A novel synthesis method of apogossypolone and its antitumor activity

Letters in Drug Design and Discovery

Volumn 6, Issue 2, 2009, Pages 129-132

  Zhan, Yonghua ^a   Jia, Guangfeng ^a  

^a XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

Apogossypolone; Gossypol; In vitro growth inhibition; Proteins; Synthesis

Indexed keywords

APOGOSSYPOLONE; GOSSYPOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CANCER INHIBITION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROSTATE CANCER; STRUCTURE ANALYSIS;

EID: 61949231424     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018009787582589     Document Type: Article

References (23)

1. Xu, L.; Yang, D.J.; Wang, S.M.; Tang, W.H.; Coleska, Z.N.; Liu, H.P.; Wu, X.H.; Ji, M.; Chen, J.Y.; Ling, Y.; Tomita, Y.; Lippman, M.E. Improved anti-tumor efficacy of chemotherapy by (-)-gossypol, a potent small molecule inhibitor of anti-apoptotic protein Bcl-XL. Clin. Cancer Res., 2003, 9(16 Suppl), 6155S-55S.
2. (a) Saleh, M.; Pitot, H.; Hartung, J.; Holmlund, J.; Albert LoBuglio, A.Forero. A. Phase I trial of AT-101, an orally bioavailable inhibitor of Bcl-2, in patients with advanced malignancies. Presented at the 2005 AACR-NCI-EORTC international conference on molecular targets and cancer therapeutics: Discovery, biology, and clinical applications, November 14-18, 2005, Philadelphia, Pennsylvania, Abstract C89;
3. (b) Wang, S.; Yang, D. Small molecule antagonists of Bcl-2 family proteins. U.S. 20030008924, 2002.
4. Xu , L.; Yang , D.J.; Wang, S.M.; Tang, W.H.; Liu, M.L.; Davis, M.; Chen, J.Y.; Rae, J.M.; Lawrence, T.; Lippman, M.E. (-)-gossypol enhances response to radiation therapy and results in tumor regression of human prostate cancer. Mol. Cancer Ther., 2005, 4(2), 197-205.
5. (a) Adams, J.M.; Cory, S. The Bcl-2 protein family: Arbiters of cell survival. Science, 1998, 281, 1322-26;
6. (b) Reed, J.C. Bcl-2 family proteins: Strategies for overcoming chemoresistance in cancer. Adv. Pharmacol., 1997, 41, 501-53;
7. (c) Chao, D.T.; Korsmeyer, S.J. Bcl-2 family: Regulators of cell death. Annu. Rev. Immunol., 1998, 16, 395-19;
8. (d) Minn, A.J.; Swain, R.E.; Ma A.; Thompson, C.B. Recent progress on the regulation of apoptosis by Bcl-2 family members. AdV. Immunol., 1998, 70, 245-79;
9. (e) Sattler, M.; Liang, H.; Nettesheim, D.; Meadows, R.P.; Harlan, J.E.; Eberstadt, M.; Yoon, H.S.; Shuker, S.B.; Chang, B.S.; Minn, A.J.; Thompson, C.B.; Fesik, S.W. Structure of Bcl-xL-Bak peptide complex: Recognition between regulators of apoptosis. Science, 1997, 275, 983-86;
10. (f) Wang, J.L.; Liu, D.; Zhang, Z.J.; Shan, S.; Han, X.; Srinivasula, S.M.; Croce, C.M.; Alnemri, E.S.; Huang, Z. Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. USA, 2000, 97, 7124-29;
11. (g) Petros, A.M.; Nettesheim, D.G.; Wang, Y.; Olejniczak, E.T.; Meadows, R.P.; Mack, J.; Swift, K.; Matayoshi, E.D.; Zhang, H.; Thompson, C.B.; Fesik, S.W. Rationale for Bcl-xL/Bad peptide complex formation from structure, mutagenesis, and biophysical studies. Protein Sci., 2000, 9, 2528-34.
