메뉴 건너뛰기




Volumn 274, Issue 1, 2009, Pages 54-60

Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450

Author keywords

CYP1A1; CYP1B1; Flavone; MCF 7 cells; Natural products

Indexed keywords

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; DIOSMETIN; ESTROGEN RECEPTOR; LUTEOLIN;

EID: 57749091536     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.canlet.2008.08.032     Document Type: Article
Times cited : (74)

References (43)
  • 1
    • 57749107418 scopus 로고    scopus 로고
    • World Cancer Research Fund/American Institute for Cancer Research, Food, Nutrition, Physical Activity, and the Prevention of Cancer: a Global Perspective, The Second Expert Report, AICR, Washington DC, 2007.
    • World Cancer Research Fund/American Institute for Cancer Research, Food, Nutrition, Physical Activity, and the Prevention of Cancer: a Global Perspective, The Second Expert Report, AICR, Washington DC, 2007.
  • 2
    • 33845213347 scopus 로고    scopus 로고
    • Therapeutic intervention of experimental breast cancer bone metastasis by indole-3-carbinol in SCID-human mouse model
    • Rahman K.M., Sarkar F.H., Banerjee S., Wang Z., Liao D.J., Hong X., et al. Therapeutic intervention of experimental breast cancer bone metastasis by indole-3-carbinol in SCID-human mouse model. Mol. Cancer Ther. 5 (2006) 2747-2756
    • (2006) Mol. Cancer Ther. , vol.5 , pp. 2747-2756
    • Rahman, K.M.1    Sarkar, F.H.2    Banerjee, S.3    Wang, Z.4    Liao, D.J.5    Hong, X.6
  • 3
    • 0037299799 scopus 로고    scopus 로고
    • Relevance of mitogen activated protein kinase (MAPK) and phosphotidylinositol-3-kinase/protein kinase B (PI3K/PKB) pathways to induction of apoptosis by curcumin in breast cells
    • Squires M.S., Hudson E.A., Howells L., Sale S., Houghton C.E., Jones J.L., et al. Relevance of mitogen activated protein kinase (MAPK) and phosphotidylinositol-3-kinase/protein kinase B (PI3K/PKB) pathways to induction of apoptosis by curcumin in breast cells. Biochem. Pharmacol. 65 (2003) 361-376
    • (2003) Biochem. Pharmacol. , vol.65 , pp. 361-376
    • Squires, M.S.1    Hudson, E.A.2    Howells, L.3    Sale, S.4    Houghton, C.E.5    Jones, J.L.6
  • 5
  • 6
    • 0033861887 scopus 로고    scopus 로고
    • Anti-apoptotic effect of quercetin: intervention in the JNK- and ERK-mediated apoptotic pathways
    • Ishikawa Y., and Kitamura M. Anti-apoptotic effect of quercetin: intervention in the JNK- and ERK-mediated apoptotic pathways. Kidney Int. 58 (2000) 1078-1087
    • (2000) Kidney Int. , vol.58 , pp. 1078-1087
    • Ishikawa, Y.1    Kitamura, M.2
  • 7
    • 33748355855 scopus 로고    scopus 로고
    • Modulation of activator protein-1 (AP-1) and MAPK pathway by flavonoids in human prostate cancer PC3 cells
    • Gopalakrishnan A., Xu C.J., Nair S.S., Chen C., Hebbar V., and Kong A.N. Modulation of activator protein-1 (AP-1) and MAPK pathway by flavonoids in human prostate cancer PC3 cells. Arch. Pharm. Res. 8 (2006) 633-644
    • (2006) Arch. Pharm. Res. , vol.8 , pp. 633-644
    • Gopalakrishnan, A.1    Xu, C.J.2    Nair, S.S.3    Chen, C.4    Hebbar, V.5    Kong, A.N.6
  • 8
    • 27744476241 scopus 로고    scopus 로고
    • Effects of hydroxyl group numbers on the B-ring of 5, 7-dihydroxyflavones on the differential inhibition of human CYP1A and CYP1B1 enzymes
    • Kim H.J., Lee S.B., Park S.K., Kim H.M., Park Y.I., and Dong M.S. Effects of hydroxyl group numbers on the B-ring of 5, 7-dihydroxyflavones on the differential inhibition of human CYP1A and CYP1B1 enzymes. Arch. Pharm. Res. 28 (2005) 1114-1121
