Nε-Modified lysine containing inhibitors for SIRT1 and SIRT2

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 15, 2010, Pages 5616-5625

  Huhtiniemi, Tero ^a   Suuronen, Tiina ^a   Lahtela Kakkonen, Maija ^a   Bruijn, Tanja ^a   Jääskeläinen, Sanna ^a   Poso, Antti ^a   Salminen, Antero ^a,b   Leppänen, Jukka ^a   Jarho, Elina ^a,c  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b KUOPIO UNIVERSITY HOSPITAL   (Finland)

^c UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Histone deacetylases; NAD+ dependent deacetylation; Sirtuin inhibitors

Indexed keywords

2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (3 METHYLBUT 2 ENAMIDO)HEXANAMIDO)PROPANOIC ACID; 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (3 METHYLBUTANAMIDO)HEXANAMIDO)PROPANOIC ACID; 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (3 METHYLBUTANETHIOAMIDO)HEXANAMIDO)PROPANOIC ACID; 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (4,4,4 TRIFLUORO 3 METHYLBUT 2 ENAMIDO)HEXANAMIDO)PROPANOIC ACID; 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 ETHANESELENOAMIDOHEXANAMIDO)PROPANOIC ACID; 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 ETHANETHIOAMIDOHEXANAMIDO)PROPANOIC ACID; 2 (2 ACETAMIDOPROPANAMIDO) N (1 (METHYLAMINO) 1 OXOPROPAN 2 YL) 6 PIVALAMIDOHEXANAMIDE; 2 (6 ACETAMIDO 2 (2 ACETAMIDOPROPANAMIDO) HEXANAMIDO)PROPANOIC ACID; 6 ACETAMIDO 2 (2 ACETAMIDOPROPANAMIDO) N (1 (METHYLAMINO) 1 OXOPROPAN 2 YL)HEXANAMIDE; ACETIC ACID DERIVATIVE; BENZYL 6 (DIMETHYLPHOSPHOROTHIOYLAMINO) 1 OXO 1 (PHENYLAMINO)HEXAN 2 YLCARBAMATE; BENZYL 6 ETHANESELENOAMIDO 1 OXO 1 (PHENYLAMINO)HEXAN 2 YLCARBAMATE; BENZYL 6 ETHANETHIOAMIDO 1 OXO 1 (PHENYLAMINO)HEXAN 2 YLCARBAMATE; CARBOXYLIC ACID; HISTONE DEACETYLASE INHIBITOR; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (2 (PYRIDIN 2 YL)ACETAMIDO)HEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (2 (PYRIDIN 3 YL)ACETAMIDO)HEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (3,3 DIMETHYLUREIDO)HEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (BUT 2 ENAMIDO)HEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (CYCLOHEX 1 ENECARBOXAMIDO)HEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (NICOTINAMIDO)HEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 (PICOLINAMIDO)HEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 BENZAMIDOHEXANAMIDO)PROPANOATE; METHYL 2 (2 (2 ACETAMIDOPROPANAMIDO) 6 PIVALAMIDOHEXANAMIDO)PROPANOATE; METHYL 2 (6 ACETAMIDO 2 (2 ACETAMIDOPROPANAMIDO)HEXANAMIDO)PROPANOATE; N (5 (2 ACETAMIDOPROPANAMIDO) 6 (1 (METHYLAMINO) 1 OXOPROPAN 2 YLAMINO) 6 OXOHEXYL) 1H PYRROLE 2 CARBOXAMIDE; SIRTUIN 1; SIRTUIN 2; SIRTUIN INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; DRUG DERIVATIVE; LYSINE; PEPTIDE;

ARTICLE; DEACETYLATION; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SYNTHESIS; HYDROGENATION; SOLID PHASE SYNTHESIS; AMINO ACID SEQUENCE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINO ACID SEQUENCE; HISTONE DEACETYLASE INHIBITORS; HUMANS; LYSINE; PEPTIDES; SIRTUIN 1; SIRTUIN 2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77955419658     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.06.035     Document Type: Article

References (36)

