A new type of five-membered heterocyclic inhibitors of basic metallocarboxypeptidases

European Journal of Medicinal Chemistry

Volumn 44, Issue 8, 2009, Pages 3266-3271

  Fernández, Daniel ^a   Avilés, Francesc X ^a   Vendrell, Josep ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

1,3,4 Oxadiazole; High throughput screening; Human carboxypeptidase B; Metallocarboxypeptidase; Molecular docking; Protease M14 family

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; CARBOXYPEPTIDASE B; METALLOCARBOXYPEPTIDASE INHIBITOR; METALLOPROTEINASE INHIBITOR; N (3 CHLOROPHENYL) 4 [[5 (3 METHOXYBENZYLTHIO) 1,3,4 OXADIAZOL 2 YL]METHYL]THIAZOL 2 AMINE; UNCLASSIFIED DRUG;

ARTICLE; BIOINFORMATICS; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; MOLECULAR DOCKING; MOLECULAR MODEL;

ANIMALS; CARBOXYPEPTIDASE B; CARBOXYPEPTIDASES A; COMPUTATIONAL BIOLOGY; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; HETEROCYCLIC COMPOUNDS; HUMANS; LEPIDOPTERA; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXAZOLES;

EID: 67349104395     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.03.034     Document Type: Article

References (44)

