Solubilization of moderately hydrophobic 17α-ethinylestradiol by mono- and di-rhamnolipid solutions

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 445, Issue , 2014, Pages 12-20

  Guo, Yan Ping ^b   Hu, Yong You ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b Guangdong Vocational College of Environmental Protection Engineering   (China)

Author keywords

Aggregate morphology; Estrogen; Moderately hydrophobic solubilizate; Rhamnolipidic homologue

Indexed keywords

AGGREGATES; HYDROPHOBICITY; LIPIDS; MIXTURES; MORPHOLOGY; SOLUBILITY; SPECTRUM ANALYSIS; SURFACE ACTIVE AGENTS; TRANSMISSION ELECTRON MICROSCOPY;

AGGREGATE MORPHOLOGY; AQUATIC ENVIRONMENTS; ENVIRONMENTAL REMEDIATION; ESTROGEN; MODERATELY HYDROPHOBIC SOLUBILIZATE; MULTICOMPONENT MIXTURE; RHAMNOLIPIDIC HOMOLOGUE; SURFACTANT AGGREGATES;

EXPERIMENTS;

DIRHAMNOLIPID; ETHINYLESTRADIOL; MONORHAMNOLIPID; RHAMNOLIPID; SURFACTANT; UNCLASSIFIED DRUG;

AQUATIC ENVIRONMENT; ARTICLE; DYNAMIC LIGHT SCATTERING; ECOSYSTEM RESTORATION; HYDROPHOBICITY; LIGHT SCATTERING; MICELLIZATION; PRIORITY JOURNAL; SOLUBILIZATION; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY;

EID: 84893051298     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2013.12.076     Document Type: Article

References (36)

