Hydrazinyldiene-chroman-2,4-diones in inducing growth arrest and apoptosis in breast cancer cells: Synergism with doxorubicin and correlation with physicochemical properties

1. A. M. Stuckey, Breast cancer: epidemiology and risk factors, Clin. Obst. Gynecol. 54 (2011) 96-102; DOI: 10.1097/GRF.0b013e3182080056.10.1097/GRF.0b013e3182080056Search in Google Scholar

2. F. C. Thorn, C. Oshiro, S. Marsh, T. Hernandez-Boussard, H. McLeod, T. Klein and B. R. Altman, Doxorubicin pathways: pharmacodynamics and adverse effects, Pharmacogenet. Genom. 21 (2011) 440-446; DOI: 10.1097/FPC.0b013e32833ffb56.10.1097/FPC.0b013e32833ffb56Search in Google Scholar

3. A. Jashari, F. Imeri, L. Ballazhi, A. Shabani, B. Mikhova, G. Dräger, E. Popovski and A. Huwiler, Synthesis and cellular characterization of novel isoxazolo- and thiazolohydrazinyldiene-chroman-2,4-diones on cancer and non-cancer cell growth and death, Bioorg. Med. Chem. 22 (2014) 2655-2661; DOI: 10.1016/j.bmc.2014.03.026.10.1016/j.bmc.2014.03.026Search in Google Scholar

4. S. Chen, M. Cho, K. Karlsberg, D. Zhou and Y. Yuan, Biochemical and biological characterization of a novel anti-aromatase coumarin derivative, J. Biol. Chem. 279 (2004) 48071-48078; DOI: 10.1074/ jbc.M406847200.10.1074/jbc.M406847200Search in Google Scholar

5. L. Woo, A. Purohit, B. Malini, M. Reed and B. Potter, Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates, Chem. Biol. 7 (2000) 773-791; DOI: 10.1016/S1074-5521(00)00023-5.10.1016/S1074-5521(00)00023-5Search in Google Scholar

6. M. Musa, J. Cooperwood and M. Khan, A review of coumarin derivatives in pharmacotherapy of breast cancer, Curr. Med. Chem. 15 (2008) 2664-2679; DOI: 10.2174/092986708786242877.10.2174/092986708786242877377264418991629Search in Google Scholar

7. S. Kirkiacharian, A. Lormier, H. Chidiack, F. Bouchoux and E. Cérède, Synthesis and binding affinity to human alpha and beta estrogen receptors of various 7-hydroxycoumarins substituted at 4- and 3,4- positions, Farmaco 59 (2004) 981-986; DOI: 10.1016/j.farmac.2004.08.004.10.1016/j.farmac.2004.08.00415598433Search in Google Scholar

8. M. Halasi, H. Zhao, H. Dahari, U. G. Bhat, E. B. Gonzalez, A. V. Lyubimo, D. A. Tonetti and A. L. Gartel, Thiazole antibiotics against breast cancer, Cell Cycle 9 (2010) 1214-1217; DOI: 10.4161/ cc.9.6.10955.10.4161/cc.9.6.1095520410687Search in Google Scholar

9. J. Shaw, B. Chen, J. P. Bourgault, H. Jiang, K. Narendra, M. Jayshree, A. V. Frederick, M. Joe, B. Kevin, P. Halina, E. Matthew and R. A. Peter, Synthesis and biological evaluation of novel nphenyl-5-carboxamidyl isoxazoles as potential chemotherapeutic agents for colon cancer, Am. J. Biomed. Sci. 4 (2012) 14-25; DOI: 10.5099/aj120100014.10.5099/aj120100014418295325285182Search in Google Scholar

10. P. Poma, M. Notarbartolo, M. Labbozzetta, A. Maurici, V. Carina, A. Alaimo, M. Rizzi, D. Simoni and N. D’Alessandro, The antitumor activities of curcumin and of its isoxazole analogue are not affected by multiple gene expression changes in an MDR model of the MCF-7 breast cancer cell line: analysis of the possible molecular basis, Int. J. Mol. Med. 20 (2007) 329-335; DOI: 10.3892/ ijmm.20.3.329.Search in Google Scholar

