Naphthalimides exhibit in vitro antiproliferative and antiangiogenic activities by inhibiting both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs)

European Journal of Medicinal Chemistry

Volumn 65, Issue , 2013, Pages 477-486

  Wang, Xin ^a   Chen, Zhuo ^a,b   Tong, Linjiang ^b   Tan, Shaoying ^a   Zhou, Wei ^a   Peng, Ting ^b   Han, Kun ^b   Ding, Jian ^b   Xie, Hua ^b   Xu, Yufang ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Angiogenesis; Multitarget; Naphthalimide; Topoisomerase II; Tyrosine kinase

Indexed keywords

DNA TOPOISOMERASE (ATP HYDROLYSING); FIBROBLAST GROWTH FACTOR RECEPTOR 1; NAPHTHALIMIDE DERIVATIVE; PLATELET DERIVED GROWTH FACTOR ALPHA RECEPTOR; TYROSINE KINASE RECEPTOR; VASCULOTROPIN RECEPTOR 2;

ANGIOGENESIS; ANTIANGIOGENIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MICROVASCULAR ENDOTHELIAL CELL; MIGRATION INHIBITION;

EID: 84884218592     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.05.002     Document Type: Article

References (39)

1. G.I. Giles, R.P. Sharma, Topoisomerase enzymes as therapeutic targets for cancer chemotherapy, Med. Chem. 1 (2005) 383-394.
2. J.A.W. Byl, S.D. Cline, T. Utsugi, T. Kobunai, Y. Yamada, N. Osheroff, DNA topoisomerase II as the target for the anticancer drug TOP-53: mechanistic basis for drug action, Biochemistry 40 (2001) 712-718. (Pubitemid 32096856)
3. K. Chikamori, A.G. Grozav, T. Kozuki, D. Grabowski, R. Ganapathi, M.K. Ganapathi, DNA topoisomerase II enzymes as molecular targets for cancer chemotherapy, Curr. Cancer Drug Targets 10 (2010) 758-771.
4. L.H. Hurley, DNA and its associated processes as targets for cancer therapy, Nat. Rev. Cancer 2 (2002) 188-200. (Pubitemid 37328788)
5. M.A. Lemmon, J. Schlessinger, Cell signaling by receptor tyrosine kinases, Cell 141 (2010) 1117-1134.
6. Z. Fu, L. Malureanu, J. Huang, W. Wang, H. Li, J.M. van Deursen, D.J. Tindall, J. Chen, Plk1-dependent phosphorylation of FoxM1 regulates a transcriptional programme required for mitotic progression, Nat. Cell. Biol. 10 (2008) 1076-1082.
7. K. Gotink, H. Verheul, Anti-angiogenic tyrosine kinase inhibitors: what is their mechanism of action? Angiogenesis 13 (2010) 1-14.
8. J. Drevs, M. Medinger, C. Schmidt-Gersbach, R. Weber, C. Unger, Receptor tyrosine kinases: the main targets for new anticancer therapy, Curr. Drug Targets 4 (2003) 113-121. (Pubitemid 36559490)
9. N. Ferrara, R.S. Kerbel, Angiogenesis as a therapeutic target, Nature 438 (2005) 967-974. (Pubitemid 43093963)
10. M. Tsanakopoulou, T. Cottin, A. Buttner, V. Sarli, E. Malamidou-Xenikaki, S. Spyroudis, A. Giannis, Indeno[1,2-d]pyrido[1,2-a]pyrimidines: a new class of receptor tyrosine kinase inhibitors, Chemmedchem 3 (2008) 429-433.
11. S.K. Jung, K.W. Lee, S. Byun, E.J. Lee, J.E. Kim, A.M. Bode, Z. Dong, H.J. Lee, Myricetin inhibits UVB-induced angiogenesis by regulating PI-3 kinase in vivo, Carcinogenesis 31 (2010) 911-917.
12. M. Presta, P. Dell'Era, S. Mitola, E. Moroni, R. Ronca, M. Rusnati, Fibroblast growth factor/fibroblast growth factor receptor system in angiogenesis, Cytokine Growth Factor Rev. 16 (2005) 159-178. (Pubitemid 40616114)
