Synthesis and evaluation of new tripeptide phosphonate inhibitors of MMP-8 and MMP-2

被引：23
|
作者：
Agamennone, M
Campestre, C
Preziuso, S
Consalvi, V
Crucianelli, M
Mazza, F
Politi, V
Ragno, R
Tortorella, P
Gallina, C
机构：
[1] Univ G dAnnunzio, Dipartimento Sci Farmaco, I-66013 Chieti, Italy
[2] Univ Roma La Sapienza, Dipartimento Sci Biochim, I-00185 Rome, Italy
[3] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Coppito, Italy
[4] Polifarma Res Ctr, I-00185 Rome, Italy
[5] Univ Bari, Dipartimento Farmacochim, I-70125 Bari, Italy
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2005年 / 40卷 / 03期
关键词：
MMP; matrix metalloproteinases inhibitors; tripeptide phosphonates; right-hand inhibitors; left-hand inhibitors;
D O I：
10.1016/j.ejmech.2004.10.013
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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.
引用
收藏
页码：271 / 279
页数：9
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