Generation of human metabolites of 7-ethoxycoumarin by bacterial cytochrome P450 BM3

Drug Metabolism and Disposition

Volumn 36, Issue 11, 2008, Pages 2166-2170

  Kim, Dong Hyun ^a   Kim, Keon Hee ^a   Kim, Dae Hwan ^a   Liu, Kwang Hyeon ^b   Jung, Heung Chae ^c   Pan, Jae Gu ^c   Yun, Chul Ho ^a  

^a Chonnam National University   (South Korea)

^b Inje University College of Medicine   (South Korea)

^c Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHOXYCOUMARIN; CYTOCHROME P450 BM3;

ARTICLE; CATALYSIS; DRUG HYDROXYLATION; DRUG OXIDATION; ENZYME ACTIVITY; ENZYME KINETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROGEN BOND; NONHUMAN; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS;

BACTERIAL PROTEINS; COUMARINS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; MUTATION; NADPH-FERRIHEMOPROTEIN REDUCTASE; SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS);

EID: 54349095608     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.021220     Document Type: Article

References (27)

1. Bernhardt R (2006) Cytochromes P450 as versatile biocatalysts. J Biotechnol 124:128-145.
2. Carmichael AB and Wong LL (2001) Protein engineering of Bacillus megaterium CYP102: the oxidation of polycyclic aromatic hydrocarbons. Eur J Biochem 268:3117-3125.
3. Di Nardo G, Fantuzzi A, Sideri A, Panicco P, Sassone C, Giunta C, and Gilardi G (2007) Wild-type CYP102A1 as a biocatalyst: turnover of drugs usually metabolised by human liver enzymes. J Biol Inorg Chem 12:313-323.
4. Farinas ET, Schwaneberg U, Glieder A, and Arnold FH (2001) Directed evolution of a cytochrome P450 monooxygenase for alkane oxidation. Adv Synth Catal 343:601-606.
5. Guengerich FP (2002a) Cytochrome P450 enzymes in the generation of commercial products. Nat Rev Drug Discov 1:359-366.
6. Guengerich FP (2002b) Rate-limiting steps in cytochrome P450 catalysis. Biol Chem 383:1553-1564.
7. Harada N, Miwa GT, Walsh JS, and Lu AYH (1984) Kinetic isotope effects on cytochrome P-450-catalyzed oxidation reactions: evidence for the irreversible formation of an activated oxygen intermediate of cytochrome P-448. J Biol Chem 259:3005-3010.
8. Hussain HA and Ward JM (2003) Enhanced heterologous expression of two Streptomyces griseolus cytochrome P450s and Streptomyces coelicolor ferredoxin reductase as potentially efficient hydroxylation catalysts. Appl Environ Microbiol 69:373-382.
9. Keizers PH, Schraven LH, de Graaf C, Hidestrand M, Ingelman-Sundberg M, van Dijk BR, Vermeulen NP, and Commandeur JN (2005) Role of the conserved threonine 309 in mechanism of oxidation by cytochrome P450 2D6. Biochem Biophys Res Commun 338:1065-1074.
10. Kim KH, Isin EM, Yun CH, Kim DH, and Guengerich FP (2006) Kinetic deuterium isotope effects for 7-alkoxycoumarin O-dealkylation reactions catalyzed by human cytochromes P450 and in liver microsomes: rate-limiting C-H bond breaking in cytochrome P450 1A2 substrate oxidation. FEBS J 273:2223-2231.
11. Lamb DC, Waterman MR, Kelly SL, and Guengerich FP (2007) Cytochromes P450 and drug discovery. Curr Opin Biotechnol 18:504-512.
12. Landwehr M, Hochrein L, Otey CR, Kasrayan A, Bäckvall JE, and Arnold FH (2006) Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3. J Am Chem Soc 128:6058-6059.
13. Li QS, Ogawa J, Schmid RD, and Shimizu S (2001) Engineering cytochrome P450 BM-3 for oxidation of polycyclic aromatic hydrocarbons. Appl Environ Microbiol 67:5735-5739.
14. Miwa GT, Walsh JS, and Lu AYH (1984) Kinetic isotope effects on cytochrome P-450-catalyzed oxidation reactions: the oxidative O-dealkylation of 7-ethoxycoumarin. J Biol Chem 259:3000-3004.
15. Munro AW, Leys DG, McLean KJ, Marshall KR, Ost TW, Daff S, Miles CS, Chapman SK, Lysek DA, Moser CC, et al. (2002) P450 BM3: the very model of a modern flavocytochrome. Trends Biochem Sci 27:250-257.
16. Narhi LO and Fulco AJ (1986) Characterization of a catalytically self-sufficient cytochrome P-450 monooxygenase induced by barbiturates in. Bacillus megaterium. J Biol Chem 261:7160-7169.
17. Narhi LO and Fulco AJ (1982) Phenobarbital induction of a soluble cytochrome P-450-dependent fatty acid monooxygenase in Bacillus megaterium. J Biol Chem 257:2147-2150.
18. Northrop DB (1975) Steady-state analysis of kinetic isotope effects in enzymic reactions. Biochemistry 14:2644-2651.
19. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J Biol Chem 239:2379-2385.
20. Otey CR, Bandara G, Lalonde J, Takahashi K, and Arnold FH (2006) Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochrome P450. Biotechnol Bioeng 93:494-499.
21. Ueno M, Yamashita M, Hashimoto M, Hino M, and Fujie A (2005) Oxidative activities of heterologously expressed CYP107B1 and CYP105D1 in whole-cell biotransformation using Streptomyces lividans TK24. J Biosci Bioeng 100:567-572.
22. Urlacher VB and Eiben S (2006) Cytochrome P450 monooxygenases: perspectives for synthetic application. Trends Biotechnol 24:324-330.
23. van Vugt-Lussenburg BM, Damsten MC, Maasdijk DM, Vermeulen NP, and Commandeur JN (2006) Heterotropic and homotropic cooperativity by a drug-metabolising mutant of cytochrome P450 BM3. Biochem Biophys Res Commun 346:810-818.
24. van Vugt-Lussenburg BM, Stjernschantz E, Lastdrager J, Oostenbrink C, Vermeulen NP, and Commandeur JN (2007) Identification of critical residues in novel drug metabolizing mutants of cytochrome P450 BM3 using random mutagenesis. J Med Chem 50:455-461.
25. Yun CH, Kim KH, Calcutt MW, and Guengerich FP (2005) Kinetic analysis of oxidation of coumarins by human cytochrome P450 2A6. J Biol Chem 280:12279-12291.
26. Yun CH, Kim KH, Kim DH, Jung HC, and Pan JG (2007) The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol 25:289-298.
27. Yun CH, Miller GP, and Guengerich FP (2000) Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants. Biochemistry 39:11319-11329.