11. L. Ballazhi, E. Popovski, A. Jashari, F. Imeri, I. Ibrahimi, B. Mikhova and K. Mladenovska, Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases, Acta Pharm. 65 (2015) 53-63; DOI: 10.1515/acph-2015-0002.10.1515/acph-2015-000225781704Search in Google Scholar

12. A. Jashari, E. Popovski, B. Mikhova, P. R. Nikolova and L. B. Shivachev, 3-[2-(5-tert-Butyl-1,2-oxazol-3-yl)hydrazinylidene]chroman-2,4-dione, Acta Crystallogr. E69 (2013) o258; DOI: 10.1107/ S1600536813000858.Search in Google Scholar

13. L. Ballazhi, F. Imeri, A. Dimovski, A. Jashari, E. Popovski, P. B. Selmani, B. Mikhova, G. Dräger, E. Alili-Idrizi and K. Mladenovska, Synergy of novel coumarin derivatives and tamoxifen in blocking growth and inducing apoptosis of breast cancer cells, Mac. Pharm. Bull. 60 (2014) 35-44.10.33320/maced.pharm.bull.2014.60.01.005Search in Google Scholar

14. N. C. Bols, V. R. Dayeh, L. E. J. Lee and K. Schirmer, Use of Fish Cell Lines in the Toxicology and Ecotoxicology of Fish, in Biochemistry and Molecular Biology of Fishes - Environmental Toxicology (Eds. T. P. Mommsen and T. W. Moon), Vol. 6, Elsevier Science, Amsterdam 2005, pp. 43-84.10.1016/S1873-0140(05)80005-0Search in Google Scholar

15. R. Hamid, Y. Rotshteyn, L. Rabadi, R. Parikh and P. Bullock, Comparison of alamar blue and MTT assays for high through-put screening, Toxicol. In Vitro 18 (2004) 703-710; DOI: 10.1016/j. tiv.2004.03.012.Search in Google Scholar

16. W. F. Deckert and K. H. Remmer, In vitro inhibition of rat and human liver microsomal enzymes by 4-hydroxycoumarin anticoagulants and related compounds, Chem. Biol. Inter. 5 (1972) 255-263; DOI: 10.1016/0009-2797(72)90029-4.10.1016/0009-2797(72)90029-4Search in Google Scholar

17. H. Liu, Y. Wang, A. Sharma, R. Mao, N. Jiang, B. Dun and X. J. She, Derivatives containing both coumarin and benzimidazole potently induce caspase-dependent apoptosis of cancer cells through inhibition of PI3K-AKT-mTOR signaling, Anticancer Drugs 26 (2015) 667-677; DOI: 10.1097/ CAD.0000000000000232.10.1097/CAD.000000000000023225811964Search in Google Scholar

18. O. Bar-On, M. Shapira and D. D. Hershko, Differential effects of doxorubicin treatment on cell cycle arrest and Skp2 expression in breast cancer cells, Anti-Cancer Drugs 18 (2007) 1113-1121; DOI: 10.1097/CAD.0b013e3282ef4571.10.1097/CAD.0b013e3282ef457117893511Search in Google Scholar

19. R. Lüpertz, W. Wätjen, R. Kahl and Y. Chovolou, Dose- and time-dependent effects of doxorubicin on cytotoxicity, cell cycle and apoptotic cell death in human colon cancer cells, Toxicology 271 (2010) 115-121; DOI: 10.1016/j.tox.2010.03.012.10.1016/j.tox.2010.03.01220346999Search in Google Scholar

20. A. M. Musa, L. V. Badisa, M. L. Latinwo, J. Cooperwood, A. Sinclair and A. Abdullah, Cytotoxic activity of new acetoxycoumarin derivatives in cancer cell lines, Anticancer Res. 31 (2011) 2017-2022.Search in Google Scholar

