Recombinant Yeast and Bacteria that Express Human P450s: Bioreactors for Drug Discovery, Development, and Biotechnology

Modern Biooxidation: Enzymes, Reactions and Applications

Volumn , Issue , 2007, Pages 233-252

  Hanlon, Steven P ^a   Friedberg, Thomas ^b   Wolf, C Roland ^b   Ghisalba, Oreste ^c   Kittelmann, Matthias ^c  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b UNIVERSITY OF DUNDEE   (United Kingdom)

^c NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Bacteria expressing human P450s; Bioreactors for drug discovery; Biotechnology; Development; E. coli P450 expression systems in bioreactors; Modern biooxidation; Novartis experience; Recombinant yeast expressing human P450; Roche experience

Indexed keywords

EID: 84889489759     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527611522.ch10     Document Type: Chapter

References (45)

1. Smith, D.A. The long, hard road: drug metabolism in the lifetime of the DMDG-Comment. Xenobiotica 2001,31,459-610
2. Smith, D.A., Van De Waterbeemd, H. Pharmacokinetics and metabolism in early drug discovery. Curr Opin Chem Biol 1999,3,373-378
3. Gonzalez, F.J. Human cytochromes P450: problems and prospects. Trends Pharmacol Sci 1992,12,346-352
4. Narimatsu, S., Kobayashi, N., Masubuchi, Y., et al. Species difference in enantioselectivity for the oxidation of propranolol by cytochrome P450 2D enzymes. Chem Biol Interact 2000,127,73-90
5. LeCluyse, E.L., Bullock, P.L., Parkinson, A. Strategies for restoration and maintenance of normal hepatic structure and function in long-term cultures of rat hepatocytes. Adv Drug Delivery Rev 1996,22,133-186
6. Maurel P. The use of adult human hepatocytes in primary culture and other in vitro systems to investigate drugmetabolism in man. Adv Drug Delivery Rev 1996,22,105-132
7. Oesch, F., Waxman, D.J., Morrissey, J.J., Honscha, W., Kissel, W., Friedberg, T. Antibodies targeted against hypervariable and constant regions of cytochromes P450IIB1 and P450IIB2. Arch Biochem Biophys 1989,270,23-32
8. DeLozier, T.C., Lee, S.C., Coulter, S.J., Goh, B.C., Goldstein, J.A. Functional characterization of novel allelic variants of CYP2C9 recently discovered in southeast Asians. J Pharmacol Exp Ther 2005,315,1085-1090
9. Fukami, T., Nakajima, M., Higashi, E., et al. Characterization of novel CYP2A6 polymorphic alleles (CYP2A6*18 and CYP2A6*19) that affect enzymatic activity. Drug Metab Dispos 2005,33,1202-1210
10. Wolf, C.R., Smith, G. Pharmacogenetics. Br Med Bull 1999,55,366-386
11. Li, D.N., Seidel, A., Pritchard, M.P., Wolf, C.R., Friedberg, T. Polymorphisms in P450CYP1B1 affect the conversion of estradiol to the potentially carcinogenic metabolite 4-hydroxyestradiol. Pharmacogenetics 2000, 10, 343-353.
12. Brown, S.J., Ward, C.J., Yu, J., Paine, M., Wolf, C.R., Rankin, E.M. In vitro prediction of cytochrome P450 mediated interactions between chemotherapeutic drugs and common co-medications. Br J Cancer 2004, 91, S59.
13. Paine, M.J.I., McLaughlin, L.A., Flanagan, J.U., et al. Residues glutamate 216 and aspartate 301 are key determinants of substrate specificity and product regioselectivity in cytochrome p450 2D6. J Biol Chem 2003,278,4021-4010
14. He, Y.A., Roussel, F., Halpert, J.R. Analysis of homotropic and heterotropic cooperativity of diazepam oxidation by CYP3A4 using site-directed mutagenesis and kinetic modeling. Arch Biochem Biophys 2003,409,92-101
15. Williams, P.A., Cosme, J., Ward, A., Angova, H.C., Vinkovic, D.M., Jhoti, H. Crystal structure of human cytochrome P4502C9 with bound warfarin. Nature 2003,424,464-468
16. Kemp, C.A., Flanagan, J.U., Van Eldik, A.J., et al. Validation of model of cytochrome p450 2D6, An in silico tool for predicting metabolism and inhibition. J Med Chem 2004,47,5340-5346
17. Friedberg, T., Pritchard, M.P., Bandera, M., et al. Merits and limitations of recombinant models for the study of human P450-mediated drug metabolism and toxicity: An intralaboratory comparison. Drug Metab Rev 1999,31,523-544
18. Guengerich, F.P. Cytochrome P450 enzymes in the generation of commercial products. Nat Rev Drug Discov 2002,1,359-566
19. Smith, D.A., Obach, R.S. Seeing through the mist: Abundance versus percentage. Commentary on Metabolites in safety testing. Drug Metab Dispos 2005,33,1409-1110
20. Gold, L. Expression of heterologous proteins in Escherichia coli. In: Goeddel, D.V., ed. Methods in Enzymology. San Diego: Academic Press, 1990, pp. 11-310.
21. Blake, J.A.R., Pritchard, M., Ding, S., et al. Coexpression of a human P450 (CYP3A4) and P450 reductase generates a highly functional monooxygenase system in Escherichia coli. FEBS Lett 1996,397,210-214
