Hydroxychalcones exhibit differential effects on XRE transactivation

Toxicology

Volumn 207, Issue 2, 2005, Pages 303-313

  Wang, Huan ^a   Wang, Yun ^a   Chen, Zhen Yu ^a   Chan, Franky L ^a   Leung, Lai K ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

CYP1A1 1B1; DMBA DNA binding; Hydroxychalcones; XRE transactivation

Indexed keywords

2 HYDROXYCHALCONE; 2' HYDROXYCHALCONE; 4 HYDROXYCHALCONE; 7,12 DIMETHYLBENZ[A]ANTHRACENE; BUTEIN; CHALCONE DERIVATIVE; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; ENZYME; ETHOXYRESORUFIN DEETHYLASE; HYDROXYL GROUP; ISOLIQUIRITIGENIN; POLYCYCLIC AROMATIC HYDROCARBON; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG; XENOBIOTIC AGENT;

ARTICLE; CONTROLLED STUDY; COVALENT BOND; DNA BINDING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; INSECT; MICROSOME; PRIORITY JOURNAL; PROTEIN EXPRESSION; REPORTER GENE;

9,10-DIMETHYL-1,2-BENZANTHRACENE; ARYL HYDROCARBON HYDROXYLASES; CELL LINE, TUMOR; CELL SURVIVAL; CHALCONE; CYTOCHROME P-450 CYP1A1; DNA ADDUCTS; FEMALE; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENES, REPORTER; HUMANS; LUCIFERASES; RESPONSE ELEMENTS; RNA, MESSENGER; TRANS-ACTIVATION (GENETICS); XENOBIOTICS;

INSECTA;

EID: 10444286767     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2004.10.005     Document Type: Article

References (31)