13. L.Q. Chow, S.G. Eckhardt, Sunitinib: from rational design to clinical efficacy, J. Clin. Oncol. 25 (2007) 884-896. (Pubitemid 350002890)
14. A. Gangjee, N. Zaware, S. Raghavan, M. Ihnat, S. Shenoy, R.L. Kisliuk, Single agents with designed combination chemotherapy potential: synthesis and evaluation of substituted pyrimido[4,5-b]indoles as receptor tyrosine kinase and thymidylate synthase inhibitors and as antitumor agents, J. Med. Chem. 53 (2010) 1563-1578.
15. Z.F. Tao, L. Wang, K.D. Stewart, Z. Chen, W. Gu, M.H. Bui, P. Merta, H. Zhang, P. Kovar, E. Johnson, C. Park, R. Judge, S. Rosenberg, T. Sowin, N.H. Lin, Structure-based design, synthesis, and biological evaluation of potent and selective macrocyclic checkpoint kinase 1 inhibitors, J. Med. Chem. 50 (2007) 1514-1527. (Pubitemid 46564373)
16. Z.W. Cai, Y. Zhang, R.M. Borzilleri, L. Qian, S. Barbosa, D. Wei, X. Zheng, L. Wu, J. Fan, Z. Shi, B.S. Wautlet, S. Mortillo, R. Jeyaseelan, D.W. Kukral, A. Kamath, P. Marathe, C. D'Arienzo, G. Derbin, J.C. Barrish, J.A. Robl, J.T. Hunt, L.J. Lombardo, J. Fargnoli, R.S. Bhide, Discovery of brivanib alaninate ((S)-((R)-1-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2, 1-f][1,2,4]triazin-6-yloxy)propan-2-yl)2-aminopropanoate), a novel prodrug of dual vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 kinase inhibitor (BMS-540215), J. Med. Chem. 51 (2008) 1976-1980. (Pubitemid 351438880)
17. J. Ma, D.J. Waxman, Combination of antiangiogenesis with chemotherapy for more effective cancer treatment, Mol. Cancer Ther. 7 (2008) 3670-3684.
18. A.A. Borisy, P.J. Elliott, N.W. Hurst, M.S. Lee, J. Lehar, E.R. Price, G. Serbedzija, G.R. Zimmermann, M.A. Foley, B.R. Stockwell, C.T. Keith, Systematic discovery of multicomponent therapeutics, Proc. Natl. Acad. Sci. U. S. A 100 (2003) 7977-7982. (Pubitemid 36760080)
19. M.F. Braña, A. Ramos, Naphthalimides as anticancer agents: synthesis and biological activity, Curr. Med. Chem. - Anti-cancer Agents 1 (2001) 237-255.
20. L. Ingrassia, F. Lefranc, R. Kiss, T. Mijatovic, Naphthalimides and azonafides as promising anti-cancer agents, Curr. Med. Chem. 16 (2009) 1192-1213.
21. T. Mijatovic, T. Mahieu, N. De Neve, J. Dewelle, G. Simon, M.J.M. Dehoux, E. van der Aar, B. Haibe-Kains, G. Bontempi, C. Deacestecker, E. Van Quaquebeke, F. Darro, R. Kiss, UNBS5162, a novel naphthalimide that decreases CXCL chemokine expression in experimental prostate cancers, Neoplasia 10 (2008) 573-586. (Pubitemid 351770301)
22. J.G. Kuhn, H.A. Burris, S.F. Jones, D.W. Hein, N.T. Willcutt, F.A. Greco, D.S. Thompson, A.A. Meluch, R.S. Schwartz, D.M. Brown, Phase I/II dose-escalation trial of amonafide for treatment of advanced solid tumors: genotyping to optimize dose based on polymorphic metabolism, J. Clin. Oncol. 25 (2007) 2503.
23. A. Wu, Y. Xu, X. Qian, J. Wang, J. Liu, Novel naphthalimide derivatives as potential apoptosis-inducing agents: design, synthesis and biological evaluation, Eur. J. Med. Chem. 44 (2009) 4674-4680.
24. M. Lv, H. Xu, Overview of naphthalimide analogs as anticancer agents, Curr. Med. Chem. 16 (2009) 4797-4813.
