Synthesis and proteasome inhibition of N-allyl vinyl ester-based peptides

Journal of Peptide Science

Volumn 16, Issue 11, 2010, Pages 659-663

  Baldisserotto, Anna ^a   Franceschini, Christian ^a   Scalambra, Franco ^a   Trapella, Claudio ^a   Marastoni, Mauro ^a,b   Sforza, Fabio ^a   Gavioli, Riccardo ^a   Tomatis, Roberto ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b Dipartimento di Scienze Farmaceutiche   (Italy)

Author keywords

Inhibitors; N allyl derivatives; Proteasome; Pseudopeptides

Indexed keywords

ALLYL VINYL ESTER PSEUDOPEPTIDE; PROTEASOME INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; PHARMACOPHORE; PRIORITY JOURNAL;

ALLYL COMPOUNDS; HUMANS; OLIGOPEPTIDES; PROTEASE INHIBITORS; PROTEASOME ENDOPEPTIDASE COMPLEX; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78650465724     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1280     Document Type: Article

References (40)

1. Ciechanover A. The ubiquitin-proteasome proteolytic pathway. Cell 1994; 79: 13-21.
2. Reed SI. The ubiquitin-proteasome pathway in cell cycle control. Results Probl. Cell Differ. 2006; 42: 147-181.
3. Marescotti D, Destro F, Baldisserotto A, Marastoni M, Coppotelli G, Masucci M, Gavioli R. Characterization of an human leucocyte antigen A2-restricted Epstein-Barr virus nuclear antigen-1-derived cytotoxic T-lymphocyte epitope. Immunology 2010; 129: 386-395.
4. Testa U. Proteasome inhibitors in cancer therapy. Curr. Drug Targets 2009; 10: 968-981.
5. Ludwig A, Fechner M, Wilck N, Meiners S, Grimbo N, Baumann G, Stangl V, Stangl K. Potent anti-inflammatory effects of low-dose proteasome inhibition in the vascular system. J. Mol. Med. 2009; 87: 793-802.
6. Brannigan JA, Dodson G, Duggleby HJ, Moody PC, Smith JL, Tomchick DR, Murzin AG. A protein catalytic framework with an N-terminal nucleophile is capable of self-activation. Nature 1995; 378: 416-419.
7. Coux O, Tanaka K, Goldberg AL. Structure and functions of the 20S and 26S proteasomes. Annu. Rev. Biochem. 1996; 65: 801-847.
8. Orlowski RZ. The role of the ubiquitin-proteasome pathway in apoptosis. Cell Death Differ. 1999; 6: 303-313.
9. Kisselev AF, Songyang Z, Goldberg AL. Why does threonine, and not serine, function as the active site nucleophile in proteasomes? J. Biol. Chem. 2000; 275: 14831-14837.
10. Myung J, Kim KB, Crews CM. The ubiquitin-proteasome pathway and proteasome inhibitors. Med. Res. Rev. 2001; 21(4): 245-273.
11. Löwe J, Stock D, Jap B, Zwickl P, Baumeister W, Huber R. Crystal structure of the 20S proteasome from the archaeon T. acidophilum at 3.4 A resolution. Science 1995; 268: 533-539.
12. Groll M, Ditzel L, Löwe J, Stock D, Bochtler M, Bartunik HD, Huber R. Structure of 20S proteasome from yeast at 2.4 A resolution. Nature 1997; 386: 463-471.
13. Marques AJ, Palanimurugan R, Matias AC, Ramos PC, Dohmen RJ. Catalytic mechanism and assembly of the proteasome. Chem. Rev. 2009; 109: 1509-1536.
14. Moore BS, Eustáquio AS, McGlinchey RP. Advances in and applications of proteasome inhibitors. Curr. Opin. Chem. Biol. 2008; 12: 434-440.
15. Groll M, Götz M, Kaiser M, Weyher E, Moroder L. TMC-95-based inhibitor design provides evidence for the catalytic versatility of the proteasome. Chem. Biol. 2006; 13: 607-614.
16. Purandare AV, Wan H, Laing N, Benbatoul K, Vaccaro W, Poss MA. Identification of a potent and rapidly reversible inhibitor of the 20S-proteasome. Bioorg. Med. Chem. Lett. 2004; 14: 4701-4704.
17. Hines J, Groll M, Fahnestock M, Crews CM. Proteasome inhibition by fellutamide B induces nerve growth factor synthesis. Chem. Biol. 2008; 15: 501-512.
18. Nickeleit I, Zender S, Sasse F, Geffers R, Brandes G, Sörensen I, Steinmetz H, Kubicka S, Carlomagno T, Menche D, Gütgemann I, Buer J, Gossler A, Manns MP, Kalesse M, Frank R, Malek NP. Argyrin a reveals a critical role for the tumor suppressor protein p27(kip1) in mediating antitumor activities in response to proteasome inhibition. Cancer Cell 2008; 14: 23-35.
19. Loidl G, Groll M, Musiol HJ, Huber R, Moroder L. Bivalency as a principle for proteasome inhibition. Proc. Natl. Acad. Sci. U.S.A. 1999; 96: 5418-5422.
