Double blockade of cell cycle at G1-S transition and M phase by 3-iodoacetamido benzoyl ethyl ester, a new type of tubulin ligand

Cancer Research

Volumn 62, Issue 21, 2002, Pages 6080-6088

  Jiang, Jian Dong ^a,d   Denner, Larry ^b   Ling, Yi He ^c   Li, Jian Nong ^d   Davis, Ashley ^e   Wang, Yue ^a   Li, Yan ^a   Roboz, Julia ^a   Wang, Long Gui ^a   Perez Soler, Roman ^c   Marcelli, Marco ^f   Bekesi, George ^a   Holland, James F ^a  

^a MOUNT SINAI SCHOOL OF MEDICINE   (United States)

^b TEXAS BIOTECHNOLOGY CORPORATION   (United States)

^c ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^d INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

^e Cytoskeleton Inc   (United States)

^f BAYLOR COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 IODOACETAMIDOBENZOYL ETHYL ESTER; CASPASE 3; CASPASE 6; CASPASE 8; CASPASE 9; CYCLIN DEPENDENT KINASE 2; CYCLIN DEPENDENT KINASE INHIBITOR; CYCLIN E; DNA FRAGMENT; IODOACETAMIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PHYTOHEMAGGLUTININ; PROTEIN BCL 2; PROTEIN P53; RETINOBLASTOMA PROTEIN; TUBULIN; UNCLASSIFIED DRUG; VINCRISTINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE; CELL CYCLE G1 PHASE; CELL CYCLE S PHASE; CONTROLLED STUDY; DEPHOSPHORYLATION; DNA DEGRADATION; DRUG PROTEIN BINDING; ENZYME ACTIVITY; GROWTH INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA; LIVER CELL CARCINOMA; LYMPHOMA; MICROTUBULE ASSEMBLY; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; PROTEIN INTERACTION; PROTEIN PHOSPHORYLATION; SIGNAL TRANSDUCTION; SOLID TUMOR;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARCINOMA, HEPATOCELLULAR; CELL CYCLE; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IODOACETAMIDE; LIGANDS; LIVER NEOPLASMS; MALE; MICE; MICE, NUDE; MICROTUBULES; PHOSPHORYLATION; PROTO-ONCOGENE PROTEINS C-BCL-2; TUBULIN; TUMOR CELLS, CULTURED; TUMOR SUPPRESSOR PROTEIN P53; U937 CELLS; VINCRISTINE; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 0036828201     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. Wilson, L., and Jordan, M. A. Microtubule dynamics: Taking aim at a moving target. Chem. Biol., 2: 569-573, 1995.
2. Hyams, J. S., and Lloyd, C. W. Microtubules. New York: Wiley-Liss, Inc., 1994.
3. Alberts, B., Bray, D., Lewis, J., Raff, M., Roberts, K., and Watson, J. D. The cytoskeleton. In. B. Alberts, D. Bray, J. Lewis, M. Raff, K. Roberts, and J. D. Watson (eds.). Molecular Biology of the Cell, pp. 787-861. New York: Garland Publishing. Inc., 1994.
4. Rowinsky, E. K., and Donehower, R. C. The clinical pharmacology and use of antimicrotubule agents in cancer chemotherapeutics. Pharmacol. Ther., 52: 35-84, 1991.
5. Jordan, M. A., and Wilson, L. Microtubules and actin filaments: Dynamic targets for cancer chemotherapy. Curr. Opin. Cell Biol., 10: 123-130, 1998.
6. Donehower, R. C., and Rowinsky, E. K. An overview of experience with Taxol (paclitaxel) in the U. S. A. Cancer Treat. Rev., 19 (Suppl. C): 63-78, 1993.
7. Nakajima, O., Sugishita, T., Hashimoto, Y., and Iwasaki, S. Increase in the chemically induced differentiation of human leukemia cell lines by tubulin disrupters. Biol. Pharm. Bull., 17: 742-744, 1994.
8. Li, Y. M., and Broome, J. D. Arsenic targets tubulins to induce apoptosis in myeloid leukemia cells. Cancer Res., 59: 776-780, 1999.
9. Li, W., and Chou, I. N. Effects of sodium arsenic on the cytoskeleton and cellular glutathione levels in cultured cells. Toxicol. Appl. Pharmacol., 114: 132-139, 1992.
10. Jiang, J. D., Davis, A. S., Middleton, K., Ling, Y. H., Perez-Soler, R., Holland, I. 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.
11. Jiang, J. D., Roboz, J., Weisz, I., Deng, L., Holland, J. F., and Bekesi, J. G. Synthesis cancericidal and antimicrotubule activities of 3-(haloacetamido) -benzoylureas. AntiCancer Drug Des., 13: 735-747, 1998.
