Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 8054-8062

  Kiviranta, Päivi H ^a   Salo, Heikki S ^a   Leppänen, Jukka ^a   Rinne, Valtteri M ^a   Kyrylenko, Sergiy ^a   Kuusisto, Erkki ^b   Suuronen, Tiina ^a   Salminen, Antero ^a,c   Poso, Antti ^a   Lahtela Kakkonen, Maija ^a   Wallén, Erik A A ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b NATIONAL PUBLIC HEALTH INSTITUTE   (Finland)

^c KUOPIO UNIVERSITY HOSPITAL   (Finland)

Author keywords

Cluster analysis; Enzyme inhibitors; Molecular docking; SIRT2; Structure activity relationship

Indexed keywords

HISTONE DEACETYLASE; N (3 PHENYLPROPENOYL)GLYCINE TRYPTAMIDE; N [3 (4 HYDROXYPHENYL)PROPENOYL]AMINO ACID TRYPTAMIDE; NICOTINAMIDE; PROTEIN INHIBITOR; SIRTUIN; SIRTUIN 2; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; PROTEIN CONFORMATION; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

BINDING SITES; CINNAMATES; CLUSTER ANALYSIS; COMPUTER SIMULATION; ENZYME INHIBITORS; GLYCINE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; SIRTUINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPTAMINES;

EID: 50349100008     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.059     Document Type: Article

References (53)

