4-Amino-5-benzoyl-2-(4-methoxyphenylamino)thiazole (DAT1): A cytotoxic agent towards cancer cells and a probe for tubulin-microtubule system

British Journal of Pharmacology

Volumn 145, Issue 8, 2005, Pages 1076-1083

  Sengupta, Suparna ^a   Smitha, Sasidharan L ^a   Thomas, Nisha E ^a   Santhoshkumar, Thankaiyyan R ^a   Devi, Satyabhama K C ^b   Sreejalekshmi, Kumaran G ^b   Rajasekharan, Kallikat N ^b  

^a RAJIV GANDHI CENTRE FOR BIOTECHNOLOGY   (India)

^b UNIVERSITY OF KERALA   (India)

Author keywords

Antimitotic agent; Cytotoxicity; Diaminoketothiazole; Microtubules; Tubulin

Indexed keywords

4 AMINO 5 BENZOYL 2(4 METHOXYPHENYLAMINO)THIAZOLE; ANILINE DERIVATIVE; ANTIMITOTIC AGENT; COLCHICINE; THIAZOLE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CELL CYCLE ARREST; CHROMOSOME; CONTROLLED STUDY; CYTOTOXICITY; DISSOCIATION CONSTANT; DRUG MECHANISM; DRUG PROTEIN BINDING; HUMAN; HUMAN CELL; MICROTUBULE; MITOSIS; MITOSIS SPINDLE; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; BINDING SITES; BRAIN; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICROTUBULES; MITOTIC INDEX; PROTEIN BINDING; TRIAZOLES; TUBULIN;

EID: 30544450012     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1038/sj.bjp.0706276     Document Type: Article

References (40)

