Novel fluorinated pseudopeptides as proteasome inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 1, 2009, Pages 83-86

  Formicola, Lucia ^a   Maréchal, Xavier ^b   Basse, Nicolas ^b   Bouvier Durand, Michelle ^b   Bonnet Delpon, Danièle ^a   Milcent, Thierry ^a   Reboud Ravaux, Michèle ^b   Ongeri, Sandrine ^a  

^a IPSIT   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

Fluorine; Proteasome inhibitors; Pseudopeptide; Trifluoromethyl hydrazino

Indexed keywords

CALPAIN 1; CATHEPSIN B; FLUORINE; HYDRAZINE DERIVATIVE; PROTEASOME; PROTEASOME INHIBITOR; PSEUDOPEPTIDE; REAGENT; TRIFLUOROMETHYL BETA HYDRAZINO ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; FLUORINATION; HUMAN; HUMAN CELL; NONHUMAN; RABBIT; STRUCTURE ACTIVITY RELATION;

ORYCTOLAGUS CUNICULUS;

EID: 57849087338     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.012     Document Type: Article

References (40)

1. Hershko A., and Ciechanover A. Annu. Rev. Biochem. 67 (1998) 425
2. Groll M., Ditzel L., Lowe J., Bochtler M., Bartunik H., and Huber R. Nature (1997) 463
3. Groll M., Heinemeyer W., Jâger S., Ullrich T., Bochtler M., Wolf D.H., and Huber R. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 10976
4. Adams J. Nat. Rev. Cancer 4 (2004) 349
5. Adams J. Cancer Cell 5 (2003) 417
6. Demo S.D., Kirk C.J., Aujay M.A., Buchholz T.J., Dajee M., Ho M.N., Jiang J., Laidig G.J., Lewis E.R., Parlati F., Shenk K.D., Smyth M.S., Sun C.M., Vallone M.K., Woo T.M., Molineaux C.J., and Bennett M.K. Cancer Res. 67 (2007) 6383
7. Chauhan D., Catley L., Li G., Podar K., Hideshima T., Velankar M., Mitsiades C., Mitsiades N., Yasui H., Letai A., Ovaa H., Berkers C., Nicholson B., Chao T.-H., Neuteboom S.T.C., Richardson P., Palladino M.A., and Anderson K.C. Cancer Cell 8 (2005) 407
8. Piva R., Ruggeri B., Williams M., Costa G., Tamagno I., Ferrero D., Giai V., Coscia M., Peola S., Massaia M., Pezzoni G., Allievi C., Pescalli N., Cassin M., di Giovine S., Nicoli P., de Feudis P., Strepponi I., Roato I., Ferracini R., Bussolati B., Camussi G., Jones-Bolin S., Hunter K., Zhao H., Neri A., Palumbo A., Berkers C., Ovaa H., Bernareggi A., and Inghirami G. Blood 111 (2008) 2765
9. Borissenko L., and Groll M. Chem. Rev. 107 (2007) 687
10. Garcia-Echeverria C. Int. J. Pept. Res. Ther. 12 (2006) 49
11. Kisselev A.F., and Goldberg A.L. Chem. Biol. 8 (2001) 739
12. Furet P., Imbach P., Noorani M., Koeppler J., Laumen K., Lang M., Guagnano P.F., Roesel J., Zimmerman J., and Garcia-Echeverria C. J. Med. Chem. 47 (2004) 4810
13. Schmidtke G., Holzhutter H.G., Bogyo M., Kairies N., Groll M., de Giuli R., Emch S., and Groettrup M. J. Biol. Chem. 274 (1999) 35734
14. Basse N., Papapostolou D., Pagano M., Bernard E., Felten A.S., Vanderesse R., and Reboud-Ravaux M. Bioorg. Med. Chem. Lett. 16 (2006) 3277
15. Kohno J., Kogushi Y., Nishio M., Nakao K., Kuroda M., Shimizu R., Ohnuki T., and Komatsubara S. J. Org. Chem. 65 (2000) 990
16. Groll M., Götz M., Kaiser M., Weyher E., and Moroder L. Chem. Biol. 13 (2006) 607
17. Basse N., Piguel S., Papapostolou D., Ferrier-Berthelot A., Richy N., Pagano M., Sarthou P., Sobczak-Thépot J., Reboud-Ravaux M., and Vidal J. J. Med. Chem. 50 (2007) 2842
18. Bégué J.-P., and Bonnet-Delpon D. J. Fluorine Chem. 127 (2006) 992
19. Hagmann W.K. J. Med. Chem. 51 (2008) 4359
20. Isanbor C., and O'Hagan D. J. Fluorine Chem. 127 (2006) 303
21. Ismail F.M.D. J. Fluorine Chem. 118 (2002) 27
22. Bégué J.-P., and Bonnet-Delpon D. In Bioorganic and Medicinal Chemistry of Fluorine (2008), Wiley-VCH Ltd. p. 279
23. Bohm H.J., Banner D., Bendels S., Kansy M., Kuhn B., Muller K., Obst-Sander U., and Stahl M. Chembiochem 5 (2004) 637
24. Zanda M. New J. Chem. 28 (2004) 1401
25. Martinelli M., Milcent T., Ongeri S., and Crousse B. Beilstein J. Org. Chem. (2008) 4
26. Magueur G., Crousse B., and Bonnet-Delpon D. Eur. J. Org. Chem. (2008) 1527
27. Bonnamour J., Legros J., Crousse B., and Bonnet-Delpon D. Tetrahedron Lett. 48 (2007) 8360
28. Tam N.T.N., Magueur G., Ourévitch M., Crousse B., Begue J.P., and Bonnet-Delpon D. J. Org. Chem. 70 (2005) 699
29. Rinaudo G., Narizuka S., Askari N., Crousse B., and Bonnet-Delpon D. Tetrahedron Lett. 47 (2006) 2065
30. Magueur G., Crousse B., and Bonnet-Delpon D. Tetrahedron Lett. 46 (2005) 2219
31. Aubin S., Martin B., Delcros J.-G., Arlot-Bonnemains Y., and Baudy-Floc'h M. J. Med. Chem. 48 (2005) 330
32. Guy L., Vidal J., Collet A., Amour A., and Reboud-Ravaux M. J. Med. Chem. 41 (1998) 4833
33. Juaristi, E.; Soloshonok, V. A. Enantioselective Synthesis of beta-Amino Acids (second edition); Wiley-VCH Ltd., 2005.
34. Cheng R.P., Gellman S.H., and DeGrado W.F. Chem. Rev. 101 (2001) 3219
35. Seebach D., Hook D.F., and Glättli A. Peptide Sci. 84 (2006) 23
36. McBee E.T., Pierce O.R., and Smith D.D. J. Am. Chem. Soc. 76 (1954) 3722
37. Jagodzinska M., Huguenot F., and Zanda M. Tetrahedron 63 (2007) 2042
38. m values of the fluorogenic substrates in our experimental conditions were: 30 ± 5 μM (Suc-LLVY-AMC), 77 ± 4 μM (Z-LLE-βNA) and 26 ± 6 μM (Boc-LRR-AMC).
39. 4, 1 mM EDTA, 1 mM DTT, respectively.
40. Proteasome Glo Cell-Based Assay (Promega) using MG-132 as a standard.