amino acid surfactants on micelle formation: an isothermal titration calorimetry study. Colloids Surf. A 2008, 317:316.
25. Miyagishi S., Suzuki H., Asakawa T. Microviscosity and aggregation number of potassium N-acylalaninate micelles in potassium chloride solution. Langmuir 1996, 12:2900.
26. Khatua D., Dey J. Fluorescence, circular dichroism, light scattering, and microscopic characterization of vesicles of sodium salts of three N-acyl peptides. J. Phys. Chem. B 2007, 111:124.
27. Lin B.F., Missirlis D., Krogstad D.V., Tirrell M. Structural effects and lipid membrane interactions of the pH-responsive GALA peptide with fatty acid acylation. Biochemistry 2012, 51:4658.
28. Ptak M., Charlier M.E., Sanson A., Bouloussa O. A NMR study of the ionization of fatty acids, fatty amines and N-acylamino acids incorporated in phosphatidylcholine vesicles. Biochim. Biophys. Acta 1980, 600:387.
29. Eastoe J., Nave S., Downer A., Paul A., Rankin A., Tribe K. Adsorption of ionic surfactants at the air-solution Interface. Langmuir 2000, 16:4511.
30. Lu J.R., Li Z.X., Su T.J., Thomas R.K., Penfold J. Structure of adsorbed layers of ethylene glycol monododecyl ether surfactants with one, two, and four ethylene oxide groups, as determined by neutron. Langmuir 1993, 9:2408.
31. Li Z.X., Lu J.R., Thomas R.K. Neutron reflectivity studies of the adsorption of aerosol-OT at the air/water Interface: the surface excess. Langmuir 1997, 13:3681.
32. Miyagishi S., Takeuchi N., Asakawa T., Inoh M. Micellar growth of N-dodecanoyl-alaninates with different counterions and its quantitative relation with some factors. Colloids Surf. A 2002, 197:125.
33. Kanthimathi M., Dhathathreyan A. Langmuir and Langmuir-Blodgett films of N-(4-octadecyloxy-2-hydroxybenzylidene) derivatives of amino acids. J. Colloid Interface Sci. 2007, 310:337.
34. Ghosh A., Dey J. Effect of hydrogen bonding on the physicochemical properties and bilayer self-assembly formation of N-(2-hydroxydodecyl)-l-alanine in aqueous solution. Langmuir 2008, 24:6018.
35. Roy S., Dey J. Spontaneously formed vesicles of sodium N-(11-acrylamidoundecanoyl)-glycinate and l-alaninate in water. Langmuir 2005, 21:10362.
36. Mohanty A., Dey J. Spontaneous formation of vesicles and chiral self-assemblies of sodium N-(4-dodecyloxybenzoyl)-l-valinate in water. Langmuir 2004, 20:8452.
37. Miyagishi S., Akasohu W., Hashimoto T., Asakawa A. Effect of NaCl on aggregation number, microviscosity, and cmc of N-dodecanoyl amino acid surfactant micelles. J. Colloid Interface Sci. 1996, 184:527.
38. Billiot F.H., McCarroll M., Billiot E.J., Rugutt J.K., Morris K., Warner I.M. Comparison of the aggregation behavior of 15 polymeric and monomeric dipeptide surfactants in aqueous Solution. Langmuir 2002, 18:2993.
39. Shinitzky M., Barenholz Y. Dynamics of the hydrocarbon layer in liposomes of lecithin and sphingomyelin containing dicetylphosphate. J. Biol. Chem. 1974, 249:2652.
40. Lakowicz J.R., Prendergast F.G., Hogen D. Differential polarized phase fluorometric investigations of diphenylhexatriene in lipid bilayers. Quantitation of hindered depolarizing rotations. Biochemistry 1979, 18:508.
41. Prendergast F.G., Haugland R.P., Callahan P.J. 1-[4-(Trimethylamino) phenyl]-6-phenylhexa-1, 3,5-triene: synthesis, fluorescence properties and use as a fluorescence probe of lipid bilayers. Biochemistry 1981, 20:7333.
42. Lentz B.R. Use of fluorescent probes to monitor molecular order and motions within liposome bilayers. Chem. Phys. Lipids 1993, 64:99.
43. Cogan U., Shinitzky M., Weber G., Nishida T. Microviscosity and order in the hydrocarbon region of phospholipid and phospholipid-cholesterol dispersions determined with fluorescent probes. Biochemistry 1973, 12:521.
