4-(E)-((p-tolylimino)-methylbenzene-1,2-diol), 1 a novel resveratrol analog, differentially regulates estrogen receptors α and β in breast cancer cells

Toxicology and Applied Pharmacology

Volumn 301, Issue , 2016, Pages 1-13

  Ronghe, Amruta ^a   Chatterjee, Anwesha ^a   Singh, Bhupendra ^b   Dandawate, Prasad ^c   Abdalla, Fatma ^a   Bhat, Nimee K ^a   Padhye, Subhash ^c   Bhat, Hari K ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

^b UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^c UNIVERSITY OF PUNE   (India)

Author keywords

Breast cancer inhibition; Estrogen receptors; Resveratrol analogs; TIMBD

Indexed keywords

4 [(4 TOLYLIMINO) METHYLBENZENE 1,2 DIOL]; ANTINEOPLASTIC AGENT; CYCLIN D1; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; MESSENGER RNA; MYC PROTEIN; PROTEIN P21; PROTEIN P53; RESVERATROL; UNCLASSIFIED DRUG; 4-(E)-((P-TOLYLIMINO)-METHYLBENZENE-1,2-DIOL); ESTROGEN RECEPTOR ALPHA, HUMAN; SMALL INTERFERING RNA; STILBENE DERIVATIVE;

ARTICLE; BRDU ASSAY; BREAST CANCER; BREAST CANCER CELL LINE; CANCER GROWTH; CELL DEATH; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DOSE RESPONSE; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MCF 7 CELL LINE; ONCOGENE C MYC; PROMOTER REGION; PROTEIN EXPRESSION; TUMOR SUPPRESSOR GENE; BREAST TUMOR; CELL LINE; CELL SURVIVAL; DRUG EFFECTS; GENETICS; METABOLISM; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HUMANS; RNA, MESSENGER; RNA, SMALL INTERFERING; STILBENES;

EID: 84962855654     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2016.03.003     Document Type: Article

References (44)

