메뉴 건너뛰기




Volumn 27, Issue 2, 2004, Pages 199-205

Potent inhibition of human cytochrome P450 1 enzymes by dimethoxyphenylvinyl thiophene

Author keywords

Cytochrome P450 1 enzyme; Dimethoxyphenylvinyl thiophene; Enzyme inhibitor

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOCHROME P450; CYTOCHROME P450 1A1; DIMETHOXYPHENYLVINYL THIOPHENE; ENZYME INHIBITOR; ISOENZYME; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RECOMBINANT PROTEIN; THIOPHENE DERIVATIVE;

EID: 4644226790     PISSN: 02536269     EISSN: 02536269     Source Type: Journal    
DOI: 10.1007/BF02980107     Document Type: Article
Times cited : (4)

References (33)
  • 1
    • 0022357068 scopus 로고
    • Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450
    • Burke, M. D., Thompson, S., Elcombe, C. R., Halpert, J., Haaparanta, T., and Mayer, R. T., Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450. Biochem. Pharmacol., 34, 3337-3345 (1985).
    • (1985) Biochem. Pharmacol. , vol.34 , pp. 3337-3345
    • Burke, M.D.1    Thompson, S.2    Elcombe, C.R.3    Halpert, J.4    Haaparanta, T.5    Mayer, R.T.6
  • 2
    • 0029897471 scopus 로고    scopus 로고
    • Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins
    • Cai, Y., Baer-Dubowska, W., Ashwood-Smith, M. J., Ceska, O., Tachibana, S., and DiGiovanni, J., Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins. Chem. Res. Toxicol., 9, 729-736 (1996).
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 729-736
    • Cai, Y.1    Baer-Dubowska, W.2    Ashwood-Smith, M.J.3    Ceska, O.4    Tachibana, S.5    DiGiovanni, J.6
  • 3
    • 0033679373 scopus 로고    scopus 로고
    • Trans-resveratrol modulates the catalytic activity and mRNA expression of the procarcinogen-activating human cytochrome P450 1B1
    • Chang, T. K., Lee, W. B., and Ko, H. H., Trans-resveratrol modulates the catalytic activity and mRNA expression of the procarcinogen-activating human cytochrome P450 1B1. Can. J. Physiol. Pharmacol., 78, 874-881 (2000).
    • (2000) Can. J. Physiol. Pharmacol. , vol.78 , pp. 874-881
    • Chang, T.K.1    Lee, W.B.2    Ko, H.H.3
  • 4
    • 0032971740 scopus 로고    scopus 로고
    • Anti-allergic action of resveratrol and related hydroxystilbenes
    • Cheong, H., Ryu, S. Y., and Kim, K. M., Anti-allergic action of resveratrol and related hydroxystilbenes. Planta Med., 65, 266-268 (1999).
    • (1999) Planta Med. , vol.65 , pp. 266-268
    • Cheong, H.1    Ryu, S.Y.2    Kim, K.M.3
  • 5
    • 0033584453 scopus 로고    scopus 로고
    • Resveratrol is a selective human cytochrome P450 1A1 inhibitor
    • Chun, Y. J., Kim, M. Y., and Guengerich, F. P., Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem. Biophys. Res. Commun., 262, 20-24 (1999).
    • (1999) Biochem. Biophys. Res. Commun. , vol.262 , pp. 20-24
    • Chun, Y.J.1    Kim, M.Y.2    Guengerich, F.P.3
  • 6
    • 0035890772 scopus 로고    scopus 로고
    • A new selective and potent inhibitor of human cytochrome P450 1B1 and its application to antimutagenesis
    • Chun, Y. J., Kim, S., Kim, D., Lee, S. K., and Guengerich, F. P., A new selective and potent inhibitor of human cytochrome P450 1B1 and its application to antimutagenesis. Cancer Res., 61, 8164-8170 (2001a).
    • (2001) Cancer Res. , vol.61 , pp. 8164-8170
    • Chun, Y.J.1    Kim, S.2    Kim, D.3    Lee, S.K.4    Guengerich, F.P.5
  • 7
    • 0035064593 scopus 로고    scopus 로고
    • Mechanismbased inhibition of human cytochrome P450 1A1 by rhapontigenin
    • Chun, Y. J., Ryu, S. Y., Jeong, T. C., and Kim, M. Y., Mechanismbased inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metab. Dispos., 29, 389-393 (2001b).
    • (2001) Drug Metab. Dispos. , vol.29 , pp. 389-393
    • Chun, Y.J.1    Ryu, S.Y.2    Jeong, T.C.3    Kim, M.Y.4
  • 8
    • 0032126507 scopus 로고    scopus 로고
    • Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity
    • Ciolino, H. P., Wang, T. T., and Yeh, G. C., Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res., 58, 2754-2760 (1998).
    • (1998) Cancer Res. , vol.58 , pp. 2754-2760
    • Ciolino, H.P.1    Wang, T.T.2    Yeh, G.C.3
  • 9
    • 0033014568 scopus 로고    scopus 로고
    • The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor
    • Ciolino, H. P. and Yeh, G. C., The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Br. J. Cancer, 79, 1340-1346 (1999).
