Physicochemical characterization and toxicity evaluation of steroid-based surfactants designed for solubilization of poorly soluble drugs

European Journal of Pharmaceutical Sciences

Volumn 44, Issue 5, 2011, Pages 595-601

  Ménard, Nathalie ^a,b,c   Tsapis, Nicolas ^b,c   Poirier, Cécile ^a   Arnauld, Thomas ^a   Moine, Laurence ^b,c   Lefoulon, Franois ^a   Péan, Jean Manuel ^a   Fattal, Elias ^b,c  

^a INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c UNIV PARIS SUD   (France)

Author keywords

Cytotoxicity; Insoluble drug; Micelle; Self assembling; Solubilization; Surfactant

Indexed keywords

CHOLESTEROL DERIVATIVE; CHOLESTERYLGLUTAMIC ACID; CHOLESTERYLPOLY(N 2 HYDROXYETHYLGLUTAMINE); LACTATE DEHYDROGENASE; POLYSORBATE 80; PYRENE; STEROID; SURFACTANT; UNCLASSIFIED DRUG; URSODEOXYCHOLANYLCHOLESTERYLPOLY(N 2 HYDROXYETHYLGLUTAMINE); URSODEOXYCHOLANYLPOLYGLUTAMIC ACID; WATER;

ANALYTICAL PARAMETERS; ANIMAL CELL; ARTICLE; CELL VIABILITY; CHEMICAL MODEL; CONTROLLED STUDY; CRITICAL AGGREGATION CONCENTRATION; CYTOTOXICITY; DRUG SOLUBILITY; ENZYME RELEASE; FLUORESCENCE SPECTROSCOPY; HEMOLYSIS; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; LIGHT SCATTERING; MEMBRANE DAMAGE; MICELLE; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RAT; SYNTHESIS; UMBILICAL VEIN ENDOTHELIAL CELL;

ANIMALS; CELL SURVIVAL; CHOLESTEROL ESTERS; GLUTAMIC ACID; HEMOLYSIS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; L-LACTATE DEHYDROGENASE; PARTICLE SIZE; PEPTIDES; POLYGLUTAMIC ACID; POLYSORBATES; RATS; RATS, WISTAR; SOLUBILITY; SPECTROMETRY, FLUORESCENCE; SURFACE-ACTIVE AGENTS; URSODEOXYCHOLIC ACID; WATER;

EID: 82155168245     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.10.006     Document Type: Article

References (30)

