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A8227

Sigma-Aldrich

AH23848 hemicalcium salt

≥90% (HPLC), powder

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Synonym(s):
(4Z)-7-[(rel-1S,2S,5R)-5-((1,1′-Biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]- 4-heptenoic acid hemicalcium salt
Empirical Formula (Hill Notation):
C29H34NO5 · 0.5 Ca
CAS Number:
81496-19-7
Molecular Weight:
496.62
MDL number:
MFCD05665139
UNSPSC Code:
12352200
PubChem Substance ID:
24724400
NACRES:
NA.77

Quality Level

100

Assay

≥90% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear
H2O: insoluble

originator

GlaxoSmithKline

storage temp.

−20°C

SMILES string

O=C(C[C@@H](OCC1=CC=C(C2=CC=CC=C2)C=C1)[C@H]3CC/C=C\CCC(O[Ca]OC(CC/C=C\CC[C@@H]4[C@H](OCC5=CC=C(C6=CC=CC=C6)C=C5)CC([C@H]4N7CCOCC7)=O)=O)=O)[C@H]3N8CCOCC8

InChI

1S/2C29H35NO5.Ca/c2*31-26-20-27(35-21-22-12-14-24(15-13-22)23-8-4-3-5-9-23)25(10-6-1-2-7-11-28(32)33)29(26)30-16-18-34-19-17-30;/h2*1-5,8-9,12-15,25,27,29H,6-7,10-11,16-21H2,(H,32,33);/q;;+2/p-2/b2*2-1-;/t2*25-,27-,29+;/m11./s1

InChI key

JDEBIDDIERGZQY-XVFRBOAOSA-L

Related Categories

Application

AH23848 has been used as an prostaglandin E2 receptor 4 (EP4) receptor antagonist to study its effect on cAMP accumulation in monocrotaline (MCT28d) rat pulmonary arterial smooth muscle cells (PASMCs) and human T cell enriched peripheral blood mononuclear cells (PBMC). It has also been used to study its effect on the expressions of collagen-I, metalloproteinase (MMP-1), MMP-3, and EP4 gene expression in human tendon fibroblasts following interleukin (IL)-1β treatment.

Biochem/physiol Actions

AH23848 regulates nitric oxide (NO) production and reduces endogenous cAMP accumulation. This is carried out by declination of inducible nitric oxide synthase (iNOS) gene expression and acceleration of iNOS protein degradation in glomerular mesangial cells.
EP4 prostanoid receptor antagonist with TP blocking activity.

Features and Benefits

This compound is featured on the Prostanoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Role of the prostanoid EP4 receptor in iloprost-mediated vasodilatation in pulmonary hypertension
Lai YJ, et al.
American Journal of Respiratory and Critical Care Medicine, 178(2), 188-196 (2008)
Lipoic acid stimulates cAMP production in T lymphocytes and NK cells
Schillace RV, et al.
Biochemical and biophysical research communications, 354(1), 259-264 (2007)
AH23848 accelerates inducible nitric oxide synthase degradation through attenuation of cAMP signaling in glomerular mesangial cells
Lin YS, et al.
Nitric Oxide, 18(2), 93-104 (2008)
EP4 receptor regulates collagen type-I, MMP-1, and MMP-3 gene expression in human tendon fibroblasts in response to IL-1$\beta$ treatment
Thampatty BP, et al.
Gene, 386(1-2), 154-161 (2007)
Christina L Jones et al.
The Journal of pharmacology and experimental therapeutics, 341(2), 552-563 (2012-03-01)
Oxidative stress is implicated in the pathogenesis of many inflammatory pulmonary diseases, including cystic fibrosis (CF). Delineating how oxidative stress stimulates CF transmembrane conductance regulator (CFTR) in airway epithelial cells is useful, both to increase the understanding of airways host
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