25. Z. Chen, X. Liang, H.Y. Zhang, H. Xie, J.W. Liu, Y.F. Xu, W.P. Zhu, Y. Wang, X. Wang, S.Y. Tan, D. Kuang, X.H. Qian, A new class of naphthalimide-based antitumor agents that inhibit topoisomerase II and induce lysosomal membrane permeabilization and apoptosis, J. Med. Chem. 53 (2010) 2589-2600.
26. N. Iranpoor, H. Firouzabadi, G. Aghapour, A.R. Vaezzadeh, Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions, Tetrahedron 58 (2002) 8689-8693.
27. M.F. Brana, M. Cacho, A. Gradillas, B. de Pascual-Teresa, A. Ramos, Intercalators as anticancer drugs, Curr. Pharm. Des. 7 (2001) 1745-1780. (Pubitemid 32998336)
28. H. Zhu, M. Huang, F. Yang, Y. Chen, Z.H. Miao, X.H. Qian, Y.F. Xu, Y.X. Qin, H.B. Luo, X. Shen, M.Y. Geng, Y.J. Cai, J. Ding, R16, a novel amonafide analogue, induces apoptosis and G(2)-M arrest via poisoning topoisomerase II, Mol. Cancer Ther. 6 (2007) 484-495. (Pubitemid 46332450)
29. K. Tanabe, Y. Ikegami, R. Ishida, T. Andoh, Inhibition of topoisomerase-II by antitumor agents bis(2,6-dioxopiperazine) derivatives, Cancer Res. 51 (1991) 4903-4908.
30. Z.Y. Tian, S.Q. Xie, Z.H. Mei, J. Zhao, W.Y. Gao, C.J. Wang, Conjugation of substituted naphthalimides to polyamines as cytotoxic agents targeting the Akt/mTOR signal pathway, Org. Biomol. Chem. 7 (2009) 4651-4660.
31. S.Q. Xie, Q. Li, Y.H. Zhang, J.H. Wang, J. Zhao, C.J. Wang, NNINspm, naphthalimide-polyamine conjugate, induces hepatoma HepG2 cell apoptosis via PI3K/Akt pathways, Chin. Pharm. Bull. 26 (2010) 169-174.
32. J. Marx, Angiogenesis: a boost for tumor starvation, Science 301 (2003) 452-454.
33. C.J. Powers, S.W. McLeskey, A. Wellstein, Fibroblast growth factors, their receptors and signaling, Endocr. Relat. Cancer 7 (2000) 165-197.
34. S. Tan, H. Yin, Z. Chen, X. Qian, Y. Xu, Oxo-heterocyclic fused naphthalimides as antitumor agents: synthesis and biological evaluation, Eur. J. Med. Chem. 62 (2013) 130-138.
35. J. Alsenz, M. Kansy, High throughput solubility measurement in drug discovery and development, Adv. Drug Delivery Rev. 59 (2007) 546-567. (Pubitemid 47285404)
36. L.J. Tong, H. Xie, T. Peng, X.F. Liu, X.L. Xin, X. Huang, S.M. Chen, H.Y. Liu, H.L. Li, M.Y. Geng, M. Yin, J. Ding, Establishment of platform for screening insulin-like growth factor-1 receptor inhibitors and evaluation of novel inhibitors, Acta Pharmacol Sin 32 (2011) 930-938.
37. K.L. Osusky, D.E. Hallahan, A. Fu, F. Ye, Y. Shyr, L. Geng, The receptor tyrosine kinase inhibitor SU11248 impedes endothelial cell migration, tubule formation, and blood vessel formation in vivo, but has little effect on existing tumor vessels, Angiogenesis 7 (2004) 225-233.
38. A. Kruczynski, M. Poli, R. Dossi, E. Chazottes, G. Berrichon, C. Ricome, R. Giavazzi, B.T. Hill, G. Taraboletti, Anti-angiogenic, vascular-disrupting and anti-metastatic activities of vinflunine, the latest vinca alkaloid in clinical development, Eur. J. Cancer 42 (2006) 2821-2832. (Pubitemid 44584664)
39. H. Xie, L. Lin, L. Tong, Y. Jiang, M. Zheng, Z. Chen, X. Jiang, X. Zhang, X. Ren, W. Qu, Y. Yang, H. Wan, Y. Chen, J. Zuo, H. Jiang, M. Geng, J. Ding, AST1306, a novel irreversible inhibitor of the epidermal growth factor receptor 1 and 2, exhibits antitumor activity both in vitro and in vivo, PLoS One 6 (2011) e21487.