Apoptosis induced by 2-acetyl-3-(6-methoxybenzothiazo)-2-yl-amino-acrylonitrile in human leukemia cells involves ROS-mitochondrial mediated death signaling and activation of p38 MAPK

Cancer Letters

Volumn 277, Issue 1, 2009, Pages 55-63

  Repicky, A ^a   Jantova, S ^a   Cipak, L ^b  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b CANCER RESEARCH INSTITUTE   (Slovakia)

Author keywords

Apoptosis; Benzothiazole derivative; Leukemia; p38 MAPK; Reactive oxygen species

Indexed keywords

2 ACETYL 3 (6 METHOXYBENZOTHIAZO) 2 YLAMINOACRYLONITRILE; ACRYLONITRILE; CASPASE 3; CASPASE 9; CYTOCHROME C; MITOGEN ACTIVATED PROTEIN KINASE P38; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL STRAIN HL 60; CELL STRAIN U937; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG MECHANISM; ENZYME ACTIVATION; HUMAN; HUMAN CELL; LEUKEMIA CELL; MITOCHONDRIAL MEMBRANE POTENTIAL; PRIORITY JOURNAL; SIGNAL TRANSDUCTION;

ACRYLONITRILE; ANTINEOPLASTIC AGENTS; APOPTOSIS; BENZOTHIAZOLES; CASPASES; DOSE-RESPONSE RELATIONSHIP, DRUG; HL-60 CELLS; HUMANS; MITOCHONDRIA; P38 MITOGEN-ACTIVATED PROTEIN KINASES; REACTIVE OXYGEN SPECIES; U937 CELLS;

EID: 61849154200     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.canlet.2008.11.026     Document Type: Article

References (26)

