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Volumn 12, Issue 4, 1999, Pages 317-322

Mechanism-based inactivation of cytochromes P450 2B1 and P450 2B6 by n- propylxanthate

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 ISOENZYME; IODOSOBENZENE; N PROPYLXANTHIC ACID; OXIDIZING AGENT; PENTOXYRESORUFIN DEALKYLASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

EID: 0032940229     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9802421     Document Type: Article
Times cited : (33)

References (38)
  • 1
    • 0025784027 scopus 로고
    • Cytochrome P450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms
    • Porter, T. D., and Coon, M. J. (1991) Cytochrome P450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J. Biol. Chem. 266, 13469-13472.
    • (1991) J. Biol. Chem. , vol.266 , pp. 13469-13472
    • Porter, T.D.1    Coon, M.J.2
  • 2
    • 0024236331 scopus 로고
    • The molecular biology of cytochrome P450s
    • Gonzalez, F. J. (1988) The molecular biology of cytochrome P450s. Pharm. Rev. 40, 243-288.
    • (1988) Pharm. Rev. , vol.40 , pp. 243-288
    • Gonzalez, F.J.1
  • 4
    • 0028989491 scopus 로고
    • Structural basis of selective cytochrome P450 inhibition
    • Halpert, J. R. (1995) Structural basis of selective cytochrome P450 inhibition. Annu. Rev. Pharmacol. Toxicol. 35, 29-53.
    • (1995) Annu. Rev. Pharmacol. Toxicol. , vol.35 , pp. 29-53
    • Halpert, J.R.1
  • 6
    • 0023645035 scopus 로고
    • High-resolution crystal structure of cytochrome P450 cam
    • Poulos, T. L., Finzel, B. C., and Howard, A. J. (1987) High-resolution crystal structure of cytochrome P450 cam. J. Mol. Biol. 195, 687-700.
    • (1987) J. Mol. Biol. , vol.195 , pp. 687-700
    • Poulos, T.L.1    Finzel, B.C.2    Howard, A.J.3
  • 7
    • 0027326717 scopus 로고
    • Crystal structure of hemoprotein domain of P450 BM-3, a prototype for microsomal P450s
    • Ravichandran, K. G., Boddupalli, S. S., Hasemann, C. A., Peterson, J. A., and Deisenhofer, J. (1993) Crystal structure of hemoprotein domain of P450 BM-3, a prototype for microsomal P450s. Science 261, 731-736.
    • (1993) Science , vol.261 , pp. 731-736
    • Ravichandran, K.G.1    Boddupalli, S.S.2    Hasemann, C.A.3    Peterson, J.A.4    Deisenhofer, J.5
  • 8
    • 0028267490 scopus 로고
    • Crystal structure and refinement of cytochrome P450terp at 2.3 Å resolution
    • Hasemann, C. A., Ravichandran, K. G., Peterson, J. A., and Deisenhofer, J. (1994) Crystal structure and refinement of cytochrome P450terp at 2.3 Å resolution. J. Mol. Biol. 236, 1169-1185.
    • (1994) J. Mol. Biol. , vol.236 , pp. 1169-1185
    • Hasemann, C.A.1    Ravichandran, K.G.2    Peterson, J.A.3    Deisenhofer, J.4
  • 9
    • 0029586252 scopus 로고
    • Structure of cytochrome P450eryF involved in erythromycin biosynthesis
    • Cupp-Vickery, J. R., and Poulos, T. L. (1995) Structure of cytochrome P450eryF involved in erythromycin biosynthesis. Nat. Struct. Biol. 2, 144-153.
    • (1995) Nat. Struct. Biol. , vol.2 , pp. 144-153
    • Cupp-Vickery, J.R.1    Poulos, T.L.2
  • 10
    • 0027275796 scopus 로고
    • Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: Identification of an active site peptide
    • Roberts, E. S., Hopkins, N. E., Alworth, W. L., and Hollenberg, P. F. (1993) Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: Identification of an active site peptide. Chem. Res. Toxicol. 6, 470-479.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 470-479
    • Roberts, E.S.1    Hopkins, N.E.2    Alworth, W.L.3    Hollenberg, P.F.4
  • 12
    • 0029862643 scopus 로고    scopus 로고
    • Identification of the heme adduct and an active site peptide modified during mechanism-based inactivation of rat liver cytochrome P450 2B1 by secobarbital
    • He, K., Falick, A. M., Chen, B., Nilsson, F., and Correia, M. A. (1996) Identification of the heme adduct and an active site peptide modified during mechanism-based inactivation of rat liver cytochrome P450 2B1 by secobarbital. Chem. Res. Toxicol. 9, 614-622.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 614-622
    • He, K.1    Falick, A.M.2    Chen, B.3    Nilsson, F.4    Correia, M.A.5