    • (2005) Arch. Pharm. Res. , vol.28 , pp. 1114-1121
    • Kim, H.J.1    Lee, S.B.2    Park, S.K.3    Kim, H.M.4    Park, Y.I.5    Dong, M.S.6
  • 9
    • 33646131391 scopus 로고    scopus 로고
    • Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: Identification of isorhamnetin, kaempherol, and quercetin as potent inhibitors of CYP1B1
    • Chang T.K.H., Chen J., and Yeung E.Y.H. Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: Identification of isorhamnetin, kaempherol, and quercetin as potent inhibitors of CYP1B1. Toxicol. Appl. Pharmacol. 213 (2006) 18-26
    • (2006) Toxicol. Appl. Pharmacol. , vol.213 , pp. 18-26
    • Chang, T.K.H.1    Chen, J.2    Yeung, E.Y.H.3
  • 10
    • 1142275258 scopus 로고    scopus 로고
    • Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1
    • Shimada T., and Kuriyama Y.F. Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1. Cancer Sci. 95 (2004) 1-6
    • (2004) Cancer Sci. , vol.95 , pp. 1-6
    • Shimada, T.1    Kuriyama, Y.F.2
  • 11
    • 18344372908 scopus 로고    scopus 로고
    • The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1
    • Potter G.A., Patterson L.H., Wanogho E., Perry P.J., Butler P.C., Ijaz T., et al. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer 86 (2002) 774-778
    • (2002) Br. J. Cancer , vol.86 , pp. 774-778
    • Potter, G.A.1    Patterson, L.H.2    Wanogho, E.3    Perry, P.J.4    Butler, P.C.5    Ijaz, T.6
  • 12
    • 0032487988 scopus 로고    scopus 로고
    • 7,3′-Dihydroxy-4′-methoxyflavone from seeds of Acacia farnesiana
    • Sahu N.P., Achari B., and Banerjee S. 7,3′-Dihydroxy-4′-methoxyflavone from seeds of Acacia farnesiana. Phytochemistry 49 (1998) 1425-1426
    • (1998) Phytochemistry , vol.49 , pp. 1425-1426
    • Sahu, N.P.1    Achari, B.2    Banerjee, S.3
  • 14
    • 13244295506 scopus 로고    scopus 로고
    • Analysis and quantification of flavonoidic compounds from Portuguese olive (Olea europaea L.) leaf cultivars
    • Meirinhos J., Silva B.M., Valentao P., Seabra R.M., Pereira J.A., Dias A., et al. Analysis and quantification of flavonoidic compounds from Portuguese olive (Olea europaea L.) leaf cultivars. Nat. Prod. Res. 19 (2005) 189-195
    • (2005) Nat. Prod. Res. , vol.19 , pp. 189-195
    • Meirinhos, J.1    Silva, B.M.2    Valentao, P.3    Seabra, R.M.4    Pereira, J.A.5    Dias, A.6
  • 15
    • 22844440224 scopus 로고    scopus 로고
    • Flavonoid glycosides inhibit oral cancer cell proliferation-role of cellular uptake and hydrolysis to the aglycones
    • Browning A.M., Walle U.K., and Walle T. Flavonoid glycosides inhibit oral cancer cell proliferation-role of cellular uptake and hydrolysis to the aglycones. J. Pharm. Pharmacol. 57 (2005) 1037-1042
    • (2005) J. Pharm. Pharmacol. , vol.57 , pp. 1037-1042
    • Browning, A.M.1    Walle, U.K.2    Walle, T.3
  • 16
    • 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.Y., and Yeh G.C. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res. 58 (1998) 2754-2760
    • (1998) Cancer Res. , vol.58 , pp. 2754-2760
    • Ciolino, H.P.1    Wang, T.T.Y.2    Yeh, G.C.3
  • 17
    • 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 (2000) 31-38
    • (2000) Toxicology , vol.144 , pp. 31-38
    • Doostdar, H.1    Burke, M.D.2    Mayer, R.T.3
  • 18
    • 0028978209 scopus 로고
    • Different response of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-sensitive genes in human breast cancer MCF-7 and MDA-MB 231 cells
