Document Detail

Synthesis and contractile activity of new pseudopeptido and thioaromatic analogues of leukotriene D4.
MedLine Citation:
PMID:  1312247     Owner:  NLM     Status:  MEDLINE    
Seven new pseudopeptido and thioaromatic leukotriene analogues were synthesized and their agonist-antagonist and binding activities investigated. The synthesis led to the pleasing observation that the analogue in which the cysteinyl-glycine moiety was replaced by a 6-mercapto-3-(E)-hexenoic acid, not only exhibited potent affinity (guinea-pig lung parenchyma, IC50: 5 x 10(-9) M) but also showed 30% of the LTD4 agonist activity (guinea-pig ileum, ED 50: 2.7 x 10(-9)) giving very important key information on LTD4 geometry to the receptor. This compound was the first stable new pseudopeptido-leukotriene with such agonist activity and should contribute to the understanding of the metabolism of leukotriene D4. In addition, inversion of chirality at C5 and C6 carbon atoms of the leukotriene chain or replacement of the cysteinyl-glycine moiety by a thioaromatic acid led to new weak antagonists of the LTD4.
N Niel; E Rechencq; A Muller; J P Vidal; R Escale; T Durand; J P Girard; J C Rossi; C Bonne
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Publication Detail:
Type:  In Vitro; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Prostaglandins     Volume:  43     ISSN:  0090-6980     ISO Abbreviation:  Prostaglandins     Publication Date:  1992 Jan 
Date Detail:
Created Date:  1992-04-10     Completed Date:  1992-04-10     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0320271     Medline TA:  Prostaglandins     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  45-54     Citation Subset:  IM    
Laboratoire de Chimie des Mediateurs et Physicochimie des Interactions Biologiques associe au C.N.R.S., Faculte de Pharmacie, Universite Montpellier I, France.
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MeSH Terms
Guinea Pigs
Ileum / drug effects
Lung / metabolism
Muscle Contraction / drug effects
Receptors, Immunologic / drug effects
Receptors, Leukotriene
SRS-A / analogs & derivatives*,  chemical synthesis,  pharmacology
Reg. No./Substance:
0/Receptors, Immunologic; 0/Receptors, Leukotriene; 0/SRS-A

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