    • (1999) Br. J. Cancer , vol.79 , pp. 1340-1346
    • Ciolino, H.P.1    Yeh, G.C.2
  • 10
    • 0038407728 scopus 로고    scopus 로고
    • Methoxyestrogens exert feedback inhibition on cytochrome P450 1A1 and 1B1
    • Dawling, S., Roodi, N., and Parl, F. F., Methoxyestrogens exert feedback inhibition on cytochrome P450 1A1 and 1B1. Cancer Res., 63, 3127-3132 (2003).
    • (2003) Cancer Res. , vol.63 , pp. 3127-3132
    • Dawling, S.1    Roodi, N.2    Parl, F.F.3
  • 11
    • 0034599543 scopus 로고    scopus 로고
    • Bioflavonoids: Selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1
    • Doostdar, H., Burke, M. D., and Mayer, R. T., Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology, 144, 31-38 (2000).
    • (2000) Toxicology , vol.144 , pp. 31-38
    • Doostdar, H.1    Burke, M.D.2    Mayer, R.T.3
  • 12
    • 0034645693 scopus 로고    scopus 로고
    • Biological effects of resveratrol
    • Fremont, L., Biological effects of resveratrol. Life Sci., 66, 663-673 (2000).
    • (2000) Life Sci. , vol.66 , pp. 663-673
    • Fremont, L.1
  • 13
    • 0002254766 scopus 로고
    • Analysis and characterization of enzymes
    • Hayes, A.W. (Ed). Raven Press, New York
    • Guengerich, F. P., Analysis and characterization of enzymes, In Hayes, A.W. (Ed). Principles and Methods of Toxicology. Raven Press, New York, pp. 1259-1313, (1994).
    • (1994) Principles and Methods of Toxicology , pp. 1259-1313
    • Guengerich, F.P.1
  • 14
    • 0029757089 scopus 로고    scopus 로고
    • Purification of functional recombinant P450s from bacteria
    • Guengerich, F. P., Martin, M. V., Guo, Z., and Chun, Y. J., Purification of functional recombinant P450s from bacteria. Methods Enzymol., 272, 35-44 (1996).
    • (1996) Methods Enzymol. , vol.272 , pp. 35-44
    • Guengerich, F.P.1    Martin, M.V.2    Guo, Z.3    Chun, Y.J.4
  • 15
    • 0025992864 scopus 로고
    • Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes
    • Guengerich, F. P. and Shimada, T., Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol., 4, 391-407 (1991).
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 391-407
    • Guengerich, F.P.1    Shimada, T.2
  • 16
    • 0033938614 scopus 로고    scopus 로고
    • Inhibitory effects of 1,4-naphthoquinone derivatives on rat cytochrome P4501A1-dependent monooxygenase activity in recombinant yeast microsomes
    • Inouye, K., Saito, A., Orita, M., Tonomura, B., Imaishi, H., and Ohkawa, H., Inhibitory effects of 1,4-naphthoquinone derivatives on rat cytochrome P4501A1-dependent monooxygenase activity in recombinant yeast microsomes. J. Biochem., 127, 1041-1046 (2000).
    • (2000) J. Biochem. , vol.127 , pp. 1041-1046
    • Inouye, K.1    Saito, A.2    Orita, M.3    Tonomura, B.4    Imaishi, H.5    Ohkawa, H.6
  • 17
    • 0029910243 scopus 로고    scopus 로고
    • Oxidation of tienilic acid by human yeastexpressed cytochromes P-450 2C8, 2C9, 2C18 and 2C19. Evidence that this drug is a mechanism-based inhibitor specific for cytochrome P-450 2C9
    • Jean, P., Lopez-Garcia, P., Dansette, P., Mansuy, D., and Goldstein, J. L., Oxidation of tienilic acid by human yeastexpressed cytochromes P-450 2C8, 2C9, 2C18 and 2C19. Evidence that this drug is a mechanism-based inhibitor specific for cytochrome P-450 2C9. Eur. J. Biochem., 241, 797-804 (1996).
    • (1996) Eur. J. Biochem. , vol.241 , pp. 797-804
    • Jean, P.1    Lopez-Garcia, P.2    Dansette, P.3    Mansuy, D.4    Goldstein, J.L.5
  • 18
    • 0037011901 scopus 로고    scopus 로고
    • Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors
    • Kim, S., Ko, H., Park, J. E., Jung, S., Lee, S. K., and Chun, Y. J., Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. J. Med. Chem., 45, 160-164 (2002a).
    • (2002) J. Med. Chem. , vol.45 , pp. 160-164
    • Kim, S.1    Ko, H.2    Park, J.E.3    Jung, S.4    Lee, S.K.5    Chun, Y.J.6
  • 19
    • 0037013315 scopus 로고    scopus 로고
    • Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action
    • Kim, Y. M., Yun, J., Lee, C. K., Lee, H., Min, K. R., and Kim, Y., Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action. J. Biol. Chem., 277, 16340-16344 (2002b).
    • (2002) J. Biol. Chem. , vol.277 , pp. 16340-16344
    • Kim, Y.M.1    Yun, J.2    Lee, C.K.3    Lee, H.4    Min, K.R.5    Kim, Y.6