1. R.J. Anto, K. Sukumaran, G. Kuttan, M.N.A. Rao, V. Subbaragju, and R. Kuttan Anticancer and antioxidant activity of synthetic chalcones and related compounds Cancer Lett. 97 1995 33 37
2. M. Backlund, I. Johansson, S. Mkrtchian, and M. Ingelman-Sundberg Signal transduction-mediated activation of the aryl hydrocarbon receptor in rat hepatoma H4IIE cells J. Biol. Chem. 272 1997 31755 31763
3. D.G. Batt, R. Goodman, D.G. Jones, J.S. Kerr, L.R. Mantegna, C. Macallister, R.C. Newton, S. Nurnberg, P.K. Welch, and M.B. Covington 2′-Substituted chalcone derivatives as inhibitor of interleukin-I biosynthesis J. Med. Chem. 36 1993 1434 1442
4. R.J. Bertz, and G.R. Granneman Use of in vitro and in vivo data to estimate the likelihood of metabolic pharmacokinetic interactions Clin. Parmacokinet. 32 1997 210 258
5. J.T. Buters, S. Sakai, T. Richter, T. Pineau, D.L. Alexander, U. Savas, J. Doehmer, J.M. Ward, C.R. Jefcoate, and F.J. Gonzalez Cytochrome P450 CYP1B1 determines susceptibility to 7,12-dimethylbenz[a]anthracene-induced lymphomas Proc. Natl. Acad. Sci. U.S.A. 96 1999 1977 1982
6. C.A. Calliste, J.C. Le Bail, P. Trouillas, C. Pouget, G. Habrioux, A.J. Chulia, and J.L. Duroux Chalcones: structural requirements for antioxidant, estrogenic and anti-proliferative activities Anticancer Res. 21 2001 3949 3956
7. H.Y. Chan, H. Wang, Z.Y. Chen, D.S.C. Tsang, and L.K. Leung Screening of chemopreventive tea polyphenols against PAH genotoxicity in breast cancer cells by a XRE-luciferase reporter construct Nutr. Cancer 46 2003 93 100
8. H.P. Ciolino, P.J. Daschner, T.T. Wang, and G.C. Yeh Effect of curcumin on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells Biochem. Pharmacol. 56 1998 197 206
9. H.P. Ciolino, P.J. Daschner, and G.C. Yeh The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor Br. J. Cancer 79 1999 1340 1346
10. 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 differentially Biochem. J. 340 1999 715 722
11. H.P. Ciolino, and G.C. Yeh Inhibition of aryl hydrocarbon-induced cytochrome P-450 1A1 enzyme activity and CYP1A1 expression by resveratrol Mol. Pharmacol. 56 1999 760 767
12. S.D. Dertinger, H.B. Lantum, A.E. Silverstone, and T.A. Gasiewicz Effect of 3′-methoxy-4′-nitroflavone on benzo[a]pyrene toxicity. Aryl hydrocarbon receptor-dependent and -independent mechanisms Biochem. Pharmacol. 60 2000 189 196
13. O. Dohr, C. Vogel, and J. Abel 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
14. W.E. Evans, and M.V. Relling Pharmacogenomics: translating functional genomics into rational therapeutics Science 286 1999 487 491
15. K. Hayashi, T. Nagamatsu, S. Honda, and Y. Suzuki Butein (3,4,2′,4′-tetrahydroxychalcone) ameliorates experimental anti-glomerular basement membrane antibody-associated glomerulonephritis Eur. J. Pharmacol. 316 1996 297 306
16. H. Haraguchi, H. Ishikawa, K. Mizutani, Y. Tamura, and T. Kinoshita Antioxidative and superoxide scavenging activities of retrochalcones in Glycyrrhiza inflata Bioorg. Med. Chem. 6 1998 339 347
17. M.C. Henderson, C.L. Miranda, J.F. Stevens, M.L. Deinzer, and D.R. Buhler In vitro inhibition of human p450 enzymes by prenylated flavonoids from hops, Humulus lupulus Xenobiotica 30 2000 235 251
18. H.K. Hsieh, T.H. Lee, J.P. Wong, F.N. Ko, and C.M. Teng Synthesis and anti-inflammatory effect of chalcones and related compounds Pharm. Res. 15 1998 39 46
19. Y.P. Kim, H.S. Ban, S.S. Lim, N. Kimura, S.H. Jung, J. Ji, S. Lee, N. Ryu, S.R. Keum, K.H. Shin, and K. Ohuchi Inhibition of prostaglandin E2 production by 2′-hydroxychalcone derivatives and the mechanism of action J. Pharm. Pharmacol. 53 2001 1295 1302
20. S. Kronenberg, C. Esser, and C. Carlberg An aryl hydrocarbon receptor conformation acts as the functional core of nuclear dioxin signaling Nucleic Acids Res. 28 2000 2286 2291
21. C.N. Lin, T.H. Lee, M.F. Hsu, J.P. Wang, F.N. Ko, and C.M. Teng 2′,5′-Dihydroxychalcone as a potent chemical mediator and cyclooxygenase inhibitor J. Pharm. Pharmacol. 49 1997 530 536
22. M. Machala, R. Kubinova, P. Haravova, and V. Suchy Chemoprotective potentials of homoisoflavonoids and chalcones of dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity Phytother. Res. 15 2001 114 118
23. B. Madan, S. Batra, and B. Ghosh 2′-Hydroxychalcone inhibits nuclear factor-κB and blocks tumor necrosis factor-α and lipopolysaccharide-induced adhesion of neutrophils to human umbilical vein endothelial cells Mol. Pharmacol. 58 2000 526 534
24. K. Monostory, V. Tamasi, L. Vereczkey, and P. Perjesi A study on CYP1A inhibitory action of E-2-(4′-methoxybenzylidene)-1-benzosuberone and some related chalcones and cyclic chalcone analogues Toxicology 184 2003 203 210
25. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
26. S. Safe Molecular biology of the Ah receptor and its role in carcinogenesis Toxicol. Lett. 120 2001 1 7 (review)
27. T. Shimada, and Y. Fujii-Kuriyama Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes p450 1A1 and 1B1 Cancer Sci. 95 2004 1 6
28. Y. Shimizu, Y. Nakatsuru, M. Ichinose, Y. Takahashi, H. Kume, J. Mimura, Y. Fujii-Kuriyama, and T. Ishikawa Benzo[a]pyrene carcinogenicity is lost in mice lacking the aryl hydrocarbon receptor Proc. Natl. Acad. Sci. U.S.A. 97 2000 779 782
29. R. Stoll, C. Renner, S. Hansen, S. Palme, C. Klein, A. Belling, W. Zeslawski, M. Kamionka, T. Rehm, P. Muhlhahn, R. Schumacher, F. Hesse, B. Kaluza, W. Voelter, R.A. Engh, and T.A. Holak Chalcone derivatives antagonize interactions between the human oncoprotein MDM2 and p53 Biochemistry 40 2001 336 344
30. R.D. Vincenzo, C. Ferlini, M. Distefano, C. Gaggini, A. Riva, E. Bombardelli, P. Morazzoni, P. Valenti, F. Belluti, F.O. Ranelletti, S. Mancuso, and G. Scambia In vitro evaluation of newly developed chalcone analogues in human cancer cells Cancer Chemother. Pharmacol. 46 2000 305 312
31. K. Zhang, K.P. Wong, and P. Chow Conjugtion of chlorambucil with GSH by GST purified from human colon adenocarcinoma cells and its inhibition by plant polyphenols Life Sci. 72 2003 2629 2640