Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone

Steroids

Volumn 74, Issue 13-14, 2009, Pages 1007-1014

  Quintana, Paula G ^a   Baldessari, Alicia ^a  

^a UMYMFOR ^*  (Argentina)

Author keywords

Hydrocortisone fatty acid esters; Lipase catalyzed reactions

Indexed keywords

21 9 OCTADECANOYLOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 21 9,12 OCTADECADIENOYLOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 21 9,12,15 OCTADECATRIENOYLOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 21 ACETOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 21 DECANOYLOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 21 HEXANOYLOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 21 OCTADECANOYLOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 21 OCTANOYLOXY 11BETA,17ALPHA DIHYDROXYPREGN 4 EN 3,20 DIONE; 3,11BETA,17ALPHA TRIACETOXY 21 HYDROXYPREGNA 3,5 DIEN 20 ONE; FATTY ACID ESTER; HYDROCORTISONE DERIVATIVE; HYDROCORTISONE FATTY ACID ESTER DERIVATIVE; SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ALCOHOLYSIS; ARTICLE; BIOCATALYST; CANDIDA ANTARCTICA; CATALYSIS; ENZYME SUBSTRATE; ESTERIFICATION; METHODOLOGY; STEREOCHEMISTRY; TEMPERATURE; TRANSESTERIFICATION;

CANDIDA; ESTERIFICATION; FATTY ACIDS; HYDROCORTISONE; LIPASE;

CANDIDA ANTARCTICA;

EID: 70350783862     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2009.07.010     Document Type: Article

References (36)

