메뉴 건너뛰기




Volumn 25, Issue 2, 2012, Pages 357-365

Inhibition of cytochrome P450 enzymes by quinones and anthraquinones

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 4 CHLORO 2 METHYLANTHRACENE 9,10 DIONE; 1 AMINO 4 HYDROXYANTHRACENE 9,10 DIONE; 2,6 DI TERT BUTYL 5 HYDROXYNAPHTHALENE 1,4 DIONE; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 2B1; CYTOCHROME P450 INHIBITOR; EMODIN; METHYL GROUP; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84859786014     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx2004163     Document Type: Article
Times cited : (44)

References (44)
  • 1
    • 3042519587 scopus 로고    scopus 로고
    • Cytochrome P450: What have we learned and what are the future issues?
    • DOI 10.1081/DMR-120033996
    • Guengerich, F. P. (2004) Cytochrome P450: What have we learned and what are the future issues? Drug Metab. Rev. 36, 159-197. (Pubitemid 38802485)
    • (2004) Drug Metabolism Reviews , vol.36 , Issue.2 , pp. 159-197
    • Guengerich, F.P.1
  • 4
    • 0034868937 scopus 로고    scopus 로고
    • Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5
    • Wang, H. W., Chen, T. L., Yang, P. C., and Ueng, T. H. (2001) Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5. Drug Metab. Dispos. 29, 1229-1235.
    • (2001) Drug Metab. Dispos. , vol.29 , pp. 1229-1235
    • Wang, H.W.1    Chen, T.L.2    Yang, P.C.3    Ueng, T.H.4
  • 5
    • 0033668698 scopus 로고    scopus 로고
    • The role of cytochrome P450 in tumour development and progression and its potential in therapy
    • Murray, G. I. (2000) The role of cytochrome P450 in tumour development and progression and its potential in therapy. J. Pathol. 192, 419-426.
    • (2000) J. Pathol. , vol.192 , pp. 419-426
    • Murray, G.I.1
  • 13
    • 33646155334 scopus 로고    scopus 로고
    • Systematic search for gastric cancer-specific genes based on SAGE data: Melanoma inhibitory activity and matrix metalloproteinase-10 are novel prognostic factors in patients with gastric cancer
    • Aung, P. P., Oue, N., Mitani, Y., Nakayama, H., Yoshida, K., Noguchi, T., Bosserhoff, A. K., and Yasui, W. (2006) Systematic search for gastric cancer-specific genes based on SAGE data: Melanoma inhibitory activity and matrix metalloproteinase-10 are novel prognostic factors in patients with gastric cancer. Oncogene 25, 2546-2557.
    • (2006) Oncogene , vol.25 , pp. 2546-2557
    • Aung, P.P.1    Oue, N.2    Mitani, Y.3    Nakayama, H.4    Yoshida, K.5    Noguchi, T.6    Bosserhoff, A.K.7    Yasui, W.8
  • 14
    • 0032804346 scopus 로고    scopus 로고
    • Metabolism-based polycyclic aromatic acetylene inhibition of CYP1B1 in 10T1/2 cells potentiates aryl hydrocarbon receptor activity
    • Alexander, D. L., Zhang, L., Foroozesh, M., Alworth, W. L., and Jefcoate, C. R. (1999) Metabolism-based polycyclic aromatic acetylene inhibition of CYP1B1 in 10T1/2 cells potentiates aryl hydrocarbon receptor activity. Toxicol. Appl. Pharmacol. 161, 123-139.
    • (1999) Toxicol. Appl. Pharmacol. , vol.161 , pp. 123-139
    • Alexander, D.L.1    Zhang, L.2    Foroozesh, M.3    Alworth, W.L.4    Jefcoate, C.R.5
  • 22
    • 77949356275 scopus 로고    scopus 로고
    • In silico studies of polyaromatic hydrocarbon inhibitors of cytochrome P450 enzymes 1A1, 1A2, 2A6, and 2B1
    • Sridhar, J., Jin, P., Liu, J., Foroozesh, M., and Stevens, C. L. (2010) In silico studies of polyaromatic hydrocarbon inhibitors of cytochrome P450 enzymes 1A1, 1A2, 2A6, and 2B1. Chem. Res. Toxicol. 23, 600-607.
