Structural modification of an angiogenesis inhibitor discovered from traditional chinese medicine and a structure-activity relationship study

Journal of Medicinal Chemistry

Volumn 51, Issue 1, 2008, Pages 77-85

  Yang, Sheng Ping ^a   Cai, Yu Jun ^a   Zhang, Bang Le ^a   Tong, Lin Jiang ^a   Xie, Hua ^a   Wu, Yan ^a   Lin, Li Ping ^a   Ding, Jian ^a   Yue, Jian Min ^a  

^a Shanghai Jiao Tong University Affiliated Sixth People s Hospital   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; CHINESE DRUG; PSEUDOLARIC ACID B; PSEUDOLARIC ACID B DERIVATIVE; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL MIGRATION; CELL PROLIFERATION; CHEMICAL MODIFICATION; CHINESE MEDICINE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HERBAL MEDICINE; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

ANGIOGENESIS INHIBITORS; CELL LINE; CELL LINE, TUMOR; CELL MOVEMENT; CELL PROLIFERATION; DITERPENES; DRUG SCREENING ASSAYS, ANTITUMOR; DRUGS, CHINESE HERBAL; ENDOTHELIAL CELLS; HUMANS; MICROCIRCULATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 37849036510     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070906g     Document Type: Article

References (28)

1. (a) Carmeliet, P.; Jain, R. K. Angiogenesis in cancer and other diseases. Nature 2000, 407, 249-257.
2. (b) St Croix, B.; Rago, C.; Velculescu, V.; Traverso, G.; Romans, K. E.; Montgomery, E.; Lal, A.; Riggins, G. J.; Lengauer, C.; Vogelstein, B.; Kinzler, K. W. Genes expressed in human tumor endothelium. Science 2000, 289, 1197-1202.
3. (a) Unger, C. New therapeutic approaches in cancer treatment. Drugs Future 1997, 22 (12), 1337-1345.
4. (b) Halim, N. S. Small molecules in large proteins. The Scientist 2000, 14, 20-21.
5. Pan, D. J.; Li, Z. L.; Hu, C. Q.; Chen, K.; Chang, J. J.; Lee, K. H. The cytotoxic principles of Pseudolarix kaempferi: Pseudolaric acid-A and -B and related derivatives. Planta Med. 1990, 56, 383-385.
6. (a) Li, Z. L.; Pan, D. J.; Hu, C. Q.; Wu, Q. L.; Yang, S. S.; Xue, G. Y. Studies on the novel diterpenic constituents of Tu-Jin-Pi. Acta Chim. Sin. 1982, 40, 447-457.
7. (b) Zhou, B. N.; Ying, B. P.; Song, G. Q.; Chen, Z. X.; Han, J.; Yan, Y. F. Pseudolaric acids from Pseudolarix kaempferi. Planta Med. 1983, 47, 35-38.
8. (c) Li, E.; Clark, A. M.; Hufford, C. D. Antifungal evaluation of pseudolaric acid B, a major constituent of. Pseudolarix kaempferi. J. Nat. Prod. 1995, 58, 57-67.
9. (d) Yang, S. P.; Dong, L.; Wang, Y.; Wu, Y.; Yue, J. M. Antifungal diterpenoids of Pseudolarix kaempferi and their structure-activity relationship study. Bioorg. Med. Chem. 2003, 11, 4577-4584.
10. (a) Wang, W. C.; Lu, R. F.; Zhao, S. X.; Zhu, Y. Z. Antifertility effect of pseudolaric acid B. Yaoxue Xuebao 1982, 3, 188-192.
11. (b) Zhang, Y. L.; Lu, R. Z.; Yan, A. L. Inhibition of ova fertilizability by pseudolaric acid B in hamster. Yaoxue Xuebao 1990, 11, 60-62.
12. (c) Wang, W. C.; Lu, R. F.; Zhao, S. X.; Gu, Z. P. Comparison of early pregnancy-terminating effect and toxicity between pseudolaric acids A and B. Yaoxue Xuebao 1988, 9, 445-448.
13. (a) Chen, B.; Ko, R. Y. Y.; Yuen, M. S. M.; Cheng, K. F.; Chiu, P. A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids. J. Org. Chem. 2003, 68, 4195-4205.