1. Munk A. Glucorticoid biology-a historical perspective. In: Goulding N.J., and Flower R.J. (Eds). Glucocorticoids (milestones in drug therapy) (2001), Birkhauser Verlag, Basel 17-34
2. Brunton L.L., Lazo J.S., and Parker K.L. Goodman and Gilman's the pharmacological basis of therapeutics. 11th ed. (2006), The Mc-Graw Hill Companies, Inc, New York
3. Hughes J., and Rustin M. Corticosteroids Clin Dermatol 15 (1997) 715-721
4. Wiedersberg S., Leopold C.S., and Guy R.H. Bioavailability and bioequivalence of topical glucocorticoids. Eur J Pharm Biopharm 68 (2008) 453-466
5. Ponec M., Kempenaar J.A., and De Kloet E.R. Corticoids and cultured hyman epidermal keratinocytes: specific intracellular binding and clinical efficacy. J Invest Dermatol 76 (1981) 211-214
6. Ponec M., and Kempenaar J.A. Biphasic entry of glucocorticoids into cultured human skin keratinocytes and fibroblasts. Arch Dermatol Res 275 (1983) 334-344
7. Caron D., Queille-Roussel C., Shah V.P., and Schaefer H. Correlation between the drug penetration and the balanching effect of topically applied hydrocortisone creams in human beings. J Am Acad Dermatol 23 (1990) 458-462
8. Kasuya Y., Ishimaru H., Shibasaki H., and Furuta T. Stable isotope methodology for kinetic sutdies of interconversion of cortisol and cortisone in a human subject. Steroids 63 (1998) 122-129
9. Brazzini B., and Pimpinelli N. New and established topical corticosteroids in dermatology: clinical pharmacology and therapeutic use. Am J Clin Dermatol 3 (2002) 47-58
10. Bommarius A.S., and Riebel B.R. Biocatalysis, fundamentals and applications (2004), Wiley-VCH, Weinheim
11. Buchholz K., Kasche V., and Bornscheuer U.T. Biocatalysis and enzyme technology (2005), Wiley-VCH, Weinheim
12. Saha B.C., and Demirjian D.C. Applied biocatalysis in specialty chemicals and pharmaceuticals (2000), ACS, Washington, DC
13. In: Carrea G., and Riva S. (Eds). Organic synthesis with enzymes in non-aqueous media (2008), Wiley-VCH, Weinheim
14. In: Gotor V., Alfonso I., and García-Urdiales E. (Eds). Asymmetric organic synthesis with enzymes (2007), Wiley-VCH, Weinheim
15. Ferrero M., and Gotor V. In: Patel R.M. (Ed). Stereoselective biocatalysis (2000), Marcel Dekker, New York 579-631
16. Cruz Silva M.M., Riva S., and Sá e Melo M.L. Regioselective enzymatic acylation of vicinal diols of steroids. Tetrahedron 61 (2005) 3065-3073
17. Cruz Silva M.M., Sá e Melo M.M., Parolin M., Tessaro D., Riva S., and Danieli B. Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids. Tetrahedron Asymm 15 (2004) 1173-1179
18. Bertinotti A., Carrea G., Ottolina G., and Riva S. Regioselective esterification of polyhydroxylated steroids by Candida antarctica lipase B. Tetrahedron 50 (1994) 13165-13172
19. Baldessari A., Maier M.S., and Gros E.G. Enzymatic deacteylation of steroids bearing labile functions. Tetrahedron Lett 36 (1995) 4349-4352
20. Baldessari A., Bruttomeso A.C., and Gros E.G. Lipase-catalysed regioselective deacetylation of androstane derivatives. Helv Chim Acta 79 (1996) 999-1004
21. Brutomesso A.C., and Baldessari A. Lipase-catalysed deacetylation of androstane and pregnane derivatives: influence of ring D substitution. J Mol Catal B: Enzym 29 (2004) 149-153
22. Brutomesso A.C., Tiscornia A., and Baldessari A. Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone. Biocatal Biotransf 22 (2004) 215-220
23. Rustoy E.M., Ruiz Arias I.E., and Baldessari A. Regioselective enzymatic synthesis of estradiol 17-fatty acid esters. ARKIVOC xii (2005) 175-188
24. Monsalve L.N., Machado Rada M.Y., Ghini A.A., and Baldessari A. An efficient enzymatyic preparation of 20-pregnanes succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5α H-pregnan-3-one. Tetrahedron 64 (2008) 1721-1730
25. Faramarzi M.A., Yazdi M.T., Sahfiee A., and Zarrini G. Microbial transformation of hydrocortisone by Acremonium strictum PTCC 5282. Steroids 67 (2002) 869-872
26. Baldessari A., and Mangone C.P. One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals. J Mol Catal B: Enzym 11 (2001) 335-541
27. Marwah P., Marwah A., and Lardy H.A. Microwave induced selective enolization of steroidal ketones and efficient acetylation of sterols in semisolid state. Tetrahedron 59 (2003) 2273-2287
28. Antonucci R., Bernstein S., Heller M., Lenhard R., Littell R., and Williams J.H. Steroidal cyclic ketals. III. Hydrocortisone and related steroids. J Org Chem 18 (1953) 70-72
29. 1H NMR spectra of the steroid hormones, their hydroxylated derivatives and related compounds. J Chem Soc Perkin Trans II 9 (1990) 1567-1594
30. Hickey J.P., Butler I.S., and Pouskouleli G. Carbon NMR spectra of some representative hormonal steroids. J Magn Reson 38 (1969) 501-506
31. Priego J., Ortíz-Nava C., Carrillo-Morales M., López-Munguía A., Escalante J., and Castillo E. Solvent engineering: an effective tool to direct chemoselectivity in a lipase-catalyzed Michael addition. Tetrahedron 65 (2009) 536-539
32. Laane C., Boeren S., Vos K., and Veeger C. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30 (1987) 81-87
33. Baldessari A., and Mangone C.P. Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity. Biocatal Biotransf 20 (2002) 275-279
34. Monsalve L.N., Rosselli S., Bruno M., and Baldessari A. Lipase-catalysed preparation of acyl derivatives of the germacranolide cnicin. J Mol Catal B: Enzym 57 (2009) 40-47
35. Procopiou P.A., Baugh S.P.D., Flack S.S., and Inglis G.G.A. An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethanesulfonate. J Org Chem 63 (1998) 2342-2347
36. Furuta T., Eguchi N., Yokokawa A., Shibasaki H., and Kasuya Y. Synthesis of multi-labeled cortisols and cortisones with 2H and 13C for study of cortisol metabolism in humans. Steroids 65 (2000) 180-189