1. Vendrell J., Aviles F.X., and Fricker L.D. Metallocarboxypeptidases. In: Messerschmidt A., Bode W., and Cygler M. (Eds). Handbook of Metalloproteins (2004), John Wiley and Sons Ltd., Chichester 176-189
2. Rodriguez de la Vega M., Sevilla R.G., Hermoso A., Lorenzo J., Tanco S., Diez A., Fricker L.D., Bautista J.M., and Aviles F.X. FASEB J. 21 (2007) 851-865
3. Wang H., Zhou Q., Kesinger J.W., Norris C., and Valdez C. Exp. Biol. Med. (Maywood) 232 (2007) 1170-1180
4. Zhou Q., Law A.C., Rajagopal J., Anderson W.J., Gray P.A., and Melton D.A. Dev. Cell 13 (2007) 103-114
5. Muller C.A., Appelros S., Uhl W., Buchler M.W., and Borgstrom A. Gut 51 (2002) 229-235
6. Asai S., Sato T., Tada T., Miyamoto T., Kimbara N., Motoyama N., Okada H., and Okada N. J. Immunol. 173 (2004) 4669-4674
7. Willemse J.L., and Hendriks D.F. Front. Biosci. 12 (2007) 1973-1987
8. Fialka F., Gruber R.M., Hitt R., Opitz L., Brunner E., Schliephake H., and Kramer F.J. Oral Oncol. 44 (2008) 941-948
9. Hataji O., Taguchi O., Gabazza E.C., Yuda H., D'Alessandro-Gabazza C.N., Fujimoto H., Nishii Y., Hayashi T., Suzuki K., and Adachi Y. Am. J. Hematol. 76 (2004) 214-219
10. P. Cronet, W. Knecht, C.A.-C. Malmborg Hager, M. Andersson, C. Furebring, Sequences of modified human carboxypeptidase U (CPU) with increased thermal stability for treating hemorrhage disorders, Astrazeneca AB, Swed., Astrazeneca UK Limited, Application: WO. Patent No. 2005052149, 2005.
11. S. Golz, U. Brueggemeier, A. Geerts, Diagnostics and therapeutics for diseases associated with human carboxypeptidase A3 based on tissue expression profiling, Bayer Healthcare AG, Germany, Application: WO. Patent No. 2006010495, 2006.
12. S. Golz, U. Brueggemeier, A. Geerts, Diagnostics and therapeutics for diseases associated with human carboxypeptidase A2 based on tissue expression profiling, Bayer Healthcare AG, Germany, Application: WO. Patent No. 2006010499, 2006.
13. Matsugi S., Hamada T., Shioi N., Tanaka T., Kumada T., and Satomura S. Clin. Chim. Acta 378 (2007) 147-153
14. Yanes O., Villanueva J., Querol E., and Aviles F.X. Nat. Protoc. 2 (2007) 119-130
15. Buchanan M.S., Carroll A.R., Edser A., Sykes M., Fechner G.A., Forster P.I., Guymer G.P., and Quinn R.J. Bioorg. Med. Chem. Lett. 18 (2008) 1495-1497
16. Wang S.H., Wang S.F., Xuan W., Zeng Z.H., Jin J.Y., Ma J., and Tian G.R. Bioorg. Med. Chem. 16 (2008) 3596-3601
17. Wang Y.X., da Cunha V., Vincelette J., Zhao L., Nagashima M., Kawai K., Yuan S., Emayan K., Islam I., Hosoya J., Sullivan M.E., Dole W.P., Morser J., Buckman B.O., and Vergona R. Thromb. Haemostasis 97 (2007) 54-61
18. Wang Y.X., Zhao L., Nagashima M., Vincelette J., Sukovich D., Li W., Subramanyam B., Yuan S., Emayan K., Islam I., Hrvatin P., Bryant J., Light D.R., Vergona R., Morser J., and Buckman B.O. Thromb. Haemostasis 97 (2007) 45-53
19. Fernandez D., Illa O., Aviles F.X., Branchadell V., Vendrell J., and Ortuno R.M. Bioorg. Med. Chem. 16 (2008) 4823-4828
20. Tully W.R., Gardner C.R., Gillespie R.J., and Westwood R. J. Med. Chem. 34 (1991) 2060-2067
21. Orlek B.S., Blaney F.E., Brown F., Clark M.S., Hadley M.S., Hatcher J., Riley G.J., Rosenberg H.E., Wadsworth H.J., and Wyman P. J. Med. Chem. 34 (1991) 2726-2735
22. Ladduwahetty T., Baker R., Cascieri M.A., Chambers M.S., Haworth K., Keown L.E., MacIntyre D.E., Metzger J.M., Owen S., Rycroft W., Sadowski S., Seward E.M., Shepheard S.L., Swain C.J., Tattersall F.D., Watt A.P., Williamson D.W., and Hargreaves R.J. J. Med. Chem. 39 (1996) 2907-2914
23. Mullican M.D., Wilson M.W., Connor D.T., Kostlan C.R., Schrier D.J., and Dyer R.D. J. Med. Chem. 36 (1993) 1090-1099
24. Borg S., Vollinga R.C., Labarre M., Payza K., Terenius L., and Luthman K. J. Med. Chem. 42 (1999) 4331-4342
25. Smith D.H. Drugs 68 (2008) 1207-1225
26. Winum J.Y., Scozzafava A., Montero J.L., and Supuran C.T. Med. Res. Rev. 26 (2006) 767-792
27. Frampton J.E., and Scott L.J. Drugs 68 (2008) 993-1016
28. Pakes G.E., Brogden R.N., Heel R.C., Speight T.M., and Avery G.S. Drugs 22 (1981) 81-110
29. Bayes A., Comellas-Bigler M., Rodriguez de la Vega M., Maskos K., Bode W., Aviles F.X., Jongsma M.A., Beekwilder J., and Vendrell J. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 16602-16607
30. Byers L.D., and Wolfenden R. Biochemistry 12 (1973) 2070-2078
31. McKay T.J., Phelan A.W., and Plummer Jr. T.H. Arch. Biochem. Biophys. 197 (1979) 487-492
32. Barrow J.C., Nantermet P.G., Stauffer S.R., Ngo P.L., Steinbeiser M.A., Mao S.S., Carroll S.S., Bailey C., Colussi D., Bosserman M., Burlein C., Cook J.J., Sitko G., Tiller P.R., Miller-Stein C.M., Rose M., McMasters D.R., Vacca J.P., and Selnick H.G. J. Med. Chem. 46 (2003) 5294-5297
33. Bunnage M.E., Blagg J., Steele J., Owen D.R., Allerton C., McElroy A.B., Miller D., Ringer T., Butcher K., Beaumont K., Evans K., Gray A.J., Holland S.J., Feeder N., Moore R.S., and Brown D.G. J. Med. Chem. 50 (2007) 6095-6103
34. Han M.S., and Kim D.H. Bioorg. Med. Chem. Lett. 11 (2001) 1425-1427
35. Lee K.J., Joo K.C., Kim E.J., Lee M., and Kim D.H. Bioorg. Med. Chem. 5 (1997) 1989-1998
36. Nantermet P.G., Barrow J.C., Lindsley S.R., Young M., Mao S.S., Carroll S., Bailey C., Bosserman M., Colussi D., McMasters D.R., Vacca J.P., and Selnick H.G. Bioorg. Med. Chem. Lett. 14 (2004) 2141-2145
37. Ventura S., Villegas V., Sterner J., Larson J., Vendrell J., Hershberger C.L., and Aviles F.X. J. Biol. Chem. 274 (1999) 19925-19933
38. Cheng Y., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099-3108
39. Joy S., Nair P.S., Hariharan R., and Pillai M.R. In Silico Biol. 6 (2006) 601-605
40. Krier M., Bret G., and Rognan D. J. Chem. Inf. Model. 46 (2006) 512-524
41. Gasteiger J., Rudolph C., and Sadowski J. Tetrahedron Comput. Methodol. 3 (1990) 537-547
42. Miteva M.A., Violas S., Montes M., Gomez D., Tuffery P., and Villoutreix B.O. Nucleic Acids Res. 34 (2006) W738-W744
43. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639-1662
44. Collaborative Computational Project. Acta Crystallogr., Sect. D: Biol. Crystallogr. 50 (1994) 760-776