Premium
Aminopeptidase Inhibitory Properties and Analgesic Activity of (2 S ,3,7‐3,7‐Diamino‐2‐hydroxy‐heptanoic Acid Containing Tripeptide Analogues of the N ‐Terminal Tripeptide of Probestin
Author(s) -
Herranz Rosario,
Vinuesa Soledad,
Pérez Concepción,
GarcíaLópez M. Teresa,
De Ceballos María L.,
Murillo Francisco M.,
Del Río Joaquín
Publication year - 1992
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19923250812
Subject(s) - tripeptide , dipeptide , chemistry , stereochemistry , aminopeptidase , enkephalin , analgesic , peptide , inhibitory postsynaptic potential , enzyme inhibitor , in vitro , amino acid , biochemistry , opioid , pharmacology , leucine , receptor , medicine , neuroscience , biology
(2 S ,3 R )‐3,7‐Diamino‐2‐hydroxy‐heptanoyl‐Leu‐Pro‐OH [(2 S ,3 R )‐DAHHA‐Leu‐Pro‐OH, 4], analogue of the N ‐terminal tripeptide of probestin, has been synthesized, and tested as inhibitor of AP‐B, Leu‐AP, AP‐M, and enkephalin‐degrading APs, and as analgesic. In order to establish structure‐activity relationships the dipeptide (2 S ,3 R )‐DAHHA‐Pro‐OH ( 5 ) and the tripeptide (2 S , 3 R )‐DAHHA‐Ala‐Pro‐OH ( 6 ) were also prepared. Compounds 4 and 6 were potent and selective inhibitors of enkephalin‐degrading APs and showed a prolonged antinociceptive effect.