Bioflavonoids: Selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1

Toxicology

Volumn 144, Issue 1-3, 2000, Pages 31-38

  Doostdar, Hamed ^a   Burke, M Danny ^b   Mayer, Richard T ^a  

^a U S HORTICULTURAL RESEARCH LABORATORY   (United States)

^b DE MONTFORT UNIVERSITY   (United Kingdom)

Author keywords

Cytochrome P450; Flavonoids; Human; Inhibitors; Substrates

Indexed keywords

ACACETIN; CYTOCHROME P450; CYTOCHROME P450 ISOENZYME; DIOSMETIN; ERIODICTYOL; ETHOXYRESORUFIN DEETHYLASE; FLAVANONE; FLAVONOID; HESPERETIN; NARINGENIN;

ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; HUMAN; HUMAN CELL; HUMAN TISSUE; LIVER MICROSOME METABOLISM; PRIORITY JOURNAL; XENOBIOTIC METABOLISM;

ARYL HYDROCARBON HYDROXYLASES; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; ENZYME INHIBITORS; FLAVONOIDS; HESPERIDIN; HUMANS; KINETICS; MICROSOMES, LIVER;

EID: 0034599543     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0300-483X(99)00215-2     Document Type: Article

References (40)

1. Abul-Hajj Y.J., Thijssen J.H.H., Blankenstein M.A. Metabolism of estradiol in human breast cancer. Eur. J. Cancer Clin. Oncol. 24:1988;1171-1178.
2. Alexander D.L., Eltom S.E., Jefcoate C.R. Ah receptor regulation of CYP1B1 expression in primary mouse embryo-derived cells. Cancer Res. 57:1997;4498-4506.
3. Ameer B., Weintraub R.A., Jhonson J.V., Yost R.A., Rouseff R.L. Flavanone absorption after naringin, hesperidin, and citrus administration. Clin. Pharmacol. Ther. 60(1):1996;34-40.
4. Barnes T.S., Burke M.D., Melvin W.T. Differences in adult and fetal human cytochrome P-450 forms recognized by monoclonal antibodies with specificity for the P450III family. Biochem. J. 260:1989;635-640.
5. Burke M.D., Thompson S., Weaver R.J., Wolf C.R., Mayer R.T. Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol. 48(5):1994;923-936.
6. Canivenc-Lavier M.C., Brunold C., Siess M.H., Suschetet M. Evidence of tangeretin O-demethylation by rat and human liver microsomes. Xenobiotica. 23(23):1993;259-266.
7. Crespi C.L., Penman B.W., Steimel D.T., Smith T., Yang C.S., Sutter T.R. Development of a human lymphoblastoid cell line constitutively expressing human CYP1B1 cDNA: substrate specificity with model substrates and promutagens. Mutagenesis. 12(2):1997;83-89.
8. Dai R., Zhai S., Wei X., Pincus M.R., Vestal R.E., Friedman F.K. Inhibition of human cytochrome P4501A2 by flavones: a molecular modeling study. J. Protein Chem. 17:1998;643-650.
9. Doostdar H., Shapiro J.P., Niedz R., Burke M.D., McCollum T.G., McDonald R.E., Mayer R.T. A cytochrome P450 mediated naringenin 3′-hydroxylase from sweet orange cell cultures. Plant Cell Physiol. 36(1):1995;69-77.
10. Edwards R.J., Adams D.A., Watts P.S., Davies D.S., Boobis A.R. Development of a comprehensive panel of antibodies against the major xenobiotic metabolising forms of cytochrome P450 in humans. Biochem. Pharmacol. 56:1998;377-387.
11. Eltom S.E., Larsen M.C., Jefcoate C.R. Expression of CYP1B1 but not CYP1A1 by primary cultured human mammary stromal fibroblasts constitutively and in response to dioxin exposure: role of the Ah receptor. Carcinogenesis. 19:1998;1437-1444.
12. Gonzalez F.J., Gelboin H.V. Role of human cytochromes P450 in metabolic activation of chemical carcinogens and toxins. Drug Metab. Rev. 40:1994;243-288.
13. Hakkola J., Pasanen M., Pelkonen O., Hukkanen J., Evisalmi S., Anttila S., Rane A., Mantyla M., Purkunen R., Saarikoski S., Tooming M., Raunio H. Expression of CYP1B1 in human adult and fetal tissues and differential inducibility of CYP1B1 and CYP1A1 by Ah receptor ligands in human placenta and cultured cells. Carcinogenesis. 18:1997;391-397.
14. Harborne J.B., Baxter H., Moss G.P. Phytochemical Dictionary. 1999;1-976 Taylor & Francis, Philadelphia, PA.
15. Hellmold H., Rylander T., Magnusson M., Reihner E., Warner M., Gustafsson J.A. Characterization of cytochrome P450 enzymes in human breast tissue from reduction mammaplasties. J. Clin. Endocrin. Metab. 83:1998;886-895.
16. Huang Z., Fasco M.J., Figge H.L., Keyomars K., Kaminsky L.S. Expression of cytochromes P450 in human breast tissue and tumor. Drug Metab. Dispos. 24(8):1996;899-905.
17. Lee H., Wang H.W., Su H.Y., Hao N.J. The structure-activity relationships of flavonoids as inhibitors of cytochrome P-450 enzymes in rat liver microsomes and the mutagenicity of 2-amino-3-methyl-imidazo[4,5-f]quinoline. Mutagenesis. 9(2):1994;101-106.
18. Liehr J.G. Dual role of oestrogens as hormones and pro-carcinogens: tumour initiation by metabolic activation of oestrogens. Eur. J. Cancer Prev. 6:1997;3-10.