    • Döhr O., Vogel C., and Abel J. Different response of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-sensitive genes in human breast cancer MCF-7 and MDA-MB 231 cells. Arch. Biochem. Biophys. 321 (1995) 405-412
    • (1995) Arch. Biochem. Biophys. , vol.321 , pp. 405-412
    • Döhr, O.1    Vogel, C.2    Abel, J.3
  • 19
    • 0023277545 scopus 로고
    • Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction
    • Chomczynski P., and Sacchi N. Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal. Biochem. 162 (1987) 156-159
    • (1987) Anal. Biochem. , vol.162 , pp. 156-159
    • Chomczynski, P.1    Sacchi, N.2
  • 20
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilising the principles of protein-dye binding
    • Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilising the principles of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 21
    • 0032428485 scopus 로고    scopus 로고
    • Applications and limitations of interspecies scaling and in vitro extrapolation in pharmacokinetics
    • Lin J.H. Applications and limitations of interspecies scaling and in vitro extrapolation in pharmacokinetics. Drug Metab. Dispos. 26 (1998) 1202-1212
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 1202-1212
    • Lin, J.H.1
  • 22
    • 0026079024 scopus 로고
    • General occurrence of binding to acetylcholinesterase-substrate complex in noncompetitive inhibition and in inhibition by substrate
    • Cohen S.G., Chishti S.B., Bell D.A., Howard S.I., Salih E., and Cohen J.B. General occurrence of binding to acetylcholinesterase-substrate complex in noncompetitive inhibition and in inhibition by substrate. Biochim. Biophys. Acta 1076 (1991) 112-122
    • (1991) Biochim. Biophys. Acta , vol.1076 , pp. 112-122
    • Cohen, S.G.1    Chishti, S.B.2    Bell, D.A.3    Howard, S.I.4    Salih, E.5    Cohen, J.B.6
  • 23
    • 31444433077 scopus 로고    scopus 로고
    • Nitric oxide inhibition of respiration involves both competitive (heme) and non competitive (copper) binding to cytochrome c oxidase
    • Mason M.G., Nicholls P., Wilson M.T., and Cooper C.E. Nitric oxide inhibition of respiration involves both competitive (heme) and non competitive (copper) binding to cytochrome c oxidase. Proc. Natl. Acad. Sci. USA 103 (2006) 708-713
    • (2006) Proc. Natl. Acad. Sci. USA , vol.103 , pp. 708-713
    • Mason, M.G.1    Nicholls, P.2    Wilson, M.T.3    Cooper, C.E.4
  • 25
    • 0036146585 scopus 로고    scopus 로고
    • Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2 and CYP2C9
    • Otake Y., and Walle T. Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2 and CYP2C9. Drug Metab. Dispos. 30 (2002) 103-105
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 103-105
    • Otake, Y.1    Walle, T.2
  • 26
    • 3242676024 scopus 로고    scopus 로고
    • Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes
    • Piver B., Fer M., Vitrac X., Merrilon J.M., Dreano Y., Berthou F., et al. Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem. Pharmacol. 68 (2004) 773-782
    • (2004) Biochem. Pharmacol. , vol.68 , pp. 773-782
    • Piver, B.1    Fer, M.2    Vitrac, X.3    Merrilon, J.M.4    Dreano, Y.5    Berthou, F.6
  • 28
    • 18144383865 scopus 로고    scopus 로고
    • Overexpression of cytochrome P450 1A1 and its novel spliced variant in ovarian cancer cells: alternative subcellular enzyme compartmentation may contribute to carcinogenesis
    • Leung Y.K., Lau K.M., Mobley J., Jiang Z., and Ho S.M. Overexpression of cytochrome P450 1A1 and its novel spliced variant in ovarian cancer cells: alternative subcellular enzyme compartmentation may contribute to carcinogenesis. Cancer Res. 65 (2005) 3726-3734
