Ester and carbamate ester derivatives of Biochanin A: Synthesis and in vitro evaluation of estrogenic and antiproliferative activities

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 9, 2012, Pages 2962-2970

  Fokialakis, Nikolas ^a   Alexi, Xanthippi ^b   Aligiannis, Nektarios ^a   Siriani, Despina ^b   Meligova, Aggeliki K ^b   Pratsinis, Harris ^c   Mitakou, Sofia ^a   Alexis, Michael N ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b INSTITUTE OF BIOLOGY   (Greece)

^c Institute of Biology   (Greece)

Author keywords

Biochanin A; Carbamate; Chemoprevention; Ester; Estrogenic activity; Ishikawa cells; MCF 7

Indexed keywords

1,3,5 TRIS(4 HYDROXYPHENYL) 4 PROPYLPYRAZOLE; 5 HYDROXY 3 (4 METHOXYPHENYL) 4 OXO 4H CHROMEN 7 YL 2 BROMOACETATE; 5 HYDROXY 3 (4 METHOXYPHENYL) 4 OXO 4H CHROMEN 7 YL 2 BROMOETHYLCARBAMATE; 5 HYDROXY 3 (4 METHOXYPHENYL) 4 OXO 4H CHROMEN 7 YL 2 CHLOROACETATE; 5 HYDROXY 3 (4 METHOXYPHENYL) 4 OXO 4H CHROMEN 7 YL 2 CHLOROETHYLCARBAMATE; 5 HYDROXY 3 (4 METHOXYPHENYL) 4 OXO 4H CHROMEN 7 YL 2 UNDECYLCARBAMATE; 5 HYDROXY 3 (METHOXYPHENYL) 4 OXO 4H CHROMEN 7 YL 2 CHLOROACETATE; ANTINEOPLASTIC AGENT; BIOCHANIN A; DIARYLPROPIONITRILE; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HORMONE RECEPTOR STIMULATING AGENT; METHYLPIPERIDINO PYRAZOLE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CANCER INHIBITION; CELL PROLIFERATION; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STABILITY; DRUG SYNTHESIS; ESTROGEN ACTIVITY; GENE INDUCTION; HUMAN; HUMAN CELL; IC 50; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CARBAMATES; CELL LINE, TUMOR; CELL PROLIFERATION; ESTERS; GENISTEIN; HUMANS; TRIFOLIUM;

TRIFOLIUM PRATENSE;

EID: 84859919978     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.03.012     Document Type: Article

References (45)

