N-(2,6-dimethoxypyridine-3-yl)-9-methylcarbazole-3-sulfonamide as a novel tubulin ligand against human cancer

Clinical Cancer Research

Volumn 14, Issue 19, 2008, Pages 6218-6227

  Wang, Yue Ming ^a   Hu, Lai Xing ^a,c   Liu, Zhen Ming ^b   You, Xue Fu ^a   Zhang, Sheng Hua ^a   Qu, Jing Rong ^d   Li, Zhuo Rong ^a   Li, Yan ^d   Kong, Wei Jia ^a   He, Hong Wei ^a   Shao, Rong Guang ^a   Zhang, Liang Ren ^d   Peng, Zong Gen ^a   Boykin, David W ^c   Jiang, Jian Dong ^a  

^a INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^c GEORGIA STATE UNIVERSITY   (United States)

^d MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE; COLCHICINE; DOXORUBICIN; GLYCOPROTEIN P; IG 105; N (2,6 DIMETHOXYPIRIDINE 3 YL) 9 METHYLCARBAZOLE 3 SULFONAMIDE; OXALIPLATIN; PROTEIN BCL 2; SULFONAMIDE; TUBULIN; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CARBAZOLE DERIVATIVE; LIGAND; N (2,6 DIMETHOXYPYRIDINE 3 YL) 9 METHYLCARBAZOLE 3 SULFONAMIDE; N-(2,6-DIMETHOXYPYRIDINE-3-YL)-9-METHYLCARBAZOLE-3-SULFONAMIDE; TUBULIN MODULATOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BODY REGIONS; BREAST CANCER; CANCER GROWTH; CELL CYCLE ARREST; CELL CYCLE M PHASE; CONTROLLED STUDY; DRUG BINDING; DRUG MECHANISM; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; IC 50; LEUKEMIA; LIVER CELL CARCINOMA; MICROTUBULE ASSEMBLY; MONOTHERAPY; MOUSE; NONHUMAN; PRIORITY JOURNAL; SOLID TUMOR; TUMOR CLASSIFICATION; ANIMAL; CANCER TRANSPLANTATION; CHEMISTRY; DRUG SCREENING; FEMALE; HUMAN; METABOLISM; MICROTUBULE; NEOPLASM; NUDE MOUSE; PATHOLOGY; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CARBAZOLES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; INHIBITORY CONCENTRATION 50; LIGANDS; MICE; MICE, NUDE; MICROTUBULES; NEOPLASM TRANSPLANTATION; NEOPLASMS; P-GLYCOPROTEIN; SULFONAMIDES; TUBULIN; TUBULIN MODULATORS;

EID: 58149163334     PISSN: 10780432     EISSN: None     Source Type: Journal    
DOI: 10.1158/1078-0432.CCR-08-0550     Document Type: Article

References (46)

