메뉴 건너뛰기




Volumn 25, Issue 1, 1997, Pages 116-122

Substituent elimination from p-substituted phenols by cytochrome P450 ipso-substitution by the oxygen atom of the active species

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; HYDROQUINONE; PHENOL DERIVATIVE;

EID: 0031012608     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (62)

References (41)
  • 1
    • 33845469510 scopus 로고
    • Chemical mechanisms of catalysis by cytochromes P-450: A unified view
    • F. P. Guengerich and T. L. Macdonald: Chemical mechanisms of catalysis by cytochromes P-450: a unified view. Acc. Chem. Res. 17, 9-16 (1984).
    • (1984) Acc. Chem. Res. , vol.17 , pp. 9-16
    • Guengerich, F.P.1    Macdonald, T.L.2
  • 2
    • 0025895757 scopus 로고
    • Reactions and significance of cytochrome P-450 enzymes
    • F. P. Guengerich: Reactions and significance of cytochrome P-450 enzymes. J. Biol. Chem. 266, 10019-10022 (1991).
    • (1991) J. Biol. Chem. , vol.266 , pp. 10019-10022
    • Guengerich, F.P.1
  • 3
    • 0025784027 scopus 로고
    • Cytochrome P-450
    • T. D. Porter and M. J. Coon: Cytochrome P-450. J. Biol. Chem. 266, 13469-13472 (1991).
    • (1991) J. Biol. Chem. , vol.266 , pp. 13469-13472
    • Porter, T.D.1    Coon, M.J.2
  • 4
    • 0026536546 scopus 로고
    • Cytochrome P450: Advances and prospects
    • F. P. Guengerich: Cytochrome P450: advances and prospects. FASEB J. 6, 667-668 (1992).
    • (1992) FASEB J. , vol.6 , pp. 667-668
    • Guengerich, F.P.1
  • 5
    • 0026564816 scopus 로고
    • Cytochrome P450: Progress and predictions
    • M. J. Coon, X. Ding, S. J. Pernecky, and A. D. N. Vaz: Cytochrome P450: progress and predictions. FASEB J. 6, 669-673 (1992).
    • (1992) FASEB J. , vol.6 , pp. 669-673
    • Coon, M.J.1    Ding, X.2    Pernecky, S.J.3    Vaz, A.D.N.4
  • 6
    • 0008265496 scopus 로고
    • Regulation of synthesis and activity of cytochrome P-450 enzymes in physiological pathway
    • P. R. Ortiz de Montellano, ed., Plenum Press, New York
    • M. R. Waterman, M. E. John, and E. R. Simpson: Regulation of synthesis and activity of cytochrome P-450 enzymes in physiological pathway. In "Cytochrome P-450, Structure, Mechanism, and Biochemistry" (P. R. Ortiz de Montellano, ed.), pp. 345-386. Plenum Press, New York, 1986.
    • (1986) Cytochrome P-450, Structure, Mechanism, and Biochemistry , pp. 345-386
    • Waterman, M.R.1    John, M.E.2    Simpson, E.R.3
  • 7
    • 0011697055 scopus 로고
    • Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage
    • B. Meunier: Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem. Rev. 92, 1411-1456 (1992).
    • (1992) Chem. Rev. , vol.92 , pp. 1411-1456
    • Meunier, B.1
  • 8
    • 0024354761 scopus 로고
    • Application of chemical P450 model systems to studies on drug metabolism. I. Phencyclidine: A multi-functional model substrate
    • H. Masumoto, K. Takeuchi, S. Ohta, and M. Hirobe: Application of chemical P450 model systems to studies on drug metabolism. I. Phencyclidine: a multi-functional model substrate. Chem. Pharm. Bull. 37, 1788-1794 (1989).
