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Basic Information

ID: ALA1140240

Journal: Bioorg Med Chem Lett

Title: Glutamic acid analogues as potent dipeptidyl peptidase IV and 8 inhibitors.

Authors: Lu IL, Lee SJ, Tsu H, Wu SY, Kao KH, Chien CH, Chang YY, Chen YS, Cheng JH, Chang CN, Chen TW, Chang SP, Chen X, Jiaang WT.

Abstract: To find potent and selective inhibitors of dipeptidyl peptidase IV (DPP-IV), we synthesized a series of 2-cyanopyrrolidine with P2-site 4-substituted glutamic acid derivatives and tested their activities against DPP-IV, DPP8, and DPP-II. Analogues that incorporated a bulky substituent at the first carbon position of benzylamine or isoquinoline showed over 30-fold selectivity for DPP-IV over both DPP8 and DPP-II. From structure-activity relationship studies, we speculate that the S2 site of DPP8 might be similar to that of DPP-IV, while DPP-IV inhibitor with N-substituted glycine in the P2 site and/or with a moiety involving in hydrophobic interaction with the side chain of Phe357 might provide a better selectivity for DPP-IV over DPP8.

CiteXplore: 15927466

DOI: 10.1016/j.bmcl.2005.04.051