Human CYP2B6: Expression, inducibility and catalytic activities

Pharmacogenetics

Volumn 9, Issue 3, 1999, Pages 295-306

  Gervot, L ^a   Rochat, B ^a,b   Gautier, J C ^a,c   Bohnenstengel, F ^d   Kroemer, H ^d   De Berardinis, V ^e   Martin, H ^f   Beaune, P ^a   De Waziers, Isabelle ^a  

^a INSERM   (France)

^b UNIVERSITY OF KANSAS   (United States)

^c NESTLÉ RESEARCH CENTER   (Switzerland)

^d DR MARGARETE FISCHER BOSCH INSTITUTE OF CLINICAL PHARMACOLOGY   (Germany)

^e CNRS   (France)

^f Serv de Toxicologie Experimentale   (France)

Author keywords

CYP2B6; Heterologous expression; Inducibility; Tissue expression

Indexed keywords

COMPLEMENTARY DNA; CYCLOPHOSPHAMIDE; CYTOCHROME; ETHOXYCOUMARIN; ETHOXYRESORUFIN; PENTOXYRESORUFIN; PHENOBARBITAL; TESTOSTERONE;

ARTICLE; BRAIN; DRUG METABOLISM; ESCHERICHIA COLI; GENE EXPRESSION; HUMAN; IMMUNOBLOTTING; INTESTINE; KIDNEY; KINETICS; LIVER MICROSOME; LUNG; MOLECULAR CLONING; NONHUMAN; PHARMACOGENETICS; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; TRACHEA;

ESCHERICHIA COLI; SACCHAROMYCES CEREVISIAE;

EID: 0032791111     PISSN: 0960314X     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008571-199906000-00004     Document Type: Article

References (56)

