Human 20α-hydroxysteroid dehydrogenase (AKR1C1)-dependent biotransformation with recombinant fission yeast Schizosaccharomyces pombe

Journal of Biotechnology

Volumn 150, Issue 1, 2010, Pages 161-170

  Naumann, Julia Maria ^a   Messinger, Josef ^b   Bureik, Matthias ^a  

^a PomBioTech GmbH   (Germany)

^b Solvay Pharmaceuticals GmbH   (Germany)

Author keywords

20 hydroxysteroid dehydrogenase; AKR1C1; Aldo keto reductase; Progesterone; Schizosaccharomyces pombe; Whole cell biotransformation

Indexed keywords

AKR1C1; ALDO-KETO REDUCTASE; HYDROXYSTEROID DEHYDROGENASE; PROGESTERONE; SCHIZOSACCHAROMYCES POMBE; WHOLE-CELL BIOTRANSFORMATIONS;

BIOCONVERSION; BIOMOLECULES; ENZYME ACTIVITY; FERMENTATION; METABOLISM; METABOLITES; SAFETY TESTING; YEAST;

SYNTHESIS (CHEMICAL);

20ALPHA DIHYDROPROGESTERONE; 20ALPHA DIHYRODYDROGESTERONE; 20ALPHA HYDROXYSTEROID DEHYDROGENASE; ALDOSTERONE; CORTICOSTERONE; CORTODOXONE; DEOXYCORTICOSTERONE; DRUG METABOLITE; DYDROGESTERONE; HYDROCORTISONE; HYDROXYPROGESTERONE; OXIDOREDUCTASE; PREGNENOLONE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BIOTECHNOLOGY; BIOTRANSFORMATION; FERMENTATION; HUMAN; NONHUMAN; PRIORITY JOURNAL; SCHIZOSACCHAROMYCES POMBE; SYNTHESIS; YEAST;

20-ALPHA-DIHYDROPROGESTERONE; 20-HYDROXYSTEROID DEHYDROGENASES; BIOTRANSFORMATION; CELL COUNT; CLONING, MOLECULAR; FERMENTATION; GLUCOSE; HUMANS; PROGESTERONE; RECOMBINANT PROTEINS; SCHIZOSACCHAROMYCES;

SCHIZOSACCHAROMYCES POMBE; SCHIZOSACCHAROMYCETACEAE;

EID: 77957377046     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2010.08.004     Document Type: Article

References (32)