12. (a) Degterev, A.; Lugovskoy, A.; Cardone, M.; Mulley, B.; Wagner, G.; Mitchison, T.; Yuan, J. Identification of small-molecule inhibitors of interaction between the BH3 domain and Bcl-xL. Nat. Cell Biol., 2001, 3, 173-82;
13. (b) Tzung, S.P.; Kim, K.M.; Basanez, G.; Giedt, C.D.; Simon, J.; Zimmerberg, J.; Zhang, K.Y.; Hockenbery, D.M. Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3. Nat. Cell Biol., 2001, 3, 183-91;
14. (c) Enyedy, I.J.; Ling, Y.; Nacro, K.; Tomita, Y.; Wu, X.; Cao, Y.; Guo, R.; Li, B.; Zhu, X.; Huang, Y.; Long, Y.Q.; Roller, P.P.; Yang, D.; Wang, S. Discovery of small-molecule inhibitors of Bcl-2 through structure-based computer screening. J. Med. Chem., 2001, 44, 4313-24.
15. (a) Kitada, S.; Leone, M.; Sareth, S.; Zhai, D.; Reed, J.C.; Pellecchia, M. Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-Cell lymphocyte/leukemia-2 proteins. J. Med. Chem., 2003, 46, 4259-64;
16. (b) Oltersdorf, T.; Elmore, S.W.; Shoemaker, A.R.; Armstrong, R.C.; Augeri, D.J.; Belli, B.A.; Bruncko, M.; Deckwerth, T.L.; Dinges, J.; Hajduk, P.J.; Joseph, M.K.; Kitada, S.; Korsmeyer, S.J.; Kunzer, A.R.; Letai, A.; Li, C.; Mitten, M.J.; Nettesheim, D.G.; Ng. S.; Nimmer, P.M.; O'Connor, J.M.; Oleksijew, A.; Petros, A.M.; Reed, J.C.; Shen, W.; Tahir, S.K.; Thompson, C.B.; Tomaselli, K.J.; Wang, B.; Wendt, M.D.; Zhang, H.; Fesik, S.W.; Rosenberg, S.H. An inhibitor of Bcl-2 family proteins induces regression of solid tumours. Nature, 2005, 435, 677-81.
17. (a) Clark, E.P. Studies on gossypol. V. J. Biol. Chem., 1929, 75, 1475-78;
18. (b) Clark, E.P. Studies on gossypol. IV. J. Biol. Chem., 1928, 74, 159-66;
19. (c) Clark E.P. Studies on gossypol.V. The action of chromiic acid upon some gossypol derivatives. J. Am. Chem. Soc., 1929, 51(5), 1475-78.
20. Wang, S.M.; Yang, D.J.; Xu, L. Small molecule antagonists of Bcl-2 family proteins. US. 7432304. B2, 2008.
21. (a) Alan, A.A.; Amro, A.; Chen, J.Y.; Yang, D.J.; Wang, S.M.; Ayad, A.; Ramzi, M. M. Preclinical studies of Apogossypolone: A new nonpeptidic pan small-molecule inhibitor of Bcl-2, Bcl-XL and Mcl-1 proteins in Follicular Small Cleaved Cell Lymphoma model. J. Mol. Cancer, 2008, 7, 20;
22. (b) Hu, Z.Y.; Zhu, X.F.; Zhong, Z.D.; Sun, J.; Wang, J.; Yang, D.; Zeng, Y.X. ApoG2, a novel inhibitor of antiapoptotic Bcl-2 family proteins, induces apoptosis and suppresses tumor growth in nasopharyngeal carcinoma xenografts. Int. J. Cancer, 2008, 123(10), 2418-29.
23. Yang, D.J.; Chen, J.Y.; Xu, L.; Gao, W.; Guo, J.; Qiu, S.; Jon, H.; Mel, S.; Wang, S.M. AT-101 and ApoG2, highly potent and orally active small molecule inhibitors of Mcl-1 protein and potential application for apoptosis-targeted anticancer therapy. AACR-NCTEORTC international conference molecular targetsand cancer therapeutic, November 14-18,2005. philadelphia, PA. Clin. Cancer Res., 2005, 11(24 Suppl), 9154S-54S.