Evaluation of the effect of the new methoxy-stilbenes on expression of receptors and enzymes involved in estrogen synthesis in cancer breast cells

Molecular and Cellular Biochemistry

Volumn 444, Issue 1-2, 2018, Pages 53-62

  Licznerska, Barbara ^a   Szaefer, Hanna ^a   Wierzchowski, Marcin ^a   Mikstacka, Renata ^b   Papierska, Katarzyna ^a   Baer Dubowska, Wanda ^a  

^a POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^b NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

AhR; Breast cancer epithelial cells; CYP1A1; CYP1B1; ER ; Methoxy stilbenes

Indexed keywords

3,4,2' TRIMETHOXY TRANS STILBENE; 3,4,2',4' TETRAMETHOXY TRANS STILBENE; 3,4,2',4',6' PENTAMETHOXY TRANS STILBENE; AROMATASE; AROMATIC HYDROCARBON RECEPTOR; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; CYTOCHROME P450 FAMILY 19; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR ALPHA; MESSENGER RNA; RECOMBINANT PROTEIN; RESVERATROL; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; AHR PROTEIN, HUMAN; BASIC HELIX LOOP HELIX TRANSCRIPTION FACTOR; CYTOCHROME P450; ESTROGEN RECEPTOR ALPHA, HUMAN; TUMOR PROTEIN;

ARTICLE; BREAST CANCER; CELL VIABILITY; CONTROLLED STUDY; DRUG EFFECT; ENZYME ACTIVITY; ESTROGEN SYNTHESIS; EVALUATION STUDY; HORMONE METABOLISM; HUMAN; HUMAN CELL; IC50; MCF-7 CELL LINE; MDA-MB-231 CELL LINE; METASTASIS; PROTEIN EXPRESSION; QUANTITATIVE ASSAY; REAL TIME POLYMERASE CHAIN REACTION; WESTERN BLOTTING; BIOSYNTHESIS; BREAST TUMOR; CHEMISTRY; DRUG SCREENING; FEMALE; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; PATHOLOGY;

BASIC HELIX-LOOP-HELIX TRANSCRIPTION FACTORS; BREAST NEOPLASMS; CYTOCHROME P-450 ENZYME SYSTEM; DRUG SCREENING ASSAYS, ANTITUMOR; ESTROGEN RECEPTOR ALPHA; ESTROGENS; FEMALE; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; MCF-7 CELLS; NEOPLASM PROTEINS; RECEPTORS, ARYL HYDROCARBON; STILBENES;

EID: 85035784495     PISSN: 03008177     EISSN: 15734919     Source Type: Journal    
DOI: 10.1007/s11010-017-3230-7     Document Type: Article

References (30)