1. M.C. Haigis, and D.A. Sinclair Annu. Rev. Pathol. 5 2010 253
2. S. Lavu, O. Boss, P.J. Elliott, and P.D. Lambert Nat. Rev. Drug Disc. 7 2008 841
3. J.C. Milne, P.D. Lambert, S. Schenk, D.P. Carney, J.J. Smith, D.J. Gagne, L. Jin, O. Boss, R.B. Perni, C.B. Vu, J.E. Bemis, R. Xie, J.S. Disch, P.Y. Ng, J.J. Nunes, A.V. Lynch, H. Yang, H. Galonek, K. Israelian, W. Choy, A. Iffland, S. Lavu, O. Medvedik, D.A. Sinclair, J.M. Olefsky, M.R. Jirousek, P.J. Elliott, and C.H. Westphal Nature 450 2007 712
4. D.M. Taylor, M.M. Maxwell, R. Luthi-Carter, and A.G. Kazantsev Cell. Mol. Life Sci. 65 2008 4000
5. F.J. Alcain, and J.M. Villalba Expert Opin. Ther. Patents 19 2009 283
6. V. Guarani, and M. Potente Curr. Opin. Pharmacol. 10 2010 139
7. B. Peck, C.Y. Chen, K.K. Ho, P. Di Fruscia, S.S. Myatt, R.C. Coombes, M.J. Fuchter, C.D. Hsiao, and E.W. Lam Mol. Cancer Ther. 9 2010 844
8. A. Mai, and L. Altucci Int. J. Biochem. Cell Biol. 41 2009 199
9. R.C. Neugebauer, W. Sippl, and M. Jung Curr. Pharm. Des. 14 2008 562
10. R. Luthi-Carter, D.M. Taylor, J. Pallos, E. Lambert, A. Amore, A. Parker, H. Moffitt, D.L. Smith, H. Runne, O. Gokce, A. Kuhn, Z. Xiang, M.M. Maxwell, S.A. Reeves, G.P. Bates, C. Neri, L.M. Thompson, J.L. Marsh, and A.G. Kazantsev Proc. Natl. Acad. Sci. U.S.A. 107 2010 7927
11. T.F. Outeiro, E. Kontopoulos, S.M. Altmann, I. Kufareva, K.E. Strathearn, A.M. Amore, C.B. Volk, M.M. Maxwell, J.C. Rochet, P.J. McLean, A.B. Young, R. Abagyan, M.B. Feany, B.T. Hyman, and A.G. Kazantsev Science 317 2007 516
12. B.C. Smith, W.C. Hallows, and J.M. Denu Chem. Biol. 15 2008 1002
13. M.T. Borra, M.R. Langer, J.T. Slama, and J.M. Denu Biochemistry 43 2004 9877
14. J.L. Avalos, J.D. Boeke, and C. Wolberger Mol. Cell 13 2004 639
15. K. Zhao, R. Harshaw, X. Chai, and R. Marmorstein Proc. Natl. Acad. Sci. U.S.A. 101 2004 8563
16. A.A. Sauve, I. Celic, J. Avalos, H. Deng, J.D. Boeke, and V.L. Schramm Biochemistry 40 2001 15456
17. B.C. Smith, and J.M. Denu Biochemistry 45 2006 272
18. M.D. Jackson, M.T. Schmidt, N.J. Oppenheimer, and J.M. Denu J. Biol. Chem. 278 2003 50985
19. A.A. Sauve, and V.L. Schramm Biochemistry 42 2003 9249
20. T. Huhtiniemi, T. Suuronen, V.M. Rinne, C. Wittekindt, M. Lahtela-Kakkonen, E. Jarho, E.A. Wallen, A. Salminen, A. Poso, and J. Leppanen J. Med. Chem. 51 2008 4377
21. T. Huhtiniemi, C. Wittekindt, T. Laitinen, J. Leppanen, A. Salminen, A. Poso, and M. Lahtela-Kakkonen J. Comput. Aided Mol. Des. 20 2006 589
22. P.H. Kiviranta, J. Leppanen, S. Kyrylenko, H.S. Salo, M. Lahtela-Kakkonen, A.J. Tervo, C. Wittekindt, T. Suuronen, E. Kuusisto, T. Jarvinen, A. Salminen, A. Poso, and E.A. Wallen J. Med. Chem. 49 2006 7907
23. P.H. Kiviranta, J. Leppanen, V.M. Rinne, T. Suuronen, O. Kyrylenko, S. Kyrylenko, E. Kuusisto, A.J. Tervo, T. Jarvinen, A. Salminen, A. Poso, and E.A. Wallen Bioorg. Med. Chem. Lett. 17 2007 2448
24. P.H. Kiviranta, H.S. Salo, J. Leppanen, V.M. Rinne, S. Kyrylenko, E. Kuusisto, T. Suuronen, A. Salminen, A. Poso, M. Lahtela-Kakkonen, and E.A. Wallen Bioorg. Med. Chem. 16 2008 8054
25. A.J. Tervo, S. Kyrylenko, P. Niskanen, A. Salminen, J. Leppanen, T.H. Nyronen, T. Jarvinen, and A. Poso J. Med. Chem. 47 2004 6292
26. A.J. Tervo, T. Suuronen, S. Kyrylenko, E. Kuusisto, P.H. Kiviranta, A. Salminen, J. Leppanen, and A. Poso J. Med. Chem. 49 2006 7239
27. D.G. Fatkins, A.D. Monnot, and W. Zheng Bioorg. Med. Chem. Lett. 16 2006 3651
28. D.G. Fatkins, and W. Zheng Int. J. Mol. Sci. 9 2008 1
29. B.C. Smith, and J.M. Denu Biochemistry 46 2007 14478
30. W.F. Hawse, K.G. Hoff, D.G. Fatkins, A. Daines, O.V. Zubkova, V.L. Schramm, W. Zheng, and C. Wolberger Structure 16 2008 1368
31. L. Jin, W. Wei, Y. Jiang, H. Peng, J. Cai, C. Mao, H. Dai, W. Choy, J.E. Bemis, M.R. Jirousek, J.C. Milne, C.H. Westphal, and R.B. Perni J. Biol. Chem. 284 2009 24394
32. T. Asaba, T. Suzuki, R. Ueda, H. Tsumoto, H. Nakagawa, and N. Miyata J. Am. Chem. Soc. 131 2009 6989
33. P.H. Kiviranta, T. Suuronen, E.A. Wallen, J. Leppanen, J. Tervonen, S. Kyrylenko, A. Salminen, A. Poso, and E.M. Jarho J. Med. Chem. 52 2009 2153
34. B.C. Smith, and J.M. Denu J. Biol. Chem. 282 2007 37256
35. T. Suzuki, T. Asaba, E. Imai, H. Tsumoto, H. Nakagawa, and N. Miyata Bioorg. Med. Chem. Lett. 19 2009 5670
36. B. Heltweg, F. Dequiedt, B.L. Marshall, C. Brauch, M. Yoshida, N. Nishino, E. Verdin, and M. Jung J. Med. Chem. 47 2004 5235