Document Detail

N-Amino acid linoleoyl conjugates: anti-inflammatory activities.
MedLine Citation:
PMID:  22217875     Owner:  NLM     Status:  MEDLINE    
Several N-linked amino acid-linoleic acid conjugates were studied for their potential as anti inflammatory agents. The parent molecule, N-linoleoylglycine was tested in an in vivo model, the mouse peritonitis assay where it showed activity in reducing leukocyte migration at doses as low as 0.3mg/kg when administered by mouth in safflower oil. Harvested peritoneal cells produced elevated levels of the inflammation-resolving eicosanoid 15-deoxy-Δ(13,14)-PGJ(2). These results are similar to those obtained in earlier studies with N-arachidonoylglycine. An in vitro model using mouse macrophage RAW cells was used to evaluate a small group of structural analogs for their ability to stimulate 15-deoxy-Δ(13,14)-PGJ(2) production. The d-alanine derivative was the most active while the d-phenylalanine showed almost no response. A high degree of stereo specificity was observed comparing the d and l alanine isomers; the latter being the less active. It was concluded that linoleic acid conjugates could provide suitable templates in a drug discovery program leading to novel agents for promoting the resolution of chronic inflammation.
Sumner Burstein; Catherine McQuain; Rebecca Salmonsen; Benjamin Seicol
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2011-12-16
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  22     ISSN:  1464-3405     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2012-01-13     Completed Date:  2012-08-24     Revised Date:  2014-09-21    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  872-5     Citation Subset:  IM    
Copyright Information:
Copyright © 2011. Published by Elsevier Ltd.
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MeSH Terms
Amino Acids / chemistry*
Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis,  chemistry,  pharmacology*
Cell Line
Dose-Response Relationship, Drug
Linoleic Acid / chemistry*
Macrophages / drug effects,  immunology
Molecular Structure
Structure-Activity Relationship
Grant Support
DA-023635/DA/NIDA NIH HHS; R21 DA017969/DA/NIDA NIH HHS; R21 DA017969-01/DA/NIDA NIH HHS; R21 DA017969-02/DA/NIDA NIH HHS; R21 DA017969-03/DA/NIDA NIH HHS; R21 DA017969-03S1/DA/NIDA NIH HHS
Reg. No./Substance:
0/Amino Acids; 0/Anti-Inflammatory Agents, Non-Steroidal; 9KJL21T0QJ/Linoleic Acid

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