1. N.E. Allen, K.K. Tsilidis, T.J. Key, L. Dossus, R. Kaaks, E. Lund, K. Bakken, O. Gavrilyuk, K. Overvad, A. Tjønneland, A. Olsen, A. Fournier, A. Fabre, F. Clavel-Chapelon, N. Chabbert-Buffet, C. Sacerdote, V. Krogh, B. Bendinelli, R. Tumino, S. Panico, M. Bergmann, M. Schuetze, F.J. Van Duijnhoven, H.B. Bueno-de-Mesquita, N.C. Onland-Moret, C.H. Van Gils, P. Amiano, A. Barricarte, M.D. Chirlaque, M.E. Molina-Montes, M.L. Redondo, E.J. Duell, K.T. Khaw, N. Wareham, S. Rinaldi, V. Fedirko, T. Mouw, D.S. Michaud, and E. Riboli Am. J. Epidemiol. 172 2010 1394
2. R.T. Chlebowski, G.L. Anderson, M. Gass, D.S. Lane, A.K. Aragaki, L.H. Kuller, J.E. Manson, M.L. Stefanick, J. Ockene, G.E. Sarto, K.C. Johnson, J. Wactawski-Wende, P.M. Ravdin, R. Schenken, S.L. Hendrix, A. Rajkovic, T.E. Rohan, S. Yasmeen, and R.L. Prentice JAMA 304 2010 1684
3. J.A. Gustafsson Climacteric 9 2006 156
4. A.M. Shaaban, C. Jarvis, F. Moore, C. West, A. Dodson, and C.S. Foster Am. J. Surg. Pathol. 29 2005 1593
5. W. Wuttke, H. Jarry, T. Becker, A. Schultens, V. Christoffel, C. Gorkow, and D. Seidlová-Wuttke Maturitas 61 2008 159
6. Y.J. Moon, B.S. Shin, G. An, and M.E. Morris Pharm. Res. 25 2008 2158
7. M. Suetsugi, L. Su, K. Karlsberg, Y.C. Yuan, and S. Chen Mol. Cancer Res. 1 2003 981
8. S. Schrepfer, T. Deuse, T. Münzel, H. Schäfer, W. Braendle, and H. Reichenspurner Menopause 13 2006 489
9. C. Atkinson, R.M. Warren, E. Sala, M. Dowsett, A.M. Dunning, C.S. Healey, S. Runswick, N.E. Day, and S.A. Bingham Breast Cancer Res. 6 2004 R170
10. B. Baber Maturitas 66 2010 344
11. V.S. Lagari, and S. Levis Curr. Opin. Endocrinol. Diab. 17 2010 546
12. Y.J. Moon, K. Sagawa, K. Frederick, S. Zhang, and M.E. Morris AAPS J. 8 2006 E433
13. W.H. Tolleson, D.R. Doerge, M.I. Churchwell, M.M. Marques, and D.W. Roberts J. Agric. Food Chem. 50 2002 4783
14. J.M. Férriz, and J. Vinsová Curr. Pharm. Des. 16 2010 2033
15. K.T. Hansen, P. Faarup, and H. Bundgaard J. Pharm. Sci. 80 1991 793
16. M. Badeau, M.J. Tikkanen, S.E. Appt, H. Adlercreutz, T.B. Clarkson, A. Hoikkala, K. Wähälä, and T.S. Mikkola Biochim. Biophys. Acta 1738 2005 115
17. K. Wahala, and T.A. Hase J. Chem. Soc., Perkin Trans. 1 1991 3005
18. S. Djiogue, M. Halabalaki, X. Alexi, D. Njamen, Z.T. Fomum, M.N. Alexis, and A.L. Skaltsounis J. Nat. Prod. 72 2009 1603
19. N.I. Chantzi, A.K. Meligova, E. Dhimolea, C.C. Petrou, D.J. Mitsiou, V. Magafa, A. Pechtelidou, I. Florentin, E. Kitraki, P. Cordopatis, D.G. Tiniakos, and M.N. Alexis Steroids 76 2011 974
20. N. Fokialakis, G. Lambrinidis, N. Aligiannis, S. Mitakou, A.L. Skaltsounis, H. Pratsinis, E. Mikros, and M.N. Alexis Chem. Biol. 11 2004 397
21. M. Halabalaki, X. Alexi, N. Aligiannis, G. Lambrinidis, H. Pratsinis, I. Florentin, S. Mitakou, E. Mikros, A.L. Skaltsounis, and M.N. Alexis Planta Med. 72 2006 488
22. X. Alexi, K.M. Kasiotis, N. Fokialakis, G. Lambrinidis, A.K. Meligova, E. Mikros, S.A. Haroutounian, and M.N. Alexis J. Steroid Biochem. Mol. Biol. 117 2009 159
23. A.D. Gritzapis, C.N. Baxevanis, I. Missitzis, E.S. Katsanou, M.N. Alexis, J. Yotis, and M. Papamichail Breast Cancer Res. Treat. 80 2003 1
24. G. Lazennec, J.L. Alcorn, and B.S. Katzenellenbogen Mol. Endocrinol. 13 1999 969
25. A.A. Van Landeghem, J. Poortman, M. Nabuurs, and J.H. Thijssen Cancer Res. 45 1985 2900
26. C. Villalonga-Barber, A.K. Meligova, X. Alexi, B.R. Steele, C.E. Kouzinos, C.G. Screttas, E.S. Katsanou, M. Micha-Screttas, and M.N. Alexis Bioorg. Med. Chem. 19 2011 339
27. T. Calogeropoulou, N. Avlonitis, V. Minas, X. Alexi, A. Pantzou, I. Charalampopoulos, M. Zervou, V. Vergou, E.S. Katsanou, I. Lazaridis, M.N. Alexis, and A. Gravanis J. Med. Chem. 52 2009 6569
28. A.C. Pike, A.M. Brzozowski, R.E. Hubbard, T. Bonn, A.G. Thorsell, O. Engström, J. Ljunggren, J.A. Gustafsson, and M. Carlquist EMBO J. 18 1999 4608
29. S. Paruthiyil, H. Parmar, V. Kerekatte, G.R. Cunha, G.L. Firestone, and D.C. Leitman Cancer Res. 64 2004 423
30. V. Bombail, F. Collins, P. Brown, and P.T. Saunders Mol. Cell Endocrinol. 314 2010 53
31. G. Leclercq, M. Lacroix, I. Laïos, and G. Laurent Curr. Cancer Drug Targets 6 2006 39
32. M. Rossi, D. Colecchia, C. Iavarone, A. Strambi, F. Piccioni, A. Verrotti di Pianella, and M. Chiariello J. Biol. Chem. 286 2011 8507
33. M.P. Murphy, and R.A. Smith Annu. Rev. Pharmacol. Toxicol. 47 2007 629
34. E.L. Robb, and J.A. Stuart Free Radic. Biol. Med. 50 2011 821
35. J.Q. Chen, M. Delannoy, C. Cooke, and J.D. Yager Am. J. Physiol. Endocrinol. Metab. 286 2004 E1011
36. A. Pedram, M. Razandi, D.C. Wallace, and E.R. Levin Mol. Biol. Cell. 17 2006 2125
37. E.R. Jang, S.J. Lim, E.S. Lee, G. Jeong, T.Y. Kim, Y.J. Bang, and J.S. Lee Oncogene 23 2004 1724
38. L. Markiewicz, J. Garey, H. Adlercreutz, and E. Gurpide J. Steroid Biochem. Mol. Biol. 45 1993 399
39. S.M. Johnson, M. Maleki-Dizaji, J.A. Styles, and I.N. White Endocr. Relat. Cancer 14 2007 337
40. Z. Weihua, S. Saji, S. Mäkinen, G. Cheng, E.V. Jensen, M. Warner, and J.A. Gustafsson Proc. Natl. Acad. Sci. U.S.A. 97 2000 5936
41. E.R. Levin Trends Endocrinol. Metab. 20 2009 477
42. H. Bundgaard, A. Buur, and V.H. Lee Acta Pharm. Suec. 25 1988 293 306
43. L. Campbell, E. Emmerson, F. Davies, S.C. Gilliver, A. Krust, P. Chambon, and G.S. Ashcroft J. Exp. Med. 2010 1825 207
44. P.G. Sator, M.O. Sator, J.B. Schmidt, H. Nahavandi, S. Radakovic, J.C. Huber, and H. Hönigsmann Climacteric 10 2007 320
45. E.S. Katsanou, M. Halabalaki, N. Aligiannis, S. Mitakou, A.L. Skaltsounis, X. Alexi, H. Pratsinis, and M.N. Alexis J. Steroid Biochem. Mol. Biol. 104 2007 228