194935-38-1

Basic information

• Product Name: DINOPROSTONE ETHANOLAMIDE
• Synonyms: DINOPROSTONE ETHANOLAMIDE;N-(2-HYDROXYETHYL)-9-OXO-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-AMIDE;PROSTAGLANDIN E2 ETHANOLAMIDE;PGE2-EA;Prostaglandin E2 Ethanolamide Lipid Maps MS Standard;(Z)-N-(2-hydroxyethyl)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enamide;Prostaglandin E2 Ethanolamide MaxSpecStandard
• CAS NO: 194935-38-1
• Molecular Formula: C22H37NO5
• Molecular Weight: 395.53
• Mol File: 194935-38-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DINOPROSTONE ETHANOLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DINOPROSTONE ETHANOLAMIDE(194935-38-1)
• EPA Substance Registry System: DINOPROSTONE ETHANOLAMIDE(194935-38-1)

Safety Data

• Hazardous Substances Data: 194935-38-1(Hazardous Substances Data)

Usage

Description

Prostaglandin E2 ethanolamide (PGE2-EA) is an analog of PGE2 with improved water solubility and stability. PGE2-EA is formed via COX-2 metabolism of arachidonoyl ethanolamide (AEA; ) and acts as an agonist at E prostanoid (EP) receptors 1-4 (Kis = 2.45, 0.46, 0.2, and 0.51 μM, respectively). It also inhibits indoleamine 2,3-dioxygenase-1 (IDO-1) in THP-1 cells and human monocytes (IC50s = 5.7 and 4.7 μM, respectively). PGE2-EA (10 μM) prevents morphological changes and F-actin rearrangement as well as reduces L-homocysteine-induced NLRP3 inflammasome formation and activation in podocytes. Ex vivo, PGE2-EA reduces luminal damage and lymphocyte infiltration in a human mucosal explant colitis model.

Uses

Prostaglandin E2 Ethanolamide-d4 is the isotope labelled analogue of Prostaglandin E2 Ethanolamide, an analogue of Prostaglandin E2 (P838610). Prostaglandin E2 is most common and most biologically potent of mammalian prostaglandins.

Upstream product

• 398138-27-7 prostaglandin H₂ 1-ethanolamide 9,11-cycloendoperoxide 
• 363-24-6 dinoprostone 
• 141-43-5 ethanolamine 

Relevant articles and documents

A Unique Collision-Induced Dissociation Reaction of Cholamine Derivatives of Certain Prostaglandins

Prostaglandins (PGs) are biologically active metabolites of arachidonic acid containing 20 carbon atoms, a cyclic moiety, and two side chains (A and B) in common. The bioassay of PGs requires high sensitivity because of their low concentration in tissues and blood and has usually been carried out by electrospray ionization tandem mass spectrometry (ESI-MS/MS) in the negative ion mode. Chemical derivatization of PG carboxylic acid groups to introduce positive charge-carrying groups is an established strategy to improve the sensitivity and selectivity of such assays. In this study, we exploited this approach for structural identification of a series of PGs using cholamine derivatization through an amidation reaction. However, we observed that collision-induced dissociation of these derivatives gave rise to unexpected product ions that we postulated were formed by unique long-range intramolecular reactions resulting in dehydration of the B chain accompanied by fragmentation of the A chain through an unusual Hofmann rearrangement. Evidence for the proposed mechanism is presented based on ESI-MS/MS and high resolution mass spectrometry studies of cholamine derivatives of PGE1, PGE2, PGD2, PGI2, and C-17 methyl deuterium-labeled limaprost. [Figure not available: see fulltext.].