메뉴 건너뛰기




Volumn 25, Issue 12, 1997, Pages 1407-1415

Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8- methoxypsoralen

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN; CYTOCHROME P450; METHOXSALEN; PILOCARPINE; POTASSIUM FERRICYANIDE; REACTIVE OXYGEN METABOLITE; RECOMBINANT ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

EID: 0031451433     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (152)

References (55)
  • 1
    • 0026781890 scopus 로고
    • Species differences and interindividual variation in liver microsomal cytochrome P450 2A enzymes: Effects on coumarin, dicoumarol, and testosterone oxidation
    • R. Pearce, D. Greenway, and A. Parkinson: Species differences and interindividual variation in liver microsomal cytochrome P450 2A enzymes: effects on coumarin, dicoumarol, and testosterone oxidation. Arch. Biochem. Biophys. 298, 211-225 (1992).
    • (1992) Arch. Biochem. Biophys. , vol.298 , pp. 211-225
    • Pearce, R.1    Greenway, D.2    Parkinson, A.3
  • 2
    • 0029996291 scopus 로고    scopus 로고
    • Ethnic-related differences in coumarin 7-hydroxylation activities catalyzed by cytochrome P4502A6 in liver microsomes of Japanese and Caucasian populations
    • T. Shimada, H. Yamazaki, and F. P. Guengerich: Ethnic-related differences in coumarin 7-hydroxylation activities catalyzed by cytochrome P4502A6 in liver microsomes of Japanese and Caucasian populations. Xenobiotica 26, 395-403 (1996).
    • (1996) Xenobiotica , vol.26 , pp. 395-403
    • Shimada, T.1    Yamazaki, H.2    Guengerich, F.P.3
  • 4
    • 0025022689 scopus 로고
    • The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes
    • S. Yamano, J. Tatsuno, and F. J. Gonzalez: The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 29, 1322-1329 (1990).
    • (1990) Biochemistry , vol.29 , pp. 1322-1329
    • Yamano, S.1    Tatsuno, J.2    Gonzalez, F.J.3
  • 5
    • 0025214234 scopus 로고
    • Identification of the human liver cytochrome P-450 responsible for coumarin 7-hydroxylase activity
    • J. S. Miles, A. W. McLaren, L. M. Forrester, M. J. Glancey, M. A. Lang, and C. R. Wolf: Identification of the human liver cytochrome P-450 responsible for coumarin 7-hydroxylase activity. Biochem. J. 267, 365-371 (1990).
    • (1990) Biochem. J. , vol.267 , pp. 365-371
    • Miles, J.S.1    McLaren, A.W.2    Forrester, L.M.3    Glancey, M.J.4    Lang, M.A.5    Wolf, C.R.6
  • 6
    • 0025841777 scopus 로고
    • Purification and characterization of human liver microsomal cytochrome P-450 2A6
    • C. Yun, T. Shimada, and F. P. Guengerich: Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol. Pharmacol. 40, 679-685 (1991).
    • (1991) Mol. Pharmacol. , vol.40 , pp. 679-685
    • Yun, C.1    Shimada, T.2    Guengerich, F.P.3
  • 10
    • 0344106760 scopus 로고    scopus 로고
    • Baculovirus Mediated Expression, Purification, and Catalytic Activity of Human CYP2A6
    • Abstr. 109
    • S. J. Thompson, L. L. Koenigs, M. Fisher, D. Slone, D. Eaton, and A. E. Rettie: Baculovirus Mediated Expression, Purification, and Catalytic Activity of Human CYP2A6. Toxicologist 36, 22 (Abstr. 109) (1997).
    • (1997) Toxicologist , vol.36 , pp. 22
    • Thompson, S.J.1    Koenigs, L.L.2    Fisher, M.3    Slone, D.4    Eaton, D.5    Rettie, A.E.6
  • 11
    • 0029982314 scopus 로고    scopus 로고
    • Metabolic activation of 2,6-dichlorobenzonitrile, an olfactory-specific toxicant, by rat, rabbit, and human cytochromes P450
    • X. Ding, D. C. Spink, J. K. Bhama, J. J. Sheng, A. D. N. Vaz, and M. J. Coon: Metabolic activation of 2,6-dichlorobenzonitrile, an olfactory-specific toxicant, by rat, rabbit, and human cytochromes P450. Mol. Pharmacol. 49, 1113-1121 (1996).
