Catalytic properties of an expressed cytochrome P450 2B1 from a Wistar- Kyoto rat liver cDNA library

Drug Metabolism and Disposition

Volumn 26, Issue 10, 1998, Pages 1026-1030

  Kobayashi, Yasuna ^a   Strobel, Sharon M ^b   Hopkins, Nancy Eddy ^c   Alworth, William L ^c   Halpert, James R ^c  

^a SHOWA UNIVERSITY   (Japan)

^b University of Texas Medical Branch School of Medicine   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHOXYCOUMARIN DEETHYLASE; 9 ETHYNYLPHENANTHRENE; ACETAMIDE DERIVATIVE; ALANINE; ANDROSTENEDIONE; CHLORAMPHENICOL; COMPLEMENTARY DNA; CYTOCHROME P450 INHIBITOR; CYTOCHROME P450 ISOENZYME; ETHOXYCOUMARIN; GLUTAMIC ACID; LYSINE; N [2 (4 NITRO)PHENETHYL]CHLOROFLUOROACETAMIDE; PENTOXYRESORUFIN DEALKYLASE; PHENANTHRENE DERIVATIVE; UNCLASSIFIED DRUG; VALINE;

AMINO ACID SUBSTITUTION; ANIMAL TISSUE; ARTICLE; CATALYSIS; COMPUTER MODEL; CONTROLLED STUDY; DNA LIBRARY; DRUG METABOLISM; ENZYME ACTIVE SITE; ENZYME PURIFICATION; ESCHERICHIA COLI; LIVER; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

AMINO ACID SUBSTITUTION; ANIMALS; CATALYSIS; CYTOCHROME P-450 CYP2B1; DNA, COMPLEMENTARY; MALE; MASS SPECTROMETRY; RATS; RATS, INBRED WKY;

ANIMALIA; ESCHERICHIA COLI; TRIXIS;

