Novel arylsulfoanilide-oxindole hybrid as an anticancer agent that inhibits translation initiation

Journal of Medicinal Chemistry

Volumn 47, Issue 21, 2004, Pages 4979-4982

  Natarajan, Amarnath ^a   Guo, Yuhong ^a   Harbinski, Frederick ^a   Fan, Yun Hua ^a   Chen, Han ^a   Luus, Lia ^a   Diercks, Jana ^a   Aktas, Huseyin ^a   Chorev, Michael ^a   Halperin, Jose A ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE; ANTINEOPLASTIC AGENT; INITIATION FACTOR 2; OXINDOLE; SULFOANILIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM CELL LEVEL; CALCIUM DEPLETION; CANCER INHIBITION; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENCY; HUMAN; HUMAN CELL; LUNG CANCER; PHOSPHORYLATION; PROSTATE CANCER; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; TRANSLATION INITIATION;

ANILINE COMPOUNDS; ANIMALS; ANTINEOPLASTIC AGENTS; CALCIUM; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; MICE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 4744344334     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0496234     Document Type: Article

References (25)

1. Clemens, M. J.; Bommer, U. A. Translational control: the cancer connection. Int. J. Biochem. Cell Biol. 1999, 31, 1-23.
2. De Benedetti, A.; Harris, A. L. eIF4E expression in tumors: its possible role in progression of malignancies. Int. J. Biochem. Cell Biol. 1999, 31, 59-72.
3. Willis, A. E. Translational control of growth factor and proto-oncogene expression. Int. J. Biochem. Cell Biol. 1999, 31, 73-86.
4. Meric, F.; Hunt, K. K. Translation initiation in cancer: a novel target for therapy. Mol. Cancer Ther. 2002, 1, 971-979.
5. Pain, V. M. Initiation of protein synthesis in eukaryotic cells. Eur. J. Biochem. 1998, 236, 747-771.
6. Brostrom, C. O.; Brostrom, M. A. Regulation of translational initiation during cellular responses to stress. Prog. Nucleic Acid Res. Mol. Biol. 1998, 58, 79-125.
7. Sudhakar, A.; Ramachandran, A.; Ghosh, S.; Hasnain, S. E.; Kaufman, R. J.; Ramaiah, K. V. Phosphorylation of serine 51 in initiation factor 2 α (eIF2 α) promotes complex formation between eIF2 α(P) and eIF2B and causes inhibition in the guanine nucleotide exchange activity of eIF2B. Biochemistry 2000, 39, 12929-12938.
8. Clemens, M. J. Initiation factor eIF2 alpha phosphorylation in stress responses and apoptosis. Prog. Mol. Subcell. Biol. 2001, 27, 57-89.
9. Benzaquen, L. R.; Brugnara, C.; Byers, H. R.; Gatton-Celli, S.; Halperin, J. A. Clotrimazole inhibits cell proliferation in vitro and in vivo. Nat. Med. 1995, 1, 534-540.
10. Palakurthi, S. S.; Fluckiger, R.; Aktas, H.; Changolkar, A. K.; Shahsafaei, A.; Halperin, J. A. Inhibition of translation initiation mediates the anticancer effect of the n-3 polyunsaturated fatty acid eicosapentaenoic acid. Cancer Res. 2000, 60, 2919-2925.
11. Palakurthi, S. S.; Aktas, H.; Grubissich, L. M.; Mortensen, R. M.; Halperin, J. A. Anticancer effects of thiazolidinediones are independent of peroxisome proliferator-activated receptor gamma and mediated by inhibition of translation initiation. Cancer Res. 2001, 61, 6213-6218.
12. 2+ stores, phosphorylation of eIF2alpha, and sustained inhibition of translation initiation mediate the anticancer effects of clotrimazole. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 8280-8285.
13. Brostrom, C. O.; Chin, K. V.; Wong, W. L.; Cade, C.; Brostrom, M. A. Inhibition of translational initiation in eukaryotic cells by calcium ionophore. J. Biol. Chem. 1989, 264, 1644-1649.
14. Natarajan, A.; Fan, Y. H.; Chen, H.; Guo, Y.; Iyasere, J.; Harbinski, F.; Christ, W. J.; Aktas, H.; Halperin, J. A. 3,3-Diaryl-1,3-dihydromdol-2-ones as antiproliferatives mediated by translation initiation inhibition. J. Med. Chem. 2004, 47, 1882-1885.
15. Fan, Y. H.; Chen, H.; Natarajan, A.; Guo, Y.; Harbinski, F.; Iyasere, J.; Christ, W. J.; Aktas, H.; Halperin, J. A. Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium. Bioorg. Med. Chem. Lett. 2004, 14, 2547-2550.
16. Casini, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Sulfonamides and sulfonylated derivatives as anticancer agents. Curr. Cancer Drug Targets 2002, 2, 55-75.
17. Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. T. Anticancer and antiviral sulfonamides. Curr. Med. Chem. 2003, 10, 925-953.
18. Owa, T.; Yoshino, H.; Okauchi, T.; Yoshimatsu, K.; Ozawa, Y.; Sugi, N. H.; Nagasu, T.; Koyanagi, N.; Kitoh, K. Discovery of novel antitumor sulfonamides targeting G1 phase of the cell cycle. J. Med. Chem. 1999, 42, 3789-3799.
19. Dittrich, C.; Dumez, H.; Calvert, H.; Hanauske, A.; Faber, M.; Wanders, J.; Yule, M.; Ravic, M.; Fumoleau, P. Phase I and pharmacokinetic study of E7070, a chloroindolyl-sulfonamide anticancer agent, administered on a weekly schedule to patients with solid tumors. Clin. Cancer Res. 2003, 9, 5195-5204.
20. Abbate, F.; Casini, A.; Owa, T.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg. Med. Chem. Lett. 2004, 14, 217-223.
21. Hewawasam, P.; Gribkoff, V. K.; Pendri, Y.; Dworetzky, S. I.; Meanwell, N. A.; Martinez, E.; Boissard, C. G.; Post-Munson, D. J.; Trojnacki, J. T. Yeleswaram, K.; Pajor, L. M.; Knipe, J.; Gao, Q.; Perrone, R.; Starrett, J. E., Jr. The synthesis and characterization of BMS-204352 (MaxiPost) and related 3-fluorooxindoles as openers of maxi-K potassium channels. Bioorg. Med. Chem. Lett. 2002, 12, 1023-1026.
22. Caddick, S.; Wilden, J. D.; Judd, D. B. Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids. J. Am. Chem. Soc. 2004, 126, 1024-1025.
23. 2+ influx. Two independently regulated mechanisms of influx stimulation coexist in neuro-secretory PC12 cells. J. Biol. Chem. 1992, 267, 2164-2172.
24. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Jenney, S.; Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
25. Aktas, H.; Cai, H.; Cooper, G. M. Ras links growth factor signaling to the cell cycle machinery via regulation of cyclin D1 and the Cdk inhibitor p27KIP1. Mol. Cell Biol. 1997, 17, 3850-3857.