Effects of flavonoids on CYP1 expression in RL95-2 endometrial carcinoma cells

Food Chemistry

Volumn 133, Issue 3, 2012, Pages 912-922

  Master, Zankhana ^a   Chaudhary, Amit ^a   Sutter, Thomas R ^b   Willett, Kristine L ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MEMPHIS   (United States)

Author keywords

CYP1A1; CYP1B1; Endometrial cells; Flavonoids; Kaempferol; Quercetin

Indexed keywords

2 ,3 ,7 ,8 TETRACHLORODIBENZO P DIOXINS; BASAL LEVELS; BENZO(A)PYRENE; CELL LINES; CHEMOPREVENTATIVE; CYP1A1; CYP1B1; CYTOCHROME P450; ENDOMETRIAL CANCER CELLS; ENDOMETRIAL CARCINOMAS; INHIBITORY EFFECT; INTACT CELLS; KAEMPFEROL; MRNA EXPRESSION; MYRICETIN; PROTEIN EXPRESSIONS; QUERCETIN;

CELL CULTURE; CELLS; FATTY ACIDS; GENE EXPRESSION; PHENOLS; PROTEINS;

FLAVONOIDS;

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; AMENTOFLAVONE; BENZO[A]PYRENE; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; FLAVONOID; KAEMPFEROL; MESSENGER RNA; MYRICETIN; QUERCETIN;

ARTICLE; CANCER CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; ENDOMETRIUM CARCINOMA; ENZYME INHIBITION; HUMAN; HUMAN TISSUE; IC 50; PROTEIN EXPRESSION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

EID: 84858340807     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.02.002     Document Type: Article

References (56)

