Synthesis and biological evaluation of novel tetrahydro-β-carboline derivatives as antitumor growth and metastasis agents through inhibiting the transforming growth factor-β signaling pathway

Journal of Medicinal Chemistry

Volumn 57, Issue 3, 2014, Pages 600-612

  Zheng, Cong ^a   Fang, Yuanzhang ^a   Tong, Weiguang ^a   Li, Guoliang ^a   Wu, Haigang ^a   Zhou, Wenbo ^a   Lin, Qingxiang ^a   Yang, Feifei ^a   Yang, Zhengfeng ^a   Wang, Peng ^a   Peng, Yangrui ^a   Pang, Xiufeng ^a   Yi, Zhengfang ^a   Luo, Jian ^a   Liu, Mingyao ^a,b   Chen, Yihua ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMALS; ANTINEOPLASTIC AGENTS; CARBOLINES; CELL LINE, TUMOR; CELL MOVEMENT; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; LUNG NEOPLASMS; MAMMARY NEOPLASMS, EXPERIMENTAL; MICE; MICE, INBRED BALB C; MICE, NUDE; MOLECULAR DOCKING SIMULATION; NEOPLASM METASTASIS; NEOPLASM TRANSPLANTATION; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFORMING GROWTH FACTOR BETA;

EID: 84894086704     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401117t     Document Type: Article

References (37)

