Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators

Journal of Medicinal Chemistry

Volumn 48, Issue 1, 2005, Pages 287-291

  De Medina, Philippe ^a   Casper, Robert ^b   Savouret, Jean François ^c   Poirot, Marc ^a  

^a INSTITUT CLAUDIUS REGAUD   (France)

^b MOUNT SINAI HOSPITAL   (Canada)

^c INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4' CHLOROPHENYL) 2 (3,5 DICHLOROPHENYL)ETHENE; 1 (4' HYDROXYPHENYL) 2 (3,5 DIHYDROXYPHENYL)ETHENE; 1 (4' METHOXYPHENYL) 2 (3,5 DICHLOROPHENYL)ETHENE; 1 (4' TRIFLUOROMETHYLPHENYL) 2 (3,5 DICHLOROPHENYL)ETHENE; 1 (4' TRIFLUOROMETHYLPHENYL) 2 (3,5 DITRIFLUOROMETHYLPHENYL)ETHENE; AROMATIC HYDROCARBON RECEPTOR; ESTROGEN RECEPTOR; ETHYLENE; RESVERATROL; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

ANIMALS; BIOCHEMISTRY; CELL LINE; CELLS, CULTURED; CHLORAMPHENICOL O-ACETYLTRANSFERASE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; ESTRADIOL; HUMANS; RABBITS; RECEPTORS, ARYL HYDROCARBON; RECEPTORS, ESTRADIOL; STILBENES; TETRACHLORODIBENZODIOXIN; TOXICITY TESTS; TRANS-ACTIVATION (GENETICS);

EID: 12144249989     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0498194     Document Type: Article

References (33)

