Azaspirene, a fungal product, inhibits angiogenesis by blocking Raf-1 activation

Cancer Science

Volumn 99, Issue 9, 2008, Pages 1853-1858

  Asami, Yukihiro ^a,d   Kakeya, Hideaki ^a,e   Komi, Yusuke ^a   Kojima, Soichi ^a   Nishikawa, Kiyohiro ^b   Beebe, Kristin ^c   Neckers, Len ^c   Osada, Hiroyuki ^a  

^a RIKEN   (Japan)

^b NIPPON KAYAKU CO LTD   (Japan)

^c NATIONAL CANCER INSTITUTE   (United States)

^d UNIVERSITY OF TOKYO   (Japan)

^e KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; AZASPIRENE; MITOGEN ACTIVATED PROTEIN KINASE; PACLITAXEL; RAF PROTEIN; VASCULOTROPIN; VASCULOTROPIN RECEPTOR 2;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DRUG EFFICACY; DRUG SPECIFICITY; DRUG STRUCTURE; ENDOTHELIUM CELL; ENZYME INACTIVATION; FEMALE; HUMAN; HUMAN CELL; IN VIVO STUDY; KIDNEY CARCINOMA; MOLECULAR DYNAMICS; MOUSE; NONHUMAN; OPTIMAL DRUG DOSE; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; TUMOR VASCULARIZATION; TUMOR VOLUME;

ANGIOGENESIS INHIBITORS; ANIMALS; CHICK EMBRYO; ENDOTHELIAL CELLS; HUMANS; NEOVASCULARIZATION, PATHOLOGIC; PROTO-ONCOGENE PROTEINS C-RAF; PYRROLIDINONES; SPIRO COMPOUNDS; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 50149111972     PISSN: 13479032     EISSN: 13497006     Source Type: Journal    
DOI: 10.1111/j.1349-7006.2008.00890.x     Document Type: Article

References (39)