  • 13
    • 25344454998 scopus 로고    scopus 로고
    • RT-PCR analysis of cytochrome P450 profile in normal and tumor samples from human breast
    • Rylander, T. M., Hellmold, H., Reihnér, E., Warner, M., and Gustafsson J.-Å. (1997) RT-PCR analysis of cytochrome P450 profile in normal and tumor samples from human breast. FASEB J. 11, P343.
    • (1997) FASEB J. , vol.11
    • Rylander, T.M.1    Hellmold, H.2    Reihnér, E.3    Warner, M.4    Gustafsson, J.-Å.5
  • 14
    • 0027333559 scopus 로고
    • Upregulation of estradiol C16 alpha-hydroxylation in human breast tissue: A potential biomarker of breast cancer risk
    • Osborne, M. P., Bradlow, H. L., Wong, G. Y., and Telang, T. N. (1993) Upregulation of estradiol C16 alpha-hydroxylation in human breast tissue: a potential biomarker of breast cancer risk. J. Natl. Cancer Inst. 85, 1917-1920.
    • (1993) J. Natl. Cancer Inst. , vol.85 , pp. 1917-1920
    • Osborne, M.P.1    Bradlow, H.L.2    Wong, G.Y.3    Telang, T.N.4
  • 16
    • 0028237729 scopus 로고
    • 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
    • Shimada, T., Yamazki, H., Mimura, M., Inui, Y., and Guengerich, F. P. (1994) 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. 270, 414-423.
    • (1994) J. Pharmacol. Exp. Ther. , vol.270 , pp. 414-423
    • Shimada, T.1    Yamazki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 17
    • 0000335714 scopus 로고    scopus 로고
    • Identification and characterization of cytochrome P450 2B6 (CYP2B6) in human liver microsomes and its induction in primary cultures of human hepatocytes
    • Los Angeles, CA, July 21-24, 1996
    • Madan, A., LeCluyse, E. L., Foster, J., Carroll, K., Lantham, J. D., Yang, D., and Parkinson, A. (1996) Identification and characterization of cytochrome P450 2B6 (CYP2B6) in human liver microsomes and its induction in primary cultures of human hepatocytes. XI International Symposium on Microsomes and Drug Oxidations, UCLA, Los Angeles, CA, July 21-24, 1996, p 203.
    • (1996) XI International Symposium on Microsomes and Drug Oxidations, UCLA , pp. 203
    • Madan, A.1    LeCluyse, E.L.2    Foster, J.3    Carroll, K.4    Lantham, J.D.5    Yang, D.6    Parkinson, A.7
  • 19
    • 0026677396 scopus 로고
    • Cotinine formation by cDNA-expressed human cytochromes P450
    • McCracken, N. W., Cholerton, S., and Idle, J. R. (1992) Cotinine formation by cDNA-expressed human cytochromes P450. Med. Sci. Res. 20, 877-878.
    • (1992) Med. Sci. Res. , vol.20 , pp. 877-878
    • McCracken, N.W.1    Cholerton, S.2    Idle, J.R.3
  • 21
    • 0028035492 scopus 로고
    • Genotoxicity of tamoxifen, tamoxifen epoxide and tormifene in human lymphoblastoid cells containing human cytochrome P450s
    • Styles, J. A., Davies, A., Lim, C. K., DeMatteis, F., Stanley, L. A., White, I. N. H., Yuan, Z.-X., and Smith, L. L. (1994) Genotoxicity of tamoxifen, tamoxifen epoxide and tormifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis 15, 5-9.
    • (1994) Carcinogenesis , vol.15 , pp. 5-9
    • Styles, J.A.1    Davies, A.2    Lim, C.K.3    DeMatteis, F.4    Stanley, L.A.5    White, I.N.H.6    Yuan, Z.-X.7    Smith, L.L.8
  • 22
    • 0030056594 scopus 로고    scopus 로고
    • Specificity of substrate and inhibitor probes for cytochrome P450s: Evaluation of in vitro metabolism using cDNA expressed human P450s and human liver microsomes
    • Ono, S., Hatanaka, T., Hotta, H., Satoh, T., Gonzalez, F. J., and Tsutsui, M. (1996) Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA expressed human P450s and human liver microsomes, Xenobiotica 26, 681-693.
    • (1996) Xenobiotica , vol.26 , pp. 681-693
    • Ono, S.1    Hatanaka, T.2    Hotta, H.3    Satoh, T.4    Gonzalez, F.J.5    Tsutsui, M.6
  • 23
    • 0030064194 scopus 로고    scopus 로고
    • 7-Ethoxycoumarin O-deethylation catalyzed by cytochromes P4501A2 and 2E1 in human liver microsomes
    • Yamazaki, H., Inoue, K., Mimura, M., Oda, Y., Guengerich, F. P., and Shimada, T. (1996) 7-Ethoxycoumarin O-deethylation catalyzed by cytochromes P4501A2 and 2E1 in human liver microsomes. Biochem. Pharmacol. 51, 313-319.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 313-319
