Unusual, pH-induced, self-assembly of sophorolipid biosurfactants

ACS Nano

Volumn 6, Issue 6, 2012, Pages 4763-4776

  Baccile, Niki ^a,b,c   Babonneau, Florence ^a,b,c   Jestin, Jacques ^d   Pehau Arnaudet, Gerard ^e   Van Bogaert, Inge ^f  

^a SORBONNE UNIVERSITÉ   (France)

^b CNRS   (France)

^c Centre de Recherche Interdisciplinaire en Biologie   (France)

^d CEA SACLAY   (France)

^e INSTITUT PASTEUR   (France)

^f GHENT UNIVERSITY   (Belgium)

Author keywords

biosurfactants; cryo TEM; ionization degree; microbial derived surfactants; pH responsive; self assembly; small angle neutron scattering; sophorolipids

Indexed keywords

BIO-SURFACTANTS; CRYO-TEM; IONIZATION DEGREE; PH-RESPONSIVE; SOPHOROLIPIDS;

BIOMOLECULES; GLUCOSE; IONIZATION; MICELLES; NEUTRON SCATTERING; SELF ASSEMBLY; SPHERES; SUPRAMOLECULAR CHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY; YEAST;

SURFACE ACTIVE AGENTS;

GLYCOLIPID; NANOPARTICLE; SURFACTANT;

ARTICLE; CANDIDA; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; MACROMOLECULE; MATERIALS TESTING; METHODOLOGY; PARTICLE SIZE; PH; SURFACE PROPERTY; ULTRASTRUCTURE;

CANDIDA; CRYSTALLIZATION; GLYCOLIPIDS; HYDROGEN-ION CONCENTRATION; MACROMOLECULAR SUBSTANCES; MATERIALS TESTING; MOLECULAR CONFORMATION; NANOPARTICLES; PARTICLE SIZE; SURFACE PROPERTIES; SURFACE-ACTIVE AGENTS;

EID: 84862856175     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn204911k     Document Type: Article

References (62)