20. Nazif T, Bogyo M. Global analysis of proteasomal substrate specificity using positional-scanning libraries of covalent inhibitors. Proc. Natl. Acad. Sci. U.S.A. 2001; 98: 2967-2972.
21. Furet P, Imbach P, Noorani M, Koeppler J, Laumen K, Lang M, Guagnano V, Fuerst P, Roesel J, Zimmermann J, García-Echeverría C. Entry into a new class of potent proteasome inhibitors having high antiproliferative activity by structure-based design. J. Med. Chem. 2004; 47: 4810-4813.
22. Hogan PC, Corey EJ. Proteasome inhibition by a totally synthetic beta-lactam related to salinosporamide A and omuralide. J. Am. Chem. Soc. 2005; 127: 15386-15387.
23. Kohno J, Koguchi Y, Nishio M, Nakao K, Kuroda M, Shimizu R, Ohnuki T, Komatsubara S. Structures of TMC-95A-D: novel proteasome inhibitors from Apiospora montagnei sacc. TC 1093. J. Org. Chem. 2000; 65: 990-995.
24. Momose I, Umezawa Y, Hirosawa S, Iinuma H, Ikeda D. Structure-based design of derivatives of tyropeptin A as the potent and selective inhibitors of mammalian 20S proteasome. Bioorg. Med. Chem. Lett. 2005; 15: 1867-1871.
25. Kaiser M, Milbradt AG, Siciliano C, Assfalg-Machleidt I, Machleidt W, Groll M, Renner C, Moroder L. TMC-95A analogues with endocyclic biphenyl ether group as proteasome inhibitors. Chem. Biodivers. 2004; 1: 161-173.
26. Kaiser M, Groll M, Renner C, Huber R, Moroder L. The core structure of TMC-95A is a promising lead for reversible proteasome inhibition. Angew. Chem. Int. Ed. Engl. 2002; 41: 780-783.
27. Adams J. The development of proteasome inhibitors as anticancer drugs. Cancer Cell 2004; 5(5): 417-421.
28. Adams J. The proteasome: a suitable antineoplastic target. Nat. Rev. Cancer 2004; 4: 349-360.
29. Groll M, Schellenberg B, Bachmann AS, Archer CR, Huber R, Powell TK, Lindow S, Kaiser M, Dudler R. A plant pathogen virulence factor inhibits the eukaryotic proteasome by a novel mechanism. Nature 2008; 452: 755-758.
30. Clerc J, Florea BI, Kraus M, Groll M, Huber R, Bachmann AS, Dudler R, Driessen C, Overkleeft HS, Kaiser M. Syringolin A selectively labels the 20 S proteasome in murine EL4 and wild-type and bortezomib-adapted leukaemic cell lines. ChemBiochem 2009; 10: 2638-2643.
31. Clerc J, Groll M, Illich DJ, Bachmann AS, Huber R, Schellenberg B, Dudler R, Kaiser M. Synthetic and structural studies on syringolin A and B reveal critical determinants of selectivity and potency of proteasome inhibition. Proc. Natl. Acad. Sci. U.S.A. 2009; 106: 6507-6512.
32. Marastoni M, Baldisserotto A, Cellini S, Gavioli R, Tomatis R. Peptidyl vinyl ester derivatives: new class of selective inhibitors of proteasome trypsin-like activity. J. Med. Chem. 2005; 48: 5038-5042.
33. Marastoni M, Baldisserotto A, Trapella C, Gavioli R, Tomatis R. P3 and P4 position analysis of vinyl ester pseudopeptide proteasome inhibitors. Bioorg. Med. Chem. Lett. 2006; 16: 3125-3130.
34. Baldisserotto A, Marastoni M, Gavioli R, Tomatis R. New cyclic peptide proteasome inhibitors. Bioorg. Med. Chem. Lett. 2009; 19: 1966-1969.
35. Baldisserotto A, Destro F, Vertuani G, Marastoni M, Gavioli R, Tomatis R. N-terminal-prolonged vinyl ester-based peptides as selective proteasome beta1 subunit inhibitors. Bioorg. Med. Chem. 2009; 17: 5535-5540.
36. Baldisserotto A, Marastoni M, Trapella C, Gavioli R, Ferretti V, Pretto L, Tomatis R. Glutamine vinyl ester proteasome inhibitors selective for trypsin-like (beta2) subunit. Eur. J. Med. Chem. 2007; 42: 586-592.
37. Radin NS. Meta-analysis of anticancer drug structures-significance of their polar allylic moieties. Anticancer Agents Med. Chem. 2007; 7: 209-222.
38. Gavioli R, Vertuani S, Masucci MG. Proteasome inhibitors reconstitute the presentation of cytotoxic T-cell epitopes in Epstein-Barr virus-associated tumors. Int. J. Cancer 2002; 101: 532-538.
39. Hendil KB, Uerkvitz W. The human multicatalytic proteinase: affinity purification using a monoclonal antibody. J. Biochem. Biophys. Methods 1991; 22: 159-165.
40. Kaiser M, Groll M, Siciliano C, Assfalg-Machleidt I, Weyher E, Kohno J, Milbradt AG, Renner C, Huber R, Moroder L. Binding mode of TMC-95A analogues to Eukaryotic 20S proteasome. ChemBiochem 2004; 5: 1256-1266.