21. A. Goel, K. A. Prasad, S. V. Parmar, B. Ghosh and N. Saini, 7,8-Dihydroxy-4-methylcoumarin induces apoptosis of human lung adenocarcinoma cells by ROS-independent mitochondrial pathway through partial inhibition of ERK/MAPK signaling, FEBS Lett. 581 (2007) 2447-2454; DOI: 10.1016/j.febslet.2007.04.052.10.1016/j.febslet.2007.04.05217485089Search in Google Scholar

22. D. Alesiani, R. Cicconi, M. Mattei, C. Montesano, R. Bei and A. Canini, Cell cycle arrest and differentiation induction by 5,7-dimethoxycoumarin in melanoma cell lines, Int. J. Oncol. 32 (2008) 425-434; DOI: 10.3892/ijo.32.2.425.10.3892/ijo.32.2.425Search in Google Scholar

23. F. Haghighi, M. M. Matin, A. R. Bahrami, M. Iranshahi, F. B. Rassouli and A. Haghighitalab, The cytotoxic activities of 7-isopentenyloxycoumarin on 5637 cells via induction of apoptosis and cell cycle arrest in G2/M stage, DARU J. Pharm. Sci. 22 (2014) Article ID: 3 (10 pages); DOI: 10.1186/2008-2231-22-3.10.1186/2008-2231-22-3389859824393601Search in Google Scholar

24. C. Barthomeuf, S. Lim, M. Iranshahi and P. Chollet, Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu metastatic pigmented malignant melanoma cells through cell-cycle arrest in G1 and induction of caspase-dependent apoptosis, Phytomedicine 15 (2008) 103-111; DOI: 10.1016/j.phymed.2007.04.001.10.1016/j.phymed.2007.04.00117689942Search in Google Scholar

25. Y. J. Chuang, F. Y. Huang, F. H. Lu, C. H. Ho, S. J. Yang, M. T. Li, W. N. Chang and G. J. Chung, Coumarin induces cell cycle arrest and apoptosis in human cervical cancer HeLa cells through a mitochondria- and caspase-3 dependent mechanism and NF-kappaB down-regulation, In Vivo 21 (2007) 1003-1010.Search in Google Scholar

26. M. Kielbus, K. Skalicka-Wozniak, A. Grabarska, W. Jeleniewicz, M. Dmoszynska-Graniczka, A. Marston, K. Polberg, P. Gawda, J. Klatka and A. Stepulak, 7-Substituted coumarins inhibit proliferation and migration of laryngeal cancer cells in vitro, Anticancer Res. 33 (2013) 4347-4356.Search in Google Scholar

27. D. Yang, T. Gu, T. Wang, Q. Tang and C. Ma, Effects of osthole on migration and invasion in breast cancer cells, Biosci. Biotechnol. Biochem. 74 (2010) 1430-1434; DOI: 1271/bbb.100110.10.1271/bbb.100110Search in Google Scholar

28. W. F. van der Giesen and L. H. Janssen, Influence of ionization and ion-pair formation on lipophilicity of some 4-hydroxy-coumarin derivatives in the octanol-water system, Int. J. Pharm. 12 (1982) 231-249; DOI: 10.1016/0378-5173(82)90122-3.10.1016/0378-5173(82)90122-3Search in Google Scholar

29. H. Schönherr and T. Cernak, Profound methyl effects in drug discovery and a call for new C-H methylation reactions, Angew. Chem. Int. Ed. Engl. 52 (2013) 12256-12267; DOI: 10.1002/ anie.201303207.10.1002/anie.20130320724151256Search in Google Scholar

30. S. C. Leung, S. S. Leung, J. R. Tirado and L. W. Jorgensen, Methyl effects on protein-ligand binding, J. Med. Chem. 55 (2012) 4489-4500; DOI: 10.1021/jm3003697. 10.1021/jm3003697335332722500930Search in Google Scholar