EID: 0031724344     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Aoyama T, Korzekwa K, Nagata K, Adesnik M, Reiss A, Lapenson DP, Gillette J, Gelboin HV, Waxman DJ and Gonzalez FJ (1989) Sequence requirements for cytochrome P-450IIB1 catalytic activity: Alteration of the stereospecificity and regioselectivity of steroid hydroxylation by a simultaneous change of two hydrophobic amino acid residues to phenylalanine. J Biol Chem 264:21327-21333.
2. Fang X, Kobayashi Y and Halpert JR (1997) Stoichiometry of 7-ethoxycoumarin metabolism by cytochrome P450 2B1 wild-type and five active-site mutants. FEBS Lett 426:77-80.
3. Foroozesh M, Primrose G, Guo Z, Bell LC, Alworth WL and Guengerich FP (1997) Aryl acetylene as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes. Chem Res Toxicol 10:91-102.
4. Fujii-Kuriyama Y, Mizukami Y, Kawajiri K, Sogawa K and Muramatsu M (1982) Primary structure of a cytochrome P-450: Coding nucleotide sequence of phenobarbital-inducible cytochrome P-450 cDNA from rat liver. Proc Natl Acad Sci USA 79:2793-2797.
5. Gotoh O (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J Biol Chem 267:83-90.
6. Grimm SW, Bend JR and Halpert JR (1995) Selectivity and kinetics of inactivation of rabbit hepatic cytochromes P450 2B4 and 2B5 by N-aralkylated derivatives of 1-aminobenzotriazole. Drug Metab Dispos 23:577-583.
7. Grimm SW, Dyroff MC, Philpot RM and Halpert JR (1994) Catalytic selectivity and mechanism-based inactivation of stably expressed and hepatic cytochromes P450 2B4 and 2B5: implications of the cytochrome P450 2B5 polymorphism. Mol Pharmacol 46:1090-1099.
8. Hall M, Parker DK, Grover PL, Lu J-YL, Hopkins NE and Alworth WA (1990) Effects of 1-euiynylpyrene and related inhibitors of P450 isozymes upon benzo[a]pyrene metabolism by liver microsomes. Chem Biol Interact 76:181-192.
9. Halpert JR and He YA (1993) Engineering of cytochrome P450 2B1 specificity. Conversion of an androgen 16/3-hydroxylase to 15α-hydroxylase. J Biol Chem 268:4453-4457.
10. Halpert J, Jaw JY, Balfour C and Kaminsky LS (1990) Selective inactivation by chlorofluoro-acetamides of the major phenobarbital-inducible form(s) of rat liver cytochrome P-450. Drug Metab Dispos 18:168-174.
11. Halpert J, Naslund B and Betner I (1982) Suicide inactivation of rat liver cytochrome P-450 by chloramphenicol in vivo and in vitro. Mol Pharmacol 23:445-452.
12. Harlow GR and Halpert JR (1997) Alanine-scanning metagenesis of a putative substrate recognition site in human cytochrome P450 3A4. J Biol Chem 272:5396-5402.
13. He YA, Balfour CA, Kedzie KM and Halpert JR (1992) Role of residue 478 as a determinant of the substrate specificity of cytochrome P450 2B1. Biochemistry 31:9220-9226.
14. He YA, Luo Z, Klekotka PA, Burnett VL and Halpert JR (1994) Structural determinants of cytochrome P450 2B1 specificity: Evidence for five substrate recognition sites. Biochemistry 33:4419-4424.
15. He YQ, He YA and Halpert JR (1995) Escherichia coli expression of site-directed mutants of cytochrome P450 2B1 from six substrate recognition sites: Substrate specificity and inhibitor selectivity studies. Chem Res Toxicol 8:574-579.
16. Hopkins NE, Foroozesh MK and Alworth WL (1992) Suicide inhibitors, of cytochrome P450 1A1 and P450 2B1. Biochem Pharmacol 44:787-796.
17. John GH, Hasler J, He YA and Halpert JR (1994) Escherichia coli expression and characterization of cytochrome P450 2B11, 2B1 and 2B5. Arch Biochem Biophys 314:367-375.
18. Kedzie KM, Balfour CA, Escobar GY, Grimm SW, He YA, Pepperl DJ, Regan JW, Stevens JC and Halpert JR (1991) Molecular basis for a functionally unique cytochrome P450IIB1 variant. J Biol Chem 266:22515-22521.
19. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (Lond) 227:680-685.
20. Miller NE and Halpert JR (1986) Analogues of chloramphenicol as mechanism-based inactivators of rat liver cytochrome P-450: Modifications of the propendiol side chain, the p-nitro group, and the dichloromethyl moiety. Mol Pharmacol 29:391-398.
21. Mizukami Y, Sogawa K, Suwa U, Muramatsu J and Fujii-Kuriyama Y (1983) Gene structure of a phenobarbital-indudble cytochrome P-450 in rat liver. Proc Natl Acad Sci USA 80:3958-3962.
22. Nelson DR. (1995) Cytochrome P450: Structure, Mechanism, and Biochemistry (Ortiz de Montellano PR ed) 2nd ed, pp 575-606, Plenum Press, New York.
23. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. J Biol Chem 239:2379-2387.
24. Ortiz de Montellano PR and Kunze KL (1980) Self-catalylzed inactivation of hepatic cytochrome P-450 by ethynyl substrates. J Biol Chem 255:5578-5585.
25. Roberts ES, Ballou DP, Hopkins NE, Alworth WA and Hollenberg PF (1995) Mechanistic studies of 9-ethynylphenanthrene-inactivated cytochrome P450 2B1. Arch Biochem Biophys 322:303-312.
26. Robots ES, Hopkins NE, Foroozesh M, Alworth WL, Halpert JR and Hollenberg PF (1996) Inactivation of cytochrome P450s 2B1, 2B4, 2B5, 2B6 and 2B11 by arylalkynes. Drug Metab Dispos 25:1242-1248.
27. Strobel SM and Halpert JR Jr (1997) Reassessment of cytochrome P450 2B2: Catalytic specificity and identification of four active site residues. Biochemistry 36:11697-11706.
28. Szklarz GD, He YA and Halpert JR (1995) Site-directed mutagenesis as a tool for modeling of cytochrome P450 2B1. Biochemistry 34:14312-14322.
29. Szklarz GD, He YQ, Kedzie KM, Halpert JR and Burnett VL (1996) Eludidation of amino acid residues critical for unique activities of rabbit cytochrome P450 2B5 using hybrid enzymes and reciprocal site-directed mutagenesis with rabbit cytochrome P450 2B4. Arch Biochem Biophys 327:308-318.
30. 19 steroids by five highly purified and reconstituted rat hepatic cytochrome P-450 isozymes. J Biol Chem 258:8839-8847.
31. Yamano S, Nhamburo PT, Aoyama T, Meyer UA, Inaba T, Kalow W, Gelboin HB, McBride OW and Gonzalez FJ (1989) cDNA cloning and sequence and cDNA-directed expression of human P450 IIBI: Identification of a normal and two variant cDNAs derived from the CYP2B locus on chromosome 19 and differential expression of the IIB mRNAs in human liver. Biochemistry 28:7340-7348.