High-Throughput Functional Screening of Steroid Substrates with Wild-Type and Chimeric P450 Enzymes

BioMed Research International

Volumn 2014, Issue , 2014, Pages

  Urban, Philippe ^a,b,c   Truan, Gilles ^a,b,c   Pompon, Denis ^a,b,c  

^a UNIVERSITÉ DE TOULOUSE   (France)

^b UMR792 INGÉNIERIE DES SYSTÈMES BIOLOGIQUES ET DES PROCÉDÉS   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 1A; STEROID; CYTOCHROME P450; HYBRID PROTEIN; MIFEPRISTONE; NOOTKATONE; SESQUITERPENE;

ARTICLE; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME STRUCTURE; HIGH THROUGHPUT SCREENING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; STEREOCHEMISTRY; STEROID METABOLISM; WILD TYPE; AMINO ACID SEQUENCE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; METABOLISM; MICROSOME; MOLECULAR GENETICS; PROCEDURES; SACCHAROMYCES CEREVISIAE; SEQUENCE ALIGNMENT;

AMINO ACID SEQUENCE; CYTOCHROME P-450 ENZYME SYSTEM; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; MICROSOMES; MIFEPRISTONE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; RECOMBINANT FUSION PROTEINS; SACCHAROMYCES CEREVISIAE; SEQUENCE ALIGNMENT; SESQUITERPENES; STEROIDS; SUBSTRATE SPECIFICITY;

EID: 84921298433     PISSN: 23146133     EISSN: 23146141     Source Type: Journal    
DOI: 10.1155/2014/764102     Document Type: Article

References (34)

