Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 40, Issue 3, Pages 271-279Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2004.10.013
Keywords
MMP; matrix metalloproteinases inhibitors; tripeptide phosphonates; right-hand inhibitors; left-hand inhibitors
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The phosphotryptophan derivative L-Pro-L-LeU-L-(P)Trp(OH)(2) (2b) was reported as the first example of left-hand-side(1) phosphonate inhibitor of MMP-8. Its uncommon mode of binding to MMP-8 was mainly ascribed to the presence of the proline residue in P, Ten new analogues of 2b were obtained by replacement of the aminoterminal L-Pro with aminoacid residues bearing small side chains. Most of the new analogues show an increase of affinity for MMP-2 and MMP-8, and different profiles of selectivity. Computer simulations were performed to explain the effects of substitutions on the preferred mode of binding. They reveal that most of the new analogues are probably accommodated in the right. rather than left-hand side of MMP-8 active site. (c) 2005 Elsevier SAS. All rights reserved.
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