Novel tail and head group prostamide probes.

Authors :: Finnegan DF
Shelnut EL
Nikas SP
Chiang N
Serhan CN
Makriyannis A
Source :: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2015 Mar 15; Vol. 25 (6), pp. 1228-31. Date of Electronic Publication: 2015 Feb 04.
Publication Year :: 2015
Abstract: We report the design and synthesis of novel prostaglandin-ethanolamide (PGE2-EA) analogs containing head and tail group modifications to aid in the characterization of a putative prostamide receptor(s). Our synthetic approach utilizes Horner-Wadsworth-Emmons and Wittig reactions to construct the head and the tail moieties of the key PGE2 precursor, which leads to the final products through a peptide coupling, Swern oxidation and HF/pyridine assisted desilylation. The synthesized analogs were shown not to interact significantly with endocannabinoid proteins and recombinant EP1, EP3 and EP4 receptors and suggest a yet to be identified prostamide receptor as their site(s) of action.<br /> (Copyright © 2015 Elsevier Ltd. All rights reserved.)