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Merck

A8227

Sigma-Aldrich

AH23848 hemicalcium salt

≥90% (HPLC), powder

Sinónimos:

(4Z)-7-[(rel-1S,2S,5R)-5-((1,1′-Biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]- 4-heptenoic acid hemicalcium salt

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About This Item

Fórmula empírica (notación de Hill):
C29H34NO5 · 0.5 Ca
Número de CAS:
Peso molecular:
496.62
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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)
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)
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)
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)
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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