Biotechnological synthesis of drug metabolites using human cytochrome P450 isozymes heterologously expressed in fission yeast

Bioanalysis

Volumn 1, Issue 4, 2009, Pages 821-830

  Peters, Frank T ^a   Bureik, Matthias ^b   Maurer, Hans H ^c  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b PomBioTech GmbH   (Germany)

^c SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; DESIGNER DRUG; ISOENZYME;

ANIMAL; BIOTECHNOLOGY; ENZYMOLOGY; HUMAN; METABOLISM; METHODOLOGY; RAT; REVIEW; SCHIZOSACCHAROMYCES; TRANSGENIC ORGANISM;

ANIMALS; BIOTECHNOLOGY; CYTOCHROME P-450 ENZYME SYSTEM; DESIGNER DRUGS; HUMANS; ISOENZYMES; ORGANISMS, GENETICALLY MODIFIED; RATS; SCHIZOSACCHAROMYCES;

EID: 76749093063     PISSN: 17576180     EISSN: 17576199     Source Type: Journal    
DOI: 10.4155/bio.09.53     Document Type: Review

References (47)

1. Guengerich FP. Human cytochrome P450 enzymes. In: Cytochrome P450-Structure, Mechanism, and Biochemistry. Ortiz-de-Montellano PR (Ed.). Kluwer Academic/Plenum Publishers NY, USA 377-530 (2005).
2. Bernhardt R. Cytochrome P-450. In: Encyclopedia of Biological Chemistry. Lennarz W, Lane M, Modrich P, Dixon J, Carafoli E, Exton J, Cleveland D (Eds). Academic Press, UK 544-549 (2005).
3. Hannemann F, Bichet A, Ewen KM, Bernhardt R. Cytochrome P450 systems-biological variations of electron transport chains. Biochim. Biophys. Acta 1770(3), 330-344 (2007).
4. Meyer UA. Pharmacogenetics and adverse drug reactions. Lancet 356(9242), 1667-1671 (2000).
5. Kaufer NF, Simanis V, Nurse P. Fission yeast Schizosaccharomyces pombe correctly excises a mammalian RNA transcript intervening sequence. Nature 318(6041), 78-80 (1985).
6. Russell P, Nurse P. Schizosaccharomyces pombe and Saccharomyces cerevisiae: a look at yeasts divided. Cell 45(6), 781-782 (1986).
7. Jones RH, Moreno S, Nurse P, Jones NC. Expression of the SV40 promoter in fssion yeast: identifcation and characterization of an AP-1-like factor. Cell 53(4), 659-667 (1988).
8. Brys R, Nelles L, van der SE, Silvestre N, Huylebroeck D, Remacle JE. Identical cis-acting elements and related trans-acting factors control activity of nonviral promoter in Schizosaccharomyces pombe and mammalian cells. DNA Cell Biol. 17(4), 349-358 (1998).
9. Giga-Hama Y, Kumagai H. Expression system for foreign genes using the fssion yeast Schizosaccharomyces pombe. Biotechnol. Appl. Biochem. 30 (Pt 3), 235-244 (1999).
10. Yun CH, Yim SK, Kim DH, Ahn T. Functional expression of human cytochrome P450 enzymes in Escherichia coli. Curr. Drug Metab. 7(4), 411-429 (2006).
11. Wood V, Gwilliam R, Rajandream MA et al. The genome sequence of Schizosaccharomyces pombe. Nature 415(6874), 871-880 (2002).
12. Alfa C, Fantes P, Hyams J, McLeod M, Warbrick E. Experiments with Fission Yeast. A Laboratory Course Manual. Cold Spring Harbor Press, NY, USA (1993).
13. Dragan CA, Zearo S, Hannemann F, Bernhardt R, Bureik M. Effcient conversion of 11-deoxycortisol to cortisol (hydrocortisone) by recombinant fssion yeast Schizosaccharomyces pombe. FEMS Yeast Res. 5(6-7), 621-625 (2005).
14. Bureik M, Hubel K, Dragan CA et al. 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 fbrosis and hypertension. Mol. Cell Endocrinol. 217(1-2), 249-254 (2004).
15. Bureik M, Schiffer B, Hiraoka Y, Vogel F, Bernhardt R. Functional expression of human mitochondrial CYP11B2 in fssion yeast and identifcation of a new internal electron transfer protein, etp1. Biochemistry 41(7), 2311-2321 (2002).