1. Siegel, R.; Naishadham, D.; Jemal, A. Cancer statistics, 2013 Ca-Cancer J. Clin. 2013, 63, 11-30
2. Siegel, R.; Naishadham, D.; Jemal, A. Cancer statistics, 2012 Ca-Cancer J. Clin. 2012, 62, 10-29
3. Chen, L.; Yang, S.; Jakoncic, J.; Zhang, J. J.; Huang, X. Y. Migrastatin analogues target fascin to block tumour metastasis Nature 2010, 464, 1062-1066
4. Mehlen, P.; Puisieux, A. Metastasis: a question of life or death Nat. Rev. Cancer 2006, 6, 449-458
5. Levy, L.; Hill, C. S. Alterations in components of the TGF-beta superfamily signaling pathways in human cancer Cytokine Growth Factor Rev. 2006, 17, 41-58
6. Miyazono, K.; Kusanagi, K.; Inoue, H. Divergence and convergence of TGF-beta/BMP signaling J. Cell Physiol. 2001, 187, 265-276
7. Leask, A.; Abraham, D. J. TGF-beta signaling and the fibrotic response FASEB J. 2004, 18, 816-827
8. Agrotis, A.; Kalinina, N.; Bobik, A. Transforming growth factor-beta, cell signaling and cardiovascular disorders Curr. Vasc. Pharmacol. 2005, 3, 55-61
9. Bierie, B.; Moses, H. L. Tumour microenvironment: TGFbeta: the molecular Jekyll and Hyde of cancer Nat. Rev. Cancer 2006, 6, 506-520
10. Eichhorn, P. J.; Rodon, L.; Gonzalez-Junca, A.; Dirac, A.; Gili, M.; Martinez-Saez, E.; Aura, C.; Barba, I.; Peg, V.; Prat, A.; Cuartas, I.; Jimenez, J.; Garcia-Dorado, D.; Sahuquillo, J.; Bernards, R.; Baselga, J.; Seoane, J. USP15 stabilizes TGF-beta receptor I and promotes oncogenesis through the activation of TGF-beta signaling in glioblastoma Nat. Med. 2012, 18, 429-435
11. Li, H. Y.; McMillen, W. T.; Heap, C. R.; McCann, D. J.; Yan, L.; Campbell, R. M.; Mundla, S. R.; King, C. H.; Dierks, E. A.; Anderson, B. D.; Britt, K. S.; Huss, K. L.; Voss, M. D.; Wang, Y.; Clawson, D. K.; Yingling, J. M.; Sawyer, J. S. Optimization of a dihydropyrrolopyrazole series of transforming growth factor-beta type I receptor kinase domain inhibitors: Discovery of an orally bioavailable transforming growth factor-beta receptor type I inhibitor as antitumor agent J. Med. Chem. 2008, 51, 2302-2306
12. Nagaraj, N. S.; Datta, P. K. Targeting the transforming growth factor-beta signaling pathway in human cancer Expert Opin. Investig. Drugs 2010, 19, 77-91
13. Schade, D.; Lanier, M.; Willems, E.; Okolotowicz, K.; Bushway, P.; Wahlquist, C.; Gilley, C.; Mercola, M.; Cashman, J. R. Synthesis and SAR of b-annulated 1,4-dihydropyridines define cardiomyogenic compounds as novel inhibitors of TGFbeta signaling J. Med. Chem. 2012, 55, 9946-9957
14. Shimizu, T.; Kimura, K.; Sakai, T.; Kawakami, K.; Miyazaki, T.; Nakouji, M.; Ogawa, A.; Ohuchi, H.; Shimizu, K. Synthesis and evaluation of [2-(4-quinolyloxy)phenyl]methanone derivatives: Novel selective inhibitors of transforming growth factor-beta kinase J. Med. Chem. 2008, 51, 3326-3329
15. Goldberg, F. W.; Ward, R. A.; Powell, S. J.; Debreczeni, J. E.; Norman, R. A.; Roberts, N. J.; Dishington, A. P.; Gingell, H. J.; Wickson, K. F.; Roberts, A. L. Rapid generation of a high quality lead for transforming growth factor-beta (TGF-beta) type I receptor (ALK5) J. Med. Chem. 2009, 52, 7901-7905
16. Kim, D. K.; Jang, Y.; Lee, H. S.; Park, H. J.; Yoo, J. Synthesis and biological evaluation of 4(5)-(6-alkylpyridin-2-yl)imidazoles as transforming growth factor-beta type 1 receptor kinase inhibitors J. Med. Chem. 2007, 50, 3143-3147
17. Akhurst, R. J.; Hata, A. Targeting the TGFbeta signalling pathway in disease Nat. Rev. Drug Discovery 2012, 11, 790-811
18. Wang, G.; Jia, S.; Wang, T.; Chen, L.; Song, Q.; Li, W. Effect of ferrous ion on epsilon-poly-L-lysine biosynthesis by Streptomyces diastatochromogenes CGMCC3145 Curr. Microbiol. 2011, 62, 1062-1067
19. Uhl, M.; Aulwurm, S.; Wischhusen, J.; Weiler, M.; Ma, J. Y.; Almirez, R.; Mangadu, R.; Liu, Y. W.; Platten, M.; Herrlinger, U.; Murphy, A.; Wong, D. H.; Wick, W.; Higgins, L. S.; Weller, M. SD-208, a novel transforming growth factor beta receptor I kinase inhibitor, inhibits growth and invasiveness and enhances immunogenicity of murine and human glioma cells in vitro and in vivo Cancer Res. 2004, 64, 7954-7961