1. Nebert, D. W.; Roe, A. L.; Dieter, M. Z.; Solis, W. A.; Yang, Y.; et al. Role of the aromatic hydrocarbon receptor and [Ah] gene battery in the oxidative stress response, cell cycle control, and apoptosis. Biochem. Pharmacol. 2000, 59, 65-85.
2. Denison, M. S.; Nagy, S. R. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 2003, 43, 309-334.
3. Mimura, J.; Fujii-Kuriyama, Y. Functional role of AhR in the expression of toxic effects by TCDD. Biochim. Biophys. Acta 2003, 1619, 263-268.
4. Savouret, J. F.; Berdeaux, A.; Casper, R. F. The aryl hydrocarbon receptor and its xenobiotic ligands: a fundamental trigger for cardiovascular diseases. Nutr. Metab. Cardiovasc. Dis. 2003, 13, 104-113.
5. Nebert, D. W.; Dalton, T. P.; Okey, A. B.; Gonzalez, F. J. Role of aryl hydrocarbon receptor-mediated induction of the CYP1 enzymes in environmental toxicity and cancer. J. Biol. Chem. 2004, 279, 23847-23850.
6. Shimizu, Y.; Nakatsuru, Y.; Ichinose, M.; Takahashi, Y.; Kume, H.; et al. Benzo[a]pyrene carcinogenicity is lost in mice lacking the aryl hydrocarbon receptor. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 779-782.
7. Andersson, P.; McGuire, J.; Rubio, C.; Gradin, K.; Whitelaw, M. L.; et al. A constitutively active dioxin/aryl hydrocarbon receptor induces stomach tumors. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 9990-9995.
8. Moennikes, O.; Loeppen, S.; Buchmann, A.; Andersson, P.; Ittrich, C.; et al. A constitutively active dioxin/aryl hydrocarbon receptor promotes hepatocarcinogenesis in mice. Cancer Res. 2004, 64, 4707-4710.
9. Sadler, B. R.; Cho, S. J.; Ishaq, K. S.; Chae, K.; Korach, K. S. Three-dimensional quantitative structure-activity relationship study of nonsteroidal estrogen receptor ligands using the comparative molecular field analysis/cross-validated r2-guided region selection approach. J. Med. Chem. 1998, 41, 2261-2267.
10. Waller, C. L.; McKinney, J. D. Three-dimensional quantitative structure-activity relationships of dioxins and dioxin-like compounds: model validation and Ah receptor characterization. Chem. Res. Toxicol. 1995, 8, 847-858.
11. Gasiewicz, T. A.; Kende, A. S.; Rucci, G.; Whitney, B.; Willey, J. J. Analysis of structural requirements for Ah receptor antagonist activity: ellipticines, flavones, and related compounds. Biochem. Pharmacol. 1996, 52, 1787-1803.
12. Fraschini, E.; Bonati, L.; Pitea, D. Molecular polarizability as a tool for understanding the binding properties of polychlorinates dibenzo-p-dioxins: definition of a reliable computational procedure. J. Phys. Chem. 1996, 100, 10564-10569.
13. Beger, R. D.; Wilkes, J. G. Models of polychlorinated dibenzodioxins, dibenzofurans, and biphenyls binding affinity to the aryl hydrocarbon receptor developed using (13)c NMR data. J. Chem. Inf. Comput. Sci. 2001, 41, 1322-1329.
14. Mhin, B. J.; Lee, J. E.; Choi, W. Understanding the congener-specific toxicity in polychlorinated dibenzo-p-dioxins: chlorination pattern and molecular quadrupole moment. J. Am. Chem. Soc. 2002, 124, 144-148.
15. Ciolino, H. P.; Wang, T. T.; Yeh, G. C. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res. 1998, 58, 2754-2760.
16. Casper, R. F.; Quesne, M.; Rogers, I. M.; Shirota, T.; Jolivet, A.; et al. Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity. Mol. Pharmacol. 1999, 56, 784-790.
17. Ciolino, H. P.; Daschner, P. J.; Yeh, G. C. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem. J. 1999, 340 (Pt 3), 715-722.
18. Ashida, H.; Fukuda, I.; Yamashita, T.; Kanazawa, K. Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin. FEBS Lett. 2000, 476, 213-217.
19. Quadri, S. A.; Qadri, A. N.; Hahn, M. E.; Mann, K. K.; Sherr, D. H. The bioflavonoid galangin blocks aryl hydrocarbon receptor activation and polycyclic aromatic hydrocarbon-induced pre-B cell apoptosis. Mol. Pharmacol. 2000, 58, 515-525.
20. Savouret, J. F.; Antenos, M.; Quesne, M.; Xu, J.; Milgrom, E.; et al. 7-ketocholesterol is an endogenous modulator for the arylhydrocarbon receptor. J. Biol. Chem. 2001, 276, 3054-3059.
21. Zhang, S.; Qin, C.; Safe, S. H. Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. Environ. Health Perspect. 2003, 111, 1877-1882.
22. Cal, C.; Garban, H.; Jazirehi, A.; Yeh, C.; Mizutani, Y.; et al. Resveratrol and cancer: chemoprevention, apoptosis, and chemoimmunosensitizing activities. Curr. Med. Chem. Anti-Cancer Agents 2003, 3, 77-93.
23. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275, 218-220.
24. Gehm, B. D.; McAndrews, J. M.; Chien, P. Y.; Jameson, J. L. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 14138-14143.
25. Wright, J. S.; Johnson, E. R.; Dilabio, G. A. Predicting the activity of phenolic antioxidants: theorical method, analysis of substituent effects, application to major families of antioxidants. J. Am. Chem. Soc. 2001, 123, 1173-1183.
26. Stivala, L. A.; Savio, M.; Carafoli, F.; Perucca, P.; Bianchi, L.; et al. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J. Biol. Chem. 2001, 276, 22586-22594.
27. Ekena, K.; Katzenellenbogen, J. A.; Katzenellenbogen, B. S. Determinants of ligand specificity of estrogen receptor-alpha: estrogen versus androgen discrimination. J. Biol. Chem. 1998, 273, 693-699.
28. Gao, H.; Katzenellenbogen, J.; Garg, R.; Hansch, C. Comparative QSAR analysis of estrogen receptor ligands. Chem. Rev. 1999, 99, 723-744.
29. Bellucci, G.; Chiappe, C.; Lo Moro, G. Crown Ether Catalyzed Stereospecific Synthesis of Z- and E-Stilbenes by Wittig Reaction in a Solid-Liquid Two-Phases System. Tetrahedron Lett. 1996, 37, 4225-4228.
30. Cushman, M.; Nagarathnam, D.; Gopal, D.; He, H. M.; Lin, C. M.; et al. Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5- trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents. J. Med. Chem. 1992, 35, 2293-2306.
31. Sun, J.; Huang, Y. R.; Harrington, W. R.; Sheng, S.; Katzenellenbogen, J. A.; et al. Antagonists selective for estrogen receptor alpha. Endocrinology 2002, 143, 941-947.
32. Poirot, M.; De Medina, P.; Delarue, F.; Perie, J. J.; Klaebe, A.; et al. Synthesis, binding and structure-affinity studies of new ligands for the microsomal anti-estrogen binding site (AEBS). Bioorg. Med. Chem. 2000, 8, 2007-2016.
33. Doisneau-Sixou, S. F.; Cestac, P.; Chouini, S.; Carroll, J. S.; Hamilton, A. D.; et al. Contrasting effects of prenyltransferase inhibitors on estrogen-dependent cell cycle progression and estrogen receptor-mediated transcriptional activity in MCF-7 cells. Endocrinology 2003, 144, 989-998.