44. Zachariasse K.A., Kuhnle W., Weller A. Intramolecular excimer fluorescence as a probe of fluidity changes and phase transitions in phosphatidylcholine bilayers. Chem. Phys. Lett. 1980, 73:6.
45. Lakowicz J.R. Principles of Fluorescence Spectroscopy 1983, Plenum Press, New York, p. 132.
46. Sarkar D., Das P., Goswami A., Chattopadhyay N. Spectroscopic characterization of phenazinium dye aggregates in water and acetonitrile media: effect of methyl substitution on the aggregation phenomenon. J. Phys. Chem. A 2008, 112:9684.
47. Ho C., Stubbs C.D. Hydration at the membrane protein-lipid interface. Biophys. J. 1992, 63:897.
48. Stubbs C.D., Ho C., Slater S.J. Fluorescence techniques for probing water penetration into lipid bilayers. J. Fluoresc. 1995, 5:19.
49. Raghuraman H., Pradhan S.K., Chattopadhyay A. Effect of urea on the organization and dynamics of triton X-100 micelles: a fluorescence approach. J. Phys. Chem. B 2004, 108:2489.
50. Sujatha J., Mishra A.K. Phase transitions in phospholipid vesicles: excited state prototropism of 1-naphthol as a novel probe concept. Langmuir 1998, 14:2256.
51. Roy S., Mohanty A., Dey J. Microviscosity of bilayer membranes of some N-acylamino acid surfactants determined by fluorescence probe method. Chem. Phys. Lett. 2005, 414:23.
52. Guler M.O., Claussen R.C., Stupp S.I. Encapsulation of pyrene within self-assembled peptide amphiphile nanofibers. J. Mater. Chem. 2005, 15:4507.
53. Mohanty A., Dey J.A. Effect of the head group structure on the aggregation behavior and stability of self-assemblies of sodium N-[4-(n-Dodecyloxy)benzoyl]-l-aminoacidates in water. Langmuir 2007, 23:1033.
54. Wang C., Huang J., Tang S., Zhu B. Special surface and aggregation behavior of a novel amino acid amphiphile. Langmuir 2001, 17:6389.
55. Huang J.B., Zhao G.X. Formation and coexistence of the micelles and vesicles in mixed solution of cationic and anionic surfactant. Colloid Polym. Sci. 1995, 273:156.
56. 3 membranes using surfactant micelles as templates. J. Mater. Sci. 1999, 34:5315.
57. Israelachivili J.N. Intermolecular and Surface Forces 1985, Academic Press, New York.
58. Edward J.T. Molecular volumes and the Stokes-Einstein equation. J. Chem. Educ. 1970, 47:261.
59. Shinitzky M., Haimovitz R. Chiral surfaces in micelles of enantiomeric N-palmitoyl- and N-stearoylserine. J. Am. Chem. Soc. 1993, 115:12545.
60. Kunitake T., Nakashima N., Shimomara M., Okahata Y., Kano K., Ogawa T. Unique properties of chromophore-containing bilayer aggregates: enhanced chirality and photochemically induced morphological change. J. Am. Chem. Soc. 1980, 102:6642.
61. Kunitake T., Nakashima N., Morimitsu K. Enhanced circular dichroism and fluidity of disk-like aggregates of a chiral, single-chain amphiphile. Chem. Lett. 1980, 1347.
62. Sakamoto K., Hatano M. Formation of chiral aggregates of acylamino acids in solutions. Bull. Chem. Soc. Jpn. 1980, 53:339.
63. Sakamoto K., Yoshida R., Hatano M. Liquid crystals composed of N-acylamino acid. I. circular dichroism in liquid crystals composed of N-lauroyl-l-glutamic acid and aromatic solvents. Chem. Lett. 1976, 1401.
64. Sakamoto K., Yoshida R., Hatano M., Tachibana T. Liquid crystals composed of N-acyl amino acids. I. Circular dichroism and selective light transmission in cholesteric liquid crystals composed of N-acyl amino acids and organic solvents. J. Am. Chem. Soc. 1978, 100:6898.
65. Shimada T., Lee S., Bates F.S., Hotta A., Tirrell M. Wormlike micelle formation in peptide-lipid conjugates driven by secondary structure transformation of the head groups. J. Phys. Chem. B 2009, 113:13711.