1. Barski O.A., Tipparaju S.M., Bhatnagar A. The aldo-keto reductase superfamily and its role in drug metabolism and detoxification. Drug Metab. Rev. 2008, 40:553-624.
2. Bureik M., Hübel K., Dragan C.-A., Scher J., Becker H., Lenz N., Bernhardt R. Development of test systems for the discovery of selective human aldosterone synthase (CYP11B2) and 11b-hydroxylase (CYP11B1) inhibitors. Discovery of a new lead compound for the therapy of congestive heart failure, myocardial fibrosis and hypertension. Mol. Cell Endocrinol. 2004, 217:249-254.
3. Bureik M., Schiffler B., Hiraoka Y., Vogel F., Bernhardt R. Functional expression of human mitochondrial CYP11B2 in fission yeast and identification of a new internal electron transfer protein, etp1. Biochemistry 2002, 41:2311-2321.
4. D'Incan E., Loupy A., Restelli A., Seyden-Penne J., Viout P. Sélectivité de la reduction de l'androsten-2-dione-3,17 et de la progestérone par divers borohydrures. Tetrahedron 1982, 38:1755.
5. de Jong-Gubbels P., van Dijken J.P., Pronk J.T. Metabolic fluxes in chemostat cultures of Schizosaccharomyces pombe grown on mixtures of glucose and ethanol. Microbiology 1996, 142:1399-1407.
6. Deyashiki Y., Ogasawara A., Nakayama T., Nakanishi M., Miyabe Y., Sato K., Hara A. Molecular cloning of two human liver 3 alpha-hydroxysteroid/dihydrodiol dehydrogenase isoenzymes that are identical with chlordecone reductase and bile-acid binder. Biochem. J. 1994, 299(Pt 2):545-552.
7. Dragan C.-A., Hartmann R.W., Bureik M. A fission yeast based test system for the determination of IC50 values of anti prostate tumor drugs acting on CYP21. J. Enzyme Inhib. Med. Chem. 2006, 21:547-556.
8. Dragan C.-A., Zearo S., Hannemann F., Bernhardt R., Bureik M. Efficient conversion of 11-deoxycortisol to cortisol (hydrocortisone) by recombinant fission yeast Schizosaccharomyces pombe. FEMS Yeast Res. 2005, 5:621-625.
9. Dragan C.A., Blank L.M., Bureik M. Increased TCA cycle activity and reduced oxygen consumption during cytochrome P450-dependent biotransformation in fission yeast. Yeast 2006, 23:779-794.
10. Ellis E.M. Microbial aldo-keto reductases. FEMS Microbiol. Lett. 2002, 216:123-131.
11. Food and Drug Administration, C.f.D.E.a.R.C., 2008. Guidance for Industry: Safety Testing of Drug Metabolites. Services, U.S.D.o.H.a.H.
12. Forsburg S.L., Rhind N. Basic methods for fission yeast. Yeast 2006, 23:173-183.
13. Jin Y., Penning T.M. Aldo-keto reductases and bioactivation/detoxication. Annu. Rev. Pharmacol. Toxicol. 2007, 47:263-292.
14. Kohli J., Hottinger H., Munz P., Strauss A., Thuriaux P. Genetic mapping in Schizosaccharomyces pombe by mitotic and meiotic analysis and induced haploidization. Genetics 1977, 87:471-489.
15. Maundrell K. Nmt1 of fission yeast. A highly transcribed gene completely repressed by thiamine. J. Biol. Chem. 1990, 265:10857-10864.
16. Maundrell K. Thiamine-repressible expression vectors pREP and pRIP for fission yeast. Gene 1993, 123:127-130.
17. Mendel C.M. The free hormone hypothesis: a physiologically based mathematical model. Endocr. Rev. 1989, 10:232-274.
18. Moreno S., Klar A., Nurse P. Molecular genetic analysis of fission yeast Schizosaccharomyces pombe. Methods Enzymol. 1991, 194:795-823.
19. Nurse P. A long twentieth century of the cell cycle and beyond. Cell 2000, 100:71-78.
20. Pajic T., Vitas M., Zigon D., Pavko A., Kelly S.L., Komel R. Biotransformation of steroids by the fission yeast Schizosaccharomyces pombe. Yeast 1999, 15:639-645.
21. Penning T.M. Hydroxysteroid dehydrogenases. New drug targets of the aldo-keto reductase superfamily. Adv. Exp. Med. Biol. 1997, 414:475-490.
22. Penning T.M., Burczynski M.E., Jez J.M., Hung C.F., Lin H.K., Ma H., Moore M., Palackal N., Ratnam K. Human 3alpha-hydroxysteroid dehydrogenase isoforms (AKR1C1-AKR1C4) of the aldo-keto reductase superfamily: functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones. Biochem. J. 2000, 351:67-77.