    • (2010) Chem. Res. Toxicol. , vol.23 , pp. 600-607
    • Sridhar, J.1    Jin, P.2    Liu, J.3    Foroozesh, M.4    Stevens, C.L.5
  • 23
    • 84855770436 scopus 로고    scopus 로고
    • QSAR models of cytochrome P450 enzyme 1A2 inhibitors using CoMFA, CoMSIA and HQSAR
    • Sridhar, J., Foroozesh, M., and Stevens, C. K. (2011) QSAR Models of Cytochrome P450 Enzyme 1A2 Inhibitors using CoMFA, CoMSIA and HQSAR. SAR QSAR Environ. Res. 22, 681-697.
    • (2011) SAR QSAR Environ. Res. , vol.22 , pp. 681-697
    • Sridhar, J.1    Foroozesh, M.2    Stevens, C.K.3
  • 24
    • 0031793967 scopus 로고    scopus 로고
    • Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes: Bioactivation to genotoxic metabolites
    • Mueller, S. O., Stopper, H., and Dekant, W. (1998) Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes. Bioactivation to genotoxic metabolites. Drug Metab. Dispos. 26, 540-546. (Pubitemid 28498359)
    • (1998) Drug Metabolism and Disposition , vol.26 , Issue.6 , pp. 540-546
    • Mueller, S.O.1    Stopper, H.2    Dekant, W.3
  • 25
    • 0034220813 scopus 로고    scopus 로고
    • Cytochrome P4501A1-inhibitory action of antimutagenic anthraquinones in medicinal plants and the structure-activity relationship
    • Sun, M., Sakakibara, H., Ashida, H., Danno, G., and Kanazawa, K. (2000) Cytochrome P4501A1-inhibitory action of antimutagenic anthraquinones in medicinal plants and the structure-activity relationship. Biosci., Biotechnol., Biochem. 64, 1373-1378.
    • (2000) Biosci., Biotechnol., Biochem. , vol.64 , pp. 1373-1378
    • Sun, M.1    Sakakibara, H.2    Ashida, H.3    Danno, G.4    Kanazawa, K.5
  • 26
    • 0042206721 scopus 로고    scopus 로고
    • Emodin induces apoptosis of human cervical cancer cells through poly(ADP-ribose) polymerase cleavage and activation of caspase-9
    • DOI 10.1016/S0014-2999(03)01976-9
    • Srinivas, G., Anto, R. J., Srinivas, P., Vidhyalakshmi, S., Senan, V. P., and Karunagaran, D. (2003) Emodin induces apoptosis of human cervical cancer cells through poly(ADP-ribose) polymerase cleavage and activation of caspase-9. Eur. J. Pharmacol. 473, 117-125. (Pubitemid 36929875)
    • (2003) European Journal of Pharmacology , vol.473 , Issue.2-3 , pp. 117-125
    • Srinivas, G.1    Anto, R.J.2    Srinivas, P.3    Vidhyalakshmi, S.4    Senan, V.P.5    Karunagaran, D.6
  • 27
    • 20444505248 scopus 로고    scopus 로고
    • Emodin induces apoptosis in human lung adenocarcinoma cells through a reactive oxygen species-dependent mitochondrial signaling pathway
    • Su, Y. T., Chang, H. L., Shyue, S. K., and Hsu, S. L. (2005) Emodin induces apoptosis in human lung adenocarcinoma cells through a reactive oxygen species-dependent mitochondrial signaling pathway. Biochem. Pharmacol. 70, 229-241.
    • (2005) Biochem. Pharmacol. , vol.70 , pp. 229-241
    • Su, Y.T.1    Chang, H.L.2    Shyue, S.K.3    Hsu, S.L.4
  • 28
    • 0037114436 scopus 로고    scopus 로고
    • Emodin induces apoptosis in human promyeloleukemic HL-60 cells accompanied by activation of caspase 3 cascade but independent of reactive oxygen species production
    • Chen, Y. C., Shen, S. C., Lee, W. R., Hsu, F. L., Lin, H. Y., Ko, C. H., and Tseng, S. W. (2002) Emodin induces apoptosis in human promyeloleukemic HL-60 cells accompanied by activation of caspase 3 cascade but independent of reactive oxygen species production. Biochem. Pharmacol. 64, 1713-1724.