1. Adlercreutz H. Phytoestrogens: epidemiology and a possible role in cancer protection. Environ. Health Perspect. 1995, 103:103-112.
2. Adlercreutz H. Epidemiology of phytoestrogens. Bailliere Clin. Endocrinol. Metab. 1998, 12:605-623.
3. Adlercreutz H. Phytoestrogens and breast cancer. J. Steroid Biochem. Mol. Biol. 2002, 83:113-118.
4. Aggarwal B.B., Bhardwaj A., Aggarwal R.S., Seeram N.P., Shishodia S., Takada Y. Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Res. 2004, 24:2783-2840.
5. Aiyer H.S., Warri A.M., Woode D.R., Hilakivi-Clarke L., Clarke R. Influence of berry polyphenols on receptor signaling and cell-death pathways: implications for breast cancer prevention. J. Agric. Food Chem. 2012, 60:5693-5708.
6. An J., Tzagarakis-Foster C., Scharschmidt T.C., Lomri N., Leitman D.C. Estrogen receptor beta-selective transcriptional activity and recruitment of coregulators by phytoestrogens. J. Biol. Chem. 2001, 276:17808-17814.
7. Banerjee S., Bueso-Ramos C., Aggarwal B.B. Suppression of 7,12-dimethylbenz(a)anthracene-induced mammary carcinogenesis in rats by resveratrol: role of nuclear factor-kappaB, cyclooxygenase 2, and matrix metalloprotease 9. Cancer Res. 2002, 62:4945-4954.
8. Bhat H.K., Vadgama J.V. Role of estrogen receptor in the regulation of estrogen induced amino acid transport of system A in breast cancer and other receptor positive tumor cells. Int. J. Mol Med. 2002, 9:271-279.
9. Bhat K.P., Lantvit D., Christov K., Mehta R.G., Moon R.C., Pezzuto J.M. Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models. Cancer Res. 2001, 61:7456-7463.
10. Bowers J.L., Tyulmenkov V.V., Jernigan S.C., Klinge C.M. Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta. Endocrinology 2000, 141:3657-3667.
11. Cai Y.J., Wei Q.Y., Fang J.G., Yang L., Liu Z.L., Wyche J.H., Han Z. The 3,4-dihydroxyl groups are important for trans-resveratrol analogs to exhibit enhanced antioxidant and apoptotic activities. Anticancer Res. 2004, 24:999-1002.
12. Carter L.G., D'Orazio J.A., Pearson K.J. Resveratrol and cancer: focus on in vivo evidence. Endocr. Relat. Cancer. 2014, 21:R209-R225.
13. Chatterjee A., Ronghe A., Singh B., Bhat N.K., Chen J., Bhat H.K. Natural antioxidants exhibit chemopreventive characteristics through the regulation of CNC b-Zip transcription factors in estrogen-induced breast carcinogenesis. J. Biochem. Mol. Toxicol. 2014, 28:529-538.
14. De Amicis F., Giordano F., Vivacqua A., Pellegrino M., Panno M.L., Tramontano D., Fuqua S.A., Ando S. Resveratrol, through NF-Y/p53/Sin3/HDAC1 complex phosphorylation, inhibits estrogen receptor alpha gene expression via p38MAPK/CK2 signaling in human breast cancer cells. FASEB J. 2011, 25:3695-3707.
15. Fulda S. Resveratrol and derivatives for the prevention and treatment of cancer. Drug Discov. Today 2010, 15:757-765.
16. Garvin S., Ollinger H.K., Dabrosin C. Resveratrol induces apoptosis and inhibits angiogenesis in human breast cancer xenografts in vivo. Cancer Lett. 2006, 231:113-122.
17. 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. USA 1997, 94:14138-14143.
18. Goldberg D.M., Yan J., Soleas G.J. Absorption of three wine-related polyphenols in three different matrices by healthy subjects. Clin. Biochem. 2003, 36:79-87.
19. Le Corre L., Chalabi N., Delort L., Bignon Y.J., Bernard-Gallon D.J. Resveratrol and breast cancer chemoprevention: molecular mechanisms. Mol. Nutr. Food Res. 2005, 49:462-471.
20. Lincoln D.W., Tsan M.F. Effect of resveratrol on growth of 4T1 breast cancer cells in vitro and in vivo. Biochem. Biophys. Res. Commun. 2002, 291:1001-1005.
21. Mense S.M., Hei T.K., Ganju R.K., Bhat H.K. Phytoestrogens and breast cancer prevention: possible mechanisms of action. Environ. Health Perspect. 2008, 116:426-433.
22. Milani A., Geuna E., Mittica G., Valabrega G. Overcoming endocrine resistance in metastatic breast cancer: current evidence and future directions. World J. Clin. Oncol. 2014, 5:990-1001.
23. Moutsatsou P. The spectrum of phytoestrogens in nature: our knowledge is expanding. Hormones (Athens) 2007, 6(3):173-193.
24. Nakagawa H., Kiyozuka Y., Uemura Y., Senzaki H., Shikata N., Hioki K., Tsubura A. Resveratrol inhibits human breast cancer cell growth and may mitigate the effect of linoleic acid, a potent breast cancer cell stimulator. J. Cancer Res. Clin. Oncol. 2001, 127:258-264.