1. V.P. Androutsopoulos, A. Papakyriakou, D. Vourloumis, and D.A. Spandidos Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids Bioorganic & Medicinal Chemistry 19 2011 2842 2849
2. E.V. Bandera, D.M. Gifkins, D.F. Moore, M.L. McCullough, and L.H. Kushi Antioxidant vitamins and the risk of endometrial cancer: A dose-response meta-analysis Cancer Causes and Control 20 2009 699 711
3. H. Bao, M. Vepakomma, and M.A. Sarkar Benzo(a)pyrene exposure induces CYP1A1 activity and expression in human endometrial cells Journal of Steroid Biochemistry and Molecular Biology 81 2002 37 45
4. R. Bhat, and E. Bresnick Glycine N-methyltransferase is an example of functional diversity. Role as a polycyclic aromatic hydrocarbon-binding receptor Journal of Biological Chemistry 272 1997 21221 21226
5. R. Bhat, C. Wagner, and E. Bresnick The homodimeric form of glycine N-methyltransferase acts as a polycyclic aromatic hydrocarbon-binding receptor Biochemistry 36 1997 9906 9910
6. J.L. Bushman Green tea and cancer in humans: A review of the literature Nutrition and Cancer 31 1998 151 159
7. J.T. Buters, S. Sakai, T. Richter, T. Pineau, D.L. Alexander, and U. Savas Cytochrome P450 CYP1B1 determines susceptibility to 7,12-dimethybenz(a) anthracene-induced lymphomas Proceedings of the National Academy of Science 96 1999 1977 1982
8. T.K. Chang, J. Chen, and E.Y. Yeung Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: Identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1 Toxicology and Applied Pharmacology 213 2006 18 26
9. A. Chaudhary, and K.L. Willett Inhibition of human cytochromes CYP1 enzymes by flavonoids of St. John's wort Toxicology 217 2006 194 205
10. Y.M. Chen, L.Y. Chen, F.H. Wong, C.M. Lee, T.J. Chang, and T.L. Yang-Feng Genomic structure, expression, and chromosomal localization of the human glycine N-methyltransferase gene Genomics 66 2000 43 47
11. J.Y. Chung, J.Y. Kim, W.R. Kim, S.G. Lee, Y.J. Kim, and J.E. Park Abundance of aryl hydrocarbon receptor potentiates benzo[a]pyrene-induced apoptosis in Hepa1c1c7 cells via CYP1A1 activation Toxicology 235 2007 62 72
12. H.P. Ciolino, P.J. Daschner, and G.C. Yeh Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differently Biochemical Journal 340 1999 715 722
13. H.P. Ciolino, T.T.Y. Wang, and G.C. Yeh Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity Cancer Research 58 1998 2754 2760
14. M.S. Denison, J.M. Fisher, and J.P. Whitlock Jr. The DNA recognition site for the dioxin-Ah receptor complex. Nucleotide sequence and functional analysis Journal of Biological Chemistry 263 1988 17221 17224
15. M.S. Denison, and S.R. Nagy Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals Annual Review of Pharmacology and Toxicology 43 2003 309 334
16. E. Dorant, P.A. van den Brandt, and R.A. Goldbohm A prospective cohort study on Allium vegetable consumption, garlic supplement use, and the risk of lung carcinoma in The Netherlands Cancer Research 54 1994 6148 6153
17. M.A. Gates, S.S. Tworoger, J.L. Hecht, V.I. De, B. Rosner, and S.E. Hankinson A prospective study of dietary flavonoid intake and incidence of epithelial ovarian cancer International Journal of Cancer 121 2007 2225 2232
18. Q.F. Gong, E.H. Liu, R. Xin, X. Huang, and N. Gao 2ME and 2OHE2 exhibit growth inhibitory effects and cell cycle arrest at G2/M in RL95-2 human endometrial cancer cells through activation of p53 and Chk1 Molecular and Cellular Biochemistry 352 2011 221 230
19. C.L. Hayes, D.C. Spink, B.C. Spink, J.Q. Cao, N.J. Walker, and T.R. Sutter 17β-estradiol hydroxylation catalyzed by human cytochrome P450 1B1 Proceedings of the National Academy of Science 93 1996 9776 9781
20. S.M. Heidel, P.S. MacWilliams, W. Baird, W.M. Dashwood, J.T. Buters, and F.J. Gonzalez Cytochrome P4501B1 mediates induction of bone marrow cytotoxicity and preleukemia cells in mice treated with 7,12-dimethylbenz[a]anthracene Cancer Research 60 2000 3454 3460