1. Xu, C.; Fu, X.; Fryd, M.; Xu, S.; Wayland, B. B.; Winey, K. I.; Composto, R. J. Reversible Stimuli-Responsive Nanostructures Assembled from Amphiphilic Block Copolymers Nano Lett. 2006, 6, 2282-2287
2. Jacquin, M.; Muller, P.; Cotter, H.; Théodoly, O. Self-assembly of charged amphiphilic diblock copolymers with insoluble blocks of decreasing hydrophobicity Langmuir 2010, 26, 18681-18693
3. Kawasaki, H.; Souda, M.; Tanaka, S.; Nemoto, N.; Karlsson, G.; Almgren, M.; Maeda, H. Reversible vesicle formation by changing pH J. Phys. Chem. B 2002, 106, 1524-1527
4. Lin, Y.; Han, X.; Huang, J.; Fu, H.; Yu, C. A Facile Route to Design pH-responsive Viscoelastic Wormlike Micelles: Smart Use of Hydrotropes J. Colloid Interface Sci. 2009, 330, 449-455
5. Chu, Z.; Feng, Y. pH-switchable Wormlike Micelles Chem. Commun. 2010, 46, 9028-9030
6. Negrini, R.; Mezzenga, R. pH-Responsive Lyotropic Liquid Crystals for Controlled Drug Delivery Langmuir 2011, 27, 5296-5303
7. Ray, S.; Das, A. K.; Banerjee, A. pH-Responsive, Bolaamphiphile-Based Smart Metallo-Hydrogels as Potential Dye-Adsorbing Agents, Water Purifier, and Vitamin B 12 Carrier Chem. Mater. 2007, 19, 1633-1639
8. Meister, A.; Bastrop, M.; Koschoreck, S.; Garamus, V. M.; Sinemus, T.; Hempel, G.; Drescher, S.; Dobner, B.; Richtering, W.; Huber, K. Structure-Properties Relationships in Stimuli-Responsive Bolaform Hydrogels Langmuir 2007, 23, 7715-7723
9. Meister, A.; Blume, A. Self-Assembly of Bipolar Amphiphiles Curr. Opin. Colloid Interf. Sci. 2007, 12, 138-147
10. Kjellin, M.; Johansson, I. Surfactants from Renewable Resources; John Wiley & Sons, Ltd.: West Sussex, 2010.
11. von Rybinski, W.; Hill, K. Alkyl Polyglycosides-Properties and Applications of a new Class of Surfactants Angew. Chem., Int. Ed. 1998, 37, 1328-1345
12. Stubenrauch, C. Sugar Surfactants - Aggregation, Interfacial, and Adsorption Phenomena Curr. Opin. Coll. Interf. Sci. 2001, 6, 160-170
13. Hoffmann, B.; Platz, G. Phase and Aggregation Behaviour of Alkylglycosides Curr. Opin. Coll. Interf. Sci. 2001, 6, 171-177
14. Baccile, N.; Nassif, N.; Malfatti, L.; Van Bogaert, I. N. A.; Soetaert, W.; Pehau-Arnaudet, G.; Babonneau, F. Sophorolipids: a Yeast-Derived Glycolipid as Greener Structure Directing Agents for Self-Assembled Nanomaterials Green Chem. 2010, 12, 1564-1567
15. Rau, U.; Hammen, S.; Heckmann, R.; Wray, V.; Lang, S. Sophorolipids: a Source for Novel Compounds Ind. Crops Prod. 2001, 13, 85-92
16. Tulloch, A. P.; Hill, A.; Spencer, J. F. T. Structure and Reactions of Lactonic and Acidic Sophorosides of 17-Hydroxyoctadecanoic Acid Can. J. Chem. 1968, 46, 3337-3351
17. Asmer, H.-J.; Lang, S.; Wagner, F.; Wray, V. Microbial Production, Structure Elucidation and Bioconversion of Sophorose Lipids J. Am. Oil Chem. Soc. 1988, 65, 1460-1466
18. Zhou, S.; Xu, C.; Wang, J.; Gao, W.; Akhverdiyeva, R.; Shah, V.; Gross, R. Supramolecular Assemblies of a Naturally Derived Sophorolipid Langmuir 2004, 20, 7926-7932
19. Develter, D. W. G.; Fleurackers, S. J. J. Surfactants from Renewable Resources; John Wiley & Sons, Ltd.: West Sussex, 2010; pp 213-238.
20. Maingault, M. Use of Sophorolipids and Cosmetic and Dermatological Compositions, WO/1995/034282A.
21. Van Bogaert, I. N. A.; Saerens, K.; De Muynck, C.; Develter, D.; Soetaert, W.; Vandamme, E. J. Microbial Production and Application of Sophorolipids Appl. Microbiol. Biotechnol. 2007, 76, 23-34
22. Shete, A. M.; Wadhawa, G.; Banat, I. M.; Chopade, B. A. Mapping of Patents on Bioemulsifier and Biosurfactant: a Review J. Sci. Ind. Res. 2006, 65, 91-11