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 1788-1794
    • Masumoto, H.1    Takeuchi, K.2    Ohta, S.3    Hirobe, M.4
  • 9
    • 0024328594 scopus 로고
    • Facile preparation of unstable metabolic intermediates; epoxide(s) of pyrazolo[1,5-a]pyridine derivatives by the cytochrome P-450 chemical model
    • Y. Nagatsu, T. Higuchi, and M. Hirobe: Facile preparation of unstable metabolic intermediates; epoxide(s) of pyrazolo[1,5-a]pyridine derivatives by the cytochrome P-450 chemical model. Chem. Pharm. Bull. 37, 1410-1412 (1989).
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 1410-1412
    • Nagatsu, Y.1    Higuchi, T.2    Hirobe, M.3
  • 10
    • 0025266069 scopus 로고
    • Application of chemical P-450 model systems to study drug metabolism. III. Metabolism of isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine
    • Y. Nagatsu, T. Higuchi, and M. Hirobe: Application of chemical P-450 model systems to study drug metabolism. III. Metabolism of isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine. Chem. Pharm. Bull. 38, 400-403 (1990).
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 400-403
    • Nagatsu, Y.1    Higuchi, T.2    Hirobe, M.3
  • 11
    • 0025899971 scopus 로고
    • Application of chemical cytochrome P-450 model systems to studies on drug metabolism. IV. Mechanism of piperidine metabolism pathway via an iminium intermediate
    • H. Masumoto, S. Ohta, and M. Hirobe: Application of chemical cytochrome P-450 model systems to studies on drug metabolism. IV. Mechanism of piperidine metabolism pathway via an iminium intermediate. Drug Metab. Dispos. 19, 768-780 (1991).
    • (1991) Drug Metab. Dispos. , vol.19 , pp. 768-780
    • Masumoto, H.1    Ohta, S.2    Hirobe, M.3
  • 12
    • 0026641280 scopus 로고
    • Oxidative decarboxylation of carboxylic acids by iron porphyrin-idosylbenzene system
    • M. Komuro, Y. Nagatsu, T. Higuchi, and M. Hirobe: Oxidative decarboxylation of carboxylic acids by iron porphyrin-idosylbenzene system. Tetrahedron Lett. 33, 4949-4952 (1992).
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4949-4952
    • Komuro, M.1    Nagatsu, Y.2    Higuchi, T.3    Hirobe, M.4
  • 13
    • 0027205460 scopus 로고
    • Application of chemical cytochrome P-450 model systems to studies on drug metabolism. VI. N,N-Coupling reaction of N-methylaniline catalyzed by polypeptide-bound porphyrinatoiron(III) and cytochrome P-450
    • T. Doi, T. Mori, T. Mashino, and M. Hirobe: Application of chemical cytochrome P-450 model systems to studies on drug metabolism. VI. N,N-Coupling reaction of N-methylaniline catalyzed by polypeptide-bound porphyrinatoiron(III) and cytochrome P-450. Biochem. Biophys. Res. Commun. 191, 737-743 (1993).
    • (1993) Biochem. Biophys. Res. Commun. , vol.191 , pp. 737-743
    • Doi, T.1    Mori, T.2    Mashino, T.3    Hirobe, M.4
  • 14
    • 0028352457 scopus 로고
    • Novel metabolic pathway of arylethers by cytochrome P450: Cleavage of the oxygen-aromatic ring bond accompanying ipso-substitution by the oxygen atom of the active species in cytochrome P450 models and cytochrome P450
    • T. Ohe, T. Mashino, and M. Hirobe: Novel metabolic pathway of arylethers by cytochrome P450: cleavage of the oxygen-aromatic ring bond accompanying ipso-substitution by the oxygen atom of the active species in cytochrome P450 models and cytochrome P450. Arch. Biochem. Biophys. 19, 402-409 (1994).
    • (1994) Arch. Biochem. Biophys. , vol.19 , pp. 402-409
    • Ohe, T.1    Mashino, T.2    Hirobe, M.3
  • 15
    • 0028951308 scopus 로고
    • Application of chemical cytochrome P-450 model systems to studies on drug metabolism. VIII. Novel metabolism of carboxylic acids via oxidative decarboxylation
    • M. Komuro, T. Higuchi, and M. Hirobe: Application of chemical cytochrome P-450 model systems to studies on drug metabolism. VIII. Novel metabolism of carboxylic acids via oxidative decarboxylation. Bioorg. Med. Chem. 3, 55-65 (1995).
