New cyclic peptide proteasome inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 7, 2009, Pages 1966-1969

  Baldisserotto, Anna ^a   Marastoni, Mauro ^a   Gavioli, Riccardo ^a   Tomatis, Roberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

Caspase like activity; Cyclic peptides; Inhibitors; Proteasome

Indexed keywords

BENZYLOXYCARBONYLLEUCYLLEUCYLLEUCINAL; CARBOXYL GROUP; CASPASE; CYCLO[GLYCYLLEUCYLLEUCYLGLUTAMYL (LEUCINE VINYL ESTER)]; CYCLO[SERYLLEUCYLLEUCYLGLUTAMYL (LEUCINE VINYL ESTER)]; CYCLO[VALYLLEUCYLLEUCYLGLUTAMYL (LEUCINE VINYL ESTER)]; CYCLOPEPTIDE; EPOXOMICIN; GLUTAMIC ACID; LEUCINE; PROTEASOME; PROTEASOME INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CELL MEMBRANE PERMEABILITY; CONCENTRATION RESPONSE; DRUG CONFORMATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; PROTEIN DEGRADATION; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; CELL LINE; HALF-LIFE; HUMANS; PEPTIDES, CYCLIC; PROTEASE INHIBITORS; PROTEASOME ENDOPEPTIDASE COMPLEX;

EID: 61849163438     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.02.046     Document Type: Article

References (34)

1. Ciechanover A. Cell 79 (1994) 13
2. Coux O., Tanaka K., and Golberg A.L. Annu. Rev. Biochem. 65 (1996) 801
3. Hershko A., and Ciechanover A. Annu. Rev. Biochem. 67 (1998) 425
4. Orlowski R.Z. Cell Death Differ. 6 1695 (1999) 19
5. Kisselev A.F., Songyang Z., and Goldberg A.L. J. Biol. Chem. 275 (2000) 14831
6. Myung J., Kim K.B., and Crews C.M. Med. Res. Rev. 21 (2001) 245
7. Boyo M., and Wang E.W. Curr. Top. Microbiol. Immunol. (2002)
8. Adams J., and Kauffman M. Cancer Invest. 22 (2004) 304
9. Löwe J., Stock D., Zwickl P., Baumeister W., and Huber H. Science 268 (1995) 533
10. Groll M., Ditzel L., Löwe J., Stock D., Bochtler M., Bartunik H.D., and Huber R. Nature 386 (1997) 463
11. Oikawa T., Sasaki T., Nakamura M., Shimamura M., Tanahashi N., Mura S., and Tanaka K. Biochem. Biophys. Res. Commun. 246 (1998) 243
12. Drexler H.C., Risau W., and Konerding M.A. FASEB J. 14 (2000) 65
13. Iqbal M., Chatterjee S., Kauer J.C., Das M., Messina P.A., Freed B., Biazzo W., and Siman R. J. Med. Chem. 38 (1995) 2276
14. Loidl G., Groll M., Musiol H.-J., Huber R., and Moroder L. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 5418
15. Nazif T., and Bogyo M. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 2967
16. Furet P., Imbach P., Noorani M., Koeppler J., Lumen K., Lang M., Guaniano V., Fuerst P., Roesel J., Zimmermann J., and Garcia-Echevevarria C. J. Med. Chem. 47 (2004) 4810
17. Momose I., Umezawa Y., Hirosawa S., Iinuma H., and Ikeda D. Bioorg. Med. Chem. Lett. 15 (2005) 1867
18. Vivier M., Jarrousse A.S., Bouchon B., Galmier M.J., Auzeloux P., Sauzieres J., and Madelmont J.C. J. Med. Chem. 48 (2005) 6731
19. Kisselev A.F., and Goldberg A.L. Chem. Biol. 8 (2001) 739
20. Garcia-Echeverria C. Int. J. Pept. Res. Ther. 12 (2006) 49
21. Groll M., Huber R., and Potts B.C.M. J. Am. Chem. Soc. 128 (2006) 5136
22. Kohno J., Koguchi Y., Nishio M., Nakao K., Kuroda M., Shimizu R., Ohnuki Y., and Komatsubara S. J. Org. Chem. 12 (2000) 1331
23. Marastoni M., Baldisserotto A., Cellini S., Gavioli R., and Tomatis R. J. Med. Chem. 48 (2005) 5038
24. Marastoni M., Baldisserotto A., Trapella C., Gavioli R., and Tomatis R. Bioorg. Med. Chem. Lett. 16 (2006) 3125
25. Marastoni M., Baldisserotto A., Trapella C., Gavioli R., and Tomatis R. Eur. J. Med. Chem. 41 (2006) 978
26. Baldisserotto A., Marastoni M., Trapella C., Gavioli R., Ferretti V., Pretto L., and Tomatis R. Eur. J. Med. Chem. 42 (2007) 586
27. Baldisserotto A., Marastoni M., Lazzari I., Trapella C., Gavioli R., and Tomatis R. Eur. J. Eur. J. Med. Chem. 43 (2008) 1403
28. Baldisserotto A., Marastoni M., Fiorini S., Pretto L., Ferretti V., Gavioli R., and Tomatis R. Bioorg. Med. Chem. Lett. 18 (2008) 1849
29. Shiori T., Ninomiya K., and Yamada S. J. Am. Chem. Soc. 94 (1972) 6203
30. Brady S.F., Freidinger R.M., Colton C.D., Homnick C.F., Whitter W.L., Curley P., Nutt R.F., and Veber D.F.J. J. Org. Chem. 52 (1987) 764
31. 3, 200 MHz): δ (ppm) 0.99 (d, 6H), 1.11 (m, 12H), 1.31 (t, 3H, J = 7.2), 1.39 (m, 2H), 1.63-1.75 (m, 7H), 1.99 (m, 2H), 2.18 (d, 2H), 2.84 (m, 2H), 3.87 (m, 2H), 4.08 (q, 2H, J = 7.3), 4.31-4.54 (m, 5H), 6.01 (d, 1H, J = 16.2), 7.06 (dd, 1H, J = 16.1), 8.02 (bs, 5H).
32. Gavioli R., Vertuani S., and Masucci M.G. Int. J. Cancer 101 (2002) 532
33. Hendil K.B., and Uerkvitz W. J. Biochem. Biophys. Methods 22 (1991) 159
34. Purification of the proteasomes and enzyme assays in vitro and in live cells are described in 'Supporting information' of Ref. 11a.