    • (1996) Mol. Pharmacol. , vol.49 , pp. 1113-1121
    • Ding, X.1    Spink, D.C.2    Bhama, J.K.3    Sheng, J.J.4    Vaz, A.D.N.5    Coon, M.J.6
  • 12
    • 0028340688 scopus 로고
    • Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: Evidence for major roles by cytochromes P450 2A6 and 2E1
    • R. J. Duescher and A. A. Elfarra: Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: evidence for major roles by cytochromes P450 2A6 and 2E1. Arch. Biochem. Biophys. 311, 342-349 (1994).
    • (1994) Arch. Biochem. Biophys. , vol.311 , pp. 342-349
    • Duescher, R.J.1    Elfarra, A.A.2
  • 13
    • 0028586852 scopus 로고
    • Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes
    • F. P. Guengerich, T. Shimada, C. Yun, H. Yamazaki, K. D. Raney, R. Thier, B. Coles, and T. M. Harris: Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes. Environ. Health Perspect. 102, 49-53 (1994).
    • (1994) Environ. Health Perspect. , vol.102 , pp. 49-53
    • Guengerich, F.P.1    Shimada, T.2    Yun, C.3    Yamazaki, H.4    Raney, K.D.5    Thier, R.6    Coles, B.7    Harris, T.M.8
  • 15
    • 0028075688 scopus 로고
    • Catalytic roles of rat and human cytochrome P450 2A enzymes in testosterone 7α- and coumarin 7-hydroxylations
    • H. Yamazaki, M. Mimura, C. Sugahara, and T. Shimada: Catalytic roles of rat and human cytochrome P450 2A enzymes in testosterone 7α- and coumarin 7-hydroxylations. Biochem. Pharmacol. 48, 1524-1527 (1994).
    • (1994) Biochem. Pharmacol. , vol.48 , pp. 1524-1527
    • Yamazaki, H.1    Mimura, M.2    Sugahara, C.3    Shimada, T.4
  • 18
    • 0016385502 scopus 로고
    • Photochemotherapy of psoriasis with oral methoxsalen and longwave ultraviolet light
    • J. A. Parrish, T. B. Fitzpatrick, L. Tanenbaum, and M. A. Pathak: Photochemotherapy of psoriasis with oral methoxsalen and longwave ultraviolet light. N. Engl. J. Med. 291, 1207-1211 (1974).
    • (1974) N. Engl. J. Med. , vol.291 , pp. 1207-1211
    • Parrish, J.A.1    Fitzpatrick, T.B.2    Tanenbaum, L.3    Pathak, M.A.4
  • 20
    • 0024434963 scopus 로고
    • Suicide inactivation of cytochrome P-450 by methoxsalen: Evidence for the covalent binding of a reactive intermediate to the protein moiety
    • G. Labbe, V. Descatoire, P. Beaune, P. Letteron, D. Larrey, and D. Pessayre: Suicide inactivation of cytochrome P-450 by methoxsalen: evidence for the covalent binding of a reactive intermediate to the protein moiety. J. Pharmacol. Exp. Ther. 250, 1034-1042 (1989).
    • (1989) J. Pharmacol. Exp. Ther. , vol.250 , pp. 1034-1042
    • Labbe, G.1    Descatoire, V.2    Beaune, P.3    Letteron, P.4    Larrey, D.5    Pessayre, D.6
  • 23
    • 0025160925 scopus 로고
    • Bioactivation of 8-methoxypsoralen and irreversible inactivation of cytochrome P-450 in mouse liver microsomes: Modification by monoclonal antibodies, inhibition of drug metabolism and distribution of covalent adducts
    • D. C. Mays, J. B. Milliard, D. D. Wong, M. A. Chambers, S. S. Park, H. V. Gelboin, and N. Gerber: Bioactivation of 8-methoxypsoralen and irreversible inactivation of cytochrome P-450 in mouse liver microsomes: modification by monoclonal antibodies, inhibition of drug metabolism and distribution of covalent adducts. J. Pharmacol. Exp. Ther. 254, 720-731 (1990).