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 55-65
    • Komuro, M.1    Higuchi, T.2    Hirobe, M.3
  • 16
    • 0028863957 scopus 로고
    • Novel oxidative pathway of parasubstituted phenols in cytochrome P450 chemical model: Substituent elimination accompanying ipso-substitution by the oxygen atom of the active species
    • T. Ohe, T. Mashino, and M. Hirobe: Novel oxidative pathway of parasubstituted phenols in cytochrome P450 chemical model: substituent elimination accompanying ipso-substitution by the oxygen atom of the active species. Tetrahedron Lett. 42, 7681-7684 (1995).
    • (1995) Tetrahedron Lett. , vol.42 , pp. 7681-7684
    • Ohe, T.1    Mashino, T.2    Hirobe, M.3
  • 17
    • 0343219002 scopus 로고    scopus 로고
    • Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ, δ- and β, γ-unsaturated carboxylic acids with an iron porphyrin-iodosylbenzene system
    • M. Komuro, T. Higuchi, and M. Hirobe: Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ, δ-and β, γ-unsaturated carboxylic acids with an iron porphyrin-iodosylbenzene system. J. Chem. Soc., 1, 2309-2313 (1996).
    • (1996) J. Chem. Soc. , vol.1 , pp. 2309-2313
    • Komuro, M.1    Higuchi, T.2    Hirobe, M.3
  • 18
    • 0020325715 scopus 로고
    • Metabolic activation and drug toxicity
    • S. D. Nelson: Metabolic activation and drug toxicity. J. Med. Chem. 25, 753-765 (1982).
    • (1982) J. Med. Chem. , vol.25 , pp. 753-765
    • Nelson, S.D.1
  • 19
    • 0028272001 scopus 로고
    • Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins
    • F. J. Gonzalez and H. V. Gelboin: Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. Drug Metab. Rev. 26, 165-183 (1994).
    • (1994) Drug Metab. Rev. , vol.26 , pp. 165-183
    • Gonzalez, F.J.1    Gelboin, H.V.2
  • 20
    • 0028074997 scopus 로고
    • Effects of fluorine substitution on drug metabolism: Pharmacological and toxicological implications
    • B. K. Park and N. R. Kitteringham: Effects of fluorine substitution on drug metabolism: pharmacological and toxicological implications. Drug Metab. Rev. 26, 605-643 (1994).
    • (1994) Drug Metab. Rev. , vol.26 , pp. 605-643
    • Park, B.K.1    Kitteringham, N.R.2
  • 21
    • 0021907369 scopus 로고
    • Catechol formation of fluoro- and bromo-substituted estradiols by hamster liver microsomes
    • J. J. Li, R. H. Purdy, E. H. Appelman, J. K. Klicka, and S. A. Li: Catechol formation of fluoro-and bromo-substituted estradiols by hamster liver microsomes. Mol. Pharmacol. 27, 559-565 (1985).
    • (1985) Mol. Pharmacol. , vol.27 , pp. 559-565
    • Li, J.J.1    Purdy, R.H.2    Appelman, E.H.3    Klicka, J.K.4    Li, S.A.5
  • 22
    • 0025288686 scopus 로고
    • Metabolic studies on pentachlorophenol (PCP) in rats
    • G. Renner and C. Hopfer: Metabolic studies on pentachlorophenol (PCP) in rats. Xenobiotica 20, 573-582 (1990).
    • (1990) Xenobiotica , vol.20 , pp. 573-582
    • Renner, G.1    Hopfer, C.2
  • 23
    • 0026598417 scopus 로고
    • A new hypothesis for the mechanism for cytochrome P-450 dependent aerobic conversion of hexahalogenated benzenes to pentahalogenated phenols
    • I. M. C. M. Rietjens and J. Vervoort: A new hypothesis for the mechanism for cytochrome P-450 dependent aerobic conversion of hexahalogenated benzenes to pentahalogenated phenols. Chem. Res. Toxicol. 5, 10-19 (1992).