21. N.R. Jana, S. Sarkar, M. Ishizuka, J. Yonemoto, C. Tohyama, and H. Sone Role of estradiol receptor-α in differential expression of 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible genes in the RL95-2 and KLE human endometrial cancer cell lines Archives of Biochemistry and Biophysics 368 1999 31 39
22. N.R. Jana, S. Sarkar, M. Ishizuka, J. Yonemoto, C. Tohyama, and H. Sone Comparative effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on MCF-7, RL95-2, and LNCaP cells: Role of target steroid hormones in cellular responsiveness to CYP1A1 induction Molecular and Cell Biology Research Communication 4 2000 174 180
23. A. Kale, S. Gawande, and S. Kotwal Cancer phytotherapeutics: Role for flavonoids at the cellular level Phytotherapy Research 22 2008 567 577
24. C. Kamps, and S. Safe Binding of polynuclear aromatic hydrocarbons to the rat 4S cytosolic binding protein: Structure-activity relationships Cancer Letters 34 1987 129 137
25. S.W. Kennedy, and S.P. Jones Simultaneous measurement of cytochrome P450 1A catalytic activity and total protein concentration with a fluorescence plate reader Analytical Biochemistry 222 1994 217 223
26. H.J. Kim, S.B. Lee, S.K. Park, H.M. Kim, Y.I. Park, and M.S. Dong Effects of hydroxyl group numbers on the B-ring of 5,7-dihydroxyflavones on the differential inhibition of human CYP 1A and CYP1B1 enzymes Archives OF Pharmacal Research 28 2005 1114 1121
27. J.H. Kim, M.E. Sherman, F.C. Curriero, F.P. Guengerich, P.T. Strickland, and T.R. Sutter Expression of cytochromes P450 1A1 and 1B1 in human lung from smokers, non-smokers, and ex-smokers Toxicology and Applied Pharmacology 199 2004 210 219
28. J.Y. Kim, J.Y. Chung, J.E. Park, S.G. Lee, Y.J. Kim, and M.S. Cha Benzo[a]pyrene induces apoptosis in RL95-2 human endometrial cancer cells by cytochrome P450 1A1 activation Endocrinology 148 2007 5112 5122
29. J.G. Liehr, M.J. Ricci, C.R. Jefcoate, E.V. Hannigan, J.A. Hokanson, and B. Ting Zhu 4-Hydroxylation of estradiol by human uterine myometrium and myoma microsomes: Implications for the mechanism of uterine tumorigenesis Proceedings of the National Academy of Science 92 1995 9220 9224
30. P. Lin, S.-W. Hu, and T.-H. Chang Correlation between gene expression of aryl hydrocarbon receptor (AhR), hydrocarbon receptor nuclear translocator (Arnt), cytochromes P4501A1 (CYP1A1) and 1B1 (CYP1B1), and inducibility of CYP1A1 and CYP1A1 in human lymphocytes Toxicological Sciences 71 2003 20 26
31. K.J. Livak, and T.D. Schmittgen Analysis of relative gene expression data using real-time quantitative PCR and the 2(-Delta Delta C(T)) method Methods 25 2001 402 408
32. A.I. Loaiza-Perez, V. Trapani, C. Hose, S.S. Singh, J.B. Trepel, and M.F. Stevens Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumor agent 2-(4-amino-3-methylphenyl) benzothiazole Molecular Pharmacology 61 2002 13 19
33. M. Lopez-Lazaro Flavonoids as anticancer agents: Structure-activity relationship study Current Medicinal Chemistry Anticancer Agents 2 2002 691 714
34. H. Luo, G.O. Rankin, Z. Li, L. Depriest, and Y.C. Chen Kaempferol induces apoptosis in ovarian cancer cells through activating p53 in the intrinsic pathway Food Chemistry 128 2011 513 519
35. L. Macpherson, and J. Matthews Inhibition of aryl hydrocarbon receptor-dependent transcription by resveratrol or kaempferol is independent of estrogen receptor alpha expression in human breast cancer cells Cancer Letters 299 2010 119 129
36. M.C.E. McFadyen, H.L. McLeod, F.C. Jackson, W.T. Melvin, J. Doehmer, and G.I. Murray Cytochrome P450 CYP1B1 protein expression: A novel mechanism of anticancer drug resistance Biochemical Pharmacology 62 2001 207 212
37. P.J. Mulholland, D.R. Ferry, D. Anderson, S.A. Hussain, A.M. Young, and J.E. Cook Pre-clinical and clinical study of QC12, a water-soluble, pro-drug of quercetin Annals of Oncology 12 2001 245 248
38. J. Niestroy, A. Barbara, K. Herbst, S. Rode, L.M. van, and P.H. Roos Single and concerted effects of benzo[a]pyrene and flavonoids on the AhR and Nrf2-pathway in the human colon carcinoma cell line Caco-2 Toxicology in Vitro 25 2011 671 683