1. Sauve A.A., Wolberger C., Schramm V.L., and Boeke J.D. Annu. Rev. Biochem. 75 (2006) 435
2. Smith J.S., Brachmann C.B., Celic I., Kenna M.A., Muhammad S., Starai V.J., Avalos J.L., Escalante-Semerena J.C., Grubmeyer C., Wolberger C., and Boeke J.D. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 6658
3. Tanner K.G., Landry J., Sternglanz R., and Denu J.M. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 14178
4. Smith B.C., and Denu J.M. Biochemistry 45 (2006) 272
5. Michan S., and Sinclair D. Biochem. J. 404 (2007) 1
6. Brachmann C.B., Sherman J.M., Devine S.E., Cameron E.E., Pillus L., and Boeke J.D. Genes Dev. 9 (1995) 2888
7. Guarente L. Genes Dev. 14 (2000) 1021
8. Lin S.J., Ford E., Haigis M., Liszt G., and Guarente L. Genes Dev. 18 (2004) 12
9. Frye R.A. Biochem. Biophys. Res. Commun. 273 (2000) 793
10. Afshar G., and Murnane J.P. Gene 234 (1999) 161
11. Vaquero A., Scher M.B., Lee D.H., Sutton A., Cheng H.L., Alt F.W., Serrano L., Sternglanz R., and Reinberg D. Genes Dev. (2006)
12. Inoue T., Hiratsuka M., Osaki M., Yamada H., Kishimoto I., Yamaguchi S., Nakano S., Katoh M., Ito H., and Oshimura M. Oncogene 26 (2007) 945
13. North B.J., Marshall B.L., Borra M.T., Denu J.M., and Verdin E. Mol. Cell 11 (2003) 437
14. Hubbert C., Guardiola A., Shao R., Kawaguchi Y., Ito A., Nixon A., Yoshida M., Wang X.F., and Yao T.P. Nature 417 (2002) 455
15. Bae N.S., Swanson M.J., Vassilev A., and Howard B.H. J. Biochem. (Tokyo) 135 (2004) 695
16. Hiratsuka M., Inoue T., Toda T., Kimura N., Shirayoshi Y., Kamitani H., Watanabe T., Ohama E., Tahimic C.G., Kurimasa A., and Oshimura M. Biochem. Biophys. Res. Commun. 309 (2003) 558
17. Outeiro T.F., Kontopoulos E., Altmann S.M., Kufareva I., Strathearn K.E., Amore A.M., Volk C.B., Maxwell M.M., Rochet J.C., McLean P.J., Young A.B., Abagyan R., Feany M.B., Hyman B.T., and Kazantsev A.G. Science 317 (2007) 516
18. Garske A.L., Smith B.C., and Denu J.M. ACS Chem. Biol. 2 (2007) 529
19. Grozinger C.M., Chao E.D., Blackwell H.E., Moazed D., and Schreiber S.L. J. Biol. Chem. 276 (2001) 38837
20. Tervo A.J., Kyrylenko S., Niskanen P., Salminen A., Leppanen J., Nyronen T.H., Jarvinen T., and Poso A. J. Med. Chem. 47 (2004) 6292
21. Mai A., Massa S., Lavu S., Pezzi R., Simeoni S., Ragno R., Mariotti F.R., Chiani F., Camilloni G., and Sinclair D.A. J. Med. Chem. 48 (2005) 7789
22. Napper A.D., Hixon J., McDonagh T., Keavey K., Pons J.F., Barker J., Yau W.T., Amouzegh P., Flegg A., Hamelin E., Thomas R.J., Kates M., Jones S., Navia M.A., Saunders J.O., DiStefano P.S., and Curtis R. J. Med. Chem. 48 (2005) 8045
23. Kiviranta P.H., Leppanen J., Kyrylenko S., Salo H.S., Lahtela-Kakkonen M., Tervo A.J., Wittekindt C., Suuronen T., Kuusisto E., Jarvinen T., Salminen A., Poso A., and Wallen E.A. J. Med. Chem. 49 (2006) 7907
24. Heltweg B., Gatbonton T., Schuler A.D., Posakony J., Li H., Goehle S., Kollipara R., DePinho R.A., Gu Y., Simon J.A., and Bedalov A. Cancer Res. 66 (2006) 4368
25. Trapp J., Jochum A., Meier R., Saunders L., Marshall B., Kunick C., Verdin E., Goekjian P., Sippl W., and Jung M. J. Med. Chem. 49 (2006) 7307
26. Trapp J., Meier R., Hongwiset D., Kassack M.U., Sippl W., and Jung M. ChemMedChem 2 (2007) 1419
27. Gey C., Kyrylenko S., Hennig L., Nguyen L.H., Buttner A., Pham H.D., and Giannis A. Angew. Chem., Int. Ed. 46 (2007) 5219
28. Tervo A.J., Suuronen T., Kyrylenko S., Kuusisto E., Kiviranta P.H., Salminen A., Leppanen J., and Poso A. J. Med. Chem. 49 (2006) 7239
29. Kiviranta P.H., Leppanen J., Rinne V.M., Suuronen T., Kyrylenko O., Kyrylenko S., Kuusisto E., Tervo A.J., Jarvinen T., Salminen A., Poso A., and Wallen E.A. Bioorg. Med. Chem. Lett. 17 (2007) 2448
30. Finnin M.S., Donigian J.R., and Pavletich N.P. Nat. Struct. Biol. 8 (2001) 621
31. Huhtiniemi T., Wittekindt C., Laitinen T., Leppanen J., Salminen A., Poso A., and Lahtela-Kakkonen M. J. Comput. Aided Mol. Des. 20 (2006) 589
32. Neugebauer R.C., Uchiechowska U., Meier R., Hruby H., Valkov V., Verdin E., Sippl W., and Jung M. J. Med. Chem. 51 (2008) 1203
33. Garcia-Lopez M.T., Gonzalez-Muniz R., Molinero M.T., Naranjo J.R., and Del Rio J. J. Med. Chem. 30 (1987) 1658
34. Lin J.H., Perryman A.L., Schames J.R., and McCammon J.A. J. Am. Chem. Soc. 124 (2002) 5632
35. Lin J.H., Perryman A.L., Schames J.R., and McCammon J.A. Biopolymers 68 (2003) 47
36. Bottegoni G., Cavalli A., and Recanatini M. J. Chem. Inf. Model. 46 (2006) 852
37. Kelley L.A., Gardner S.P., and Sutcliffe M.J. Protein Eng. 10 (1997) 737
38. Avalos J.L., Celic I., Muhammad S., Cosgrove M.S., Boeke J.D., and Wolberger C. Mol. Cell 10 (2002) 523
39. Warren G.L., Andrews C.W., Capelli A.M., Clarke B., LaLonde J., Lambert M.H., Lindvall M., Nevins N., Semus S.F., Senger S., Tedesco G., Wall I.D., Woolven J.M., Peishoff C.E., and Head M.S. J. Med. Chem. 49 (2006) 5912
40. Leach A.R., Shoichet B.K., and Peishoff C.E. J. Med. Chem. 49 (2006) 5851
41. Andrianaivoravelona J.O., Terreaux C., Sahpaz S., Rasolondramanitra J., and Hostettmann K. Phytochemistry 52 (1999) 1145
42. Sato H., Kawgishi H., Nishimura T., Yoneyama S., Yoshimoto Y., Sakamura S., Furusaki A., Katsuragi S., and Matsumoto T. Agric. Biol. Chem. 49 (1985) 2969
43. Takii T., Kawashima S., Chiba T., Hayashi H., Hayashi M., Hiroma H., Kimura H., Inukai Y., Shibata Y., Nagatsu A., Sakakibara J., Oomoto Y., Hirose K., and Onozaki K. Int. Immunopharmacol. 3 (2003) 273
44. Van Der Spoel D., Lindahl E., Hess B., Groenhof G., Mark A.E., and Berendsen H.J. J. Comput. Chem. 26 (2005) 1701
45. van Gunsteren, W. F; Billeter, S. R.; Eising, A. A.; Hünenberger, P. H.; Krüger, P.; Mark, A. E.; Scott, W. R. P.; Tironi, I. G. In Biomolecular Simulation: The GROMOS96 Manual and User Guide, Hochschulverlag AG an der ETH Zürich: Zürich, Switzerland, 1996.
46. Berendsen H.J.C., Postma J.P.M., van Gunsteren W.F., and Hermans J. In: Pullman B. (Ed). Intermolecular Forces (1981), D. Reidel Publishing Company Dordrecht 331-342
47. Darden T., York D., and Pedersen L. J. Chem. Phys. 98 (1993) 10089
48. Essmann U., Perera L., Berkowitz M.L., Darden T., Lee H., and Pedersen L.G. J. Chem. Phys. 103 (1995) 8577
49. Berendsen H.J.C., Postma J.P.M., DiNola A., and Haak J.R. J. Chem. Phys. 81 (1984) 3684
50. Daura X., Gademann K., Jaun B., Seebach J.D., van Gunsteren W.F., and Mark A.E. Angew. Chem., Int. Ed. 38 (1999) 236
51. Sybyl 7.3, Tripos International, 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA.
52. Jones G., Willett P., Glen R.C., Leach A.R., and Taylor R. J. Mol. Biol. 267 (1997) 727
53. In R Development Core Team (2005). R: A language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, Austria, 2008. http://www.R-project.org.