23. Peters F.T., Dragan C.A., Kauffels A., Schwaninger A.E., Zapp J., Bureik M., Maurer H.H. Biotechnological synthesis of the designer drug metabolite 4'-Hydroxymethyl-alpha-pyrrolidinohexanophenone in fission yeast heterologously expressing human cytochrome P450 2D6-A versatile alternative to multistep chemical synthesis. J. Anal. Toxicol. 2009, 33:190-197.
24. Peters F.T., Dragan C.A., Schwaninger A.E., Sauer C., Zapp J., Bureik M., Maurer H.H. Use of fission yeast heterologously expressing human cytochrome P450 2B6 in biotechnological synthesis of the designer drug metabolite N-(1-phenylcyclohexyl)-2-hydroxyethanamine. Forensic Sci. Int. 2009, 184:69-73.
25. Peters F.T., Dragan C.A., Wilde D.R., Meyer M.R., Zapp J., Bureik M., Maurer H.H. Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4'-hydroxymethyl-alpha-pyrrolidinobutyrophenone. Biochem. Pharmacol. 2007, 74:511-520.
26. Robinson C.H., Hofer P. N.M.R. spectra of C(20)-substituted pregnanes. Chem. Ind. 1966, 377-378.
27. Steckelbroeck S., Jin Y., Gopishetty S., Oyesanmi B., Penning T.M. Human cytosolic 3alpha-hydroxysteroid dehydrogenases of the aldo-keto reductase superfamily display significant 3beta-hydroxysteroid dehydrogenase activity: implications for steroid hormone metabolism and action. J. Biol. Chem. 2004, 279:10784-10795.
28. Suga M., Hatakeyama T. A rapid and simple procedure for high-efficiency lithium acetate transformation of cryopreserved Schizosaccharomyces pombe cells. Yeast 2005, 22:799-804.
29. Wood V., Gwilliam R., Rajandream M.A., Lyne M., Lyne R., Stewart A., Sgouros J., Peat N., Hayles J., Baker S., Basham D., Bowman S., Brooks K., Brown D., Brown S., Chillingworth T., Churcher C., Collins M., Connor R., Cronin A., Davis P., Feltwell T., Fraser A., Gentles S., Goble A., Hamlin N., Harris D., Hidalgo J., Hodgson G., Holroyd S., Hornsby T., Howarth S., Huckle E.J., Hunt S., Jagels K., James K., Jones L., Jones M., Leather S., McDonald S., McLean J., Mooney P., Moule S., Mungall K., Murphy L., Niblett D., Odell C., Oliver K., O'Neil S., Pearson D., Quail M.A., Rabbinowitsch E., Rutherford K., Rutter S., Saunders D., Seeger K., Sharp S., Skelton J., Simmonds M., Squares R., Squares S., Stevens K., Taylor K., Taylor R.G., Tivey A., Walsh S., Warren T., Whitehead S., Woodward J., Volckaert G., Aert R., Robben J., Grymonprez B., Weltjens I., Vanstreels E., Rieger M., Schafer M., Muller-Auer S., Gabel C., Fuchs M., Dusterhoft A., Fritzc C., Holzer E., Moestl D., Hilbert H., Borzym K., Langer I., Beck A., Lehrach H., Reinhardt R., Pohl T.M., Eger P., Zimmermann W., Wedler H., Wambutt R., Purnelle B., Goffeau A., Cadieu E., Dreano S., Gloux S., Lelaure V., Mottier S., Galibert F., Aves S.J., Xiang Z., Hunt C., Moore K., Hurst S.M., Lucas M., Rochet M., Gaillardin C., Tallada V.A., Garzon A., Thode G., Daga R.R., Cruzado L., Jimenez J., Sanchez M., del Rey F., Benito J., Dominguez A., Revuelta J.L., Moreno S., Armstrong J., Forsburg S.L., Cerutti L., Lowe T., McCombie W.R., Paulsen I., Potashkin J., Shpakovski G.V., Ussery D., Barrell B.G., Nurse P. The genome sequence of Schizosaccharomyces pombe. Nature 2002, 415:871-880.
30. Zehentgruber D., Dr Gan C.L., Bureik M., Lutz S. Challenges of steroid biotransformation with human cytochrome P450 monooxygenase CYP21 using resting cells of recombinant Schizosaccharomyces pombe. J. Biotechnol. 2010.
31. Zhao Y., Lieberman H.B. Schizosaccharomyces pombe: a model for molecular studies of eukaryotic genes. DNA Cell Biol. 1995, 14:359-371.
32. Zöllner A., Dragan C.A., Pistorius D., Müller R., Bode H.B., Peters F.T., Maurer H.H., Bureik M. Human CYP4Z1 catalyzes the in-chain hydroxylation of lauric acid and myristic acid. Biol. Chem. 2009, 390:313-317.