19. Liehr J.G., Ricci M.J., Jefcoate C.R., Hannigan E.V., Hokanson J.A., Zhu B.T. 4-Hydroxylation of estradiol by human uterine myometrium and myoma microsomes: implications for the mechanism of uterine tumorigenesis. Proc. Nat. Acad. Sci. USA. 92:1995;9220-9224.
20. Martucci C.P., Fishman J. P450 enzymes of estrogen metabolism. Pharmacol. Ther. 57:1993;237-257.
21. Mayer R.T., Jermyn J.W., Burke M.D. Methoxyresorufin as a substrate for the fluorometric assay of insect microsomal O-dealkylase. Pestic. Biochem. Physiol. 7:1977;349-354.
22. McKay J.A., Melvin W.T., Ah-See A.K., Ewen S.W.B., Greenlee W.F., Marcus C.B., Burke M.D., Murray G.I. Expression of cytochrome P450 CYP1B1 in breast cancer. FEBS Lett. 374:1995;270-272.
23. Miyake Y., Yamamoto K., Osawa T. Metabolism of antioxidants in lemon fruit (citrus limon BURM. f.) by human intestinal bacteria. J. Agric. Food Chem. 45:1997;3738-3742.
24. Mouly P.P., Arzouyan C.R., Gaydou E.M., Estienne J.M. Differentiation of citrus juices by factorial discriminant analysis using liquid chromatography of flavanone glycosides. J. Agric. Food Chem. 42:1994;70-79.
25. Murray G.I., Foster C.O., Barnes T.S., Weaver R.J., Snyder C.P., Ewen S.W.B., Melvin W.T., Burke M.D. Cytochrome P450IA expression in adult and fetal human liver. Carcinogenesis. 13:1992;165-169.
26. Murray G.I., Taylor M.C., McFadyne M.C.E., McKay J.A., Greenlee W.F., Burke M.D., Melvin W.T. Tumor-specific expression of cytochrome P450 CYP1B1. Cancer Res. 57:1997;3026-3031.
27. Nelson D.R., Koymans L., Kamotaki T., Stegeman J.J., Feyercisen R., Waxman D.J., Waterman M.R., Gotoh O., Coon J.M., Estabrook R.W., Gunsalus I.C., Nebert D.W. P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics. 6:1996;1-42.
28. Obermeier M.T., White R.E., Yang C.S. Effects of bioflavonoids on hepatic CYP activities. Xenobiotica. 25(6):1995;575-584.
29. Shen L., Qui S., Chen Y., Zhang F., van Breemen R.B., Nikolic D., Bolton J.L. Alkylation of 2′-deoxynucleosides and DNA by the Premarin metabolite 4-hydroxyequilenin semiquinone radical. Chem. Res. Toxicol. 11(2):1998;94-101.
30. Shimada T., Hayes C.L., Yamazaki H., Amin S., Hecht S.S., Guengerich F.P., Sutter T.R. Activation of chemically diverse procarcinogens by human cytochrome-P-450 1B1. Cancer Res. 56:1996;2979-2984.
31. Shimada T., Gillam E.M.J., Sutter T.R., Strickland P.T., Guengerich F.P., Yamazaki H. Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab. Dispos. 25:1997;617-622.
32. So F.V., Guthrie N., Chambers A.F., Moussa M., Carroll K.K. Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices. Nutr. Cancer. 26:1996;167-181.
33. Spink D.C., Spink B.C., Cao J.Q., DePasquale J.A., Pentecost B.T., Fasco M.J., Li Y., Sutter T.R. Differential expression of CYP1A1 and CYP1B1 in human breast epithelial cells and breast tumor cells. Carcinogenesis. 19:1998;291-298.
34. Sutter T.R., Tang Y.M., Hayes C.L., Wo Y.Y.P., Jabe E.W., Li X., Yin H., Cody C.W., Greenlee W.F. Complete cDNA sequence of a human dioxin-inducible mRNA identifies a new gene subfamily of cytochrome P450 that maps to chromosome 2. J. Biol. Chem. 269(18):1994;13092-13099.
35. Tanaka T., Makita H., Ohnishi M., Mori H., Satoh K., Hara A., Sumida T., Fukutani K., Tanaka T., Ogawa H. Chemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis in rats by flavonoids diosmin and hesperedin, each alone and in combination. Cancer Res. 57:1997;246-252.
36. Tsyrlov I.B., Mikhailenko V.M., Gelboin H.V. Isozyme- and species-specific susceptibility of cDNA-expressed CYP1A P-450s to different flavonoids. Biochem. Biophys. Acta. 1205:1994;325-335.
37. Vadlamuri S.V., Glover D.D., Turner T., Sarkar M.A. Regiospecific expression of cytochrome P4501A1 and 1B1 in human uterine tissue. Cancer Lett. 122:1998;143-150.
38. Weaver R.J., Dickins M., Burke M.D. Cytochrome P4502C9 is responsible for hydroxylation of the naphthoquinone antimalarial drug 58C80 in human liver. Biochem. Pharmacol. 46:1993;1183-1197.
39. Willey J.C., Coy E.L., Frampton M.W., Torres A., Apostolakos M.J., Hoehn G., Schuermann W.H., Thilly W.G., Olson D.E., Hammersley J.R., Crespi C.L., Utell M.J. Quantitative RT-PCR measurement of cytochromes p4501A1, 1B1, and 2B7, microsomal epoxide hydrolase, and NADPH oxidoreductase expression in lung cells of smokers and non-smokers. Am. J. Resp. Cell. Mol. Biol. 17:1997;114-124.
40. Zhai S., Dai R., Wei X., Friedman F.K., Vestal R.E. Inhibition of methoxyreorufin demethylase activity by flavonoids in human liver microsomes. Life Sci. 63(8):1998;119-123.