23. Fu, S. L.; Wallner, S. R.; Bowne, W. B.; Hagler, M. D.; Zenilman, M. E.; Gross, R.; Bluth, M. H. Sophorolipids and Their Derivatives are Lethal Against Human Pancreatic Cancer Cells J. Surg. Res. 2008, 148, 77-82
24. Ishigami, Y.; Gama, Y.; Nagahora, H.; Yamaguchi, M.; Nakahara, H.; Kamata, T. The pH Sensitive Conversion of Molecular Aggregates of Rhamnolipid Biosurfactant Chem. Lett. 1987, 763-766
25. Kitamoto, D.; Morita, T.; Fukuoka, T.; Konishi, M.; Imura, T. Self-Assembling Properties of Glycolipid Biosurfactants and Their Potential Applications Curr. Opin. Coll. Interf. Sci. 2009, 14, 315-328
26. Masuda, M.; Shimizu, T. Lipid Nanotubes and Microtubes: Experimental Evidence for Unsymmetrical Monolayer Membrane Formation from Unsymmetrical Bolaamphiphiles Langmuir 2004, 20, 5969-5977
27. Zimmels, Y.; Lin, I. J. Stepwise Association Properties of Some Surfactant Aqueous Solutions Colloid Polym. Sci. 1974, 252, 594-612
28. Maeda, H.; Eguchi, Y.; Suzuki, M. Hydrogen Ion Titration of Oleic Acid in Aqueous Media J. Phys. Chem. 1992, 96, 10487-10491
29. Bendejacq, D.; Joanicot, M.; Ponsinet, V. Pearling Instabilities in Water-Dispersed Copolymer Cylinders With Charged Brushes Eur. Phys. J. E 2005, 17, 83-92
30. Reiss-Husson, F.; Luzzati, V. The Structure of the Micellar Solutions of Some Amphiphilic Compounds in Pure Water as Determined by Absolute Small-Angle X-Ray Scattering Techniques J. Phys. Chem. 1964, 68, 3504-3511
31. Ekwall, P.; Mandel, L.; Solyom, P. The Aqueous Cetyltrimethylammonium Bromide Solutions J. Colloid Interface Sci. 1971, 35 (4) 519-528
32. Quirion, F.; Magid, L. J. Growth and Counterion Binding of Cetyltrimethylammonium Bromide Aggregates at 25 Degree: a Neutron and Light Scattering Study J. Phys. Chem. 1986, 90, 5435-5441
33. Goyal, P. S.; Dasannacharya, B. A.; Kelkar, V. K.; Manohar, C.; Srinivasa Rao, K.; Valaulikar, B. S. Shapes and Sizes of Micelles in CTAB Solutions Physica B 1991, 174, 196-199
34. 3 Solutions: Rheology, SANS and Cryo-TEM Analysis J. Colloid Interface Sci. 2008, 323, 403-409
35. Glatter, O.; Fritz, G.; Lindner, H.; Brunner-Popela, J.; Mittelbach, R.; Strey, R.; Egelhaaf, S. U. Nonionic Micelles Near the Critical Point: Micellar Growth and Attractive Interaction Langmuir 2000, 16, 8692-8701
36. Shrestha, R. G.; Shrestha, L. K.; Sharma, S. C.; Aramaki, K. Phase Behavior and Microstructures of Nonionic Fluorocarbon Surfactant in Aqueous Systems J. Phys. Chem. B 2008, 112, 10520-10527
37. Hickl, P.; Ballauff, M.; Jada, A. Small-Angle X-ray Contrast-Variation Study of Micelles Formed by Poly(styrene)-Poly(ethylene oxide) Block Copolymers in Aqueous Solution Macromolecules 1996, 29, 4006-4014
38. Zhang, R.; Marone, P. A.; Thiyagarajan, P.; Tiede, D. M. Structure and Molecular Fluctuations of n-Alkyl-β-d-glucopyranoside Micelles Determined by X-ray and Neutron Scattering Langmuir 1999, 15, 7510-7519
39. Milkereit, G.; Garamus, V. M.; Veermans, K.; Willumeit, R.; Vill, V. Structures of Micelles formed by Synthetic Alkyl glycosides with Unsaturated alkyl Chains J. Colloid Interface Sci. 2005, 284, 704-713
40. Sodermann, O.; Johansson, I. Polyhydroxyl-Based Surfactants and Their Physico-Chemical Properties and Applications Curr. Opin. Coll. Interf. Sci 2000, 4, 391-401
41. Kwon, S. Y. Length Control in Rigid Cylindrical Nanoassembly by Tuning Molecular Interactions in Aqueous Solutions Langmuir 2008, 24, 10674-10679
42. Shimizu, T.; Masuda, M.; Minamikawa, H. Supramolecular Nanotube Architectures Based on Amphiphilic Molecules Chem. Rev. 2005, 105, 1401-1443