22. Pritchard, M.P., Glancey, M.J., Blake, J.A.R., et al. Functional coexpression of CYP2D6 and human cytochrome P450 reductase in Escherichia coli. Pharmacogenetics 1998,8,33-42
23. Pritchard, M.P., Ossetian, R., Li, D.N., et al. A general strategy for the expression of recombinant human cytochrome P450s in Escherichia coli using bacterial signal peptides: Expression of CYP3A4, CYP2A6, and CYP2E1. Arch Biochem Biophys 1997,345,342-354
24. Pritchard, M.P., McLaughlin, L.A., Friedberg, T. Establishment of functional human cytochrome P450 monooxygenase systems in Escherichia coli. In: Phillips, I. R., Shephard, E.A., eds. Cytochrome P450 Protocols. Totowa, NJ: Humana Press, 2006, pp. 19-29
25. Campbell, I., Duffus, J.H., eds. Yeast: A Practical Approach. Washington: IRL Press, 1988.
26. Emr, S.D. Heterologous gene expression in yeast. In: Goeddel, D.V., ed. Methods in Enzymology. San Diego: Academic Press, 1990, pp. 231-279
27. Urban, P., Truan, G., Bellamine, A., Laine, R., Gautier, J.C., Pompon, D. Engineered yeast simulating P450- dependent metabolism: Tricks, myths and reality. In: Kingsley N, ed. Drug Metabolism and Interactions. London: Freund Publishing, 1994, pp. 169-200
28. Shkumatov, V.M., Usova, E.V., Radyuk, V.G., et al. Oxidation of 17 alpha,20 beta- and 17 alpha,20 alphadihydroxypregn- 4-en-3-ones, side products of progesterone biotransformation with recombinant microorganisms expressing cytochrome P-45017 alpha. Russian J Bioorg Chem 2003,29,581-610
29. Nthangeni, M.B., Urban, P., Pompon, D., Smit, M.S., Nicaud, J.M. The use of Yarrowia lipolytica for the expression of human cytochrome P450CYP1A1. Yeast 2004,21,583-592
30. Dietrich, M., Grundmann, L., Kurr, K., et al. Recombinant production of human microsomal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris. Chembiochem 2005,6,2014-2022
31. Cullin, C., Pompon, D. Synthesis of functional cytochromes P450 P1 and chimeric P-450 P3-1 in the yeast Saccharomyces cerevisiae. Gene 1988,65,203-210
32. Bligh, H.F.J., Wolf, C.R., Smith, G., Beggs, J.D. Production of cytochrome P450 reductase yeast-rat hybrid proteins in Saccharomyces cerevisiae. Gene 1992,110,33-39
33. Pompon, D., Louerat, B., Bronine, A., Urban, P. Yeast expression of animal and plant P450s in optimized redox environments. In: Johnson, E.F., Waterman, M.R., eds. Methods in Enzymology. San Diego: Academic Press, 1996. pp. 51-64
34. Paine, M.J.I., Gilham, D., Roberts, G.C.K., Wolf, C.R. Functional high-level expression of cytochrome-P450 CYP2D6 using baculoviral expression systems. Arch Biochem Biophys 1996,328,143-150
35. Yamazaki, H., Guo, Z., Persmark, M. et al. Bufuralol hydroxylation by cytochrome P450 2D6 and 1A2 enzymes in human liver microsomes. Mol Pharmacol 1994,46,568-710
36. Lee, C.A., Kadwell, S.H., Kost, T.A., Serabjit-Singh, C.J. CYP3A4 expressed by insect cells infected with a recombinant baculovirus containing both CYP3A4 and human NADPH-cytochrome P450 reductase is catalytically similar to human liver microsomal CYP3A4. Arch Biochem Biophys 1995,319,157-610
37. Renaud, J.P., Peyronneau, M.A., Urban, P., et al. Recombinant yeast in drug-metabolism. Toxicology 1993,82,39-52
38. Voice, M.W., Zhang, Y., Wolf, C.R., Burchell, B., Friedberg, T. Effects of human cytochrome b(5) on CYP3A4 activity and stability in vivo. Arch Biochem Biophys 1999,366,116-124
39. Shimada, T., Yamazaki, H., Mimura, M., Inui, Y., Guengerich, F.P. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 1994,270,414-423
40. McGinnty, D., Griffine, S.J., Moody, G.C., et al. Rapid characterization of the major drug-metabolizing human hepatic cytochrome P450 enzymes expressed in E. coli. Drug Metab Dispos 1999,27,1017-1023
41. Weaver, R., Graham, K.S., Beattie, I.G., Riley, R.J. Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation. Drug Metab Dispos 2003,31,955-966
42. Vail, R.B., Homann, M.J., Hanna, I., Zaks, A. Preparative synthesis of drug metabolites using human cytochrome P450s 3A4, 2C9 and 1A2 with NADPHP450 reductase expressed in Escherichiacoli. J Indust Microbiol Biotechnol 2005,32,67-74
43. Shimada, T., Yamazaki, H., Mimura, M., Inui, Y., Guengerich, F.P. Interindividual veriations in human liver cytochrome P450 systems involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 1994,270,414-423
44. Barnes, H.J., Arlotto, M.F., Waterman, M.R. Expression and enzymatic activity of recombinant cytochrome P450 17α-hydroxylase in Escherichia coli. Proc Natl Acad Sci USA 1991,88,5597-5601
45. Cox, K.A., Clarke, N.J., Rindgen, N.J., Korfmacher, W.A. Higher throughput metabolite identifcation in drug discovery. Am Pharm Rev 2001,4,45-52