12. Jiang, J. D., Wang, Y., Roboz, J., Strauchen, J., Holland, J. F., and Bekesi, J. G. Inhibition of microtubule assembly in tumor cells by 3-bromoacetylamino benzoylurea a new cancericidal compound. Cancer Res., 58: 2126-2133, 1998.
13. Roboz, J., Jiang, J. D., Holland, J. F., and Bekesi, J. G. Selective tumor apoptosis by MF13, L-prolyl-L-m-[bis(chloroethyl)amino]-phenylalanyl-L-norvaline ethyl ester, a new sarcolysin containing tripeptide. Cancer Res., 57: 4795-4802, 1997.
14. Boyd, M. R. The NCl in vitro anticancer drug discovery screen. In: B. Teicher (ed.), Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials, and Approval, pp. 23-42. Totowa, NJ: Humana Press, Inc., 1997.
15. Monks, A., Scudiero, D. A., Skehan, P., Shoemaker, R. H., Paull, K., Vistica, D., Hose, C., Langley, J., Cronise, P., Vaigro-Wolff, A., Gray-Goodrich, M., Cambell, H., and Boyd, M. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. (Bethesda), 83: 757-766, 1991.
16. Rubinstein, L. V., Shoemaker, R. H., Paull, K. D., Simon, R. M., Tonisi, S., Skehan, P., Scudiero, D. A., Monks, A. and Boyd, M. R. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J. Natl. Cancer Inst. (Bethesda), 82: 1113-1118, 1990.
17. Ogawa, T., Mimura, Y., Isowa, K., Kato, H., Mitsuishi, M., Toyoshi, T., Kuwayama, N., Morimoto, H., Murakoshi, M., Nakayama, T. An antimicrotubule agent, TZT-1027, does not induce neuropathologic alterations which are detected after administration of vincristine or paclitaxel in animal models. Toxicol. Lett., 121: 97-106, 2001.
18. Dolan, M. E., Fleig, M. J., Feuerstein, B. G., Basu, H. S., Luk, G. D., Casero, R. A., Jr., and Marton, L. J. Effect of 1, 19-bis(ethylamino)-5, 10, 15 -triazanonadecane on human tumor xenografts. Cancer Res., 54: 4698-4702, 1994.
19. Yagi, M. J., and Bekesi, J. G. Evaluation ofp-F-Phe-m-bis-(2-chloroethyl) amino-L-Phe-Met-ethoxy HCl against transplantable and spontaneous murine neoplasia. Cancer Chemother. Pharmacol., 26: 215-220, 1990.
20. Legault, J., Gaulin, J. F., Mounetou, E., Bolduc, S., Lacroix, J., Poyet, P., and C.-Gaudreault R. Microtubule disruption induced in vivo by alkylation of β-tubulin by 1-aryl-3-(2-chloroethyl)urea, a novel class of soft alkylating agents. Cancer Res., 60: 985-992, 2000.
21. Sun, H. D., Ma, L., Hu, X. C., and Zhang, T. D. Treatment of acute promyelocytic leukemia by Aliling-1 therapy with use of syndrome differentiation of traditional -Chinese medicine. Chin. J. Comb. Trad. Chin. Med. West Med., 12: 170-171, 1992.
22. 3) in the treatment of acute promyelocytic leukemia (APL). II. Clinical efficacy and pharmacokinetics in relapsed patients. Blood, 89: 3354-3360, 1997.
23. Soignet, S. L., Maslak, P., Wang, Z. G., Jhanwar, S., Calleja, E., Dardashti, L. J., Corso, D., DeBlasio, A., Gabrilove, J., Scheinberg, D. A., Pandolfi, P. P., and Warrell, R. P. Jr. Complete remission after treatment of acute promyelocytic leukemia with arsenic trioxide. N. Engl. J. Med., 339: 1341-1348, 1998.
24. Park, W. H., Seol, J. G., Kim, E. S., Hyun, J. M., Jung, C. W., Lee, C. C., Kim, B. K., and Lee, Y. Y. Arsenic trioxide-mediated growth inhibition in MC/CAR myeloma cells via cell cycle arrest in association with induction of cyclin-dependent kinase inhibitor, p21, and apoptosis. Cancer Res., 60: 3065-3071, 2000.
25. Zhang, W., Ohnishi, K., Shigeno, K., Fujisawa, S., Naito, K., Nakamura, S., Takeshita, K., Takeshita, A., and Ohna. R. The induction of apoptosis and cell cycle arrest by arsenic trioxide in lymphoid neoplasms. Leukemia (Baltimore), 12: 1383-1391, 1998.
26. Bernier-Valentin, F., Aunis, D., and Rousset, B. Evidence for tubulin binding sites on cellular membrane: Plasma membranes, mitochondrial membranes, and secretory, granule membranes. J. Cell Biol., 97: 209-216, 1983.
