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Novel tail and head group prostamide probes.

David F Finnegan1, Erin L Shelnut1, Spyros P Nikas1

  • 1Center for Drug Discovery and Departments of Chemistry and Chemical Biology and Pharmaceutical Sciences, Northeastern University, 360 Huntington Ave, 116 Mugar Hall, Boston, MA 02115, USA.

Bioorganic & Medicinal Chemistry Letters
|February 22, 2015
PubMed
Summary

Researchers synthesized novel prostaglandin-ethanolamide (PGE2-EA) analogs to identify a specific prostamide receptor. These analogs did not bind to known receptors, suggesting a new target for PGE2-EA action.

Keywords:
Cyclooxygenase-2EndocannabinoidsProstamides

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Area of Science:

  • Medicinal Chemistry
  • Neuroscience
  • Pharmacology

Background:

  • Prostaglandin-ethanolamides (PGE2-EAs) are bioactive lipids implicated in various physiological processes.
  • The specific receptor(s) mediating PGE2-EA actions remain largely uncharacterized.
  • Existing research has not fully elucidated the molecular targets of PGE2-EAs.

Purpose of the Study:

  • To design and synthesize novel PGE2-EA analogs with modified head and tail groups.
  • To aid in the characterization of the putative prostamide receptor(s).
  • To investigate the binding interactions of these analogs with known receptors and proteins.

Main Methods:

  • Utilized Horner-Wadsworth-Emmons and Wittig reactions for synthesizing the PGE2 precursor.
  • Employed peptide coupling, Swern oxidation, and desilylation for final product synthesis.
  • Tested analog interactions with endocannabinoid proteins and recombinant EP1, EP3, and EP4 receptors.

Main Results:

  • Successfully synthesized novel PGE2-EA analogs with structural modifications.
  • The synthesized analogs showed no significant interaction with endocannabinoid proteins.
  • No significant binding was observed with recombinant EP1, EP3, and EP4 receptors.

Conclusions:

  • The novel PGE2-EA analogs are valuable tools for probing prostamide receptor function.
  • The findings suggest the existence of an unidentified receptor for PGE2-EA.
  • Further research is warranted to identify and characterize this novel prostamide receptor.