    • (1990) J. Pharmacol. Exp. Ther. , vol.254 , pp. 720-731
    • Mays, D.C.1    Milliard, J.B.2    Wong, D.D.3    Chambers, M.A.4    Park, S.S.5    Gelboin, H.V.6    Gerber, N.7
  • 26
  • 27
    • 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
    • S. Ono, T. Hatanaka, H. Hotta, T. Satoh, F. J. Gonzalez, and M. Tsutsui: 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).
    • (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
  • 28
    • 0028936655 scopus 로고
    • Metabolism of coumarin by precision-cut calf liver slices and calf liver microsomes
    • B. G. Lake, M. J. Sauer, F. Esclangon, J. A. Beamond, R. J. Price, and D. G. Walters: Metabolism of coumarin by precision-cut calf liver slices and calf liver microsomes. Xenobiotica 25, 133-141 (1995).
    • (1995) Xenobiotica , vol.25 , pp. 133-141
    • Lake, B.G.1    Sauer, M.J.2    Esclangon, F.3    Beamond, J.A.4    Price, R.J.5    Walters, D.G.6
  • 31
    • 0022630925 scopus 로고
    • Disposition of 8-methoxypsoralen in the rat: Methodology for measurement, dose-dependent pharmacokinetics, tissue distribution and identification of metabolites
    • D. C. Mays, S. L. Rogers, R. C. Guiler, D. E. Sharp, S. G. Hecht, A. E. Staubus, and N. Gerber: Disposition of 8-methoxypsoralen in the rat: methodology for measurement, dose-dependent pharmacokinetics, tissue distribution and identification of metabolites. J. Pharmacol. Exp. Ther. 236, 364-373 (1986).
    • (1986) J. Pharmacol. Exp. Ther. , vol.236 , pp. 364-373
    • Mays, D.C.1    Rogers, S.L.2    Guiler, R.C.3    Sharp, D.E.4    Hecht, S.G.5    Staubus, A.E.6    Gerber, N.7
  • 32
    • 0023228494 scopus 로고
    • Disposition of 8-methoxypsoralen in the rat: Induction of metabolism in vivo and in vitro and identification of urinary metabolites by thermospray mass spectrometry
    • D. C. Mays, S. G. Hecht, S. E. Unger, C. M. Pacula, J. M. Climie, D. E. Sharp, and N. Gerber: Disposition of 8-methoxypsoralen in the rat: induction of metabolism in vivo and in vitro and identification of urinary metabolites by thermospray mass spectrometry. Drug Metab. Dispos. 15, 318-328 (1987).
    • (1987) Drug Metab. Dispos. , vol.15 , pp. 318-328
    • Mays, D.C.1    Hecht, S.G.2    Unger, S.E.3    Pacula, C.M.4    Climie, J.M.5    Sharp, D.E.6    Gerber, N.7
  • 34
    • 0022642182 scopus 로고
    • Clinical pharmacokinetics of methoxsalen and other psoralens
    • F. A. de Wolff and T. V. Thomas: Clinical pharmacokinetics of methoxsalen and other psoralens. Clin. Pharmacokinet. 11, 62-75 (1986).
    • (1986) Clin. Pharmacokinet. , vol.11 , pp. 62-75
    • De Wolff, F.A.1    Thomas, T.V.2
  • 35
    • 0018125845 scopus 로고
    • Pharmacokinetics and metabolite-pattern of 8-methoxypsoralen in man following oral administration as compared to the pharmacokinetics in rat and dog
    • U. Busch, J. Schmid, F. W. Koss, H. Zipp, and A. Zimmer: Pharmacokinetics and metabolite-pattern of 8-methoxypsoralen in man following oral administration as compared to the pharmacokinetics in rat and dog. Arch. Dermatol. Res. 262, 255-265 (1978).