16. 50 values of anti-prostate tumor drugs acting on CYP21. J. Enzyme Inhib. Med. Chem. 21(5), 547-556 (2006).
17. Yasumori T. Expression of a human cytochrome P450 form in Schizosaccharomyces pombe: comparison with expression in Saccharomyces cerevisiae. In: Foreign Gene Expression in Fission Yeast Schizosaccharomyces pombe. Giga-Hama Y, Kumagai H (Eds). Springer-Verlag, Berlin, Germany 111-121 (1997).
18. Takanashi K, Tainaka H, Kobayashi K, Yasumori T, Hosakawa M, Chiba K. CYP2C9 Ile359 and Leu359 variants: enzyme kinetic study with seven substrates. Pharmacogenetics 10(2), 95-104 (2000).
19. Zoellner A, Dragan CA, Pistorius D et al. Human CYP4Z1 catalyzes the in-chain hydroxylation of lauric acid and myristic acid. Biol. Chem. 390(4), 313-317 (2009).
20. Yamazaki S, Sato K, Suhara K, Sakaguchi M, Mihara K, Omura T. Importance of the proline-rich region following signal-anchor sequence in the formation of correct conformation of microsomal cytochrome P-450s. J. Biochem. 114(5), 652-657 (1993).
21. Yasumori T, Chen LS, Li QH et al. Human CYP2C-mediated stereoselective phenytoin hydroxylation in Japanese: difference in chiral preference of CYP2C9 and CYP2C19. Biochem. Pharmacol. 57(11), 1297-1303 (1999).
22. Dragan CA, Blank LM, Bureik M. Increased TCA cycle activity and reduced oxygen consumption during cytochrome P450-dependent biotransformation in fssion yeast. Yeast 23(11), 779-794 (2006).
23. Peters FT, Dragan CA, Wilde DR et al. Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fssion yeast exemplifed for the designer drug metabolite 4́-hydroxymethyl-a- pyrrolidinobutyrophenone. Biochem. Pharmacol. 74(3), 511-520 (2007).
24. Peters F T, Dragan CA, Kauffels A et al. Biotechnological synthesis of the designer drug metabolite 4́-hydroxymethyl-a-pyrrolidinohexanophenone in fssion yeast heterologously expressing human cytochrome P4502D6- A versatile alternative to multi-step chemical synthesis. J. Anal. Toxicol. 33(4), 190-197 (2009).
25. Peters F T, Dragan CA, Schwaninger AE et al. Use of fssion yeast heterologously expressing human cytochrome P450 2B6 in biotechnological synthesis of the designer drug metabolite 2-[(1-phenylcyclohexyl) amino]ethanol. Forensic Sci. Int. 184(1-3), 69-73 (2009).
26. Roesner P, Junge T, Fritschi G, Klein B, Thielert K, Kozlowski M. Neue synthetische drogen: piperazin-, procyclidin-und a-aminopropiophenonderivate. Toxichem. Krimtech 66(2), 81-90 (1999).
27. Peters F T, Meyer MR, Fritschi G, Maurer HH. Studies on the metabolism and toxicological detection of the new designer drug 4́-methyl-a- pyrrolidinobutyrophenone (MPBP) in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 824(1-2), 81-91 (2005).
28. Springer D, Peters FT, Fritschi G, Maurer HH. New designer drug 4́-methyl-a-pyrrolidinohexanophenone: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 789(1) 79-91 (2003).
29. Gorelick DA, Balster RL. Phencyclidine (PCP). In: Psychopharmacology: the Fourth Generation of Progress. Bloom FE, Kupfer DJ (Ed.). Raven Press, NY, USA 1767-1776 (1995).
30. Abraham HD, McCann UD, Ricaurte GA. Psychedelic Drugs. In: Neuropsychopharmacology: the Fifth Generation of Progress. Davis KL, Charney D, Coyle JT, Nemeroff C (Eds). Lippincott Williams & Wilkins, PA, USA 1545-1556 (2002).