1. Bussolino F, Mantovani A, Persico G. Molecular mechanisms of blood vessel formation. Trends Biochem Sci 1997; 22: 251-6.
2. Inser JM, Asahara T. Angiogenesis and vasculogenesis as therapeutic strategies for postnatal neovascularization. J Clin Invest 1999; 103: 1231-6.
3. Hanhan D, Folkman J. Patterns and emerging mechanisms of the angiogenic switch during tumorigenesis. Cell 1996; 82: 353-64.
4. Folkman J. What is the evidence that tumors are angiogenesis dependent? J Natl Cancer Inst 1990; 80: 4-6.
5. Fidler IJ, Ellis LM. The implications of angiogenesis for the biology and therapy of cancer metastasis. Cell 1994; 79: 185-8.
6. Murakami M, Iwai S, Hiratsuka S et al. Signaling of vascular endothelial growth factor receptor-1 tyrosine kinase promotes rheumatoid arthritis through activation of monocytes/macrophages. Blood 2006; 108: 1849-56.
7. Shibuya M, Claesson-Welsh L. Signal transduction by VEGF receptors in regulation of angiogenesis and lymphangiogenesis. Exp Cell Res 2006; 312: 549-60.
8. He Y, Rajantie I, Pajusola K et al. Vascular endothelial cell growth factor receptor 3-mediated activation of lymphatic endothelium is crucial for tumor cell entry and spread via lymphatic vessels. Cancer Res 2005; 65: 4739-46.
9. Sridhar SS, Hedley D, Siu LL. Raf kinase as a target for anticancer therapeutics. Mol Cancer Ther 2005; 4: 677-85.
10. Olsson AK, Dimberg A, Kreuger J, Claesson-Welsh L. VEGF receptor signalling-in control of vascular function. Nat Rev Mol Cell Biol 2006; 7: 359-71.
11. Wilhelm SM, Carter C, Tang L et al. BAY 43-9006 exhibits broad spectrum oral antitumor activity and targets the RAF/MEK/ERK pathway and receptor tyrosine kinases involved in tumor progression and angiogenesis. Cancer Res 2004; 64: 7099-109.
12. Dasgupta P, Sun J, Wang S et al. Disruption of the Rb-Raf-1 interaction inhibits tumor growth and angiogenesis. Mol Cell Biol 2004; 24: 9527-41.
13. Xu L, Yoneda J, Herrera C, Wood J, Killion JJ, Fidler IJ. Inhibition of malignant ascites and growth of human ovarian carcinoma by oral administration of a potent inhibitor of the vascular endothelial growth factor receptor tyrosine kinases. Int J Oncol 2000; 16: 445-54.
14. Lyons JF, Wilhelm S, Hibner B, Bollag G. Discovery of a novel Raf kinase inhibitor. Endocr Relat Cancer 2001; 3: 219-25.
15. Hennequin LF, Stokes ES, Thomas AP et al. Novel 4-anilinoquinazolines with C-7 basic side chains: Design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors. J Med Chem 2002; 45: 1300-12.
16. Duran I, Hotte SJ, Hirte H et al. Phase I targeted combination trial of sorafenib and erlotinib in patients with advanced solid tumors. Clin Cancer Res 2007; 13: 4849-57.
17. Elser C, Siu LL, Winquist E et al. Phase II trial of sorafenib in patients with recurrent or metastatic squamous cell carcinoma of the head and neck or nasopharyngeal carcinoma. J Clin Oncol 2007; 25: 3766-73.
18. Verheul HM, Pinedo HM. Possible molecular mechanisms involved in the toxicity of angiogenesis inhibition. Nat Rev Cancer 2007; 7: 475-85.
19. Asami Y, Kakeya H, Onose R, Chang YH, Toi M, Osada H. RK-805, an endothelial-cell-growth inhibitor produced by Neosartorya sp. and a docking model with methionie aminopeptidase-2. Tetrahedron 2004; 60: 7085-91.
20. Kakeya H, Onose R, Koshino H et al. Epoxyquinol A, a highly functionalized pentaketide dimer with antiangiogenic activity isolated from fungal metabolites. J Am Chem Soc 2002; 124: 3496-7.
21. Kakeya H, Onose R, Yoshida A, Koshino H, Osada H. Epoxyquinol B, a fungal metabolite with a potent antiangiogenic activity. J Antibiot 2002; 55: 829-31.
22. Kakeya H, Onose R, Koshino H, Osada H. Epoxytwinol A, a novel unique angiogenesis inhibitor with C2 symmetry, produced by a fungus. Chem Commun 2005; 20: 2575-7.
23. Asami Y, Kakeya H, Okada G, Toi M, Osada H. RK-95113, a new angiogenesis inhibitor produced by Aspergillus fumigatus. J Antibiot 2006; 59: 724-8.
24. Asami Y, Kakeya H, Onose R, Yoshida A, Matsuzaki H, Osada H. Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp. Org Lett 2002; 17: 2845-8.
25. Kreisle R, Ershler W. Investigation of tumor angiogenesis in an id mouse model: Role of host-tumor interactions. J Natl Cancer Inst 1988; 80: 849-54.
26. Suzuki Y, Komi Y, Ashino H et al. Retinoic acid controls blood vessel formation by modulating endothelial and mural cell interaction via suppression of Tie2 signaling in vascular progenitor cells. Blood 2004; 104: 166-9.
27. Simizu S, Tamura Y, Osada H. Dephosphorylation of Bcl-2 by protein phosphatase 2A results in apoptosis resistance. Cancer Sci 2004; 95: 266-70.
28. Tamura Y, Simizu S, Osada H. The phosphorylation status and anti-apoptotic activity of Bcl-2 are regulated by ERK and protein phosphatase 2A on the mitochondria. FEBS Lett 2004; 569: 249-55.
29. Takahashi T, Ueno H, Shibuya M. VEGF activates protein kinase C-dependent, but Ras-independent Raf-MEK-MAP kinase pathway for DNA synthesis in primary endothelial cells. Oncogene 1999; 18: 2221-30.
30. Kanno S, Oda N, Abe M et al. Roles of two VEGF receptors, Flt-1 and KDR, in the signal transduction of VEGF effects in human vascular endothelial cells. Oncogene 2000; 19: 2138-46.
31. Sasaki A, Taketomi T, Kato R et al. Sprouty4 suppresses Ras-independent ERK activation by binding to Raf1. Nat Cell Biol 2003; 5: 427-32.
32. Tomanek RJ, Holifield JS, Reiter RS, Sandra A, Lin JJ. Role of VEGF family members and receptors in coronary vessel formation. Dev Dyn 2002; 225: 233-40.
33. Kuriyama M, Taniguchi T, Shirai Y, Sasaki A, Yoshimura A, Saito N. Activation and translocation of PKCδ is necessary for VEGF-induced ERK activation through KDR in HEK293T cells. Biochem Biophys Res Commun 2004; 325: 843-51.
34. Igarashi Y, Yabuta Y, Sekine A et al. Directed biosynthesis of fluorinated pseurotin A, synerazol and gliotoxin. J Antibiot 2004; 57: 748-54.
35. Hood J, Granger HJ. Protein kinase G mediates vascular endothelial growth factor-induced Raf-1 activation and proliferation in human endothelial cells. J Biol Chem 1998; 273: 23.504-8.
36. Takahashi T, Yamaguchi S, Chida K, Shibuya M. A single autophosphorylation site on KDR/Flk-1 is essential for VEGF-A-dependent activation of PLC-γ and DNA synthesis in vascular endothelial cells. EMBO J 2001; 20: 2768-78.
37. Alavi A, Hood JD, Frausto R, Stupack DG, Cheresh DA. Role of Raf in vascular protection from distinct apoptotic stimuli. Science 2003; 301: 94-6.
38. Hood JD, Frausto R, Kiosses WB, Schwartz MA, Cheresh DA. Differential αv integrin-mediated Ras-ERK signaling during two pathways of angiogenesis. J Cell Biol 2003; 162: 933-43.
39. Chong H, Vikis HG, Guan KL. Mechanisms of regulating the Raf kinase family. Cell Signal 2003; 15: 463-9.