1. ANDREU, J.M. & TIMASHEFF, S.N. (1982). Conformational states of tubulin liganded to colchicine, tropolone methyl ether, and podophyllotoxin. Biochemistry, 21, 6465-6476.
2. BACUS, S.S., GUDKOV, A.V., LOWE, M., LYASS, L., YUNG, Y., KOMAROV, A.P., KEYOMARSI, K., YARDEN, Y. & SEGER, R. (2001). Taxol-induced apoptosis depends on MAP kinase pathways (ERK and p38) and is independent of p53. Oncogens, 20, 147-155.
3. BANERJEE, A.C. & BHATTACHARYYA, B. (1979). Colcemid and colchicine binding to tubulin. Similarity and dissimilarity. FEBS Lett., 99, 333-336.
4. BECKERS, T., REISSMANN, T., SCHMIDT, M., BURGER, A.M., FIEBIG, H.H., VANHOEFER, U., PONGRATZ, H., HUFSKY, H., HOCKEMEYER, J., FRIESER, M. & MAHBOOBI, S. (2002). 2-Aroylindoles, a novel class of potent, orally active small molecule tubulin inhibitors. Cancer Res., 62, 3113-3119.
5. BEER, T.M., EL-GENEIDI, M. & EILERS, K.M. (2003). Docetaxel (taxotere) in the treatment of prostate cancer. Expert Rev. Anticancer Ther., 3, 261-268.
6. BHATTACHARYYA, B. & WOLFF, J. (1974). Promotion of fluorescence upon binding of colchicine to tubulin. Proc. Natl. Acad. Sci. U.S.A., 71, 2627-2631.
7. BHATTACHARYYA, B. & WOLFF, J. (1984). Immobilization-dependent fluorescence of colchicine. J. Biol. Chem., 259, 11836-11843.
8. BINU, R., THOMAS, K.K., JENARDANAN, G.C. & RAJASEKHARAN, K.N. (1998). Synthesis and cyclization of 1-(N-nitroamidino) thioureas to 2,4-diaminothiazoles. Org. Prep. Proced. Int., 30, 93-96.
9. BOWLER, A.N., OLESEN, P.H., SORENSEN, A.R., HANSEN, B.F., WORSAAE, H. & KURTZHALS, P. (2001). Use of 2,4-diaminothiazole derivatives. U.S. Patent Application, 20010039275.
10. BRADFORD, M.M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72, 248-254.
11. BUOLAMWINI, J.K. (2000). Cell cycle molecular targets in novel anticancer drug discovery. Curr. Pharm. Des., 6, 379-392.
12. CANTOR, C.R. & SCHIMMEL, P.R. (1980). Biophysical Chemistry, Part 3, Chapter 15, pp. 849-866. New York: WH Freeman and Co.
13. CHU, S.S., ALEGRIA, L.A., BENDER, S.L., BENEDICT, S.P., BORCHARDT, A.J., KANIA, R.S., NAMBU, M.D., TEMPCZYK-RUSSELL, A.M., SARSHAR, S., BHUMRALKAR, D., PENG, Z. & YANG, M. (2003). Thiazole compounds and pharmaceutical compositions for inhibiting protein kinases and methods for their use. US Patent, 6, 620,828.
14. CIRLA, A. & MANN, J. (2003). Combretastatins: from natural products to drug discovery. Nat. Prod. Rep., 20, 558-564.
15. COONEY, M.M., RADIVOYEVITCH, T., DOWLATI, A., OVERMOYER, B., LEVITAN, N., ROBERTSON, K., LEVINE, S.L., DECARO, K., BUCHTER, C., TAYLOR, A., STAMBLER, B.S. & REMICK, S.C. (2004). Cardiovascular safety profile of combretastatin A4 phosphate in a single-dose phase I study in patients with advanced cancer. Clin. Cancer Res., 10, 96-100.
16. CORTESE, F., BHATTACHARYYA, B. & WOLFF, J. (1977). Podophyllotoxin as a probe for the colchicine binding site of tubulin. J. Biol. Chem., 252, 1134-1140.
17. DETRICH III, H.W., WILLIAMS JR., R.C., MACDONALD, T.L., WILSON, L. & PUETT, D. (1981). Changes in the circular dichroic spectrum of colchicine associated with its binding to tubulin. Biochemistry, 20, 5999-6005.
18. DING, S., CHAMBERLAIN, M., MCLAREN, A., GOH, L., DUNCAN, I. & WOLF, C.R. (2001). Cross-talk between signalling pathways and the multidrug resistant protein MDR-1. Br. J. Cancer, 85, 1175-1184.
19. DUFLOS, A., KRUCZYNSKI, A. & BARRET, J.M. (2002). Novel aspects of natural and modified vinca alkaloids. Curr. Med. Chem. AntiCancer Agents, 2, 55-70.
20. GARLAND, D.L. (1978). Kinetics and mechanism of colchicine binding to tubulin: evidence for ligand-induced conformational change. Biochemistry, 17, 4266-4272.
21. GAUTAM, A. & KOSHKINA, N. (2003). Paclitaxel (taxol) and taxoid derivates for lung cancer treatment: potential for aerosol delivery. Curr. Cancer Drug Targets, 3, 287-296.
22. GUPTA, S. & BHATTACHARYYA, B. (2003). Antimicrotubular drugs binding to vinca domain of tubulin. Mol. Cell. Biochem., 253, 41-47.
23. HADFIELD, J.A., DUCKI, S., HIRST, N. & MCGOWN, A.T. (2003). Tubulin and microtubules as targets for anticancer drugs. Prog. Cell Cycle Res., 5, 309-325.
24. HAMEL, E., DEL CAMPO, A.A., LOWE, M.C. & LIN, CM. (1981). Interactions of taxol, microtubule-associated proteins, and guanine nucleotides in tubulin polymerization. J. Biol. Chem., 256, 11887-11894.
25. HANSEN, C.H. & BRÜNNER, N. (1994). Cell Biology, Part 1, pp. 16-18. New York: Academic Press.
26. HELBECQUE, N., MOQUIN, C., BERNIER, J.L., MOREL, E., GUYOT, M. & HENICHART, J.P. (1987). Grossularine-1 and grossularine-2, alpha carbolines from Dendrodoa grossularia, as possible intercalative agents. Cancer Biochem. Biophys., 9, 271-279.
27. HOLWELL, S.E., COOPER, P.A., THOMPSON, M.J., PETTIT, G. R., LIPPERT III, L.W., MARTIN, S.W. & BIBBY, M.C. (2002). Anti-tumor and anti-vascular effects of the novel tubulin-binding agent combretastatin A-1 phosphate. Anticancer Res., 22, 3933-3940.
28. HU, L., HOFMANN, J., LU, Y., MILLS, G.B. & JAFFE, R.B. (2002). Inhibition of phosphatidylinositol 3′-kinase increases efficacy of paclitaxel in in vitro and in vivo ovarian cancer models. Cancer Res., 62, 1087-1092.
29. HUANG, S.C. & LEE, T.C. (1998). Arsenite inhibits mitotic division and perturbs spindle dynamics in HeLa S3 cells. Carcinogenesis, 19, 889-896.
30. JIMENEZ-BARBERO, J., AMAT-GUERRI, F. & SNYDER, J.P. (2002). The solid state, solution and tubulin-bound conformations of agents that promote microtubule stabilization. Curr. Med. Chem. Anti-Cancer Agents, 2, 91-122.
31. JORDAN, A., HADFIELD, J.A., LAWRENCE, N.J. & MCGOWN, A.T. (1998). Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle. Med. Res. Rev., 18, 259-296.
32. JORDAN, M.A., THROWER, D. & WILSON, L. (1992). Effects of vinblastine, podophyllotoxin and nocodazole on mitotic spindles. Implications for the role of microtubule dynamics in mitosis. J. Cell Sci., 102, 401-416.
33. JORDAN, M.A. & WILSON, L. (2004). Microtubules as a target for anticancer drugs. Nat. Rev. Cancer, 4, 253-265.
34. LI, Q., SHAM, H.L. & ROSENBERG, S.H. (1999). Antimitotic Agents, in Annual Reports in Medicinal Chemistry, Chapter 14, pp. 139-148.
35. RAJASEKHARAN, K.N., NAIR, K.P. & JENARDANAN, G.C. (1986). Studies on the synthesis of 5-acyl-2,4-diaminothiazoles from amidinothioureas. Synthesis, 5, 353-355.
36. ROWINSKY, E.K. (1997). The development and clinical utility of the taxane class of antimicrotubule chemotherapy agents. Annu. Rev. Med., 48, 353-374.
37. SHINGU, T., YAMADA, K., HARA, N., MORITAKE, K., OSAGO, H., TERASHIMA, M., UEMURA, T., YAMASAKI, T. & TSUCHIYA, M. (2003). Synergistic augmentation of antimicrotubule agent-induced cytotoxicity by a phosphoinositide 3-kinase inhibitor in human malignant glioma cells. Cancer Res., 63, 4044-4047.
38. SLOBADA, R.D. & ROSENBAUM, J.L. (1982). Purification and assay of microtubule-associated proteins (MAPs). Methods Enzymol., 85, 409-415.
39. WILSON, L., PANDA, D. & JORDAN, M.A. (1999). Modulation of microtubule dynamics by drugs: a paradigm for the actions of cellular regulators. Cell Struct. Funct., 24, 329-335.
40. YOSHIMATSU, K., YAMAGUCHI, A., YOSHINO, H., KOYANAGI, N. & KITOH, K. (1997). Mechanism of action of E7010, an orally active sulfonamide antitumor agent: inhibition of mitosis by binding to the colchicine site of tubulin. Cancer Res., 57, 3208-3213.