Anti-proliferative and apoptotic effects of the derivatives from 4- aryl-4H-chromene family on human leukemia K562 cells

Archives of Pharmacal Research

Volumn 35, Issue 9, 2012, Pages 1573-1582

  Aryapour, Hassan ^a   Mahdavi, Majid ^b   Mohebbi, Seyed Reza ^c   Zali, Mohammad Reza ^c   Foroumadi, Alireza ^d  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF TABRIZ   (Iran)

^c SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

4 Aryl 4H chromenes; Apoptosis; Caspase 3; K562 cells; Survivin

Indexed keywords

2 AMINO 4 (3 BROMOPHENYL) 3 CYANO 7 (DIMETHYLAMINO) 4H CHROMENE; 2 AMINO 4 (3 NITROPHENYL) 3 CYANO 7 (DIMETHYLAMINO) 4H CHROMENE; 2 AMINO 4 (3 TRIFLUOROMETHYLPHENYL) 3 CYANO 7 (DIMETHYLAMINO) 4H CHROMENE; 2 AMINO 4 (4,5 METHYLENEDIOXYPHENYL) 3 CYANO 7 (DIMETHYLAMINO) 4H CHROMENE; ANTILEUKEMIC AGENT; CASPASE 3; CASPASE 9; CHROMENE DERIVATIVE; PHOSPHATIDYLSERINE; SURVIVIN; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CELL PROLIFERATION; CELL STRUCTURE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DOWN REGULATION; ENZYME ACTIVATION; ENZYME ACTIVITY; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; PROTEIN EXPRESSION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BENZOPYRANS; CASPASE 3; CASPASE 9; CELL ADHESION; CELL LINE, TUMOR; CELL NUCLEUS SHAPE; CELL PROLIFERATION; CELL SURVIVAL; DNA FRAGMENTATION; DOWN-REGULATION; DRUG DESIGN; HUMANS; INHIBITOR OF APOPTOSIS PROTEINS; INHIBITORY CONCENTRATION 50; LEUKEMIA; NEOPLASM PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; UP-REGULATION;

EID: 84872100638     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-012-0908-y     Document Type: Article

References (39)