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 10-19
    • Rietjens, I.M.C.M.1    Vervoort, J.2
  • 24
    • 0027521508 scopus 로고
    • Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product
    • C. Den Besten, P. J. Van Bladeren, E. Duizer, J. Vervoort, and I. M. C. M. Rietjens: Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product. Chem. Res. Toxicol. 6, 674-680 (1993).
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 674-680
    • Den Besten, C.1    Van Bladeren, P.J.2    Duizer, E.3    Vervoort, J.4    Rietjens, I.M.C.M.5
  • 25
    • 0000530381 scopus 로고
    • Biogenesis-like transformation of salidroside to rengyol and its related cyclohexyletanoids of Forsythia suspensa
    • K. Endo, K. Seya, and H. Hikono: Biogenesis-like transformation of salidroside to rengyol and its related cyclohexyletanoids of Forsythia suspensa. Tetrahedron 45, 3673-3682 (1989).
    • (1989) Tetrahedron , vol.45 , pp. 3673-3682
    • Endo, K.1    Seya, K.2    Hikono, H.3
  • 26
    • 0343218998 scopus 로고
    • The oxidative hydrolysis of quinol esters by periodic acid
    • C. A. Bunton and J. Hellyer: The oxidative hydrolysis of quinol esters by periodic acid. J. Am. Chem. Soc. 89, 6252-6257 (1967).
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 6252-6257
    • Bunton, C.A.1    Hellyer, J.2
  • 27
    • 0343219000 scopus 로고
    • p-Chlorophenyl salicylate
    • N. Rabjohn, ed., John Wiley and Sons, New York
    • N. G. Gaylord and P. M. Kamath: p-Chlorophenyl salicylate. In "Organic Syntheses" (N. Rabjohn, ed.), vol. 4, pp. 178-179. John Wiley and Sons, New York, 1963.
    • (1963) Organic Syntheses , vol.4 , pp. 178-179
    • Gaylord, N.G.1    Kamath, P.M.2
  • 29
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes
    • T. Omura and R. Sato: The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378 (1964).
    • (1964) J. Biol. Chem. , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 30
    • 77049138167 scopus 로고
    • The colorimetric estimation of formaldehyde by means of the Hantzsch reaction
    • T. Nash: The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J. 55, 416-421 (1953).
    • (1953) Biochem. J. , vol.55 , pp. 416-421
    • Nash, T.1
  • 31
    • 0017794681 scopus 로고
    • Assay of formaldehyde generated during microsomal oxidation reactions
    • S. Fleischer and L. Packer, eds., Academic Press, New York
    • J. Werringloer: Assay of formaldehyde generated during microsomal oxidation reactions. In "Methods in Enzymology" (S. Fleischer and L. Packer, eds.), vol. 52, pp. 297-302. Academic Press, New York, 1978.
    • (1978) Methods in Enzymology , vol.52 , pp. 297-302
    • Werringloer, J.1
  • 32
    • 84979132832 scopus 로고
    • Bemerkungen zu der Abhandlung der HH. Weselsky und Benedikt "Ueber einige Azoverbindungen."
    • P. Griess: Bemerkungen zu der Abhandlung der HH. Weselsky und Benedikt "Ueber einige Azoverbindungen." Chem. Ber. 12, 426-428 (1879).
    • (1879) Chem. Ber. , vol.12 , pp. 426-428
    • Griess, P.1
  • 34
    • 0002270104 scopus 로고
    • Cytochrome P-450 enzymes in sterol biosynthesis and metabolism
    • P. R. Ortiz de Montellano, ed., Plenum Press, New York
    • C. R. Jefcoate: Cytochrome P-450 enzymes in sterol biosynthesis and metabolism. In "Cytochrome P-450, Structure, Mechanism, and Biochemistry" (P. R. Ortiz de Montellano, ed.), pp. 387-428. Plenum Press, New York, 1986.