1. Mulligan C.N. Environmental applications for biosurfactants. Environ. Pollut. 2005, 133:183-198.
2. Zhang Y., Maier W.J., Miller R.M. Effect of rhamnolipids on the dissolution, bioavailability, and biodegradation of phenanthrene. Environ. Sci. Technol. 1997, 3:2211-2217.
3. Shin K.-H., Kim K.-W., Seagren E.A. Combined effects of pH and biosurfactant addition on solubilization and biodegradation of phenanthrene. Appl. Microbiol. Biotechnol. 2004, 65:336-343.
4. Cho Y.C., Ostrofsky E.B., Rhee G.Y. Effects of a rhamnolipid biosurfactant on the reductive dechlorination of polychlorinated biphenyls by St. Lawrence River (North America) microorganisms. Environ. Toxicol. Chem. 2004, 23:1425-1430.
5. Fiebig R., Detlef S., Chung J.-C., Lee S.-T. Biodegradation of polychlorinated biphenyls (PCBs) in the presence of a bioemulsifier produced on sunflower oil. Biodegradation 1997, 8:67-75.
6. Mata-Sandoval J.C., Karns J., Torrents A. Effect of rhamnolipids produced by Pseudomonas aeruginosa UG2 on the solubilization of pesticides. Environ. Sci. Technol. 2000, 34:4923-4930.
7. Nitschke M., Costa S.G.V.A.O., Contiero J. Rhamnolipid surfactants: an updata on the general aspects of these remarkable biomolecules. Biotechnol. Prog. 2005, 21:1593-1600.
8. Özdemir G., Peker S., Helvaci S.S. Effect of pH on the surface and interfacial behavior of rhamnolipids R1 and R 2. Colloids Surf. A 2004, 234:135-143.
9. Helvaci S.S., Peker S., Özdemir G. Effect of electrolytes on the surface behavior of rhamnolipids R1 and R2. Colloids Surf. B 2004, 35:225-233.
10. Sánchez M., Aranda F.J., Espuny M.J., Marqués A., Teruel J.A., Manresa Á., Ortiz A. Aggregation behaviour of a dirhamnolipid biosurfactant secreted by Pseudomonas aeruginosa in aqueous media. J. Colloid Interface Sci. 2007, 307:246-253.
11. Pornsuntrorntawee O., Chavadej S., Rujiravanit R. Solution properties and vesicle formation of rhamnolipid biosurfactants produced by Pseudomonas aeruginosa SP4. Colloids Surf. B 2009, 72:6-15.
12. Singh A., Van Hamme J.D., Ward O.P. Surfactants in microbiology and biotechnology: Part 2. Application aspects. Biotechnol. Adv. 2007, 25:99-121.
13. Laha S., Tansel B., Ussawarujikulchai A. Surfactant-soil interactions during surfactant-amended remediation of contaminated soils by hydrophobic organic compounds: a review. J. Environ. Manage. 2009, 90:95-100.
14. Mata-Sandoval J.C., Karns J., Torrents A. Influence of rhamnolipids and Triton X-100 on the desorption of pesticides from soils. Environ. Sci. Technol. 2002, 36:4669-4675.
15. Ying G.-G., Kookana R.S., Ru Y.-J. Occurrence and fate of hormone steroids in the environment. Environ. Int. 2002, 28:545-551.
16. Yu Z.Q., Xiao B.H., Huang W.L., Peng P. Sorption of steroid estrogens to soils and sediments. Environ. Toxicol. Chem. 2004, 23:531-539.
17. Pojana G., Gomiero A., Jonkers N., Marcomini A. Natural and synthetic endocrine disrupting compounds (EDCs) in water, sediment and biota of a coastal lagoon. Environ. Int. 2007, 33:929-936.
18. Guo Y.-P., Hu Y.-Y., Gu R.R., Lin H. Characterization and micellization of rhamnolipidic fractions and crude extracts produced by Pseudomonas aeruginosa mutant MIG-N146. J. Colloid Interface Sci. 2009, 331:356-363.
19. Champion J.T., Gilkey J.C., Lamparski H., Retterer J., Miller R.M. Electron microscopy of rhamnolipid (biosurfactant) morphology: effects of pH, cadmium, and octadecane. J. Colloid Interface Sci. 1995, 170:569-574.
20. Yu Z.Q., Huang W.L. Competitive sorption between 17α-ethinyl estradiol and naphthalene/phenanthrene by sediments. Environ. Sci. Technol. 2005, 39:4878-4885.
21. Lai K.M., Johnson K.L., Scrimshaw M.D., Lester J.N. Binding of waterborne steroid estrogens to solid phases in river and estuarine systems. Environ. Sci. Technol. 2000, 34:3890-3894.
22. Edwards D.A., Luthy R.G., Liu Z. Solubilization of polycyclic aromatic hydrocarbons in micellar nonionic surfactant solutions. Environ. Sci. Technol. 1991, 25:127-133.
23. Prak D.J.L., Abriola L.M., Weber W.J., Bocskay K.A. Solubilization rates of n-alkanes in micellar solutions of nonionic surfactants. Environ. Sci. Technol. 2000, 34:476-482.
24. Kanga S.A., Bonner J.S., Page C.A., Mills M.A., Autenrieth R.L. Solubilization of naphthalene and methyl-substituted naphthalenes from crude oil using biosurfactants. Environ. Sci. Technol. 1997, 31:556-561.
25. 7 (n=14,16) nonionic micelles. J. Colloid Interface Sci. 2008, 317:115-120.
26. De La Maza A., Coderch L., Lopez O., Parra J.L. Vesicle to micelle structural transitions involved in the interaction of dodecylbetaine with liposomes: transmission electron microscopy and light scattering studies. Micron 1998, 29:175-182.
27. Song D., Li Y., Liang S., Wang J. Micelle behaviors of sophorolipid/rhamnolipid binary mixed biosurfactant systems. Colloids Surf. A 2013, 436:201-206.
28. Guo Y., Mulligan C.N., Nieh M.-P. An unusual morphological transformation of rhamnolipid aggregates induced by concentration and addition of styrene: a small angle neutron scattering (SANS) study. Colloids Surf. A 2011, 373:42-50.
29. Keczynski M., Bednar J., Kuzmicz D., Wydro P., Nowakowska M. Spontaneous formation of densely stacked multilamellar vesicles in dioctadecyldimethylammonium bromide/oleosiloxane mixtures. Langmuir 2010, 26:1551-1556.
30. Bhat P.A., Rather G.M., Dar A.A. Effect of surfactant mixing on partitioning of model hydrophobic drug, naproxen, between aqueous and micellar phases. J. Phys. Chem. B 2009, 113:997-1006.
31. Choucair A., Eisenberg A. Interfacial solubilization of model amphiphilic molecules in block copolymer micelles. J. Am. Chem. Soc. 2003, 125:11993-12000.
32. Cang H., Brace D.D., Fayer M.D. Dynamic partitioning of an aromatic probe between the headgroup and core regions of cationic micelles. J. Phys. Chem. B 2001, 105:10007-10015.
33. 1H NMR spectroscopy. Langmuir 2001, 17:565-566.
34. Goldenberg M.S., Bruno L.A., Rennwantz E.L. Determination of solubilization sites and efficiency of water-insoluble agents in ethylene oxide-containing nonionic micelles. J. Colloid Interface Sci. 1993, 158:351-363.
35. 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, 5:763-766.
36. Ariel L.-P., Pemberton J.E., Becker B.A., Otto W.H., Larive C.K., Maier R.M. Determination of the acid dissociation constant of the biosurfactant monorhamnolipid in aqueous solution by potentiometric and spectroscopic methods. Anal. Chem. 2006, 78:7649-7658.