1. T. Baba, N. Terada, Y. Fujii, N. Ohno, S. Ohno, and S.B. Sato Ultrastructural study of echninocytes induced by poly (ethylene glycol)-cholesterol Histochem. Cell Biol. 122 2004 587 592 (Pubitemid 40174595)
2. C. Boettcher, B. Schade, and J.H. Fuhrhop Comparative cryo-electron microscopy of noncovalent n-dodecanoyl-(d- and l-)serine assemblies in vitreous toluene and water Langmuir 17 2001 873 877 (Pubitemid 32873079)
3. R.O. Brito, E.F. Marques, P. Gomes, S. Falcao, and O. Soderman Self assembly in a catanionic mixture with an aminoacid derived surfactant: from mixed micelles to spontaneous vesicles J. Phys. Chem. B 110 2006 18158 18165 (Pubitemid 44547317)
4. R.O. Brito, E.F. Marques, S.G. Silva, M.L. do Vale, P. Gomes, M.J. Araújo, J.E. Rodriguez-Borges, M.R. Infante, M.T. Garcia, I. Ribosa, M.P. Vinardell, and M. Mitjans Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles Colloids Surf. B: Biointerfaces 72 2009 80 87
5. F.K. Engels, R.A. Mathot, and J. Verweij Alternative drug formulations of docetaxel: a review Anticancer Drugs 18 2007 95 103 (Pubitemid 44967420)
6. B.M. Folmer Sterol surfactants: from synthesis to applications Adv. Colloid Interface Sci. 103 2003 99 119
7. M.F. Francis, L. Lavoie, F.M. Winnik, and J.C. Leroux Solubilization of cyclosporin A in dextran-g-polyethyleneglycolalkyl ether polymeric micelles Eur. J. Pharm. Biopharm. 56 2003 337 346 (Pubitemid 37346506)
8. M.F. Francis, M. Piredda, and F.M. Winnik Solubilization of poorly water soluble drugs in micelles of hydrophobically modified hydroxypropylcellulose copolymers J. Controlled Release 93 2003 59 68 (Pubitemid 37346268)
9. S. Güldütuna, B. Deisinger, A. Weiss, H.J. Freisleben, G. Zimmer, P. Sipos, and U. Leuschner Ursodeoxycholate stabilizes phospholipid-rich membranes and mimics the effect of cholesterol: investigations on large unilamellar vesicles Biochim. Biophys. Acta (BBA) - Biomembranes 1326 1997 265 274 (Pubitemid 27272131)
10. X.D. Guo, F. Tandiono, N. Wiradharma, D. Khor, C.G. Tan, M. Khan, Y. Qian, and Y.Y. Yang Cationic micelles self-assembled from cholesterol-conjugated oligopeptides as an efficient gene delivery vector Biomaterials 29 2008 4838 4846
11. A.V. Heydenreich, R. Westmeier, N. Pedersen, H.S. Poulsen, and H.G. Kristensen Preparation and purification of cationic solid lipid nanospheres - effects on particle size, physical stability and cell toxicity Int. J. Pharm. 254 2003 83 87 (Pubitemid 36259816)
12. S. Hirama, T. Tatsuishi, K. Iwase, H. Nakao, C. Umebayashi, Y. Nishizaki, M. Kobayashi, S. Ishida, Y. Okano, and Y. Oyama Flow-cytometric analysis on adverse effects of polysorbate 80 in rat thymocytes Toxicology 199 2004 137 143 (Pubitemid 38624525)
13. F.Q. Hu, L.N. Liu, Y.Z. Du, and H. Yuan Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles Biomaterials 30 2009 6955 6963
14. H. Igimi, and M.C. Carey PH solubility relations of chenodeoxycholic and ursodeoxycholic acids: physical, chemical basis for dissimilar solution and membrane phenomena J. Lipid Res. 21 1980 72 90 (Pubitemid 10120440)
15. A.S. Inacio, K.A. Mesquita, M. Baptista, J. Ramalho-Santos, W.L.C. Vaz, and O.V. Vieira In vitro surfactant structure-toxicity relationships: implications for surfactant use in sexually transmitted infection prophylaxis and contraception PloS ONE 6 2011 1 15
16. Y. Jin, L. Xing, Y. Tian, M. Li, C. Gao, L. Du, J. Dong, and H. Chen Self-assembled drug delivery systems. Part 4. In vitro/in vivo studies of the self-assemblies of cholesteryl-phosphonyl zidovudine Int. J. Pharm. 381 2009 40 48
17. B. Kaler, W. Morgan, A. Bomzon, and P.H. Bach The effects of bile acids on freshly isolated rat glomeruli and proximal tubular fragments Toxicol. In Vitro 12 1998 1 7 (Pubitemid 28057321)
18. M.K. Lee, S. Kim, C.H. Ahn, and J. Lee Hydrophilic and hydrophobic amino acid copolymers for nano-comminution of poorly soluble drugs Int. J. Pharm. 384 2010 173 180
19. I. Makino, and S. Nakagawa Changes in biliary lipid and biliary bile acid composition in patients after administration of ursodeoxycholic acid J. Lipid Res. 19 1978 723 728 (Pubitemid 9006235)
20. N. Mano, K. Nishimura, T. Narui, S. Ikegawa, and J. Goto Characterization of rat liver bile acid acyl glucuronosyltransferase Steroids 67 2002 257 262 (Pubitemid 34150143)
21. K. Matsuoka, M. Maeda, and Y. Moroi Micelle formation of sodium glyco- and taurocholates and sodium glyco- and taurodeoxycholates and solubilization of cholesterol into their micelles Colloid Surf. B 32 2003 87 95 (Pubitemid 37083515)
22. Y. Moroi, and M. Okabe Micelle formation of sodium ursodeoxycholate and solubilization into the micelle Colloid Surf. A 169 2000 75 84 (Pubitemid 30227386)
23. P. Mukerjee, Y. Moroi, M. Murata, and A.Y.S. Yang Bile salts as atypical surfactants and solubilizers Hepatology 4 1984 61S 65S (Pubitemid 14018145)
24. S. Nakagawa, I. Makino, T. Ishizaki, and I. Dohi Dissolution of cholesterol gallstones by ursodeoxycholic acid Lancet 310 1977 367 369 (Pubitemid 8164394)
25. A.S. Narang, D. Delmarre, and D. Gao Stable drug encapsulation in micelles and microemulsions Int. J. Pharm. 345 2007 9 25 (Pubitemid 350103649)
26. L. Sanchez, M. Mitjans, M.R. Infante, M.T. Garcia, M.A. Manresa, and M.P. Vinardell The biological properties of lysine-derived surfactants Amino Acids 32 2007 133 136 (Pubitemid 44866579)
27. A. Seret, and M.A. Bahri The CMC-like behaviour of bile salts as probed by photoexcited Rose Bengal Colloid Surf. A 339 2009 153 158
28. M.A. Vives, M. Macián, J. Seguer, M.R. Infante, and M.P. Vinardell Irritancy potential induced by surfactants derived from lysine Toxicol. In Vitro 11 1997 779 783 (Pubitemid 27504500)
29. T. Wang, C. Chipot, X. Shao, and W. Cai Structural characterization of micelles formed of cholesteryl-functionalized cyclodextrins Langmuir 27 1 2011 91 97
30. H. Xu, K.Q. Wang, Y.H. Deng, and D.W. Chen Effects of cleavable PEG-cholesterol derivatives on the accelerated blood clearance of PEGylated liposomes Biomaterials 31 2010 4757 4763