    • (2002) Biochem. Pharmacol. , vol.64 , pp. 1713-1724
    • Chen, Y.C.1    Shen, S.C.2    Lee, W.R.3    Hsu, F.L.4    Lin, H.Y.5    Ko, C.H.6    Tseng, S.W.7
  • 29
    • 0032482434 scopus 로고    scopus 로고
    • Tyrosine kinase inhibitors, emodin and its derivative repress HER-2/neu-induced cellular transformation and metastasis-associated properties
    • Zhang, L., Lau, Y. K., Xi, L., Hong, R. L., Kim, D. S., Chen, C. F., Hortobagyi, G. N., Chang, C., and Hung, M. C. (1998) Tyrosine kinase inhibitors, emodin and its derivative repress HER-2/neu-induced cellular transformation and metastasis-associated properties. Oncogene 16, 2855-2863. (Pubitemid 28383270)
    • (1998) Oncogene , vol.16 , Issue.22 , pp. 2855-2863
    • Zhang, L.1    Lau, Y.-K.2    Xi, L.3    Hong, R.-L.4    Kim, D.S.H.L.5    Chen, C.-F.6    Hortobagyi, G.N.7    Chang, C.-J.8    Hung, M.-C.9
  • 30
    • 0034846756 scopus 로고    scopus 로고
    • Effects and mechanisms of emodin on cell death in human lung squamous cell carcinoma
    • Lee, H. Z. (2001) Effects and mechanisms of emodin on cell death in human lung squamous cell carcinoma. Br. J. Pharmacol. 134, 11-20.
    • (2001) Br. J. Pharmacol. , vol.134 , pp. 11-20
    • Lee, H.Z.1
  • 31
    • 1642535590 scopus 로고    scopus 로고
    • Emodin Enhances Arsenic Trioxide-Induced Apoptosis via Generation of Reactive Oxygen Species and Inhibition of Survival Signaling
    • DOI 10.1158/0008-5472.CAN-2820-2
    • Yi, J., Yang, J., He, R., Gao, F., Sang, H., Tang, X., and Ye, R. D. (2004) Emodin enhances arsenic trioxide-induced apoptosis via generation of reactive oxygen species and inhibition of survival signaling. Cancer Res. 64, 108-116. (Pubitemid 38114088)
    • (2004) Cancer Research , vol.64 , Issue.1 , pp. 108-116
    • Yi, J.1    Yang, J.2    He, R.3    Gao, F.4    Sang, H.5    Tang, X.6    Ye, R.D.7
  • 32
    • 0028106482 scopus 로고
    • Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver
    • DOI 10.1016/0006-2952(94)90363-8
    • Burke, M. D., Thompson, S., Weaver, R. J., Wolf, C. R., and Mayer, R. T. (1994) Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol. 48, 923-936. (Pubitemid 24285170)
    • (1994) Biochemical Pharmacology , vol.48 , Issue.5 , pp. 923-936
    • Danny Burke, M.1    Thompson, S.2    Weaver, R.J.3    Roland Wolf, C.4    Mayers, R.T.5
  • 33
    • 54349098233 scopus 로고    scopus 로고
    • Application of molecular modeling for prediction of substrate specificity in cytochrome P450 1A2 mutants
    • Tu, Y., Deshmukh, R., Sivaneri, M., and Szklarz, G. D. (2008) Application of molecular modeling for prediction of substrate specificity in cytochrome P450 1A2 mutants. Drug Metab. Dispos. 36, 2371-2380.
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 2371-2380
    • Tu, Y.1    Deshmukh, R.2    Sivaneri, M.3    Szklarz, G.D.4
  • 34
    • 0027374515 scopus 로고
    • A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man. Direct fluorescence monitoring of the deethylation of 7-ethoxy-4-trifluoromethylcoumarin
    • DOI 10.1016/0006-2952(93)90326-R
    • 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. Direct fluorescence monitoring of the deethylation of 7-ethoxy-4- trifluoromethylcoumarin. Biochem. Pharmacol. 46, 1577-1584. (Pubitemid 23338491)
    • (1993) Biochemical Pharmacology , vol.46 , Issue.9 , pp. 1577-1584
    • Buters, J.T.M.1    Schiller, C.D.2    Chou, R.C.3
  • 35
    • 0023919384 scopus 로고
    • A direct, highly sensitive assay for cytochrome P-450 catalyzed O-deethylation using a novel coumarin analog
    • DeLuca, J. G., Dysart, G. R., Rasnick, D., and Bradley, M. O. (1988) A direct, highly sensitive assay for cytochrome P-450 catalyzed O-deethylation using a novel coumarin analog. Biochem. Pharmacol. 37, 1731-1739.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 1731-1739
    • Deluca, J.G.1    Dysart, G.R.2    Rasnick, D.3    Bradley, M.O.4
  • 36
    • 0026726554 scopus 로고
    • Suicide inhibitors of cytochrome P450 1A1 and P450 2B1
    • Hopkins, N. E., Foroozesh, M. K., and Alworth, W. L. (1992) Suicide inhibitors of cytochrome P450 1A1 and P450 2B1. Biochem. Pharmacol. 44, 787-796.
