Potent transglutaminase inhibitors, aryl β-aminoethyl ketones

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 1141-1144

  Ozaki, Shoichiro ^a   Ebisui, Etsuko ^a   Hamada, Kozo ^a,b   Goto, Jun Ichi ^a   Suzuki, Akinobu Z ^a   Terauchi, Akiko ^a,b   Mikoshiba, Katsuhiko ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Alzheimer's disease; Celiac disease; Huntington's disease; Parkinson's disease; Protein cross link inhibitor; Transglutaminase inhibitor

Indexed keywords

5 BROMO 2 THIENYL(N TERT BUTYL N BENZYL)AMINOETHYL KETONE; ACYLTRANSFERASE INHIBITOR; AMINE; AROMATIC COMPOUND; ARYL BETA AMINOETHYL KETONE; BENZYLAMINE DERIVATIVE; CARBONYL DERIVATIVE; ETHANOLAMINE DERIVATIVE; KETONE DERIVATIVE; LDDN 80042; N BENZYL N TERT BUTYL AMINOETHYL; THIOPHENE DERIVATIVE; TRANSGLUTAMINASE INHIBITOR; UNCLASSIFIED DRUG; KETONE; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE;

ARTICLE; CONTROLLED STUDY; CROSS LINKING; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; OLIGOMERIZATION; SUBSTITUTION REACTION; TISSUE; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECTS; ENZYMOLOGY; GUINEA PIG; LIVER; METABOLISM;

ANIMALS; GUINEA PIGS; KETONES; LIVER; TRANSGLUTAMINASES;

EID: 74049137148     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.011     Document Type: Article

References (35)

1. Griffin M., Casadio R., and Bergamini C.M. Biochem. J. 368 Pt 2 (2002) 377
2. Lorand L., and Graham R.M. Nat. Rev. Mol. Cell Biol. 4 (2003) 140
3. Candi E., Schmidt R., and Melino G. Nat. Rev. Mol. Cell Biol. 6 (2005) 328
4. Norlund M.A., Lee J.M., Zainelli G.M., and Muma N.A. Brain Res. 851 (1999) 154
5. Selkoe D.J., Abraham C., and Ihara Y. Proc. Natl. Acad. Sci. U.S.A. 79 (1982) 6070
6. Mastroberardino P.G., Iannicola C., Nardacci R., Bernassola F., De Laurenzi V., Melino G., Moreno S., Pavone F., Oliverio S., Fesus L., and Piacentini M. Cell Death Differ. 9 (2002) 873
7. Jeitner T.M., Matson W.R., Folk J.E., Blass J.P., and Cooper A.J. J. Neurochem. 106 (2008) 37
8. Karpuj M.V., Becher M.W., Springer J.E., Chabas D., Youssef S., Pedotti R., Mitchell D., and Steinman L. Nat. Med. 8 (2002) 143
9. Dedeoglu A., Kubilus J.K., Jeitner T.M., Matson S.A., Bogdanov M., Kowall N.W., Matson W.R., Cooper A.J., Ratan R.R., Beal M.F., Hersch S.M., and Ferrante R.J. J. Neurosci. 22 (2002) 8942
10. Lorand L. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 14310
11. Hoffner G., and Djian P. Front. Biosci. 10 (2005) 3078
12. Grierson A.J., Johnson G.V., and Miller C.C. Neurosci. Lett. 298 (2001) 9
13. Hartley D.M., Zhao C., Speier A.C., Woodard G.A., Li S., Li Z., and Walz T. J. Biol. Chem. 283 (2008) 16790
14. De Young L., Ballaron S., and Epstein W. J. Invest. Dermatol. 82 (1984) 275
15. Malorni W., Farrace M.G., Rodolfo C., and Piacentini M. Curr. Pharm. Des. 14 (2008) 278
16. Azari P., Rahim I., and Clarkson D.P. Curr. Eye Res. 1 (1981) 463
17. Schroeder W.T., Thacher S.M., Stewart-Galetka S., Annarella M., Chema D., Siciliano M.J., Davies P.J., Tang H.Y., Sowa B.A., and Duvic M. J. Invest. Dermatol. 99 (1992) 27
18. Choi K., Siegel M., Piper J.L., Yuan L., Cho E., Strnad P., Omary B., Rich K.M., and Khosla C. Chem. Biol. 12 (2005) 469
19. Tatsukawa H., Fukaya Y., Frampton G., Martinez-Fuentes A., Suzuki K., Kuo T.F., Nagatsuma K., Shimokado K., Okuno M., Wu J., Iismaa S., Matsuura T., Tsukamoto H., Zern M.A., Graham R.M., and Kojima S. Gastroenterology 136 (2009) 1783
20. Lorand L., Rule N.G., Ong H.H., Furlanetto R., Jacobsen A., Downey J., Oner N., and Bruner-Lorand J. Biochemistry 7 (1968) 214
21. Stenberg P., Nilsson J.L., Eriksson O., and Lunden R. Acta Pharm. Suec. 8 (1971) 415
22. Fesus L. Surv. Immunol. Res. 1 (1982) 297
23. Piper J.L., Gray G.M., and Khosla C. Biochemistry 41 (2002) 386
24. Hovhannisyan Z., Weiss A., Martin A., Wiesner M., Tollefsen S., Yoshida K., Ciszewski C., Curran S.A., Murray J.A., David C.S., Sollid L.M., Koning F., Teyton L., and Jabri B. Nature 456 (2008) 534
25. Duval E., Case A., Stein R.L., and Cuny G.D. Bioorg. Med. Chem. Lett. 15 (2005) 1885
26. Griffin M., Mongeot A., Collighan R., Saint R.E., Jones R.A., Coutts I.G., and Rathbone D.L. Bioorg. Med. Chem. Lett. 18 (2008) 5559
27. Watts R.E., Siegel M., and Khosla C. J. Med. Chem. 49 (2006) 7493
28. Pardin C., Pelletier J.N., Lubell W.D., and Keillor J.W. J. Org. Chem. 73 (2008) 5766
29. Lai T.S., Liu Y., Tucker T., Daniel K.R., Sane D.C., Toone E., Burke J.R., Strittmatter W.J., and Greenberg C.S. Chem. Biol. 15 (2008) 969
30. Arend M., Westermann B., and Risch N. Angew. Chem., Int. Ed. 37 (1998) 1044
31. Brown G.R., Bamford A.M., Bowyer J., James D.S., Rankine N., Tang E., Torr V., and Culbert E.J. Bioorg. Med. Chem. Lett. 10 (2000) 575
32. Mannkind cooporation. Intracellular Kinase Inhibitors. PCT WO 2007/136790 A2.
33. 50 values were calculated by nonlinear regression analysis to fit experimental data to the logistic function with 4 or 3 parameters using SigmaPlot.
34. Lorand L., Lockridge O.M., Campbell L.K., Myhrman R., and Bruner-Lorand J. Anal. Biochem. 44 (1971) 221
35. 22BrNOS, 380.0684.