    • (1978) Arch. Dermatol. Res. , vol.262 , pp. 255-265
    • Busch, U.1    Schmid, J.2    Koss, F.W.3    Zipp, H.4    Zimmer, A.5
  • 36
    • 0024403279 scopus 로고
    • Characteristics of warfarin hydroxylation catalyzed by human liver microsomes
    • A. E. Rettie, A. C. Eddy, L. D. Heimark, M. Gibaldi, and W. F. Trager: Characteristics of warfarin hydroxylation catalyzed by human liver microsomes. Drug Metab. Dispos. 17, 265-270 (1989).
    • (1989) Drug Metab. Dispos. , vol.17 , pp. 265-270
    • Rettie, A.E.1    Eddy, A.C.2    Heimark, L.D.3    Gibaldi, M.4    Trager, W.F.5
  • 37
    • 0030587544 scopus 로고    scopus 로고
    • Allelic variants of human cytochrome P450 2C9: Baculovirus-mediated expression, purification, structural characterization, substrate stereoselectivity, and prochiral selectivity of the wild-type and I359L mutant forms
    • R. L. Haining, A. P. Hunter, M. E. Veronese, W. F. Trager, and A. E. Rettie: Allelic variants of human cytochrome P450 2C9: baculovirus-mediated expression, purification, structural characterization, substrate stereoselectivity, and prochiral selectivity of the wild-type and I359L mutant forms. Arch. Biochem. Biophys. 333, 447-457 (1996).
    • (1996) Arch. Biochem. Biophys. , vol.333 , pp. 447-457
    • Haining, R.L.1    Hunter, A.P.2    Veronese, M.E.3    Trager, W.F.4    Rettie, A.E.5
  • 38
    • 0025885546 scopus 로고
    • NADPH-cytochrome P-450 oxidoreductase: The role of cysteine 566 in catalysis and cofactor binding
    • A. L. Shen, M. J. Christensen, and C. B. Kaspar: NADPH-cytochrome P-450 oxidoreductase: the role of cysteine 566 in catalysis and cofactor binding. J. Biol. Chem. 266, 19976-19980 (1991).
    • (1991) J. Biol. Chem. , vol.266 , pp. 19976-19980
    • Shen, A.L.1    Christensen, M.J.2    Kaspar, C.B.3
  • 42
    • 0026519541 scopus 로고
    • Hydroxylation of warfarin by human cDNA-expressed cytochrome P-450: A role for P450 2C9 in the etiology of (S)-warfarin-drug interactions
    • A. Rettie, K. Korzekwa, K. Kunze, R. Lawrence, A. Eddy, T. Aoyama, H. Gelboin, F. Gonzalez, and W. Trager: Hydroxylation of warfarin by human cDNA-expressed cytochrome P-450: a role for P450 2C9 in the etiology of (S)-warfarin-drug interactions. Chem. Res. Toxicol. 5, 54-59 (1992).
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 54-59
    • Rettie, A.1    Korzekwa, K.2    Kunze, K.3    Lawrence, R.4    Eddy, A.5    Aoyama, T.6    Gelboin, H.7    Gonzalez, F.8    Trager, W.9
  • 43
    • 0029867317 scopus 로고    scopus 로고
    • Formation of (R)-8-hydroxywarfarin in human liver microsomes: A new metabolic marker for the (S)-mephenytoin hydroxylase, P4502C19
    • L. C. Weinkers, C. J. Wurden, E. Storch, K. L. Kunze, A. E. Rettie, and W. F. Trager: Formation of (R)-8-hydroxywarfarin in human liver microsomes: a new metabolic marker for the (S)-mephenytoin hydroxylase, P4502C19. Drug Metab. Dispos. 24, 610-614 (1996).
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 610-614
    • Weinkers, L.C.1    Wurden, C.J.2    Storch, E.3    Kunze, K.L.4    Rettie, A.E.5    Trager, W.F.6
  • 44
    • 0026324040 scopus 로고
    • Bufuralol, dextromethorphan, and debrisoquine as prototype substrates for human P450IID6
    • T. Kornbach: Bufuralol, dextromethorphan, and debrisoquine as prototype substrates for human P450IID6. Methods Enzymol. 206, 509-517 (1991).