1. Sirerol JA, Rodroguez ML, Mena S, Asensi MA, Estrela JM, Ortega AL. (2016) Role of natural stilbenes in the prevention of cancer. Oxid Med Cell Longev ID 3128951. 10.1155/2016/3128951
2. Cottari CH, Nivet-Antoine V, Beaudeux JL (2014) Review of recent data on the metabolism, biological effects, and toxicity of resveratrol in humans. Mol Nutr Food Res 58:7–21. 10.1002/mnfr.201200589
3. Piotrowska H, Myszkowski K, Abraszek J, Kwiatkowska-Borowczyk E, Amarowicz R, Murias M, Wierzchowski M, Jodynis-Liebert J (2014) DMU-212 inhibits tumor growth in xenograft model of human ovarian cancer. Biomed Pharmacother 68:397–400. 10.1016/j.biopha.2014.02.00
4. Piotrowska-Kempisty H, Klupczyńska A, Trzybulska D, Kulcenty K, Sulej-Suchomska AM, Kucińska M, Mikstacka R, Wierzchowski M, Murias M, Baer-Dubowska W, Kokot Z, Jodynis-Liebert J (2017) Role of CYP1A1 in the biological activity of methylated resveratrol analogue, 3,4,5,4′-tetramethoxystilbene (DMU-212) in ovarian cancer A-2780 and non-cancerous HOSE cells. Toxicol Lett 267:59–66. 10.1016/j.toxlet.2016.12.018
5. Licznerska B, Szaefer H, Wierzchowski M, Sobierajska H, Baer-Dubowska W (2017) Resveratrol and its methoxy derivatives modulate the expression of estrogen metabolism enzymes in breast epithelial cells by AhR down-regulation. Mol Cell Biochem 425:169–179. 10.1007/s11010-016-2871-2
6. Cui J, Shen Y, Li R (2013) Estrogen synthesis and signaling pathways during ageing: from periphery to brain. Trends Mol Med 19:197–209. 10.1016/j.molmed.2012.12.007
7. Jia M, Dahlman-Wright K, Gustafsson JA (2015) Estrogen receptor alpha and beta in health and disease. Best Pract Res Clin Endocrinol Metab 29:557–568. 10.1016/j.beem.2015.04.008
8. Huang B, Omoto Y, Iwase H, Yamashita H, Toyama T, Coombes RC, Filipovic A, Warner M, Gustafsson J (2014) Differential expression of estrogen receptor alpha, beta1, and beta2 in lobular and ductal breast cancer. Proc Natl Acad Sci USA 111:1933–1938. 10.1073/pnas.1323719111
9. Couse JF, Korach KS (1999) Estrogen receptor null mice: what have we learned and where will they lead us? Endocr Rev 20:358–417
10. Yasuda MT, Sakakibara H, Shimoi K (2017) Estrogen- and stress-induced DNA damage in breast cancer and chemoprevention with dietary flavonoid. Genes Environ 39:10. 10.1186/s41021-016-0071-7
11. Ohtake F, Takeyama K, Matsumoto T, Kitagawa H, Yamamoto Y, Nohara K, Tohyama C, Krust A, Mimura J, Chambon P, Yanagisawa J, Kato S, Fujii Kuriyama Y (2003) Modulation of oestrogen receptor signalling by association with the activated dioxin receptor. Nature 423:545–550
12. Wormke M, Stoner M, Saville B, Walker K, Abdelrahim M, Burghardt R, Safe S (2003) The aryl hydrocarbon receptor mediates degradation of estrogen receptor alpha through activation of proteasomes. Mol Cell Biol 23:1843–1855
13. Zhao S, Kanno Y, Nakayama M, Makimura M, Ohara S, Inouye Y (2012) Activation of the aryl hydrocarbon receptor represses mammosphere formation in MCF-7 cells. Cancer Lett 317:192–198. 10.1016/j.canlet.2011.11.025
14. Chan MY, Huang H, Leung LK (2010) 2,3,7,8-Tetrachlorodibenzo-para-dioxin increases aromatase (CYP19) mRNA stability in MCF-7 cells. Mol Cell Endocrinol 317:8–13. 10.1016/j.mce.2009.11.012
15. Cheshenko K, Brion F, Le Page Y, Hinfray N, Pakdel F, Kah O, Segner H, Eggen RI (2007) Expression of zebra fish aromatase cyp19a and cyp19b genes in response to the ligands of estrogen receptor and aryl hydrocarbon receptor. Toxicol Sci 96:255–267. 10.1093/toxsci/kfm003
16. Saito R, Miki Y, Hata S, Ishida T, Suzuki T, Ohuchi N, Sasano H (2017) Aryl hydrocarbon receptor induced intratumoral aromatase in breast cancer. Breast Cancer Res Treat 161:399–407. 10.1007/s10549-016-4063-x
17. Casper RF, Quesne M, Rogers IM, Shirota T, Jolivet A, Milgrom E, Savouret JF (1999) Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity. Mol Pharmacol 56:784–790. http://molpharm.aspetjournals.org/content/56/4/784.long
18. Soule HD, Maloney TM, Wolman SR, Peterson WD Jr, Brenz R, McGrath CM, Russo J, Pauley RJ, Jones RF, Brooks SC (1990) Isolation and characterization of a spontaneously immortalized human breast epithelial cell line, MCF-10. Cancer Res 50:6075–6086
19. Russo J, Fernandez SV, Russo PA, Fernbaugh R, Sheriff FS, Lareef HM, Garberand J, Russo JH (2006) 17-b-Estradiol induces transformation and tumorigenesis in human breast epithelial cells. FASEB J 20:1622–1634. 10.1096/fj.05-5399com
20. Szaefer H, Krajka-Kuźniak V, Licznerska B, Bartoszek A, Baer-Dubowska W (2015) Cabbage juices and indoles modulate the expression profile of AhR, ERα, and Nrf2 in human breast cell lines. Nutr Cancer 67:1342–1354. 10.1080/01635581.2015.1082111
21. Jin RY, Gui WJ, Guo YR, Wang CM, Wu JX, Zhu GN (2008) Comparison of monoclonal antibody-based ELISA for triazophos between the indirect and direct formats. Food Agric Immunol 19:49–60. 10.1080/09540100801933454
22. Lin H-S, Ho PC (2009) A rapid HPLC method for the quantification of 3,5,4′-trimethoxy-trans-stilbene (TMS) in rat plasma and its application in pharmacokinetics study. J Pharm Biomed Anal 49:387–393. 10.1016/j.jpba.2008.10.042
23. McFadyen MCE, Rooney PH, Melvin WT, Murray GI (2003) Quantitative analysis of the Ah receptor/cytochrome P450 CYP1B1/CYP1A1 signalling pathway. Biochem Pharmacol 65:1663–1674. 10.1016/S0006-2952(03)00111-4
24. 453Ser polymorphism on the post-translational regulation of CYP1B1 expression. Mol Pharmacol 67:435–443. 10.1124/mol.104.006056
25. Wang Y, Leung LK (2007) Pharmacological concentration of resveratrol suppresses aromatase in JEG-3 cells. Toxicol Lett 173:175–180. 10.1016/j.toxlet.2007.07.009
26. Chun Y-J, Lee S-K, Kim MY (2005) Modulation of human cytochrome P450 1B1 expression by 2,4,3′,5′-tetramethoxystilbene. Drug Metab Dispos 33:1771–1776. 10.1124/dmd.105.006502
27. Kim T, Park H, Yue W, Wang J-P, Atkins KA, Zhang Z, Rogan EG, Cavalieri EL, Mohammad KS, Kim S, Santen RJ, Aiyar SE (2011) Tetra-methoxystilbene modulates ductal growth of the developing murine mammary gland. Breast Cancer Res Treat 126:779–789. 10.1007/s10549-010-1301-5
28. Mikstacka R, Wierzchowski M, Dutkiewicz Z, Gielara-Korzańska A, Korzański A, Teubert A, Sobiak S, Baer-Dubowska W (2014) 3,4,20-Trimethoxy-trans-stilbene: a potent CYP1B1 inhibitor. Med Chem Commun 5:496–501. 10.1039/C3MD00317E
29. Orsini F, Verotta L, Klimo K, Gerhäuser C (2016) Synthesis of resveratrol derivatives and in vitro screening for potential cancer chemopreventive activities. Arch Pharm 349:414–427. 10.1002/ardp.201600022
30. Mayhoub AS, Marler L, Kondratyuk TP, Park EJ, Pezzuto JM, Cushman M (2012) Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol. Bioorg Med Chem 20:2427–2434. 10.1016/j.bmc.2012.01.047