B5, a novel pyrrole-substituted indolinone, exerts potent antitumor efficacy through G2/M cell cycle arrest

Investigational New Drugs

Volumn 28, Issue 1, 2010, Pages 26-34

  Xiong, Xishan ^a   Zhang, Yingwei ^b   Gao, Xiang ^b   Dong, Zheyi ^b   Li, Lin ^b   Ji, Chengcheng ^b   Fu, Lili ^b   Luo, Xiaomin ^c   Liu, Hong ^c   Mei, Changlin ^b  

^a BEIJING INSTITUTE OF MICROBIOLOGY AND EPIDEMIOLOGY   (China)

^b SECOND MILITARY MEDICAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Cdc2; Cell cycle arrest; Cyclin B1; Cyclin dependent kinase; Pyrrole substituted indolinone

Indexed keywords

4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; ANTINEOPLASTIC AGENT; B 5; CYCLIN B1; CYCLIN DEPENDENT KINASE; DNA; EPIDERMAL GROWTH FACTOR RECEPTOR; ETHYL 3,5 DIMETHYL 4 [(INDOLIN 2 ONE 3 YLIDENE)METHYL] 1H PYRROLE 2 CARBOXYLATE; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ASSAY; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; DRUG POTENCY; ENZYME INHIBITION; EPITHELIUM CELL; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IN VITRO STUDY; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; WESTERN BLOTTING;

ANTINEOPLASTIC AGENTS; BROMODEOXYURIDINE; CDC2 PROTEIN KINASE; CELL DEATH; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CYCLIN B1; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME-LINKED IMMUNOSORBENT ASSAY; G2 PHASE; HUMANS; IMIDAZOLES; INDOLES; MITOSIS; PYRROLES; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR;

EID: 74149090586     PISSN: 01676997     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10637-008-9211-7     Document Type: Article

References (27)