    • (2005) Cancer Res. , vol.65 , pp. 3726-3734
    • Leung, Y.K.1    Lau, K.M.2    Mobley, J.3    Jiang, Z.4    Ho, S.M.5
  • 29
    • 0033637140 scopus 로고    scopus 로고
    • The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer
    • Middleton Jr. E., Kandaswami C., and Theoharides T.C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52 (2000) 673-751
    • (2000) Pharmacol. Rev. , vol.52 , pp. 673-751
    • Middleton Jr., E.1    Kandaswami, C.2    Theoharides, T.C.3
  • 31
  • 32
    • 34047110804 scopus 로고    scopus 로고
    • Luteolin inhibits insulin-like growth factor 1 receptor signaling in prostate cancer cells
    • Fang J., Zhou Q., Shi X.L., and Jiang B.H. Luteolin inhibits insulin-like growth factor 1 receptor signaling in prostate cancer cells. Carcinogenesis 28 (2007) 713-723
    • (2007) Carcinogenesis , vol.28 , pp. 713-723
    • Fang, J.1    Zhou, Q.2    Shi, X.L.3    Jiang, B.H.4
  • 33
    • 33646411225 scopus 로고    scopus 로고
    • Luteolin promotes degradation in signal transducer and activator of transcription 3 in human hepatoma cells: an implication for the antitumor potential of flavonoids
    • Selvendiran K., Koga H., Ueno T., Yoshida T., Maeyama M., Torimura T., et al. Luteolin promotes degradation in signal transducer and activator of transcription 3 in human hepatoma cells: an implication for the antitumor potential of flavonoids. Cancer Res. 66 (2006) 4826-4834
    • (2006) Cancer Res. , vol.66 , pp. 4826-4834
    • Selvendiran, K.1    Koga, H.2    Ueno, T.3    Yoshida, T.4    Maeyama, M.5    Torimura, T.6
  • 34
    • 24744449776 scopus 로고    scopus 로고
    • Protein kinase C inhibition and X-linked inhibitor of apoptosis protein degradation contribute to the sensitization effect of luteolin on tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis in cancer cells
    • Shi R.X., Ong C.N., and Shen H.M. Protein kinase C inhibition and X-linked inhibitor of apoptosis protein degradation contribute to the sensitization effect of luteolin on tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis in cancer cells. Cancer Res. 65 (2005) 7815-7823
    • (2005) Cancer Res. , vol.65 , pp. 7815-7823
    • Shi, R.X.1    Ong, C.N.2    Shen, H.M.3
  • 35
    • 7444272077 scopus 로고    scopus 로고
    • Luteolin inhibits vascular endothelial growth factor-induced angiogenesis; inhibition of endothelial cell survival and proliferation by targeting phosphatidylinositol 3′-kinase activity
    • Bagli E., Stefaniotou M., Morbidelli L., Ziche M., Psillas K., Murphy C., et al. Luteolin inhibits vascular endothelial growth factor-induced angiogenesis; inhibition of endothelial cell survival and proliferation by targeting phosphatidylinositol 3′-kinase activity. Cancer Res. 64 (2004) 7936-7946
    • (2004) Cancer Res. , vol.64 , pp. 7936-7946
    • Bagli, E.1    Stefaniotou, M.2    Morbidelli, L.3    Ziche, M.4    Psillas, K.5    Murphy, C.6
  • 36
    • 55749110433 scopus 로고    scopus 로고
    • Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1 mediated metabolism
    • Androutsopoulos V., Arroo R.R.J., Hall J.F., Surichan S., and Potter G.A. Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1 mediated metabolism. Breast Cancer Res. 10 (2008) R39
    • (2008) Breast Cancer Res. , vol.10
    • Androutsopoulos, V.1    Arroo, R.R.J.2    Hall, J.F.3    Surichan, S.4    Potter, G.A.5
  • 37
    • 9444263203 scopus 로고    scopus 로고
    • Fluorinated 2-(4-amino-3-methylphenyl)benzothiazoles induce CYP1A1 expression, become metabolised, and bind to macromolecules in sensitive human cancer cells