39. D. Puppala, C.G. Gairola, and H.I. Swanson Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation Carcinogenesis 28 2007 639 647
40. A. Raha, T. Joyce, S. Gusky, and E. Bresnick Glycine N-methyltransferase is a mediator of cytochrome P4501A1 gene expression Archives of Biochemistry and Biophysics 322 1995 395 404
41. A. Raha, C. Wagner, R.G. MacDonald, and E. Bresnick Rat liver cytosolic 4 S polycyclic aromatic hydrocarbon-binding protein is glycine N-methyltransferase Journal of Biological Chemistry 269 1994 5750 5756
42. M. Rahman, C.H. Sutter, G.L. Emmert, and T.R. Sutter Regioselective 2-hydroxylation of 17β-estradiol by rat cytochrome P4501B1 Toxicology and Applied Pharmacology 216 2006 469 478
43. G. Rajaraman, G. Yang, J. Chen, and T.K. Chang Modulation of CYP1B1 and CYP1A1 gene expression and activation of aryl hydrocarbon receptor by Ginkgo biloba extract in MCF-10A human mammary epithelial cells Canadian Journal of Physiology and Pharmacology 87 2009 674 683
44. E.H. Rodgers, and M.H. Grant The effect of the flavonoids, quercetin, myricetin and epicatechin on the growth and enzyme activities of MCF7 human breast cancer cells Chemico-Biological Interactions 116 1998 213 228
45. L. Sampson, E. Rimm, P.C. Hollman, J.H. de Vries, and M.B. Katan Flavonol and flavone intakes in US health professionals Journal of the American Dietetic Association 102 2002 1414 1420
46. D. Schwarz, P. Kisselev, W.H. Schunck, and I. Roots Inhibition of 17beta-estradiol activation by CYP1A1: Genotype- and regioselective inhibition by St. John's Wort and several natural polyphenols Biochimica et Biophysica Acta 1814 2011 168 174
47. D. Schwarz, and I. Roots In vitro assessment of inhibition by natural polyphenols of metabolic activation of procarcinogens by human CYP1A1 Biochemical and Biophysical Research Communications 303 2003 902 907
48. T. Shimada, E.M. Gillam, Y. Oda, F. Tsumura, T.R. Sutter, and F.P. Guengerich Metabolism of benzo(a)pyrene to trans-7,8-dihydroxy-7,8- dihydrobenzo(a)pyrene by recombinant human cytochrome P450 1B1 and purified liver epoxide hydrolase Chemical Research in Toxicology 12 1999 623 629
49. R. Siegel, E. Ward, O. Brawley, and A. Jemal Cancer statistics, 2011: The impact of eliminating socioeconomic and racial disparities on premature cancer deaths CA: A Cancer Journal for Clinicians 61 2011 212 236
50. P. Sundareshan, and M.J.C. Hendrix Growth, morphologic and invasive characteristics of early and late passages of a human endometrial carcinoma cell line (RL95-2) In Vitro Cellular & Developmental Biology 28A 1992 544 552
51. A.F. Trombino, R.I. Near, R.A. Matulka, S. Yang, L.J. Hafer, and P.A. Toselli Expression of the aryl hydrocarbon receptor/transcription factor (AhR) and AhR-regulated CYP1 gene transcripts in a rat model of mammary tumorigenesis Breast Cancer Research and Treatment 63 2000 117 131
52. N.J. Walker, F.G. Crofts, Y. Li, S.F. Lax, C.L. Hayes, and P.T. Strickland Induction and localization of cytochrome P450 1B1 (CYP1B1) protein in the livers of TCDD-treated rats: Detection using polyclonal antibodies raised to histidine-tagged fusion proteins produced and purified from bacteria Carcinogenesis 19 1998 395 402
53. L. Wang, I.-M. Lee, S.M. Zhang, J.B. Blumberg, J.E. Buring, and H.D. Sesso Dietary intake of selected flavonols, flavones, and flavonoid-rich foods and risk of cancer in middle-aged and older women American Journal of Clinical Nutrition 89 2009 905 912
54. D.L. Way, D.S. Grosso, J.R. Davis, E.A. Surwit, and C.D. Christian Characterization of a new human endometrial carcinoma (RL95-2) established in tissue culture In Vitro 19 1983 147 158
55. X. Wen, and T. Walle 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
56. S. Zhang, C. Qin, and S.H. Safe Flavonoids as aryl hydrocarbon receptor agonists/antagonists: Effects of structure and cell context Environmental Health Perspectives 111 2003 1877 1882