    • (1991) Methods Enzymol. , vol.206 , pp. 509-517
    • Kornbach, T.1
  • 45
    • 0025223625 scopus 로고
    • Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P450IIE1
    • R. Peter, R. Bocker, P. Beaune, M. Iwasaki, F. Guengerich, and C. Yang: Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P450IIE1. Chem. Res. Toxicol. 3, 566-573 (1990).
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 566-573
    • Peter, R.1    Bocker, R.2    Beaune, P.3    Iwasaki, M.4    Guengerich, F.5    Yang, C.6
  • 46
    • 0028860852 scopus 로고
    • Competitive inhibition of coumarin 7-hydroxylation by pilocarpine and its interaction with mouse CYP 2A5 and human CYP 2A6
    • T. Kimonen, M. Pasanen, J. Gynther, A. Poso, T. Jarvinen, E. Alhava, and R. O. Juvonen: Competitive inhibition of coumarin 7-hydroxylation by pilocarpine and its interaction with mouse CYP 2A5 and human CYP 2A6. Br. J. Pharmacol. 116, 2625-2630 (1995).
    • (1995) Br. J. Pharmacol. , vol.116 , pp. 2625-2630
    • Kimonen, T.1    Pasanen, M.2    Gynther, J.3    Poso, A.4    Jarvinen, T.5    Alhava, E.6    Juvonen, R.O.7
  • 48
    • 0022004351 scopus 로고
    • Coumarin 7-hydroxylase activity in human liver microsomes: Properties of the enzyme and interspecies comparisons
    • O. Pelkonen, E. A. Sotaniemi, and J. T. Ahokas: Coumarin 7-hydroxylase activity in human liver microsomes: properties of the enzyme and interspecies comparisons. Br. J. Clin. Pharmacol. 19, 59-66 (1985).
    • (1985) Br. J. Clin. Pharmacol. , vol.19 , pp. 59-66
    • Pelkonen, O.1    Sotaniemi, E.A.2    Ahokas, J.T.3
  • 49
    • 0026593719 scopus 로고
    • Metabolism of coumarin by rat, gerbil and human liver microsomes
    • J. H. Fentem and J. R. Fry: Metabolism of coumarin by rat, gerbil and human liver microsomes. Xenobiotica 22, 357-367 (1992).
    • (1992) Xenobiotica , vol.22 , pp. 357-367
    • Fentem, J.H.1    Fry, J.R.2
  • 50
    • 0029862553 scopus 로고    scopus 로고
    • Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2A6: Role in metabolic activation of nasal toxicants
    • C. Liu, X. Zhou, F. J. Gonzalez, and X. Ding: Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2A6: role in metabolic activation of nasal toxicants. Mol. Pharmacol. 50, 781-788 (1996).
    • (1996) Mol. Pharmacol. , vol.50 , pp. 781-788
    • Liu, C.1    Zhou, X.2    Gonzalez, F.J.3    Ding, X.4
  • 51
    • 0027380074 scopus 로고
    • Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline
    • K. L. Kunze and W. F. Trager: Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem. Res. Toxicol. 6, 649-656 (1993).
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 649-656
    • Kunze, K.L.1    Trager, W.F.2
  • 54
    • 0020086178 scopus 로고
    • In vitro metabolic activation of the pulmonary toxin. 4-ipomeanol, in nonciliated bronchiolar epithelial (Clara) and alveolar type II cells isolated from rabbit lung
    • T. R. Devereux, K. G. Jones, J. R. Bend, J. R. Fouts, C. N. Statham, and M. R. Boyd: In vitro metabolic activation of the pulmonary toxin. 4-ipomeanol, in nonciliated bronchiolar epithelial (Clara) and alveolar type II cells isolated from rabbit lung. J. Pharmacol. Exp. Ther. 220, 223-227 (1981).
    • (1981) J. Pharmacol. Exp. Ther. , vol.220 , pp. 223-227
    • Devereux, T.R.1    Jones, K.G.2    Bend, J.R.3    Fouts, J.R.4    Statham, C.N.5    Boyd, M.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.