    • Yamazaki, H.1    Inoue, K.2    Mimura, M.3    Oda, Y.4    Guengerich, F.P.5    Shimada, T.6
  • 28
    • 0020061760 scopus 로고
    • Effects of potassium ethylxanthogenate and 2,3-dimercaptopropane sulphonate sodium on the pentobarbital pharmacokinetics and metabolism in male mice
    • Yanev, S., Yanku, I., Stoychev, T., Havilk, I., and Krebs, V. (1982) Effects of potassium ethylxanthogenate and 2,3-dimercaptopropane sulphonate sodium on the pentobarbital pharmacokinetics and metabolism in male mice. Eur. J. Drug Metabol. Pharmacokinet. 7, 21-29.
    • (1982) Eur. J. Drug Metabol. Pharmacokinet. , vol.7 , pp. 21-29
    • Yanev, S.1    Yanku, I.2    Stoychev, T.3    Havilk, I.4    Krebs, V.5
  • 29
    • 0023685035 scopus 로고
    • Effects of potassium ethylxanthogenate on nitrosodiethylamine-induced DNA damage and on liver carcinogenesis
    • Hadjiolov, D., Frank, M., Hadjiolov, N., and Yanev, S. (1988) Effects of potassium ethylxanthogenate on nitrosodiethylamine-induced DNA damage and on liver carcinogenesis. Arch. Geschwulstforsch. 58, 313-318.
    • (1988) Arch. Geschwulstforsch. , vol.58 , pp. 313-318
    • Hadjiolov, D.1    Frank, M.2    Hadjiolov, N.3    Yanev, S.4
  • 30
    • 0000555228 scopus 로고    scopus 로고
    • Mechanism-based enzyme inactivators
    • (Purich, D. L., Ed.), Academic Press, San Diego, CA
    • Silverman, R. B. (1996) Mechanism-based enzyme inactivators. In Contemporary Enzyme Kinetics and Mechanisms (Purich, D. L., Ed.) pp 291-335, Academic Press, San Diego, CA.
    • (1996) Contemporary Enzyme Kinetics and Mechanisms , pp. 291-335
    • Silverman, R.B.1
  • 32
    • 0019523641 scopus 로고
    • Purification to homogeneity and characterization of a form of cytochrome P450 with high specificity for benzopyrene from β-naphthoflavone-pretreated rat liver microsomes
    • Saito, T., and Strobel, H. W. (1981) Purification to homogeneity and characterization of a form of cytochrome P450 with high specificity for benzopyrene from β-naphthoflavone-pretreated rat liver microsomes. J. Biol. Chem. 256, 984-988.
    • (1981) J. Biol. Chem. , vol.256 , pp. 984-988
    • Saito, T.1    Strobel, H.W.2
  • 33
    • 0017795019 scopus 로고
    • Purification and properties of NADPH-cytochrome P-450 reductase
    • Strobel, H. W., and Dignam, J. D. (1978) Purification and properties of NADPH-cytochrome P-450 reductase. Methods Enzymol. 52, 89-92.
    • (1978) Methods Enzymol. , vol.52 , pp. 89-92
    • Strobel, H.W.1    Dignam, J.D.2
  • 34
    • 0031822496 scopus 로고    scopus 로고
    • Role of alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities
    • Hanna, I. H., Teiber, J. F., Kokones, K. L., and Hollenberg, P. F. (1998) Role of alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities. Arch. Biochem. Biophys. 350, 324-332.
    • (1998) Arch. Biochem. Biophys. , vol.350 , pp. 324-332
    • Hanna, I.H.1    Teiber, J.F.2    Kokones, K.L.3    Hollenberg, P.F.4
  • 35
    • 0027374515 scopus 로고
    • A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man
    • Buters, J. T., Schiller, C. D., and Chou, R. C. (1993) A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man. Biochem. Pharmacol. 46, 1577-1584.
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 1577-1584
    • Buters, J.T.1    Schiller, C.D.2    Chou, R.C.3
  • 36
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemo protein nature
    • Omura, T., and Saito, R. (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemo protein nature. J. Biol. Chem. 239, 2370-2378.
    • (1964) J. Biol. Chem. , vol.239 , pp. 2370-2378
    • Omura, T.1    Saito, R.2
  • 38
    • 0024464027 scopus 로고
    • 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
    • Yamano, S., Nhamburo, P. T., Aoyama, T., Meyer, U. A., Inaba, T., Kalow, W., Gelboin, H. V., McBride, O. W., and Gonzalez, F. J. (1989) 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 28, 7340-7348.
    • (1989) Biochemistry , vol.28 , pp. 7340-7348
    • Yamano, S.1    Nhamburo, P.T.2    Aoyama, T.3    Meyer, U.A.4    Inaba, T.5    Kalow, W.6    Gelboin, H.V.7    McBride, O.W.8    Gonzalez, F.J.9


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