1. M. J. Coon, "Cytochrome P450: natures most versatile biological catalyst, " Annual Review of Pharmacology and Toxicology, vol. 45, pp. 1-25, 2005.
2. D. C. Lamb, M. R. Waterman, S. L. Kelly, and F. P. Guengerich, "Cytochromes P450 and drug discovery, " Current Opinion in Biotechnology, vol. 18, no. 6, pp. 504-512, 2007.
3. F. P. Guengerich, "Cytochrome P450 and chemical toxicology, " Chemical Research in Toxicology, vol. 21, no. 1, pp. 70-83, 2008.
4. J. McGraw and D. Waller, "Cytochrome P450 variations in different ethnic populations, " Expert Opinion on DrugMetabolism and Toxicology, vol. 8, no. 3, pp. 371-382, 2012.
5. D. J. Waxman, "Regulation of liver-specific steroidmetabolizing cytochromes P450: cholesterol 7α-hydroxylase, bile acid 6β-hydroxylase, and growth hormone-responsive steroid hormone hydroxylases, " Journal of Steroid Biochemistry and Molecular Biology, vol. 43, no. 8, pp. 1055-1072, 1992.
6. D. J. Waxman, C. Attisano, F. P. Guengerich, andD. P. Lapenson, "Human liver microsomal steroid metabolism: identification of the major microsomal steroid hormone 6β-hydroxylase cytochrome P-450 enzyme, " Archives of Biochemistry and Biophysics, vol. 263, no. 2, pp. 424-436, 1988.
7. F. P. Guengerich, "Oxidation of 17β-ethynylestradiol by human liver cytochrome P-450, " Molecular Pharmacology, vol. 33, no. 5, pp. 500-508, 1988.
8. H. Yamazaki and T. Shimada, "Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes, " Archives of Biochemistry and Biophysics, vol. 346, no. 1, pp. 161-169, 1997.
9. P. Urban, G. Truan, and D. Pompon, "High-througput enzymology and combinatorialmutagenesis for mining cytochrome P450 functions, " Expert Opinion on Drug Metabolism and Toxicology, vol. 4, no. 6, pp. 733-747, 2008.
10. S. Sansen, J. K. Yano, R. L. Reynald et al., "Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2, " The Journal of Biological Chemistry, vol. 282, no. 19, pp. 14348-14355, 2007.
11. A. A. Walsh, G. D. Szklarz, and E. E. Scott, "Human cytochrome P450 1A1 structure and utility in understanding drug and xenobiotic metabolism, " The Journal of Biological Chemistry, vol. 288, no. 18, pp. 12932-12943, 2013.
12. J. Gautier, S. Lecoeur, J. Cosme et al., "Contribution of human cytochrome P450 to benzo a]pyrene and benzo a]pyrene-7, 8-dihydrodiol metabolism, as predicted from heterologous expression in yeast, " Pharmacogenetics, vol. 6, no. 6, pp. 489-499, 1996.
13. D. Pompon, "cDNA cloning and functional expression in yeast Saccharomyces cerevisiae of β-naphthoflavone-induced rabbit liver P-450 LM4 and LM6, " European Journal of Biochemistry, vol. 177, no. 2, pp. 285-293, 1988.
14. D. Pompon, B. Louerat, A. Bronine, and P. Urban, "Yeast expression of animal and plant P450s in optimized redox environments, " Methods in Enzymology, vol. 272, pp. 51-64, 1996.
15. D. Pompon and A. Nicolas, "Protein engineering by cDNA recombination in yeasts: shuffling of mammalian cytochrome P-450 functions, " Gene, vol. 83, no. 1, pp. 15-24, 1989.
16. V. Abecassis, D. Pompon, and G. Truan, "High efficiency family shuffling based on multi-step PCR and in vivo DNA recombination in yeast: statistical and functional analysis of a combinatorial library between human cytochrome P450 1A1 and 1A2, " Nucleic Acids Research, vol. 28, no. 20, p. E88, 2000.
17. H. Hotelling, "Analysis of a complex of statistical variables into principal components, " Journal of Educational Psychology, vol. 24, no. 6, pp. 417-441, 1933.
18. W. S. Torgerson, Theory andMethods of Scaling, Academic Press, New York, NY, USA, 1958.
19. D. E. Almonacid and P. C. Babbitt, "Toward mechanistic classification of enzyme functions, " Current Opinion in Chemical Biology, vol. 15, no. 3, pp. 435-442, 2011.
20. M. Landwehr, M. Carbone, C. R. Otey, Y. Li, and F. H. Arnold, "Diversification of catalytic function in a synthetic family of chimeric cytochrome P450s, " Chemistry and Biology, vol. 14, no. 3, pp. 269-278, 2007.
21. R. A. Fisher, "The correlation between relatives on the supposition ofMendelian inheritance, " Transactions of the Royal Society of Edinburgh, vol. 52, no. 2, pp. 399-433, 1919.
22. V. Cojocaru, P. J. Winn, and R. C. Wade, "The ins and outs of cytochrome P450s, " Biochimica et Biophysica Acta, vol. 1770, no. 3, pp. 390-401, 2007.
23. L. Nikfarjam, S. Izumi, T. Yamazaki, and S. Kominami, "The interaction of cytochrome P450 17α with NADPH-cytochrome P450 reductase, investigated using chemical modification and MALDI-TOF mass spectrometry, " Biochimica et Biophysica Acta, vol. 1764, no. 6, pp. 1126-1131, 2006.
24. O. Gotoh, "Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences, " The Journal of Biological Chemistry, vol. 267, no. 1, pp. 83-90, 1992.
25. A. Parikh, P. D. Josephy, and F. P. Guengerich, "Selection and characterization of human cytochrome P450 1A2 mutants with altered catalytic properties, " Biochemistry, vol. 38, no. 17, pp. 5283-5289, 1999.
26. C.-H. Yun, G. P. Miller, and F. P. Guengerich, "Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants, " Biochemistry, vol. 39, no. 37, pp. 11319-11329, 2000.
27. D. Kim and F. P. Guengerich, "Selection of human cytochrome P450 1A2 mutants with enhanced catalytic activity for heterocyclic amine N-hydroxylation, " Biochemistry, vol. 43, no. 4, pp. 981-988, 2004.
28. J. Liu, S. S. Ericksen, M. Sivaneri, D. Besspiata, C. W. Fisher, and G. D. Szklarz, "The effect of reciprocal active sitemutations in human cytochromes P450 1A1 and 1A2 on alkoxyresorufin metabolism, " Archives of Biochemistry and Biophysics, vol. 424, no. 1, pp. 33-43, 2004.
29. I. F. Sevrioukova and T. L. Poulos, "Dissecting cytochrome P450 3A4-ligand interactions using ritonavir analogues, " Biochemistry, vol. 52, no. 26, pp. 4474-4481, 2013.
30. H. Yamazaki, M. Nakano, Y. Imai, Y. Ueng, F. P. Guengerich, and T. Shimada, "Roles of cytochrome b5 in the oxidation of testosterone and nifedipine by recombinant cytochrome P450 3A4 and by human liver microsomes, " Archives of Biochemistry and Biophysics, vol. 325, no. 2, pp. 174-182, 1996.
31. H. Yamazaki and T. Shimada, "Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 34 in human liver microsomes, " Archives of Biochemistry and Biophysics, vol. 346, no. 1, pp. 161-169, 1997.
32. Q. Ma and A. Y. H. Lu, "CYP1A induction and human risk assessment: an evolving tale of in vitro and in vivo studies, " Drug Metabolism and Disposition, vol. 35, no. 7, pp. 1009-1016, 2007.
33. M. Lewinska, U. Zelenko, F. Merzel, S. Golic Grdadolnik, J. C. Murray, and D. Rozman, "Polymorphisms of CYP51A1 from cholesterol synthesis: associations with bird weight and maternal lipid levels and impact on CYP51 protein structure, " PLoS ONE, vol. 8, no. 12, Article IDe82554, 2013.
34. L. N. Ma, Z. Z. Du, P. Lian, andD. Q. Wei, "Atheoretical studyon the mechanism of a superficial mutation inhibiting the enzyme activity of CYP1A2, " Interdisciplinary Sciences: Computational Life Sciences, vol. 6, no. 1, pp. 25-31, 2013.