14. (b) Chiu, P.; Chen, B.; Cheng, K. F. A rhodium carbene cyclization-cycloaddition cascade strategy toward the pseudolaric acids. Org. Lett. 2001, 3, 1721-1724.
15. (c) Wu, B.; Karle, J. M.; Watkins, E. B.; Avery, M. A. Toward the total synthesis of pseudolaric acid B. Preparation of a key intermediate by degradation and its use in the reassembly of the natural product. Tetrahedron Lett. 2002, 43, 4095-4098.
16. (d) Chiu, P.; Chen, B.; Cheng, K. F. A conjugated reduction- intramolecular aldol strategy toward the synthesis of pseudolaric acid A. Tetrahedron Lett. 1998, 39, 9229-9232.
17. (e) Pan, B. C.; Chang, H. Y.; Cai, G. L.; Guo, Y. S. Sythetic studies on pseudolaric acid A. Pure Appl. Chem. 1989, 61, 389-392.
18. (a) Tan, W. F.; Zhang, X. W.; Li, M. H.; Yue, J. M.; Chen, Y.; Lin, L. P.; Ding, J. Pseudolarix acid B inhibits angiogenesis by antagonizing the vascular endothelial growth factor-mediated anti-apoptotic effect. Eur. J. Pharmacol. 2004, 499, 219-228.
19. (b) Yue, J. M.; Yang, S. P.; Ding, J.; Xiao, D.; Yuan, S. T.; Wu, Y.; Tong, Y. G.; Dong, L. Pseudolaric acid-B derivatives, their preparation and pharmaceutical compositions. U.S. Patent 6,887,895 B2, 2005.
20. Li, M. H.; Miao, Z. H.; Tan, W. F.; Yue, J. M.; Zhang, C.; Lin, L. P.; Zhang, X. W.; Ding, J. Pseudolaric acid B inhibits angiogenesis and reduces hypoxia-inducible factor 1α by promoting proteasome-mediated degradation. Clin. Cancer Res. 2004, 10, 8266-8274.
21. (a) Gong, X. F.; Wang, M. W.; Tashiro, S. I.; Onodera, S.; Ikejima, T. Pseudolaric acid B induces apoptosis through P53 and Bax/Bcl-2 pathways in human melanoma A375-S2 cells. Arch. Pharm. Res. 2005, 28, 68-72.
22. (b) Gong, X. F.; Wang, M. W.; Wu, Z.; Tashiro, S. I.; Onodera, S.; Ikejima, T. Pseudolaric acid B induces apoptosis via activation of c-Jun N-terminal kinase and caspase-3 in Hela cells. Exp. Mol. Med. 2004, 36, 551-556.
23. Wong, V. K. W.; Chiu, P.; Chung, S. S. M.; Chow, L. M. C.; Zhao, Y. Z.; Yang, B. B.; Ko, B. C. B. Pseudolaric acid B, a novel microtubule-destabilizing agent that circumvents multidrug resistance phenotype and exhibits antitumor activity in vivo. Clin. Cancer Res. 2005, 11, 6002-6011.
24. Yang, S. P.; Wu, Y.; Yue, J. M. Five new diterpenoids from Pseudolarix kaempferi. J. Nat. Prod. 2002, 65, 1041-1044.
25. (a) Spivey, A. C.; McKendrick, J.; Srikaran, R.; Helm, B. A. Solid-phase synthesis of an A-B loop mimetic of the CE3 domain of human IgE: Macrocyclization by Sonogashira coupling. J. Org. Chem. 2003, 68, 1843-1851.
26. (b) Takimoto, S.; Inanga, J.; Katsuki, T.; Yamaguchi, M. Preparation of hindered esters from acid chlorides and alcohols in the presence of silver cyanide. Bull. Chem. Soc. Jpn. 1976, 49, 2335-2336.
27. Zhang, C.; Yang, F.; Zhang, X. W.; Wang, S. C.; Li, M. H.; Lin, L. P.; Ding, J. Grateloupia longifolia polysaccharide inhibits angiogenesis by downregulating tissue factor expression in HMEC-1 endothelial cells. Br. J. Pharmacol. 2006, 148, 741-751.
28. Tong, Y. G.; Zhang, X. W.; Tian, F.; Yi, Y. H.; Xu, Q. Z.; Li, L.; Tong, L. J.; Lin, L. P.; Ding, J. Philinopside A, a novel marine-derived compound possessing dual anti-angiogenic and anti-tumor effects. Int. J. Cancer 2005, 114, 843-853.