1. Bagley C, Bostick F, De Vita V. Clinical pharmacology of cyclophosphamide. Cancer Res 1973, 33:226-233.
2. Belloc C, Baird S, Cosme J, Lecoeur S, Gautier JC, Challine D, et al. Human cytochrome P450 expressed in Escherichia coli: production of specific antibodies. Toxicology 1996; 106:207-219.
3. Bhamre S, Anandatheerathavarada H, Shankar S, Boyd M, Ravindranath V. Purification of multiple forms of cytochrome P450 from a human brain and reconstitution of catalytic activities. Arch Biochem Biophys 1993; 301:251-255.
4. Bohnenstengel F, Eichelbaum M, Golbs E, Kroemer H. High-performance liquid chromatographic determination of acrolein as a marker for cyclophosphamide bioactivation in human liver microsomes. J Chromatogr 1997; 692:163-168.
5. Burke D, Thompson S, Elcombe C, Halpert J, Haaparanta T, Mayer R. Ethoxy-, pentoxy-and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochrome P450s. Biochem Pharmacol 1985; 34:3337-3345.
6. Chang T, Weber G, Crespi C, Waxman D. Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Cancer Res 1993; 53:5629-5637.
7. Chang T, Yu L, Maurel P, Waxman D. Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocytes cultures: response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines. Cancer Res 1997; 57:1946-1954.
8. Chantret I, Rodolosse A, Barbat A, Dussaulx E, Brot-Laroche E, Zweibaum A, Rousset M. Differential expression of sucrase-isomaltase in clones isolated from early and late passages of the cell line CaCO2: evidence for a glucose dependent negative regulation. J Cell Sci 1994; 107:213-225.
9. Chirgwin J, Przybyla A, MacDonald R, Rutter W. Isolation of biologically active ribonucleic acid from sources enriched in ribonuclease. Biochemistry 1979; 18:5294-5299.
10. Code E, Crespi C, Penman B, Gonzalez F, Chang T, Waxman D. Human cytochrome P4502B6: interindividual hepatic expression, substrate specificity, and role in procarcinogen activation. Drug Metabol Dipos 1997; 25:985-993.
11. Cullin C, Pompon D. Synthesis of functional mouse cytochromes P-450 P1 and chimeric P-450 P3-1 in the yeast Saccharomyces cerevisiae. Gene 1988; 65: 203-217.
12. Czerwinski M, McLemore T, Gelboin H, Gonzalez F. Quantification of CYP2B7, CYP4B1, and CYPOR messenger RNAs in normal human lung and lung tumors. Cancer Res 1994; 54:1085-1091.
13. de Waziers I, Cugnenc P, Yang C, Leroux J, Beaune P. Cytochrome P450 isoenzymes, epoxide hydrolase and glutathione transferases in rat and human hepatic and extrahepatic tissues. J Pharmacol Exp Ther 1990; 253: 387-394.
14. Doostdar H, Grant M, Melvin W, Wolf C, Burke M. The effect of inducing agents on cytochromes P450 and UDP-glucuronyl-transferase activities in human HepG2 hepatoma cells. Biochem Pharmacol 1993; 46: 629-635.
15. Ekins S, VandenBranden M, Ring B, Wrighton S. Examination of purported probes of human CYP2B6. Pharmacogenetics 1997; 7: 165-179.
16. Gaullier JM, Geze M, Santus R, Sa e Melo T, Maziere JC, et al. Subcellular localization of and photosensitization by protoporphyrin IX human keratinocytes and fibroblasts cultivated with 5-aminolevulinic acid. Photochem Photobiol 1995; 62: 114-122.
17. Gautier JC, Urban P, Beaune P, Pompon D. Engineered yeast cells as model to study coupling between human xenobiotic metabolizing enzyme. Eur J Biochem 1993; 211:63-72.
18. Gonzalez F, Gelboin H. Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxin. Drug Metab Rev 1994; 26:165-183.
19. Graham M, Shaw I, Souhami R, Sidau B, Harper P, McLean A. Decreased plasma half-life of cyclophosphamide during repeated high-dose administration. Cancer Chemother Pharmacol 1983; 10:192-193.
20. Guengerich F, Dannan G, Wright S, Martin M, Kaminski L. Purification and characterization of rat liver microsomal cytochrome P-450: electrophoretic, spectral, catalytic and immunochemical properties and inducibility of eight isoenzymes isolated from rats treated with phenobarbital or β-naphthoflavone. Biochemistry 1982; 21:1-51.
21. Guengerich F, Turvy C. Comparison of level of several human microsomal cytochrome P-450 enzymes and epoxide hydrolase in normal and disease states using immunochemical analysis of surgical liver samples. J Pharmacol Exp Ther 1991; 256:1189-1194.
22. Guengerich FP. Comparisons of catalytic selectivity of cytochromes P450 subfamily enzymes from different species. Chem Biol Interact 1997; 106:161-182.
23. Härtter S, Baier D, Dingemanse J, Ziegler G, Hiemke C. Automated determination of dextrometorphan and its main metabolites in human plasma by high-performance liquid chromatography and column switching. Ther Drug Monit 1996; 18:297-303.
24. Heyn H, White R, Steven J. Catalytic role of cytochrome P450 2B6 in the N-demethylation of S-mephenytoin. Drug Metab Dispos 1996; 24:948-953.
25. Imaoka S, Yamada T, Hiroi T, Hayashi K, Sakaki T, Yabusaki Y, Funae Y. Multiple forms of human P450 expressed in Saccharomyces cerevisiae. Biochem Pharmacol 1996; 51:1041-1050.
26. Jao J, Jusko W, Cohen J. Phenobarbital effects on cyclophosphamide pharmacokinetics in man. Cancer Res 1972; 32:2761-2764.
27. Kolars J, Schmiedlin-Ren P, Schuetz J, Fang C, Watkins B. Identification of rifampicin-inducible P450IIIA4 (CYP3A4) in human small bowel enterocytes. J Clin Invest 1992; 90:1871-1878.