    • (1986) Cytochrome P-450, Structure, Mechanism, and Biochemistry , pp. 387-428
    • Jefcoate, C.R.1
  • 35
    • 0027184205 scopus 로고
    • Oxidation of nitric oxide in aqueous solution to nitrite but not nitrate: Comparison with enzymatically formed nitric oxide from L-arginine
    • L. J. Ignarro, J. M. Fukuto, J. M. Griscavage, N. E. Rogers, and R. E. Byrns: Oxidation of nitric oxide in aqueous solution to nitrite but not nitrate: comparison with enzymatically formed nitric oxide from L-arginine. Proc. Natl. Acad. Sci. U.S.A. 90, 8103-8107 (1993).
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 8103-8107
    • Ignarro, L.J.1    Fukuto, J.M.2    Griscavage, J.M.3    Rogers, N.E.4    Byrns, R.E.5
  • 36
    • 0024350150 scopus 로고
    • Microsomal metabolism of fluoroanilines
    • I. M. C. M. Rietjens and J. Vervoort: Microsomal metabolism of fluoroanilines. Xenobiotica 19, 1297-1305 (1989).
    • (1989) Xenobiotica , vol.19 , pp. 1297-1305
    • Rietjens, I.M.C.M.1    Vervoort, J.2
  • 38
    • 0025959828 scopus 로고
    • Bioactivation of 4-fluorinated anilines to benzoquinoneimines as primary reaction products
    • I. M. C. M. Rietjens and J. Vervoort: Bioactivation of 4-fluorinated anilines to benzoquinoneimines as primary reaction products. Chem.-Biol. Interact. 77, 263-281 (1991).
    • (1991) Chem.-Biol. Interact. , vol.77 , pp. 263-281
    • Rietjens, I.M.C.M.1    Vervoort, J.2
  • 39
    • 0027076381 scopus 로고
    • Study on the regioselectivity and mechanism of the aromatic hydroxylation of monofluoroanilines
    • N. H. P. Cnubben, J. Vervoort, C. Veeger, and I. M. C. M. Rietjens: Study on the regioselectivity and mechanism of the aromatic hydroxylation of monofluoroanilines. Chem.-Biol. Interact. 85, 151-172 (1992).
    • (1992) Chem.-Biol. Interact. , vol.85 , pp. 151-172
    • Cnubben, N.H.P.1    Vervoort, J.2    Veeger, C.3    Rietjens, I.M.C.M.4
  • 40
    • 0028132823 scopus 로고
    • Molecular orbital-based quantitative structure-activity relationship for the cytochrome P450-catalyzed 4-hydroxylation of halogenated anilines
    • N. H. P. Cnubben, S. Peelen, J.-W. Borst, J. Vervoort, C. Veeger, and I. M. C. M. Rietjens: Molecular orbital-based quantitative structure-activity relationship for the cytochrome P450-catalyzed 4-hydroxylation of halogenated anilines. Chem. Res. Toxicol. 7, 590-598 (1994).
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 590-598
    • Cnubben, N.H.P.1    Peelen, S.2    Borst, J.-W.3    Vervoort, J.4    Veeger, C.5    Rietjens, I.M.C.M.6
  • 41
    • 0029049573 scopus 로고
    • The effect of varying halogen substituent patterns on the cytochrome P450 catalysed dehalogenation of 4-halogenated anilines to 4-aminophenol metabolites
    • N. H. P. Cnubben, J. Vervoort, M. G. Boersma, and I. M. C. M. Rietjens: The effect of varying halogen substituent patterns on the cytochrome P450 catalysed dehalogenation of 4-halogenated anilines to 4-aminophenol metabolites. Biochem. Pharmacol. 49, 1235-1248 (1995).
    • (1995) Biochem. Pharmacol. , vol.49 , pp. 1235-1248
    • Cnubben, N.H.P.1    Vervoort, J.2    Boersma, M.G.3    Rietjens, I.M.C.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.