  • 20
    • 0036168607 scopus 로고    scopus 로고
    • Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[ a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation
    • Kleiner, H. E., Vulimiri, S. V., Reed, M. J., Uberecken, A., and DiGiovanni, J., Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[ a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation. Chem. Res. Toxicol., 15, 226-235 (2002).
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 226-235
    • Kleiner, H.E.1    Vulimiri, S.V.2    Reed, M.J.3    Uberecken, A.4    DiGiovanni, J.5
  • 22
    • 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
    • Mays, D., Hilliard, J., Wong, D., Chambers, M., Park, S., Gelboin, H., and Gerber, N., 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.1    Hilliard, J.2    Wong, D.3    Chambers, M.4    Park, S.5    Gelboin, H.6    Gerber, N.7
  • 23
    • 0017153510 scopus 로고
    • Effects of 2,4,3′,5′-tetrahydroxystilbene on oxidative phosphorylation by rat liver mitochondria
    • Nimmanpisut, S., Chudapongse, P., and Ratanabanangkoon, K., Effects of 2,4,3′,5′-tetrahydroxystilbene on oxidative phosphorylation by rat liver mitochondria. Biochem. Pharmacol., 25, 1245-1248 (1976).
    • (1976) Biochem. Pharmacol. , vol.25 , pp. 1245-1248
    • Nimmanpisut, S.1    Chudapongse, P.2    RatanabanangkoonK3
  • 24
    • 0033917295 scopus 로고    scopus 로고
    • Inhibition of human cytochrome P450 enzymes by constituents of St. John's Wort, an herbal preparation used in the treatment of depression
    • Obach, R. S., Inhibition of human cytochrome P450 enzymes by constituents of St. John's Wort, an herbal preparation used in the treatment of depression. J. Pharmacol. Exp. Ther., 294, 88-95 (2000).
    • (2000) J. Pharmacol. Exp. Ther. , vol.294 , pp. 88-95
    • Obach, R.S.1
  • 25
    • 0142150012 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen
    • O'Donnell, J. P., Dalvie, D. K., Kalgutkar, A. S., and Obach, R. S., Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab. Dispos., 31, 1369-1377 (2003).
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 1369-1377
    • O'Donnell, J.P.1    Dalvie, D.K.2    Kalgutkar, A.S.3    Obach, R.S.4
  • 26
    • 78651165715 scopus 로고
    • The carbon-monoxide binding pigment of liver microsomes
    • Omura, T. and Sato, R., 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
  • 27
    • 0030843652 scopus 로고    scopus 로고
    • Drug metabolism by Escherichia coli expressing human cytochromes P450
    • Parikh, A., Gillam, E. M., and Guengerich, F. P., Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat. Biotechnol., 15, 784-788 (1997).
    • (1997) Nat. Biotechnol. , vol.15 , pp. 784-788
    • Parikh, A.1    Gillam, E.M.2    Guengerich, F.P.3
  • 28
    • 0242695672 scopus 로고    scopus 로고
    • Resveratrol: From grapevines to mammalian biology
    • Pervaiz, S., Resveratrol: from grapevines to mammalian biology. FASEB J., 17, 1975-1985 (2003).
    • (2003) FASEB J. , vol.17 , pp. 1975-1985
    • Pervaiz, S.1
  • 29
    • 0345707567 scopus 로고    scopus 로고
    • St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1
    • Schwarz, D., Kisselev, P., and Roots, I., St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1. Cancer Res., 63, 8062-8068 (2003).
    • (2003) Cancer Res. , vol.63 , pp. 8062-8068
    • Schwarz, D.1    Kisselev, P.2    Roots, I.3
  • 32
    • 0032040745 scopus 로고    scopus 로고
    • Inhibitory effects of hydroxystilbenes on cyclooxygenase from sheep seminal vesicles
    • Shin, N. H., Ryu, S. Y., Lee, H., Min, K. R., and Kim, Y., Inhibitory effects of hydroxystilbenes on cyclooxygenase from sheep seminal vesicles. Planta Med., 64, 283-284 (1998b).
    • (1998) Planta Med. , vol.64 , pp. 283-284
    • Shin, N.H.1    Ryu, S.Y.2    Lee, H.3    Min, K.R.4    Kim, Y.5
  • 33
    • 0031785065 scopus 로고    scopus 로고
    • Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids
    • Zhai, S., Dai, R., Friedman, F. K., and Vestal, R. E., Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids. Drug Metab. Dispos., 26, 989-992 (1998).
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 989-992
    • Zhai, S.1    Dai, R.2    Friedman, F.K.3    Vestal, R.E.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.