Synthesis and evaluation of the antiproliferative activities of derivatives of carboxyalkyl isoflavones linked to N-t-Boc-hexylenediamine

Journal of Medicinal Chemistry

Volumn 50, Issue 25, 2007, Pages 6405-6410

  Kohen, Fortune ^a   Gayer, Batya ^a   Kulik, Tikva ^a   Frydman, Veronica ^a   Nevo, Nava ^a   Katzburg, Sara ^b   Limor, Rona ^b   Sharon, Orli ^b   Stern, Naftali ^b   Somjen, Dalia ^b  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 CARBOXYPROPYL) 5,7,4' TRIHYDROXYISOFLAVONE; 2 (3 CARBOXYPROPYL) 7,5 DIHYDROXY 4' METHOXYISOFLAVONE; 2 [3 [N [6 (TERT BUTOXYCARBONYL)AMINOHEXYL]]CABOXAMIDOPROPYL] 5,7,4' TRIHYDROXYISOFLAVONE; 2 [3 CARBOXY (6 TERT BUTOXYCARBONYLAMINO)HEXYLAMINOPROPYL] 7,5 DIHYDROXY 4' METHOXYISOFLAVONE; 5 [2 [3 (4 HYDROXYPHENYL) 4 OXO 4H CHROMEN 7 YLOXY]ACETYLAMINO]PENTYL CARBAMIC ACID TERT BUTYL ESTER; BENZYLOXYCARBONYLVALYLALANYLASPARTYL FLUOROMETHYL KETONE; BIOCHANIN A; DAIDZEIN; GENISTEIN; ISOFLAVONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; CANCER CELL; CELL PROLIFERATION; CONTROLLED STUDY; DNA SYNTHESIS; DRUG ACTIVITY; DRUG ANTAGONISM; DRUG INHIBITION; DRUG SYNTHESIS; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; VASCULAR SMOOTH MUSCLE;

AMINO ACID CHLOROMETHYL KETONES; ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARBAMATES; CELL LINE, TUMOR; CHROMONES; COLONIC NEOPLASMS; DNA; DRUG INTERACTIONS; ESTROGEN ANTAGONISTS; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FEMALE; HUMANS; ISOFLAVONES; MALE; MICE; MICE, NUDE; MUSCLE, SMOOTH, VASCULAR; NEOPLASM TRANSPLANTATION; OVARIAN NEOPLASMS; OVARY; PROSTATE; RNA, MESSENGER; TRANSPLANTATION, HETEROLOGOUS;

EID: 37049029469     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070727z     Document Type: Article

References (16)

1. Aggarwal, B. B.; Shishodia, S. Molecular targets of dietary agents for prevention and therapy of cancer. Biochem. Pharmacol. 2006, 71, 1397-1421.
2. Kuiper, G. G.; Lemmen, J. G.; Carlsson, B.; Corton, J. C.; Safe, S. H.; van der Saag, P. T.; van der Burg, B.; Gustafsson, J. A. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 1998, 139, 4252-4263.
3. Harris, D. M.; Besselink, E.; Henning, S. M.; Go, V. L.; Heber, D. Phytoestrogens induce differential estrogen receptor alpha- or Beta-mediated responses in transfected breast cancer cells. Exp Biol Med (Maywood) 2005, 230, 558-568.
4. Akiyama, T.; Ishida, J.; Nakagawa, S.; Ogawara, H.; Watanabe, S.; Itoh, N.; Shibuya, M.; Fukami, Y. Genistein, a specific inhibitor of tyrosine-specific protein kinases. J. Biol. Chem. 1987, 262, 5592-5595.
5. Agarwal, R. Cell signaling and regulators of cell cycle as molecular targets for prostate cancer prevention by dietary agents. Biochem. Pharmacol. 2000, 60, 1051-1059.
6. Kim, H.; Peterson, T. G.; Barnes, S. Mechanisms of action of the soy isoflavone genistein: emerging role for its effects via transforming growth factor beta signaling pathways. Am. J. Clin. Nutr. 1998, 68, 1418S-1425S.
7. Uckun, F. M.; Narla, R. K.; Jun, X.; Zeren, T.; Venkatachalam, T.; Waddick, K. G.; Rostostev, A.; Myers, D. E. Cytotoxic activity of epidermal growth factor-genistein against breast cancer cells. Clin. Cancer Res. 1998, 4, 901-912.
8. Barve, V.; Ahmed, F.; Adsule, S.; Banerjee, S.; Kulkarni, S.; Katiyar, P.; Anson, C. E.; Powell, A. K.; Padhye, S.; Sarkar, F. H. Synthesis, molecular characterization, and biological activity of novel synthetic derivatives of chromen-4-one in human cancer cells. J. Med. Chem. 2006, 49, 3800-3808.
9. Sarkar, F. H.; Adsule, S.; Padhye, S.; Kulkarni, S.; Li, Y. The role of genistein and synthetic derivatives of isoflavone in cancer prevention and therapy. Mini-Rev. Med. Chem. 2006, 6, 401-407.
10. Kamsteeg, M.; Rutherford, T.; Sapi, E.; Hanczaruk, B.; Shahabi, S.; Flick, M.; Brown, D.; Mor, G. Phenoxodiol - an isoflavone analog - induces apoptosis in chemoresistant ovarian cancer cells. Oncogene 2003, 22, 2611-2620.
11. Gamble, J. R.; Xia, P.; Hahn, C. N.; Drew, J. J.; Drogemuller, C. J.; Brown, D.; Vadas, M. A. Phenoxodiol, an experimental anticancer drug, shows potent antiangiogenic properties in addition to its antitumour effects. Int. J. Cancer 2006, 118, 2412-2420.
12. Mor, G.; Fu, H. H.; Alvero, A. B. Phenoxodiol, a novel approach for the treatment of ovarian cancer. Curr. Opin. Invest. Drugs 2006, 7, 542-548.
13. Somjen, D.; Amir-Zaltsman, Y.; Gayer, B.; Kulik, T.; Knoll, E.; Stern, N.; Lu, L. J.; Toldo, L.; Kohen, F. 6-Carboxymethyl genistein: a novel selective oestrogen receptor modulator (SERM) with unique, differential effects on the vasculature, bone and uterus. J Endocrinol. 2002, 173, 415-427.
14. Somjen, D.; Kohen, F.; Amir-Zaltsman, Y.; Knoll, E.; Stern, N. Vitamin D analogs modulate the action of gonadal steroids in human vascular cells in vitro. Am. J. Hypertens. 2000, 13, 396-403.
15. Pelter, A.; Ward, R.; Whalley, J. A facile synthesis of 2-substituted isoflavones for immunoassay: Assembly of the isoflavonoid skeleton by means of a novel cyclisation reaction. Synthesis 1998, 1793-1802.
16. Bennetau-Pelissero, C.; Le Houerou, C.; Lamothe, V.; Le Menn, F.; Babin, P.; Bennetau, B. Synthesis of haptens and conjugates for ELISAs of phytoestrogens. Development of the immunological tests. J. Agric. Food Chem. 2000, 48, 305-311.