43. Imae, T.; Funayama, K.; Krafft, M. P.; Giulieri, F.; Tada, T.; Matsumoto, T. Small-Angle Scattering and Electron Microscopy Investigation of Nanotubules Made from a Perfluoroalkylated Glucophospholipid J. Colloid Interface Sci. 1999, 212, 330-337
44. Ernst, R. R.; Bodenhausen, G.; Wokaun, A. Principles of Nuclear Magnetic Resonance in One and Two Dimensions; Oxford University Press: New York, 1987.
45. Macura, S.; Ernst, R. R. Elucidation of Cross Relaxation in Liquids by Two-Dimensional N.M.R. Spectroscopy Mol. Phys. 1980, 41, 95
46. Zhao, J.; Fung, M. Conformational Change of Hydrocarbon Chains Upon the Formation of Micelles J. Phys. Chem. 1993, 97, 5185-5187
47. Yuan, H.-Z.; Cheng, G.-Z.; Zhao, S.; Miao, X.-J.; Yu, J.-Y.; Shen, L.-F.; Du, Y.-R. Conformational Dependence of Triton X-100 on Environment Studied by 2D NOESY and 1H NMR Relaxation Langmuir 2000, 16, 3030-3035
48. Aydogan, N.; Abbott, N. L. Interfacial Properties of Unsymmetrical Bolaform Amphiphiles with One Ionic and One Nonionic Head Group J. Colloid Interface Sci. 2001, 242, 411-418
49. Kan, P. L.; Papahadjopoulos-Sternberg, B.; Wong, D.; Waigh, R. D.; Watson, D. G.; Gray, A. I.; McCarthy, D.; McAllister, M.; Scha1tzlein, A. G.; Uchegbu, I. F. Highly Hydrophilic Fused Aggregates (Microsponges) from a C12 Spermine Bolaamphiphile J. Phys. Chem. B 2004, 108, 8129-8135
50. Tanford, C. The Hydrophobic Effect: Formation of Micelle and biological Membranes; John Wiley & Sons, Ltd.: New York, 1980.
51. Abel, S.; Dupradeau, F.-Y.; Raman, E. P.; MacKerell, A. D., Jr.; Marchi, M. Molecular Simulations of Dodecyl-β-maltoside Micelles in Water: Influence of the Headgroup Conformation and Force Field Parameters J. Phys. Chem. B 2011, 115, 487-499
52. Kaibara, K.; Iwata, E.; Eguchi, Y.; Suzuki, M.; Maeda, H. Dispersion Behavior of Oleic Acid in Aqueous Media: From Micelles to Emulsions Colloid Polym. Sci. 1997, 275, 777-783
53. de Koster, C. G.; Heerma, W.; Pepermans, H. A. M.; Groenewegen, A.; Peters, H.; Haverkamp, J. Tandem Mass Spectrometry and Nuclear Magnetic Resonance Spectroscopy Studies of Candida bombicola Sophorolipids and Product Formed on Hydrolysis by Cutinase Anal. Biochem. 1995, 230, 135-148
54. Das, S.; Bhirud, R. G.; Nayyar, N.; Narayan, K. S.; Kumar, V. V. Chemical Shift Changes on Micellization of Linear Alkyl Benzenesulfonate and Oleate J. Phys. Chem. 1992, 96, 7454-7457
55. Lang, S.; Brakemeier, A.; Heckmann, R.; Spockner, S.; Rau, U. Production of Native and Modified Sophorose Lipids Chim Oggi-Chem. Today 2000, 18, 76-79
56. Davila, A.-M.; Marchal, R.; Vandecasteele, J.-P. Sophorose Lipid Production from Lipidic Precursors - Predictive Evaluation of Industrial Substrates J. Ind. Microbiol. 1994, 13, 249-257
57. Rau, U.; Heckmann, R.; Wray, V.; Lang, S. Enzymatic Conversion of a Sophorolipid into a Glucose Lipid Biotechnol. Lett. 1999, 21, 973-977
58. Develter, D. W. G.; Lauryssen, L. M. L. Properties and Industrial Applications of Sophorolipids Eur. J. Lipid Sci. Technol. 2010, 112, 628-638
59. Imura, T.; Masuda, Y.; Minamikawa, H.; Fukuoka, T.; Konishi, M.; Morita, T.; Sakai, H.; Abe, M.; Kitamoto, D. Enzymatic Conversion of Diacetylated Sophoroselipid into Acetylated Glucoselipid: Surface-Active Properties of Novel Bolaform Biosurfactants J. Oleo. Sci. 2010, 59, 495-501
60. http://didier.lairez.fr/dokuwiki/doku.php?id=pasinet.
61. Förster, S.; Burger, C. Scattering Functions of Polymeric Core-Shell Structures and Excluded Volume Chains Macromolecules 1998, 31, 879-891
62. Glatter, O.; Kratky, O. Small Angle X-ray Scattering; Academic Press: London, 1982.