1. A Jemal R Siegel E Ward T Murray J Xu MJ Thun 2007 Cancer statistics, 2007 CA Cancer J Clin 57 43 66 10.3322/canjclin.57.1.43 17237035
2. JH Atkins LJ Gershell 2002 Selective anticancer drugs Nat Rev Drug Discov 1 491 492 10.1038/nrd842 1:CAS:528:DC%2BD38XkvFKlu78%3D 12120255
3. D Tsatas V Kanagasundaram A Kaye U Novak 2002 EGF receptor modifies cellular responses to hyaluronan in glioblastoma cell lines J Clin Neurosci 9 282 288 10.1054/jocn.2001.1063 1:CAS:528:DC%2BD38XntVCjt70%3D 12093135 (Pubitemid 34885566)
4. JE Dancey B Freidlin 2003 Targeting epidermal growth factor receptor-are we missing the mark? Lancet 362 62 64 10.1016/S0140-6736(03)13810-X 1:CAS:528:DC%2BD3sXltF2is7w%3D 12853203 (Pubitemid 36835824)
5. K Kiakos A Sato T Asao PJ McHugh M Lee JA Hartley 2007 DNA sequence selective adenine alkylation, mechanism of adduct repair, and in vivo antitumor activity of the novel achiral seco-amino-cyclopropylbenz[e]indolone analogue of duocarmycin AS-I-145 Mol Cancer Ther 6 2708 2718 10.1158/1535-7163.MCT-07-0294 1:CAS:528:DC%2BD2sXhtFKltbbE 17938264 (Pubitemid 350058151)
6. L Sun N Tran F Tang H App P Hirth G McMahon, et al. 1998 Synthesis and biological evaluations of 3-substituted indolin-2-ones: a novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases J Med Chem 41 2588 2603 10.1021/jm980123i 1:CAS:528: DyaK1cXkt12jtrw%3D 9651163 (Pubitemid 28321908)
7. BD Palmer S Trumpp-Kallmeyer DW Fry JM Nelson HD Showalter WA Denny 1997 Tyrosine kinase inhibitors. 11. Soluble analogues of pyrrolo- and pyrazoloquinazolines as epidermal growth factor receptor inhibitors: synthesis, biological evaluation, and modeling of the mode of binding J Med Chem 40 1519 1529 10.1021/jm960789h 1:CAS:528:DyaK2sXis1ahtb0%3D 9154973 (Pubitemid 27200767)
8. HH Li XH Zheng JZ Tan LL Chen H Liu XM Luo, et al. 2007 Design, synthesis, antitumor evaluations and molecular modeling studies of novel 3,5-substituted indolin-2-one derivatives Acta Pharmacol Sin 28 140 152 17184594
9. BK Banik M Cardona 2006 Bismuth nitrate-catalyzed novel synthesis of pyrrole-substituted indolinones Tetrahedron Lett 47 7385 7387 10.1016/j.tetlet.2006.07.150 1:CAS:528:DC%2BD28XptlCrsro%3D (Pubitemid 44331287)
10. B Qin H Ariyama E Baba R Tanaka H Kusaba M Harada, et al. 2006 Activated Src and Ras induce gefitinib resistance by activation of signaling pathways downstream of epidermal growth factor receptor in human gallbladder adenocarcinoma cells Cancer Chemother Pharmacol 58 577 584 10.1007/s00280-006- 0219-4 1:CAS:528:DC%2BD28Xns1Smsb4%3D 16532343 (Pubitemid 44167382)
11. H Ariyama B Qin E Baba R Tanaka K Mitsugi M Harada, et al. 2006 Gefitinib, a selective EGFR tyrosine kinase inhibitor, induces apoptosis through activation of Bax in human gallbladder adenocarcinoma cells J Cell Biochem 97 724 734 10.1002/jcb.20678 1:CAS:528:DC%2BD28Xis1CrsL4%3D 16229013
12. L Bonaccorsi S Marchiani M Muratori G Forti E Baldi 2004 Gefitinib ('IRESSA', ZD1839) inhibits EGF-induced invasion in prostate cancer cells by suppressing PI3 K/AKT activation J Cancer Res Clin Oncol 130 604 614 10.1007/s00432-004-0581-8 1:CAS:528:DC%2BD2cXns12nsbw%3D 15258753 (Pubitemid 39371330)
13. M Sassatelli E Debiton B Aboab M Prudhomme P Moreau 2006 Synthesis and antiproliferative activities of indolin-2-one derivatives bearing amino acid moieties Eur J Med Chem 41 709 716 10.1016/j.ejmech.2006.03.021 1:CAS:528:DC%2BD28XlvFygs7Y%3D 16675065 (Pubitemid 43866307)
14. M Mohammadi G McMahon L Sun C Tang P Hirth BK Yeh, et al. 1997 Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors Science 276 955 960 10.1126/science.276.5314.955 1:CAS:528:DyaK2sXjt1ans7w%3D 9139660 (Pubitemid 27209095)
15. L Sun N Tran C Liang F Tang A Rice R Schreck, et al. 1999 Design, synthesis, and evaluations of substituted 3-[(3- or 4-carboxyethylpyrrol-2-yl) methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases J Med Chem 42 5120 5130 10.1021/jm9904295 1:CAS:528: DyaK1MXnsFOmt70%3D 10602697 (Pubitemid 30020263)
16. L Sun N Tran C Liang S Hubbard F Tang K Lipson, et al. 2000 Identification of substituted 3-[(4,5,6, 7-tetrahydro-1H-indol-2-yl)methylene]- 1,3-dihydroindol-2-ones as growth factor receptor inhibitors for VEGF-R2 (Flk-1/KDR), FGF-R1, and PDGF-Rbeta tyrosine kinases J Med Chem 43 2655 2663 10.1021/jm9906116 1:CAS:528:DC%2BD3cXktFOgs7w%3D 10893303 (Pubitemid 30463914)
17. AW Murray 2004 Recycling the cell cycle: cyclins revisited Cell 116 221 234 10.1016/S0092-8674(03)01080-8 1:CAS:528:DC%2BD2cXhtValsrc%3D 14744433 (Pubitemid 38167314)
18. IH Chowdhury XF Wang NR Landau ML Robb VR Polonis DL Birx, et al. 2003 HIV-1 Vpr activates cell cycle inhibitor p21/Waf1/Cip1: a potential mechanism of G2/M cell cycle arrest Virology 305 371 377 10.1006/viro.2002.1777 1:CAS:528:DC%2BD3sXptlOruw%3D%3D 12573582 (Pubitemid 36259671)
19. LM Schang 2002 Cyclin-dependent kinases as cellular targets for antiviral drugs J Antimicrob Chemother 50 779 792 10.1093/jac/dkf227 1:CAS:528: DC%2BD38XptlOisb8%3D 12460995 (Pubitemid 36032796)
20. SV Ekholm SI Reed 2000 Regulation of G(1) cyclin-dependent kinases in the mammalian cell cycle Curr Opin Cell Biol 12 676 684 10.1016/S0955-0674(00) 00151-4 1:CAS:528:DC%2BD3cXovVagsL8%3D 11063931 (Pubitemid 30947601)
21. M Hengstschlager K Braun T Soucek A Miloloza E Hengstschlager-Ottnad 1999 Cyclin-dependent kinases at the G1-S transition of the mammalian cell cycle Mutat Res 436 1 9 10.1016/S1383-5742(98)00022-2 1:CAS:528:DyaK1cXotFWhurs%3D 9878675 (Pubitemid 29044044)
22. CY Chu RW Lim 2000 Involvement of p27(kip1) and cyclin D3 in the regulation of cdk2 activity during skeletal muscle differentiation Biochim Biophys Acta 1497 175 185 10.1016/S0167-4889(00)00064-1 1:CAS:528: DC%2BD3cXkvFSgurg%3D 10903422 (Pubitemid 30618829)
23. W Tong JW Pollard 1999 Progesterone inhibits estrogen-induced cyclin D1 and cdk4 nuclear translocation, cyclin E- and cyclin A-cdk2 kinase activation, and cell proliferation in uterine epithelial cells in mice Mol Cell Biol 19 2251 2264 1:CAS:528:DyaK1MXhsFCjsrw%3D 10022912
24. KJ Sweeney B Sarcevic RL Sutherland EA Musgrove 1997 Cyclin D2 activates Cdk2 in preference to Cdk4 in human breast epithelial cells Oncogene 14 1329 1340 10.1038/sj.onc.1200951 1:CAS:528:DyaK2sXit12jtbs%3D 9178893
25. AO Morla G Draetta D Beach JY Wang 1989 Reversible tyrosine phosphorylation of cdc2: dephosphorylation accompanies activation during entry into mitosis Cell 58 193 203 10.1016/0092-8674(89)90415-7 1:CAS:528: DyaL1MXltlWmt7Y%3D 2473839 (Pubitemid 19180091)
26. DJ Moshinsky CR Bellamacina DC Boisvert P Huang T Hui J Jancarik, et al. 2003 SU9516: biochemical analysis of cdk inhibition and crystal structure in complex with cdk2 Biochem Biophys Res Commun 310 1026 1031 10.1016/j.bbrc.2003. 09.114 1:CAS:528:DC%2BD3sXnvVyksr4%3D 14550307 (Pubitemid 37188725)
27. ME Lane B Yu A Rice KE Lipson C Liang L Sun, et al. 2001 A novel cdk2-selective inhibitor, SU9516, induces apoptosis in colon carcinoma cells Cancer Res 61 6170 6177 1:CAS:528:DC%2BD3MXmt12ktb0%3D 11507069