20. Saunier, E. F.; Akhurst, R. J. TGF beta inhibition for cancer therapy Curr. Cancer Drug Targets 2006, 6, 565-578
21. Hjelmeland, M. D.; Hjelmeland, A. B.; Sathornsumetee, S.; Reese, E. D.; Herbstreith, M. H.; Laping, N. J.; Friedman, H. S.; Bigner, D. D.; Wang, X. F.; Rich, J. N. SB-431542, a small molecule transforming growth factor-beta-receptor antagonist, inhibits human glioma cell line proliferation and motility Mol. Cancer Ther. 2004, 3, 737-745
22. de Gouville, A. C.; Boullay, V.; Krysa, G.; Pilot, J.; Brusq, J. M.; Loriolle, F.; Gauthier, J. M.; Papworth, S. A.; Laroze, A.; Gellibert, F.; Huet, S. Inhibition of TGF-beta signaling by an ALK5 inhibitor protects rats from dimethylnitrosamine-induced liver fibrosis Br. J. Pharmacol. 2005, 145, 166-177
23. Suzuki, E.; Kim, S.; Cheung, H. K.; Corbley, M. J.; Zhang, X.; Sun, L.; Shan, F.; Singh, J.; Lee, W. C.; Albelda, S. M.; Ling, L. E. A novel small-molecule inhibitor of transforming growth factor beta type I receptor kinase (SM16) inhibits murine mesothelioma tumor growth in vivo and prevents tumor recurrence after surgical resection Cancer Res. 2007, 67, 2351-2359
24. Yingling, J. M.; Blanchard, K. L.; Sawyer, J. S. Development of TGF-beta signalling inhibitors for cancer therapy Nat. Rev. Drug Discovery 2004, 3, 1011-1022
25. Roth, G. J.; Heckel, A.; Brandl, T.; Grauert, M.; Hoerer, S.; Kley, J. T.; Schnapp, G.; Baum, P.; Mennerich, D.; Schnapp, A.; Park, J. E. Design, synthesis, and evaluation of indolinones as inhibitors of the transforming growth factor beta receptor I (TGFbetaRI) J. Med. Chem. 2010, 53, 7287-7295
26. Fang, Y.; Chen, Y.; Yu, L.; Zheng, C.; Qi, Y.; Li, Z.; Yang, Z.; Zhang, Y.; Shi, T.; Luo, J.; Liu, M. Inhibition of breast cancer metastases by a novel inhibitor of TGFbeta receptor 1 J. Natl. Cancer Inst. 2013, 105, 47-58
27. Wu, T. Y.; Schultz, P. G. A versatile linkage strategy for solid-phase synthesis of N, N -dimethyltryptamines and β-carbolines Org. Lett. 2002, 4, 4033-4036
28. Luis, S. V.; Burguete, M. I. The Fischer indole synthesis of 8-methyl-5-substituted-1-oxo- β -carbolines: A remarkable high yield of a [1,2]-methyl migration Tetrahedron 1991, 47, 1737-1744
29. Lehmann, J.; Pohl, U. Indoles. VI. Lactamization of 4,9-dihydropyrano[3, 4-b]indol-1(3H)-ones with methylamine. A new synthetic route to strychnocarpine and its derivatives Arch. Pharm. (Weinheim, Ger.) 1988, 321, 411-414
30. Liu, J.; Jiang, X.; Zhao, M.; Zhang, X.; Zheng, M.; Peng, L.; Peng, S. A class of 3 S -2-aminoacyltetrahydro-β-carboline-3-carboxylic acids: Their facile synthesis, inhibition for platelet activation, and high in vivo antithrombotic potency J. Med. Chem. 2010, 53, 3106-3116
31. Yachida, S.; Jones, S.; Bozic, I.; Antal, T.; Leary, R.; Fu, B.; Kamiyama, M.; Hruban, R. H.; Eshleman, J. R.; Nowak, M. A.; Velculescu, V. E.; Kinzler, K. W.; Vogelstein, B.; Iacobuzio-Donahue, C. A. Distant metastasis occurs late during the genetic evolution of pancreatic cancer Nature 2010, 467, 1114-1117
32. Wells, A.; Grahovac, J.; Wheeler, S.; Ma, B.; Lauffenburger, D. Targeting tumor cell motility as a strategy against invasion and metastasis Trends Pharmacol. Sci. 2013, 34, 283-289
33. Palmer, T. D.; Ashby, W. J.; Lewis, J. D.; Zijlstra, A. Targeting tumor cell motility to prevent metastasis Adv. Drug Delivery Rev. 2011, 63, 568-581
34. Alex, A.; Natalia, K.; Alex, B. Transforming Growth Factor-beta, Cell Signaling and Cardiovascular Disorders Curr. Vasc. Pharmacol. 2005, 3, 55-61
35. Luo, J.; Zhou, W.; Zhou, X.; Li, D.; Weng, J.; Yi, Z.; Cho, S. G.; Li, C.; Yi, T.; Wu, X.; Li, X. Y.; de Crombrugghe, B.; Höök, M.; Liu, M. Regulation of bone formation and remodeling by G-protein-coupled receptor 48 Development 2009, 136, 2747-2756
36. Fiser, A.; Do, R. K.; Sali, A. Modeling of loops in protein structures Protein Sci. 2000, 9, 1753-1773
37. Ogunjimi, A. A.; Zeqiraj, E.; Ceccarelli, D. F.; Sicheri, F.; Wrana, J. L.; David, L. Structural basis for specificity of TGF β family receptor small molecule inhibitors Cell. Signal. 2011, 24, 476-483