Degradation-promoters of cellular inhibitor of apoptosis protein 1 based on bestatin and actinonin

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 8, 2008, Pages 4685-4698

  Sato, Shinichi ^a   Tetsuhashi, Masashi ^a   Sekine, Keiko ^a,b   Miyachi, Hiroyuki ^a   Naito, Mikihiko ^a   Hashimoto, Yuichi ^a   Aoyama, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b NIPPON KAYAKU CO LTD   (Japan)

Author keywords

Actinonin; Bestatin; cIAP1; Inhibitor; Structural development

Indexed keywords

ACTINONIN; AMIDE; BESTATIN; CARBONYL DERIVATIVE; CELL PROTEIN; ESTER DERIVATIVE; N [3 HYDROXYCARBAMOYL 2 PENTYLPROPANOYL] LEVO ALANINA METHYL ESTER; PROTEIN CIAP1; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; IC 50; PROTEIN DEGRADATION; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION;

APOPTOSIS; CELL LINE, TUMOR; HUMANS; HYDROXAMIC ACIDS; INHIBITOR OF APOPTOSIS PROTEINS; INHIBITORY CONCENTRATION 50; LEUCINE; MOLECULAR STRUCTURE; PROMOTER REGIONS (GENETICS); STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 42149103458     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.024     Document Type: Article

References (53)

