Synthesis and biological evaluation of hydroxamate-based inhibitors of glutamate carboxypeptidase II

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 13, 2003, Pages 2097-2100

  Stoermer, Doris ^a   Liu, Qun ^a   Hall, Monicia R ^a   Flanary, Juliet M ^a   Thomas, Ajit G ^a   Rojas, Camilo ^a   Slusher, Barbara S ^a   Tsukamoto, Takashi ^a  

^a GUILFORD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (HYDROXYCARBAMOYLMETHYL)PENTANEDIOIC ACID; AMINOPEPTIDASE; BACTERIAL ENZYME; CARBENE; GAMMA GLUTAMYL HYDROLASE; HYDROXAMIC ACID; HYDROXAMIC ACID DERIVATIVE; INTERSTITIAL COLLAGENASE; PEPTIDE HYDROLASE INHIBITOR; UNCLASSIFIED DRUG; VALERIC ACID;

AEROMONAS; ARTICLE; COMPARATIVE STUDY; CRYSTALLOGRAPHY; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; NONHUMAN; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

EID: 0038209460     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00407-4     Document Type: Article

References (28)

1. Carter, R. E.; Coyle, J. T. In Handbook of Proteolytic Enzymes; Barrett, A. J., Rawlings, N. D., Woessner, J. F., Eds.; Academic: New York, 1998, p 1434.
2. Rawlings N.D., Barrett A.J. Biochim. Biophys. Acta. 1339:1997;247.
3. Whelan J. Drug Discov. Today. 5:2000;171.
4. Jackson P.F., Cole D.C., Slusher B.S., Stetz S.L., Ross L.E., Donzanti B.A., Trainor D.A. J. Med. Chem. 39:1996;619.
5. Rojas C., Frazier S.T., Flanary J., Slusher B.S. Anal. Biochem. 310:2002;50.
6. Slusher B.S., Vornov J.J., Thomas A.G., Hurn P.D., Harukuni I., Bhardwaj A., Traystman R.J., Robinson M.B., Britton P., Lu X.C., Tortella F.C., Wozniak K.M., Yudkoff M., Potter B.M., Jackson P.F. Nat. Med. 5:1999;1396.
7. Jackson P.F., Tays K.L., Maclin K.M., Ko Y.S., Li W., Vitharana D., Tsukamoto T., Stoermer D., Lu X.C., Wozniak K., Slusher B.S. J. Med. Chem. 44:2001;4170.
8. Majer P., Jackson P.F., Delahanty G., Grella B.S., Ko Y.-S., Li W., Liu Q., Maclin K.M., Poláková J., Shaffer K.A., Stoermer D., Vitharana D., Wang E.Y., Zakrzewski A., Slusher B.S., Wozniak K.M., Burak E., Limsakun T., Tsukamoto T. J. Med. Chem. 46:2003;1989.
9. Whittaker M., Floyd C.D., Brown P., Gearing A.J.H. Chem. Rev. 99:1999;2735.
10. Cox R.J., Jenkins H., Schouten J.A., Stentiford R.A., Wareing K.J. J. Chem. Soc., Perkin Trans. 1. 2000;2023.
11. Liotta L.J., Gibbs R.A., Taylor S.D., Benkovic P.A., Benkovic S.J. J. Am. Chem. Soc. 117:1995;4729.
12. Hin B., Majer P., Tsukamoto T. J. Org. Chem. 67:2002;7365.
13. Chorev M., Rubini E., Gilon C., Wormser U., Selinger Z. J. Med. Chem. 26:1983;129.
14. Compounds (S)- and (R)-13, (S)-14, and 16 were purchased from Sigma-Aldrich.
15. Ames D.E., Grey T.F. J. Chem. Soc. 1955;631.
16. Barinka C., Rinnova M., Sacha P., Rojas C., Majer P., Slusher B.S., Konvalinka J. J. Neurochem. 80:2002;477.
17. Vornov J.J. J. Neurochem. 65:1995;1681.
18. Wilkes S.H., Prescott J.M. J. Biol. Chem. 258:1983;13517.
19. Baker J.O., Wilkes S.H., Bayliss M.E., Prescott J.M. Biochemistry. 22:1983;2098.
20. Wagner F.W., Wilkes S.H., Prescott J.M. J. Biol. Chem. 247:1972;1208.
21. Pinto J.T., Suffoletto B.P., Berzin T.M., Qiao C.H., Lin S., Tong W.P., May F., Mukherjee B., Heston W.D. Clin. Cancer Res. 2:1996;1445.
22. Nan F., Bzdega T., Pshenichkin S., Wroblewski J.T., Wroblewska B., Neale J.H., Kozikowski A.P. J. Med. Chem. 43:2000;772.
23. Kozikowski A.P., Nan F., Conti P., Zhang J., Ramadan E., Bzdega T., Wroblewska B., Neale J.H., Pshenichkin S., Wroblewski J.T. J. Med. Chem. 44:2001;298.
24. Rodriguez C.E., Lu H., Martinez A.R., Hu Y., Brunelle A., Berkman C.E. J. Enzyme Inhib. 16:2001;359.
25. Tsukamoto T., Flanary J.M., Rojas C., Slusher B.S., Valiaeva N., Coward J.K. Bioorg. Med. Chem. Lett. 12:2002;2189.
26. Johnson W.H., Roberts N.A., Borkakoti N. J. Enz. Inhib. 2:1987;1.
27. Jackson P.F., Slusher B.S. Curr. Med. Chem. 8:2001;949.
28. Babine R.E., Bender S.L. Chem. Rev. 97:1997;1359.