    • (1992) Biochem. Pharmacol. , vol.44 , pp. 787-796
    • Hopkins, N.E.1    Foroozesh, M.K.2    Alworth, W.L.3
  • 37
    • 0031021458 scopus 로고    scopus 로고
    • Aryl acetylenes as mechanism-based inhibitors of cytochrome P450- dependent monooxygenase enzymes
    • DOI 10.1021/tx960064g
    • Foroozesh, M., Primrose, G., Guo, Z., Bell, L. C., Alworth, W. L., and Guengerich, F. P. (1997) Aryl acetylenes as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes. Chem. Res. Toxicol. 10, 91-102. (Pubitemid 27044913)
    • (1997) Chemical Research in Toxicology , vol.10 , Issue.1 , pp. 91-102
    • Foroozesh, M.1    Primrose, G.2    Guo, Z.3    Bell, L.C.4    Alworth, W.L.5    Guengerich, F.P.6
  • 38
    • 19644374377 scopus 로고    scopus 로고
    • New AMBER force field parameters of heme iron for cytochrome P450s determined by quantum chemical calculations of simplified models
    • DOI 10.1002/jcc.20221
    • Oda, A., Yamaotsu, N., and Hirono, S. (2005) New AMBER force field parameters of heme iron for cytochrome P450s determined by quantum chemical calculations of simplified models. J. Comput. Chem. 26, 818-826. (Pubitemid 40751576)
    • (2005) Journal of Computational Chemistry , vol.26 , Issue.8 , pp. 818-826
    • Oda, A.1    Yamaotsu, N.2    Hirono, S.3
  • 40
    • 12144276704 scopus 로고    scopus 로고
    • 5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6
    • DOI 10.1021/jm049696n
    • Denton, T. T., Zhang, X., and Cashman, J. R. (2005) 5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6. J. Med. Chem. 48, 224-239. (Pubitemid 40105261)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.1 , pp. 224-239
    • Denton, T.T.1    Zhang, X.2    Cashman, J.R.3
  • 41
    • 13844316753 scopus 로고    scopus 로고
    • Cytochrome P450 activation of arylamines and heterocyclic amines
    • DOI 10.1146/annurev.pharmtox.45.120403.100010
    • Kim, D., and Guengerich, F. P. (2005) Cytochrome P450 activation of arylamines and heterocyclic amines. Annu. Rev. Pharmacol. Toxicol. 45, 27-49. (Pubitemid 40261797)
    • (2005) Annual Review of Pharmacology and Toxicology , vol.45 , pp. 27-49
    • Kim, D.1    Guengerich, F.P.2
  • 42
    • 3242660672 scopus 로고    scopus 로고
    • Inhibition of murine cytochrome P4501A by tacrine: In vitro studies
    • DOI 10.1124/dmd.32.8.805
    • Peng, J. Z., Remmel, R. P., and Sawchuk, R. J. (2004) Inhibition of murine cytochrome P4501A by tacrine: in vitro studies. Drug Metab. Dispos. 32, 805-812. (Pubitemid 38955609)
    • (2004) Drug Metabolism and Disposition , vol.32 , Issue.8 , pp. 805-812
    • Peng, J.Z.1    Remmel, R.P.2    Sawchuk, R.J.3
  • 43
    • 0024980098 scopus 로고
    • Deuterium isotope effects on toluene metabolism. Product release as a rate-limiting step in cytochrome P-450 catalysis
    • Ling, K. H., and Hanzlik, R. P. (1989) Deuterium isotope effects on toluene metabolism. Product release as a rate-limiting step in cytochrome P-450 catalysis. Biochem. Biophys. Res. Commun. 160, 844-849.
    • (1989) Biochem. Biophys. Res. Commun. , vol.160 , pp. 844-849
    • Ling, K.H.1    Hanzlik, R.P.2
  • 44
    • 0027380074 scopus 로고
    • Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline
    • Kunze, K. L., and Trager, W. F. (1993) Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem. Res. Toxicol. 6, 649-656. (Pubitemid 23290017)
    • (1993) Chemical Research in Toxicology , vol.6 , Issue.5 , pp. 649-656
    • Kunze, K.L.1    Trager, W.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.