1. Abhari, B. A. and Davoodi, J., BIR2 domain of XIAP plays a marginal role in inhibition of executioner caspases. Int. J. Biol. Macromol., 46, 337-341 (2010).
2. Cai, S. X., Drewe, J., and Kemnitzer, W., Discovery of 4-aryl- 4H-chromenes as potent apoptosis inducers using a celland caspase-based Anti-cancer Screening Apoptosis Program (ASAP): SAR studies and the identification of novel vascular disrupting agents. Anticancer Agents Med. Chem., 9, 437-456 (2009).
3. Chen, G. and Goeddel, D. V., TNF-R1 signaling: a beautiful pathway. Science, 296, 1634-1635 (2002).
4. Cohen, G. M., Caspases: the executioners of apoptosis. Biochem. J., 326 (Pt 1), 1-16 (1997).
5. Denizot, F. and Lang, R., Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods, 89, 271-277 (1986).
6. Earnshaw, W. C., Martins, L. M., and Kaufmann, S. H., Mammalian caspases: structure, activation, substrates, and functions during apoptosis. Annu. Rev. Biochem., 68, 383- 424 (1999).
7. Foroumadi, A., Dehghan, G., Samzadeh-Kermani, A., Arabsorkhi, F., Sorkhi, M., Shafiee, A., and Abdollahi, M., Synthesis and antioxidant activity of some 2-amino-4- aryl-3-cyano-7-(dimethylamino)-4H-chromenes. Asian J. Chem., 19, 1391-1396 (2007).
8. Gourdeau, H., Leblond, L., Hamelin, B., Desputeau, C., Dong, K., Kianicka, I., Custeau, D., Boudreau, C., Geerts, L., Cai, S. X., Drewe, J., Labrecque, D., Kasibhatla, S., and Tseng, B., Antivascular and antitumor evaluation of 2-amino-4- (3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a novel series of anticancer agents. Mol. Cancer Ther., 3, 1375-1384 (2004).
9. Hayashi, N., Asano, K., Suzuki, H., Yamamoto, T., Tanigawa, N., Egawa, S., and Manome, Y., Adenoviral infection of survivin antisense sensitizes prostate cancer cells to etoposide in vivo. Prostate, 65, 10-9 (2005).
10. Hengartner, M., Apoptosis. Death by crowd control. Science, 281, 1298-1299 (1998).
11. Hirokawa, N., Microtubule organization and dynamics dependent on microtubule-associated proteins. Curr. Opin. Cell Biol., 6, 74-81 (1994).
12. Hunter, A. M., Lacasse, E. C., and Korneluk, R. G., The inhibitors of apoptosis (IAPs) as cancer targets. Apoptosis, 12, 1543-1568 (2007).
13. Jiang, J. D., Davis, A. S., Middleton, K., Ling, Y. H., Perez- Soler, R., Holland, J. F., and Bekesi, J. G., 3-(Iodoacetamido)- benzoylurea: a novel cancericidal tubulin ligand that inhibits microtubule polymerization, phosphorylates bcl- 2, and induces apoptosis in tumor cells. Cancer Res., 58, 5389-5395 (1998).
14. Jin, Y., Wei, Y., Xiong, L., Yang, Y., and Wu, J. R., Differential regulation of survivin by p53 contributes to cell cycle dependent apoptosis. Cell Res., 15, 361-370 (2005).
15. Kasibhatla, S., Gourdeau, H., Meerovitch, K., Drewe, J., Reddy, S., Qiu, L., Zhang, H., Bergeron, F., Bouffard, D., Yang, Q., Herich, J., Lamothe, S., Cai, S. X., and Tseng, B., Discovery and mechanism of action of a novel series of apoptosis inducers with potential vascular targeting activity. Mol. Cancer Ther., 3, 1365-1374 (2004).
16. Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Wang, Y., Zhao, J., Jia, S., Herich, J., Labreque, D., Storer, R., Meerovitch, K., Bouffard, D., Rej, R., Denis, R., Blais, C., Lamothe, S., Attardo, G., Gourdeau, H., Tseng, B., Kasibhatla, S., and Cai, S. X., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based highthroughput screening assay. 1. Structure-activity relationships of the 4-aryl group. J. Med. Chem., 47, 6299-6310 (2004).
17. Kemnitzer, W., Kasibhatla, S., Jiang, S., Zhang, H., Zhao, J., Jia, S., Xu, L., Crogan-Grundy, C., Denis, R., Barriault, N., Vaillancourt, L., Charron, S., Dodd, J., Attardo, G., Labrecque, D., Lamothe, S., Gourdeau, H., Tseng, B., Drewe, J., and Cai, S. X., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based highthroughput screening assay. 2. Structure-activity relationships of the 7- and 5-, 6-, 8-positions. Bioorg. Med. Chem. Lett., 15, 4745-4751 (2005).
18. Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Zhao, J., Crogan-Grundy, C., Xu, L., Lamothe, S., Gourdeau, H., Denis, R., Tseng, B., Kasibhatla, S., and Cai, S. X., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 3. Structure-activity relationships of fused rings at the 7,8-positions. J. Med. Chem., 50, 2858-2864 (2007).
19. Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Crogan- Grundy, C., Labreque, D., Bubenick, M., Attardo, G., Denis, R., Lamothe, S., Gourdeau, H., Tseng, B., Kasibhatla, S., and Cai, S. X., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspasebased high throughput screening assay. 4. Structureactivity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions. J. Med. Chem., 51, 417-423 (2008a).
20. Kemnitzer, W., Jiang, S., Wang, Y., Kasibhatla, S., Crogan- Grundy, C., Bubenik, M., Labrecque, D., Denis, R., Lamothe, S., Attardo, G., Gourdeau, H., Tseng, B., Drewe, J., and Cai, S. X., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based HTS assay. Part 5: modifications of the 2- and 3-positions. Bioorg. Med. Chem. Lett., 18, 603-607 (2008b).
21. Kemnitzer, W., Jiang, S., Zhang, H., Kasibhatla, S., Crogan- Grundy, C., Blais, C., Attardo, G., Denis, R., Lamothe, S., Gourdeau, H., Tseng, B., Drewe, J., and Cai, S. X., Discovery of 4-aryl-2-oxo-2H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. Bioorg. Med. Chem. Lett., 18, 5571-5575 (2008c).
22. Kerr, J. F., Winterford, C. M., and Harmon, B. V., Apoptosis. Its significance in cancer and cancer therapy. Cancer, 73, 2013-2026 (1994).
23. Korzeniewska-Dyl, I., Caspases-structure and function. Pol. Merkur. Lekarski, 23, 403-407 (2007).
24. Krajewska, M., Krajewski, S., Banares, S., Huang, X., Turner, B., Bubendorf, L., Kallioniemi, O. P., Shabaik, A., Vitiello, A., Peehl, D., Gao, G. J., and Reed, J. C., Elevated expression of inhibitor of apoptosis proteins in prostate cancer. Clin. Cancer Res., 9, 4914-4925 (2003).
25. Lacasse, E. C., Baird, S., Korneluk, R. G., and Mackenzie, A. E., The inhibitors of apoptosis (IAPs) and their emerging role in cancer. Oncogene, 17, 3247-3259 (1998).
26. Li, F., Ambrosini, G., Chu, E. Y., Plescia, J., Tognin, S., Marchisio, P. C., and Altieri, D. C., Control of apoptosis and mitotic spindle checkpoint by survivin. Nature, 396, 580-584 (1998).
27. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J., Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193, 265-275 (1951).
28. Mahdavi, M., Davoodi, J., Zali, M. R., and Foroumadi, A., Concomitant activation of caspase-9 and down-regulation of IAP proteins as a mechanism of apoptotic death in HepG2, T47D and HCT-116 cells upon exposure to a derivative from 4-aryl-4H-chromenes family. Biomed. Pharmacother., 65, 175-182 (2011).
29. Mahmoodi, M., Aliabadi, A., Emami, S., Safavi, M., Rajabalian, S., Mohagheghi, M. A., Khoshzaban, A., Samzadeh-Kermani, A., Lamei, N., Shafiee, A., and Foroumadi, A., Synthesis and in-vitro cytotoxicity of poly-functionalized 4-(2-arylthiazol-4- yl)-4H-chromenes. Arch. Pharm. (Weinheim), 343, 411-416 (2010).
30. Messmer, U. K., Pereda-Fernandez, C., Manderscheid, M., and Pfeilschifter, J., Dexamethasone inhibits TNF-alphainduced apoptosis and IAP protein downregulation in MCF-7 cells. Br. J. Pharmacol., 133, 467-476 (2001).
31. Nachmias, B., Ashhab, Y., and Ben-Yehuda, D., The inhibitor of apoptosis protein family (IAPs): an emerging therapeutic target in cancer. Semin. Cancer Biol., 14, 231-243 (2004).
32. Otaki, M., Hatano, M., Kobayashi, K., Ogasawara, T., Kuriyama, T., and Tokuhisa, T., Cell cycle-dependent regulation of TIAP/m-survivin expression. Biochim. Biophys. Acta, 1493, 188-194 (2000).
33. Roy, N., Deveraux, Q. L., Takahashi, R., Salvesen, G. S., and Reed, J. C., The c-IAP-1 and c-IAP-2 proteins are direct inhibitors of specific caspases. EMBO J., 16, 6914-6925 (1997).
34. Salvesen, G. S. and Dixit, V. M., Caspases: intracellular signaling by proteolysis. Cell, 91, 443-446 (1997).
35. Singh, R. P. and Agarwal, R., Mechanisms of action of novel agents for prostate cancer chemoprevention. Endocr. Relat. Cancer, 13, 751-778 (2006).
36. Stennicke, H. R., Ryan, C. A., and Salvesen, G. S., Reprieval from execution: the molecular basis of caspase inhibition. Trends Biochem. Sci., 27, 94-101 (2002).
37. Wang, J. L., Liu, D., Zhang, Z. J., Shan, S., Han, X., Srinivasula, S. M., Croce, C. M., Alnemri, E. S., and Huang, Z., Structure- based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. U. S. A., 97, 7124-7129 (2000).
38. Wen, X. H. and Xu, Y. H., Differentiation of K562 cells induced by antisense oligonucleotide targeting survivin. Zhonghua Er Ke Za Zhi, 43, 279-283 (2005).
39. Wrzesien-Kus, A., Smolewski, P., Sobczak-Pluta, A., Wierzbowska, A., and Robak, T., The inhibitor of apoptosis protein family and its antagonists in acute leukemias. Apoptosis, 9, 705-715 (2004).