28. Kremers P, Beaune P, Cresteil T, De Graeve J, Columelli S, Leroux J, Gielen J. Cytochrome P450 monooxygenase activities in human and rat liver microsomes. Eur J Biochem 1981; 118:599-606.
29. Leammli UK. Cleavage of structural properties during the assembly of the head of the bacteriophage T4. Nature 1970; 227:680-685.
30. Leeman T, Transon C, Dayer P. Cytochrome P450TB (CYP2C): a major monooxygenase catalysing diclofenac 4'-hydroxylation in human liver. Life Sci 1993; 52:29-34.
31. Lessufleur T, Barbat A, Luccioni J, Beaumatin M, Claire A, Kornovski E, et al. Dihydrofolate reductase gene amplification-associated shift of differentiation in methotrexate-adapted HT-29 cells. J Cell Biol 1991; 115:1409-1418.
32. Lewis D, Lake B. Molecular modeling of mammalian CYP2B isoforms and their interaction with substrates, inhibitors and redox partners. Xenobiotica 1997; 27:443-478.
33. Macé K, Aguilar F, Wang J-S, Vautravers P, Gomez-Lechon M, Gonzales F, et al. Aflatoxin B1-induced DNA adduct formation and p53 mutations in CYP450-expressing human liver cell lines. Carcinogenesis 1997; 18:1291-1297.
34. Maniatis T. Molecular cloning. A laboratory manual. 1989; Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
35. Maurel P. The use of adult human hepatocytes in primary culture and other in vitro systems to investigate drug metabolism in man. Adv Drug Deliv Rev 1996; 22:105-132.
36. McKinnon R, Burgess W, Hall P, Robert-Thomson S, Gonzalez F, McMannus M. Characterisation of CYP3A gene subfamily expression in human gastrointestinal tissues. Gut 1995; 36:259-267.
37. Mimura M, Baba T, Yamazaki H, Ohmori S, Inui Y, Gonzalez F, et al. Characterization of cytochrome P-450 2B6 in human liver microsomes. Drug Metabol Dispos 1993; 21: 1048-1056.
38. Morel F, Beaune P, Ratanasavanh D, Flinois J-P, Yang C, Guengerich F, Guillouzo A. Expression of cytochrome P450 enzymes in cultured human hepatocytes. Eur J Biochem 1990; 191:437-442.
39. Omura T, Sato R. The carbon monoxide binding pigment of liver microsomes. J Biol Chem 1964; 239:2379-2385.
40. Ono S, Hatanaka T, Hotta H, Satoh T, Gonzalez F, Tsutsui M. Specificity of substrate and inhibitor probes for cytochromes P450s: elevation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica 1996; 26:681-693.
41. Peter R, Bocker R, Beaune P, Iwasaki M, Guengerich F, Yang C. Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1, Chem Res Toxicol 1990; 3:566-573.
42. Pompon D. cDNA cloning and functional expression in yeast Saccharomyces cerevisiae of B-naphtoflavone-induced rabbit liver cytochrome P-450 LM4 and LM6. Eur J Biochem 1988; 177: 285-293.
43. Pompon D, Louerat B, Bronine A, Urban P. Yeast expression of animal and plant P450s in optimized redox environments. Method Enzymol 1996; 272:51-64.
44. Ravindranath V, Anandatheerathavarada H, Shankar S. Xenobiotic metabolism in human brain-presence of cytochromes P-450 and associated mono-oxygenases. Brain Res 1989; 496:331-335.
45. Reinerink E, Door L, Jansen E, Van Lersel A. Measurement of enzymes activities of cytochrome P450 isoenzymes by high performance liquid chromatographic analysis of products. J Chromatogr 1991; 553:233.
46. Renaud J, Cullin C, Pompon D, Beaune P, Mansuy D. Expression of human liver cytochrome P450 IIIA4 in yeast: a functional model for the hepatic enzyme. Eur J Biochem 1990; 194:889-896.
47. Ryan D, Levin W. Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacol Ther 1990; 45:153-239.
48. Schuetz E, Schuetz J. Strom S, Thompson M, Fisher R, Molowa D, et al. Regulation of human liver cytochrome P-450 in family 3A in primary and continuous culture of human hepatocytes. Hepathology 1993; 18:1254-1262.
49. Schuler U, Ehninger G, Wagner T. Repeated high-dose cyclophosphamide administration in bone marrow transplantation: exposure to activated metabolites. Cancer Chemother Pharmacol 1987; 20:248-252.
50. Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich F. Interindividual variation 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.
51. Springate J, Zamlauski-Tucker J, Lu H, Chan K. Renal clearance of ifosfamide. Drug Metab Dispos 1997; 29: 1081-1082.
52. Srivastava P, Beaune P, Ged C, Guengerich F. Separation of human liver microsomal tolbutamide hydroxylase and (S)-mephenytoin 4'-hydroxylase cytochrome P450 enzymes. Mol Pharmacol 1991; 40:69-79.
53. Studier WF, Rosenberg AH, Dunn JJ, Dubendorf JW. Use of T7 RNA polymerase to direct expression of cloned genes. Meth Enzymol 1990; 185:60-89.
54. Urban P, Cullin C, Pompon D. Maximizing the expression of mammalian cytochrome P-450 monooxygenase activities in yeast cells. Biochimie (Paris) 1990; 472:463-472.
55. Yamano S, Nhamburo PT, Aoyama T, Meyer U, Inaba T, Kalow W, et al. cDNA cloning and sequence and cDNA-directed expression of human P450 IIB1: 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 1989; 28:7340-7348.
56. Yamazaki H, Inoue K, Mimura M, Oda Y, Guengerich F, Shimada T. 7-Ethoxycoumarin O-deethylation catalysed by cytochrome P4501A2 and 2E1 in human liver microsomes. Biochem Pharmacol 1996; 51:313-319.