27. Leterrier, J. F., Rusakov, D. A., Nelson, B. D., and Linden, M. Interactions between brain mitochondria and cytoskeleton: Evidence for specialized outer membrane domains involved in the association of cytoskeleton-associated proteins to mitochondria in situ and in vitro. Microsc. Res. Tech., 27: 233-261, 1994.
28. Shan, B., Medina, J, C., Santha, E., Frankmoelle, W. P., Chou, T. C., Learned, R. M., Marbut, M. R., Stott, D., Wu, P., Jaen, J. C., Rosen, T., Timmermans, P. B., and Beckmann, H. Selective, covalent modification of β-tubulin residue Cys-239 by T138067, and antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc. Natl. Acad. Sci. USA, 96: 5686-5691, 1999.
29. Nurse, P. Ordering S and M phases in the cell cycle. Cell, 79: 547-550, 1994.
30. Hatta, Y., and Koeffler, H. P. Role of tumor suppressor genes in the development of adult T cell leukemia/lymphoma (ATLL). Leukemia (Baltimore), 16: 1069-1085, 2002.
31. 1 checkpoint is required for E2F-induced S-phase entry. Nat. Genet., 31: 190-194, 2002.
32. Brown, V. D., Phillips, R. A. and Gallie, B. L. Cumulative effect of phosphorylation of pRb on regulation of E2F activity. Mol. Cell. Biol., 19: 3246-3256, 1999.
33. Alberts, B., Bray, D., Lewis, J., Raff, M., Roberts, K., and Watson, J. D. The cell division cycle. In: B. Alberts, D. Bray, J. Lewis, M. Raff, K. Roberts, and J. D. Watson (eds.), Molecular Biology of the Cell, pp. 863-910. New York: Garland Publishing Inc., 1994.
34. Lin, Y. H., Consoli, U., Tornos, C., Andreeff, M., and Perez-Soler, R. Accumulation of cyclin B1, activation of cyclin B1-dependent kinase and induction of programmed cell death in human epidermoid carcinoma KB cells treated with Taxol. Int. J. Cancer., 75: 925-932, 1998.
35. Schafer, K. A. The cell cycle: A review. Vet. Pathol., 35: 461-478, 1998.
36. Blagosklonny, M. V., Giannakakou, P., el-Deiry, W. S., Kingston, D. G., Higgs, P. I. Neckers, L., and Fojo, T. Raf-1/bcl-2 phosphorylation: A step from microtubule damage to cell death. Cancer Res., 57: 130-135, 1997.
37. Haldar, S., Chintapalli, J., and Croce, C. M. Taxol induced bcl-2 phosphorylation and death of prostate cancer cells. Cancer Res., 56: 1253-1255, 1996.
38. Kroemer, G. The proto-oncogene Bcl-2 and its role in regulating apoptosis. Nat. Med., 3: 614-620, 1997.
39. Susin, S. A., Lorenzo, H. K., Zamzami, N., Marzo, I., Snow, B., Brothers, G. M., Mangion, J., Jacotot, E., Costantini, P., Loeffler, M., Larochette, N., Goodlett, D. R., Aebersold, R., Siderovski, D. P., Penninger, J. M., and Kroemer, G. Molecular characterization of mitochondrial apoptosis-inducing factor. Nature (Lond.), 397: 441-446, 1999.
40. Green, D. R., and Reed, J. C. Mitochondria and apoptosis. Science (Wash. DC), 281: 1309-1312, 1998.
41. Muzio, M., Chinnaiyan, A. M., Kischkel, F. C., O’Rourke, K., Shevchenoko, A., Ni, J., Scaffidi, C., Bretz, J. D., Zhang, M., Gentz, R., Mann, M., Krammer, P. H., Peter, M. E., and Dixit, V. M. FLICE, a novel FADD-homologous ICE/CED-3-like protease, is recruited to the CD95 (Fas/APO-1) death inducing signaling complex. Cell, 85: 817-827, 1996.
42. Sun, X. M., MacFarlane, M., Zhuang, J. G., Wolf, B. B., Green, D. R., and Cohen, G. M. Distinct caspase cascades are initiated in receptor-mediated and chemical-induced apoptosis. J. Biol. Chem., 274: 5053-5060, 1999.
43. Martin, D. S., Bertino, J. R., and Koutcher, J. A. ATP depletion + pyrimidine depletion can markedly enhance cancer therapy: Fresh insight for a new approach. Cancer Res., 60: 6776-6783, 2000.
44. Ando, N., Nakajima, T., Masuda, H., Kawabata, Y., Iwai, M., Watanabe, M., Kagitani, Y., Yamada, N. and Tsukagoshi, S. Antimicrotubule effects of the novel antitumor benzoylphenylurea derivative HO-221. Cancer Chemother. Pharmacol., 37: 63-69, 1995.
45. Lobert, S., Vulevic, B., and Correia, J. J. Interaction of Vinca alkaloids with tubulin: A comparison of vinblastine, vincristine and vinorelbine. Biochemistry, 35: 6806-6814, 1996.