1. Vanx D.L., and Korsmeyer S.J. Cell 96 (1999) 245-254
2. Thompson C.B. Science 267 (1995) 1456-1462
3. Vaux D.L., and Strasser A. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 2239-2244
4. Wylie A.H. Eur. J. Cell Biol. 73 (1997) 189-197
5. Earnshaw W.C., Martins L.M., and Kaufmann S.H. Annu. Rev. Biochem. 68 (1999) 383-424
6. Garrido C., and Kroemer G. Curr. Opin. Cell Biol. 16 (2004) 639-646
7. Riedl S.J., and Shi Y. Nat. Rev. Mol. Cell Biol. 5 (2004) 897-907
8. Kroemer G., and Martin S.J. Nat. Med. 11 (2005) 725-730
9. Green D.R. Cell 102 (2000) 1-4
10. Goyal L. Cell 104 (2001) 805-808
11. Deveraux Q.L., and Reed J.C. Genes Dev. 13 (1999) 239-252
12. Duckett C.S., Nava V.E., Gedrich R.W., Clem R.J., Van Dongen J.L., Gilfilan M.C., Shiels H., Hardwick J.M., and Thompson C.B. EMBO J. 15 (1996) 2685-2694
13. Birnbaum M.J., Clem R.J., and Miller L.K. J. Virol. 68 (1994) 2521-2528
14. Liston P., Fong W.G., and Korneluk R.G. Oncogene 22 (2003) 8568-8580
15. Vaux D.X., and Silke J. Nat. Rev. Mol. Cell Biol. 6 (2005) 287-297
16. Verhagen A.M., Coulson E.J., and Vaux D.X. Genome Biol. 2 (2001) R3009
17. Miller L. Trends Cell Biol. 9 (1999) 323-328
18. Roy N., Mahadevan M.S., McLean M., Shutler G., Yaraghi Z., Farahani R., Baird S., Besner-Johnston A., Lefebvre C., Kang X., Salih M., Aubry H., Tamai K., Guan X., Ioannou P., Crawford T.O., DeJong P.J., Surh L., Ikeda J.E., Korneluk R.G., and MacKenzie A. Cell 80 (1995) 167-178
19. Rothe M., Pan M.G., Henzel W.J., Ayres T.M., and Goeddel D.V. Cell 80 (1995) 1243-1252
20. Liston P., Roy N., Tamai K., Lefebvre C., Baird S., Cherton-Horvat G., Farahani R., McLean M., Ikeda J.E., MacKenzie A., and Korneluk R.G. Nature 379 (1996) 349-353
21. Kasof G.M., and Gomes B.C. J. Biol. Chem. 276 (2001) 3238-3246
22. Chen Z., Naito M., Hori S., Mashima T., Yamori T., and Tsuruo T. Biochem. Biophys. Res. Commun. 264 (1999) 847-854
23. Richter B.W., Mir S.S., Eiben L.J., Lewis J., Reffey S.B., Frattini A., Tian L., Frank S., Youle R.J., Nelson D.L., Notarangelo L.D., Vezzoni P., Fearnhead H.O., and Duckett C.S. Mol. Cell. Biol. 21 (2001) 4292-4301
24. Ambrosini G., Adida C., and Altieri D.C. Nat. Med. 3 (1997) 917-921
25. Deveraux Q.L., Takahashi R., Salvesen G.S., and Reed J.C. Nature 388 (1997) 300-304
26. Roy N., Deveraux Q.L., Takahashi R., Salvesen G.S., and Reed J.C. EMBO J. 16 (1997) 6914-6925
27. Hay B.A., Wassarman D.A., and Rubin G.M. Cell 83 (1995) 1253-1262
28. Vucic D., Kaiser W.J., and Miller L.K. Mol. Cell. Biol. 18 (1998) 3300-3309
29. Vucic D., Kaiser W.J., and Miller L.K. J. Biol. Chem. 273 (1998) 33915-33921
30. McCarthy J.V., and Dixit V.M. J. Biol. Chem. 273 (1998) 24009-24015
31. Wilkinson J.C., Wilkinson A.S., Scott F.L., Csomos R.A., Salvesen G.S., and Duckett C.S. J. Biol. Chem. 279 (2004) 51082-51090
32. Vucic D., Franklin M.C., Wallweber H.J.A., Das K., Eckelman B.P., Shin H., Elliott L.O., Kadkhodayan S., Deshayes K., Salvesen G.S., and Fairbrother W.J. Biochem. J. 385 (2005) 11-20
33. Liu Z., Sun C., Olejniczak E.T., Meadows R.P., Betz S.F., Oost T., Herrmann J., Wu J.C., and Fesik S.W. Nature 408 (2000) 1004-1008
34. Wu G., Chai J., Suber T.L., Wu J.W., Du C., Wang X., and Shi Y. Nature 408 (2000) 1008-1012
35. Sharma S.K., Straub C., and Zawel L. Int. J. Peptide Res. Ther. 12 (2006) 21-32
36. Zobel K., Wang L., Varfolomeev E., Franklin M.C., Elliott L.O., Wallweber H.J.A., Okawa D.C., Flygare J.A., Vucic D., Fairbrother W.J., and Deshayes K. ACS Chem. Biol. 1 (2006) 525-533
37. Vince J.E., Wong W.W., Nufail K., Feltham R., Chau D., Ahmed U.A., Benetatos C.A., Chunduru S.K., Condon S.M., McKinlay M., Brink R., Leverkus M., Tergonkar V., Schneider P., Callus B.A., Koentgen F., Vaux D.L., and Silke J. Cell 131 (2007) 682-693
38. Yang Q.-H., and Du C. J. Biol. Chem. 279 (2004) 16963-16970
39. Varfolomeev E., Blankenship J.W., Wayson S.M., Fedorova A.V., Kayagaki N., Garg P., Zobel K., Dynek J.N., Elliott L.O., Wallweber H.J.A., Flygare J.A., Fairbrother W.J., Deshayes K., Dixit V.M., and Vucic D. Cell 131 (2007) 669-681
40. Umezawa H., Aoyagi T., Suda H., Hamada M., and Takeuchi T. J. Antibiot. 29 (1976) 97-99
41. Leyhausen G., Gramzow M., Zahn R.K., Steffen R., Umezawa H., and Müller W.E.G. J. Antibiot. 36 (1983) 728-734
42. Nakamura H., Suda H., Takita T., Aoyagi T., Umezawa H., and Iitaka Y. J. Antibiot. 29 (1976) 102-103
43. Sekine, K.; Takubo, K.; Nishimoto, M.; Kitagawa, M.; Abe, F.; Nishikawa, K.; Tsuruo, T.; Naito, M. J. Biol. Chem., in press, doi:10.1074/jbc.M709525200..
44. Gordon J.J., Kelly B.K., and Miller G.A. Nature 195 (1962) 701-702
45. Umezawa H., Aoyagi T., Tanaka T., Suda H., Okuyama A., Naganawa H., Hamada M., and Takeuchi T. J. Antibiot. 38 (1985) 1629-1630
46. Tillman D.M., Harwood F.G., Gibson A.A., and Houghton J.A. Cell Death Differ. 5 (1998) 450-457
47. Yoshida T., Shiraishi T., Nakata S., Horinaka M., Wakada M., Mizutani Y., Miki T., and Sakai T. Cancer Res. 65 (2005) 5662-5667
48. Herranz R., Castro-Pichel J., Vinuesa S., and García-Lopéz M.T. J. Org. Chem. 55 (1990) 2232-2234
49. Kondekar N.B., Kandula S.R.V., and Kumar P. Tetrahedron Lett. 45 (2004) 5477-5479
50. Hentges S.G., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 4263-4265
51. Ando K., Tsuji E., Ando Y., Kuwata N., Kunitomo J., Yamashita M., Ohta S., Kohno S., and Ohishi Y. Org. Biomol. Chem. 2 (2004) 625-635
52. Roush W.R., and Brown B.B. J. Org. Chem. 57 (1992) 3380-3387
53. Evans D.A., Ennis M.D., and Mathre D.J. J. Am. Chem. Soc. 104 (1982) 1737-1739