25. Polotskaia A., Hoffman S., Krett N.L., Shanmugam M., Rosen S.T., Bargonetti J. 8-Amino-adenosine activates p53-independent cell death of metastatic breast cancers. Mol. Cancer Ther. 2012, 11:2495-2504.
26. Pozo-Guisado E., Alvarez-Barrientos A., Mulero-Navarro S., Santiago-Josefat B., Fernandez-Salguero P.M. The antiproliferative activity of resveratrol results in apoptosis in MCF-7 but not in MDA-MB-231 human breast cancer cells: cell-specific alteration of the cell cycle. Biochem. Pharmacol. 2002, 64:1375-1386.
27. Pozo-Guisado E., Merino J.M., Mulero-Navarro S., Lorenzo-Benayas M.J., Centeno F., Alvarez-Barrientos A., Fernandez-Salguero P.M. Resveratrol-induced apoptosis in mcf-7 human breast cancer cells involves a caspase- independent mechanism with downregulation of bcl-2 and Nf-kappab. Int. J. Cancer 2005, 115:74-84.
28. Roberti M., Pizzirani D., Simoni D., Rondanin R., Baruchello R., Bonora C., Buscemi F., Grimaudo S., Tolomeo M. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem. 2003, 46:3546-3554.
29. Ronghe A., Chatterjee A., Singh B., Murphy L., Dandawate P., Padhye S., Bhat N.K., Bhat H.K. Differential regulation of estrogen receptors α and β by 4-(E)-((4-hydroxyphenylimino)-methylbenzene, 1,2-diol), a novel resveratrol analog. J. Steroid Biochem. Mol. Biol. 2014, 144:500-512.
30. Siddiqui A., Dandawate P., Rub R., Padhye S., Aphale S., Moghe A., Jagyasi A., Venkateswara Swamy K., Singh B., Chatterjee A., Ronghe A., Bhat H.K. Novel Aza-resveratrol analogs: synthesis, characterization and anticancer activity against breast cancer cell lines. Bioorg. Med. Chem. Lett. 2013, 23:635-640.
31. Signorelli P., Ghidoni R. Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. J. Nutr. Biochem. 2005, 16:449-466.
32. Singh B., Bhat H.K. Superoxide dismutase 3 is induced by antioxidants, inhibits oxidative DNA damage and is associated with inhibition of estrogen-induced breast cancer. Carcinogenesis 2012, 33:2601-2610.
33. Singh B., Mense S.M., Remotti F., Liu X., Bhat H.K. Antioxidant butylated hydroxyanisole inhibits estrogen-induced breast carcinogenesis in female ACI rats. J. Biochem. Mol. Toxicol. 2009, 23:202-211.
34. Singh B., Mense S.M., Bhat N.K., Putty S., Guthiel W.A., Remotti F., Bhat H.K. Dietary quercetin exacerbates the development of estrogen-induced breast tumors in female ACI rats. Toxicol. Appl. Pharmacol. 2010, 247:83-90.
35. Singh B., Bhat N.K., Bhat H.K. Partial inhibition of estrogen-induced mammary carcinogenesis in rats by tamoxifen: balance between oxidant stress and estrogen responsiveness. PLoS One 2011, 6.
36. Singh B., Bhat N.K., Bhat H.K. Induction of NAD(P)H-quinone oxidoreductase 1 by antioxidants in female ACI rats is associated with decrease in oxidative DNA damage and inhibition of estrogen-induced breast cancer. Carcinogenesis 2012, 33:156-163.
37. Singh B., Chatterjee A., Ronghe A.M., Bhat N.K., Bhat H.K. Antioxidant-mediated up-regulation of OGG1 via NRF2 induction is associated with inhibition of oxidative DNA damage in estrogen-induced breast cancer. BMC Cancer 2013, 13:253.
38. Singh B., Ronghe A.M., Chatterjee A., Bhat N.K., Bhat H.K. MicroRNA-93 regulates NRF2 expression and is associated with breast carcinogenesis. Carcinogenesis 2013, 34:1165-1172.
39. Singh B., Shoulson R., Chatterjee A., Ronghe A., Bhat N.K., Dim D.C., Bhat H.K. Resveratrol inhibits estrogen-induced breast carcinogenesis through induction of NRF2-mediated protective pathways. Carcinogenesis 2014, 35:1872-1880.
40. Ursin G., Bernstein L., Pike M.C. Breast cancer. Cancer Surv. 1994, 19-20:241-264.
41. Walle T. Bioavailability of resveratrol. Ann. N. Y. Acad. Sci. 2011, 1215:9-15.
42. Wang C., Mayer J.A., Mazumdar A., Fertuck K., Kim H., Brown M., Brown P.H. Estrogen induces c-myc gene expression via an upstream enhancer activated by the estrogen receptor and the AP-1 transcription factor. Mol. Endocrinol. 2011, 25:1527-1538.
43. Williams C., Edvardsson K., Lewandowski S.A., Strom A., Gustafsson J.A. A genome-wide study of the repressive effects of estrogen receptor beta on estrogen receptor alpha signaling in breast cancer cells. Oncogene 2008, 27:1019-1032.
44. Wong S.C., Chan J.K., Lee K.C., Hsiao W.L. Differential expression of p16/p21/p27 and cyclin D1/D3, and their relationships to cell proliferation, apoptosis, and tumour progression in invasive ductal carcinoma of the breast. J. Pathol. 2001, 194:35-42.