1. Jordan MA, Wilson L. Microtubules as a target for anticancer drugs. Nat Rev Cancer 2004;4:253-65.
2. Desai A, Mitchison TJ. Microtubule polymerization dynamics. Annu Rev Cell Dev Biol 1997;13:83-117.
3. Brangwynne CP, MacKintosh FC, Weitz DA. Force fluctuations and polymerization dynamics of intracellular microtubules. Proc Natl Acad Sci U S A 2007;104:16128-33.
4. Howard J, Hyman AA. Dynamics and mechanics of the microtubule plus end. Nature 2003;422:753-8.
5. Rusan NM, Fagerstrom CJ, Yvon AM, Wadsworth P. Cell cycle-dependent changes in microtubule dynamics in living cells expressing green fluorescent protein-α tubulin. Mol Biol Cell 2001;12:971-80.
6. Jordan MA, Thrower D, Wilson L. Mechanism of inhibition of cell proliferation by Vinca alkaloids. Cancer Res 1991;51:2212-22.
7. Yvon AM, Wadsworth P, Jordan MA. Taxol suppresses dynamics of individual microtubules in living human tumor cells. Mol Biol Cell 1999;10:947-59.
8. Wilson L, Panda D, Jordan MA. Modulation of microtubule dynamics by drugs: a paradigm for the actions of cellular regulators. Cell Struct Funct 1999;24:329-35.
9. Bhalla KN. Microtubule-targeted anticancer agents and apoptosis. Oncogene 2003;22:9075-86.
10. Jackson JR, Patrick DR, Dar MM, Huang PS. Targeted anti-mitotic therapies: can we improve on tubulin agents? Nat Rev Cancer 2007;7:107-17.
11. Mollinedo F, Gajate C. Microtubules, microtubule-interfering agents and apoptosis. Apoptosis 2003;8:413-50.
12. Openshaw H, Beamon K, Synold TW, et al. Neurophysiological study of peripheral neuropathy after high-dose paclitaxel: lack of neuroprotective effect of amifostine. Clin Cancer Res 2004;10:461-7.
13. Schmidt M, Bastians H. Mitotic drug targets and the development of novel anti-mitotic anticancer drugs. Drug Resist Updat 2007;10:162-81.
14. Tao W, South VJ, Zhang Y, et al. Induction of apoptosis by an inhibitor of the mitotic kinesin KSP requires both activation of the spindle assembly checkpoint and mitotic slippage. Cancer Cell 2005;8:49-59.
15. Lee JJ, Low JA, Croarkin E, et al. Changes in neurologic function tests may predict neurotoxicity caused by ixabepilone. J Clin Oncol 2006;24:2084-91.
16. Sampath D, Greenberger LM, Beyer C, et al. Preclinical pharmacologic evaluation of MST-997, an orally active taxane with superior in vitro and in vivo efficacy in paclitaxel- and docetaxel-resistant tumor models. Clin Cancer Res 2006;12:3459-69.
17. Dumontet C, Sikic BI. Mechanisms of action of and resistance to antitubulin agents: microtubule dynamics, drug transport, and cell death. J Clin Oncol 1999;17:1061-70.
18. Gururaja TL, Goff D, Kinoshita T, et al. R-253 disrupts microtubule networks in multiple tumor cell lines. Clin Cancer Res 2006;12:3831-42.
19. Giannakakou P, Sackett D, Fojo T. Tubulin/microtubules: still a promising target for new chemotherapeutic agents. J Natl Cancer Inst 2000;92:182-3.
20. Hu L, Li ZR, Wang YM, Wu Y, Jiang JD, Boykin DW. Novel pyridinyl and pyrimidinylcarbazole sulfonamides as antiproliferative agents. Bioorg Med Chem Lett 2007;17:1193-6.
21. Rubinstein LV, Shoemaker RH, Paull KD, et al. 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 1990;82:1113-8.
22. Jiang JD, Wang Y, Roboz J, Strauchen J, Holland JF, Bekesi JG. Inhibition of microtubule assembly in tumor cells by 3-bromoacetylamino benzoylurea, a new cancericidal compound. Cancer Res 1998;58:2126-33.
23. Ravelli RB, Gigant B, Curmi PA, et al. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature 2004;428:198-202.
24. Morris GM, Goodsell DS, Halliday RS, et al. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998;19:1639-62.
25. 1-S transition and M phase by 3-iodoacetamido benzoyl ethyl ester, a new type of tubulin ligand. Cancer Res 2002;62:6080-8.
26. Huang YH, Shang BY, Zhen YS. Antitumor efficacy of lidamycin on hepatoma and active moiety of its molecule. World J Gastroenterol 2005;11:3980-4.
27. Nurse P. Universal control mechanism regulating onset of M-phase. Nature 1990;344:503-8.
28. Mooberry SL, Weiderhold KN, Dakshanamurthy S, et al. Identification and characterization of a new tubulin-binding tetrasubstituted brominated pyrrole. Mol Pharmacol 2007;72:132-40.
29. Tishler RB, Lamppu DM, Park S, Price BD. Microtubule-active drugs Taxol, vinblastine, and nocodazole increase the levels of transcriptionally active p53. Cancer Res 1995;55:6021-5.
30. Kops GJ, Weaver BA, Cleveland DW. On the road to cancer: aneuploidy and the mitotic checkpoint. Nat Rev Cancer 2005;5:773-85.
31. Chang DC, Xu N, Luo KQ. Degradation of cyclin Bis requiredf or the onset of anaphase in mammalian cells. J Biol Chem 2003;278:37865-73.
32. Wasch R, Engelbert D. Anaphase-promoting complex-dependent proteolysis of cell cycle regulators and genomic instability of cancer cells. Oncogene 2005;24:1-10.
33. Weaver BA, Cleveland DW. Decoding the links between mitosis, cancer, andc hemotherapy: the mitotic checkpoint, adaptation, and cell death. Cancer Cell 2005;8:7-12.
34. Cory S, Adams JM. Killing cancer cells by flipping the Bcl-2/Bax switch. Cancer Cell 2005;8:5-6.
35. Green DR, Kroemer G. The pathophysiology of mitochondrial cell death. Science 2004;305:626-9.
36. Fan M, Du L, Stone AA, Gilbert KM, Chambers TC. Modulation of mitogen-activated protein kinases and phosphorylation of Bcl-2 by vinblastine represent persistent forms of normal fluctuations at G2-1. Cancer Res 2000;60:6403-7.
37. 2-terminal kinase and inhibited by the mitogen-activated protein kinase extracellular signal-regulated kinase 1/2 pathway. Clin Cancer Res 2007;13:1308-14.
38. Haldar S, Chintapalli J, Croce CM. Taxol induces bcl-2 phosphorylation and death of prostate cancer cells. Cancer Res 1996;56:1253-5.
39. Danial NN, Korsmeyer SJ. Cell death: critical control points. Cell 2004;116:205-19.
40. Kroemer G, Martin SJ. Caspase-independent cell death. Nat Med 2005;11:725-30.
41. Sun XM, MacFarlane M, Zhuang J, Wolf BB, Green DR, Cohen GM. Distinct caspase cascades are initiated in receptor-mediated and chemical-induced apoptosis. J Biol Chem1999;274:5053-60.
42. Basu A, Castle VP, Bouziane M, Bhalla K, Haldar S. Crosstalk between extrinsic andi ntrinsic cell death pathways in pancreatic cancer: synergistic action of estrogen metabolite and ligands of death receptor family. Cancer Res 2006;66:4309-18.
43. Vogel C, Kienitz A, Hofmann I, Muller R, Bastians H. Crosstalk of the mitotic spindle assembly checkpoint with p53 to prevent polyploidy. Oncogene 2004;23:6845-53.
44. Perfettini JL, Kroemer RT, Kroemer G. Fatal liaisons of p53 with Bax and Bak. Nat Cell Biol 2004;6:386-8.
45. 2 arrest instead of mitotic arrest: molecular determinants of paclitaxel-induced cytotoxicity. Oncogene 2001;20:3806-13.
46. Li JN, Song DQ, Lin YH, et al. Inhibition of microtubule polymerization by 3-bromopropionylamino benzoylurea (JIMB01), a new cancericidal tubulin ligand. Biochem Pharmacol 2003;65:1691-9.