1. Ballell L., Field R.A., Duncan K., and Young R.J. New small-molecule synthetic antimycobacterials. Antimicrobial Agents and Chemotherapy 49 (2005) 2153-2163
2. Delmas F., Avellaneda A., Di Giorgio C., Robin M., De Clercq E., Timon-David P., and Galy J.P. Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives. European Journal of Medicinal Chemistry 39 (2004) 685-690
3. Russo F., Romeo G., Santagati N.A., Caruso A., Cutuli V., and Amore D. Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties. European Journal of Medicinal Chemistry 29 (1994) 569-578
4. Holcombe R.F., McLaren C.E., and Milovanovic T. Immunomodulation with low dose levamisole in patients with colonic polyps. Cancer Detection and Prevention 30 (2006) 94-98
5. Labiche L.A., and Grotta J.C. Clinical trials for cytoprotection in stroke. Neurotherapeutics 1 (2004) 46-70
6. Choi M.M., Kim E.A., Hahn H.G., Nam K.D., Yang S.J., Choi S.Y., Kim T.U., Cho S.W., and Huh J.W. Protective effect of benzothiazole derivative KHG21834 on amyloid β-induced neurotoxicity in PC12 cells and cortical and mesencephalic neurons. Toxicology 239 (2007) 156-166
7. Trapani G., Franco M., Latrofa A., Reho A., and Liso G. Synthesis, in vitro and in vivo cytotoxicity and prediction of the intestinal absorption of substituted 2-ethoxycarbonyl-imidazol[2,1-b]benzothiazoles. European Journal of Pharmaceutical Sciences 14 (2001) 209-216
8. Hutchinson I., Bradshaw T.D., Matthews C.S., Stevens M.F., and Westwell A.D. Antitumor benzothiazoles. Part 20: 3′-cyano and 3′-alkynyl-substituted 2-(4′-aminophenyl)benzothiazoles as new potent and selective analogues. Bioorganic and Medicinal Chemistry Letters 13 (2003) 471-474
9. Yoshida M., Hayakawa I., Hayashi N., Agatsuma T., Oda Y., Tanzawa F., Iwasaki S., Koyama K., Furukawa H., Kurakata S., and Sugano Y. Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents. Bioorganic and Medicinal Chemistry Letters 15 (2005) 3328-3332
10. Sharma P., and Ghoshal N. Exploration of a binding mode of benzothiazol-2-yl acetonitrile pyrimidine core based derivatives as potent c-Jun N-terminal kinase-3 inhibitors and 3D-QSAR analyses. Journal of Chemical Information and Modeling 46 (2006) 1736-1774
11. Kamal A., Khan M.N., Reddy K.S., Srikanth Y.V., and Sridhar B. Synthesis, structural characterization and biological evaluation of novel [1, 2, 4]triazolo[1, 5-b][1, 2, 4]benzothiadiazine-benzothiazole conjugates as potent anticancer agents. Chemical Biology and Drug Design 71 (2008) 78-86
12. Prasad K.K., Toraskar M.P., and Kadam V.J. N-myristoyltransferase: a novel target. Mini Reviews in Medicinal Chemistry 8 (2008) 142-149
13. Pinar A., Yurdakul P., Yildiz I., Temiz-Arpaci O., Acan N.L., Aki-Sener E., and Yalcin I. Some fused heterocyclic compounds as eukaryotic topoisomerase II inhibitors. Biochemical and Biophysical Research Communications 317 (2004) 670-674
14. Yates P.C. Semi-empirical molecular orbital calculations on tyrosine kinase inhibitors and structurally related compounds. Journal of Molecular Structure: Theochem 231 (1991) 201-213
15. Guédat P., and Colland F. Patented small molecule inhibitors in the ubiquitin proteasome system. BMC Biochemistry 8 (2007) S14
16. Davies K.P., Zahner H., and Köhler P. Litomosoides carinii: mode of action in vitro of benzothiazole and amoscanate derivatives with antifilarial activity. Experimental Parasitology 68 (1989) 382-391
17. Trapani V., Patel V., Leong C.O., Ciolino H.P., Yeh G.C., Hose C., Trepel J.B., Stevens M.F.G., Sausville E.A., and Loaiza-Pérez A.I. DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells. British Journal of Cancer 88 (2003) 599-605
18. Bradshaw T.D., and Westwell A.D. The development of the antitumour benzothiazole prodrug, Phortress, as a clinical candidate. Current Medicinal Chemistry 11 (2004) 1009-1021
19. Stojkovic R., Karminski-Zamola G., Racane L., Tralic-Kulenovic V., Glavas-Obrovac L., Ivankovic S., and Radacic M. Antitumor efficiency of novel fluoro-substituted 6-amino-2-phenylbenzothiazole hydrochloride salts. In Vitro and In Vivo Methods and Findings in Experimental and Clinical Pharmacology 28 (2006) 347-354
20. Cernuchova P., Vo-Thanh G., Milata V., Loupy A., Jantova S., and Theiszova M. Utilization of 2-ethoxymethylene-3-oxobutanenitrile in the synthesis of heterocycles possessing biological activity. Tetrahedron 61 (2005) 5379-5387
21. Lowry O.H., Rosebrough N.J., Farr A.L., and Randal R.J. Protein measurement with the Folin phenol reagent. The Journal Biological Chemistry 143 (1951) 265-275
22. Zhu X., Yu Q.S., Cutler R.G., Culmsee C.W., Holloway H.W., Lahiri D.K., Mattson M.P., and Greig N.H. Novel p53 inactivators with neuroprotective action: syntheses and pharmacological evaluation of 2-amino-2,3,4,5,6,7-hexahydrobenzothiazole and 2-imino-2,3,4,5,6,7-hexahydrobenzoxazole derivatives. Journal of Medicinal Chemistry 45 (2002) 5090-5097
23. Pietrancosta N., Moumen A., Dono R., Lingor P., Planchamp V., Lamballe F., Bahr M., Kraus J.L., and Maina F. Imino-tetrahydro-benzothiazole derivatives as p53 inhibitors: discovery of a highly potent in vivo inhibitor and its action mechanism. Journal of Medicinal Chemistry 49 (2006) 3645-3652
24. Kurata S. Selective activation of p38 MAPK cascade and mitotic arrest caused by low level oxidative stress. The Journal of Biological Chemistry 31 (2000) 23413-23416
25. Park S.J., and Kim I.S. The role of p38 MAPK activation in auranofin-induced apoptosis of human promyelocytic leukaemia HL-60 cells. British Journal of Pharmacology 146 (2005) 506-513
26. Kondoh M., Tasaki E., Araragi S., Takiguchi M., Higashimoto M., Watanabe Y., and Sato M. Requirement of caspase and p38 MAPK activation in zinc-induced apoptosis in human leukemia HL-60 cells. European Journal of Biochemistry 269 (2002) 6204-6211