    • Brantley E., Trapani V., Alley M.C., Hose C.D., Bradshaw T.D., Stevens M.F.G., et al. Fluorinated 2-(4-amino-3-methylphenyl)benzothiazoles induce CYP1A1 expression, become metabolised, and bind to macromolecules in sensitive human cancer cells. Drug Metab. Dispos. 32 (2004) 1392-1401
    • (2004) Drug Metab. Dispos. , vol.32 , pp. 1392-1401
    • Brantley, E.1    Trapani, V.2    Alley, M.C.3    Hose, C.D.4    Bradshaw, T.D.5    Stevens, M.F.G.6
  • 38
    • 33746690306 scopus 로고    scopus 로고
    • Metabolism of the soyabean isoflavone daidzein by CYP1A2 and the extra-hepatic CYPs 1A1 and 1B1 affects biological activity
    • Atherton K., Mutch E., and Ford D. Metabolism of the soyabean isoflavone daidzein by CYP1A2 and the extra-hepatic CYPs 1A1 and 1B1 affects biological activity. Biochem. Pharmacol. 72 (2006) 624-631
    • (2006) Biochem. Pharmacol. , vol.72 , pp. 624-631
    • Atherton, K.1    Mutch, E.2    Ford, D.3
  • 39
    • 33745001652 scopus 로고    scopus 로고
    • Molecular and cellular targets
    • Bode A.M., and Dong Z. Molecular and cellular targets. Mol. Carcinogen. 45 (2006) 422-430
    • (2006) Mol. Carcinogen. , vol.45 , pp. 422-430
    • Bode, A.M.1    Dong, Z.2
  • 40
    • 33747890916 scopus 로고    scopus 로고
    • Inhibition of benzo[a]pyrene-activating enzymes and DNA binding in human bronchial epithelial BEAS-2B cells by methoxylated flavonoids
    • Tsuji P.A., and Walle T. Inhibition of benzo[a]pyrene-activating enzymes and DNA binding in human bronchial epithelial BEAS-2B cells by methoxylated flavonoids. Carcinogenesis 27 (2006) 1579-1585
    • (2006) Carcinogenesis , vol.27 , pp. 1579-1585
    • Tsuji, P.A.1    Walle, T.2
  • 41
    • 27144443044 scopus 로고    scopus 로고
    • Preferential induction of CYP1B1 by benzo[a]pyrene in human oral epithelial cells: impact on DNA adduct formation and prevention by polyphenols
    • Wen X., and Walle T. Preferential induction of CYP1B1 by benzo[a]pyrene in human oral epithelial cells: impact on DNA adduct formation and prevention by polyphenols. Carcinogenesis 26 (2005) 1774-1781
    • (2005) Carcinogenesis , vol.26 , pp. 1774-1781
    • Wen, X.1    Walle, T.2
  • 42
    • 4444223703 scopus 로고    scopus 로고
    • Aryl hydrocarbon receptor activation of an antitumor aminoflavone: basis of selective toxicity for MCF-7 breast tumor cells
    • Loaiza-Pérez A.I., Kenney S., Boswell J., Hollingshead M., Alley M.C., Hose C., Ciolino H.P., et al. Aryl hydrocarbon receptor activation of an antitumor aminoflavone: basis of selective toxicity for MCF-7 breast tumor cells. Mol. Cancer Ther. 3 (2004) 715-725
    • (2004) Mol. Cancer Ther. , vol.3 , pp. 715-725
    • Loaiza-Pérez, A.I.1    Kenney, S.2    Boswell, J.3    Hollingshead, M.4    Alley, M.C.5    Hose, C.6    Ciolino, H.P.7
  • 43
    • 0034665390 scopus 로고    scopus 로고
    • Role of CYP1A1 in modulation of antitumor properties of the novel agent 2-(4-amino-3-methylphenyl) benzothiazole (DF 203, NSC 674495) in human breast cancer cells
    • Chua M.S., Kashiyama E., Bradshaw T.D., Stinson S.F., Brantley E., Sausville E.A., et al. Role of CYP1A1 in modulation of antitumor properties of the novel agent 2-(4-amino-3-methylphenyl) benzothiazole (DF 203, NSC 674495) in human breast cancer cells. Cancer Res. 60 (2000) 5196-5203
    • (2000) Cancer Res. , vol.60 , pp. 5196-5203
    • Chua, M.S.1    Kashiyama, E.2    Bradshaw, T.D.3    Stinson, S.F.4    Brantley, E.5    Sausville, E.A.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.