31. Haerer M, Kovar KA. [Designer drugs-the phencyclidine series]. Pharm. Unserer Zeit 23(1), 52-61 (1994).
32. Sauer C, Peters FT, Staack RF, Fritschi G, Maurer HH. New designer drugs N-(1-phenylcyclohexyl)-2-ethoxyethanamine (PCEEA) and N-(1-phenylcyclohexyl)-2- methoxyethanamine (PCMEA): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom. 43(3), 305-316 (2008).
33. Sauer C, Peters FT, Schwaninger AE, Meyer MR, Maurer HH. Investigations on the cytochrome P450 (CYP) isoenzymes involved in the metabolism of the designer drugs N-(1-phenylcyclohexyl)-2-ethoxyethanamine and N-(1-phenylcyclohexyl)-2-methoxyethanamine. Biochem. Pharmacol. 77(3), 444-450 (2009).
34. Cheng J, Wan DF, Gu JR et al. Establishment of a yeast system that stably expresses human cytochrome P450 reductase: application for the study of drug metabolism of cytochrome P450s in vitro. Protein Expr. Purif. 47(2), 467-476 (2006).
35. Dietrich M, Grundmann L, Kurr K et al. Recombinant production of human microsomal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris. Chembiochem 6(11), 2014-2022 (2005).
36. Hayashi K, Sakaki T, Kominami S, Inouye K, Yabusaki Y. Coexpression of genetically engineered fused enzyme between yeast NADPH-P450 reductase and human cytochrome P450 3A4 and human cytochrome b5 in yeast. Arch. Biochem. Biophys. 381(1), 164-170 (2000).
37. Truan G, Cullin C, Reisdorf P, Urban P, Pompon D. Enhanced in vivo monooxygenase activities of mammalian P450s in engineered yeast cells producing high levels of NADPH-P450 reductase and human cytochrome b5. Gene 125(1), 49-55 (1993).
38. Michaelis W, Russel JH, Schindler O. The metabolism of pyrovalerone hydrochloride. J. Med. Chem. 13(3), 497-503 (1970).
39. Maddox VH, Godefroi EF, Parcell RF. Synthesis of phencyclidine and other 1-arylcyclohexylamines. J. Med. Chem. 8(2), 230-235 (1965).
40. Kang YS, Park SY, Yim CH et al. The CYP3A4*18 genotype in the cytochrome P450 3A4 gene, a rapid metabolizer of sex steroids, is associated with low bone mineral density. Clin. Pharmacol. Ther. 85(3), 312-318 (2009).
41. Kirchheiner J, Klein C, Meineke I et al. Bupropion and 4-OH-bupropion pharmacokinetics in relation to genetic polymorphisms in CYP2B6. Pharmacogenetics 13(10), 619-626 (2003).
42. Rodriguez-Antona C, Jande M, Rane A, Ingelman-Sundberg M. Identifcation and phenotype characterization of two CYP3A haplotypes causing different enzymatic capacity in fetal livers. Clin. Pharmacol. Ther. 77(4), 259-270 (2005).
43. Dai D, Tang J, Rose R et al. Identifcation of variants of CYP3A4 and characterization of their abilities to metabolize testosterone and chlorpyrifos. J. Pharmacol. Exp. Ther. 299(3), 825-831 (2001).
44. Scollon EJ, Starr JM, Godin SJ, DeVito MJ, Hughes MF. In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. Drug Metab. Dispos. 37(1), 221-228 (2009).
45. Godin SJ, Crow JA, Scollon EJ, Hughes MF, DeVito MJ, Ross MK. Identifcation of rat and human cytochrome p450 isoforms and a rat serum esterase that metabolize the pyrethroid insecticides deltamethrin and esfenvalerate. Drug Metab. Dispos. 35(9), 1664-1671 (2007).
46. Gillam EM. Engineering cytochrome p450 enzymes. Chem. Res. Toxicol. 21(1), 220-231 (2008).
47. Gillam EM. Extending the capabilities of nature's most versatile catalysts: directed evolution of mammalian xenobiotic-metabolizing P450s. Arch. Biochem. Biophys. 464(2), 176-186 (2007).