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A1221

Sigma-Aldrich

AH6809

≥98%, crystalline solid or supercooled liquid

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Synonym(s):
6-Isopropoxy-9-oxoxanthene-2-carboxylic acid
Empirical Formula (Hill Notation):
C17H14O5
CAS Number:
Molecular Weight:
298.29
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98%

form

crystalline solid or supercooled liquid

solubility

ethanol: soluble 2.5 mg/mL
DMSO or DMF: soluble 8 mg/mL

SMILES string

CC(C)Oc1ccc2c(Oc3ccc(cc3C2=O)C(O)=O)c1

InChI

1S/C17H14O5/c1-9(2)21-11-4-5-12-15(8-11)22-14-6-3-10(17(19)20)7-13(14)16(12)18/h3-9H,1-2H3,(H,19,20)

InChI key

AQFFXPQJLZFABJ-UHFFFAOYSA-N

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This Item
B7273V6383L6538
AH6809 ≥98%, crystalline solid or supercooled liquid

Sigma-Aldrich

A1221

AH6809

Bezafibrate ≥98%, solid

Sigma-Aldrich

B7273

Bezafibrate

Vinpocetine ≥98%, solid

Sigma-Aldrich

V6383

Vinpocetine

Limaprost ≥99%, crystalline

Sigma-Aldrich

L6538

Limaprost

form

crystalline solid or supercooled liquid

form

solid

form

solid

form

crystalline

solubility

ethanol: soluble 2.5 mg/mL, DMSO or DMF: soluble 8 mg/mL

solubility

DMF: soluble, deionized water: insoluble, methanol: soluble

solubility

DMSO: 5 mg/mL, H2O: insoluble

solubility

DMF: soluble, DMSO: soluble, ethanol: soluble

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

Application

AH6809 has been used:
  • as a prostaglandin E2 receptor 1 & 2 (EP1/2) antagonist to analyze its effects on cyclooxygenase-2 /prostaglandin E2 (COX-2/PGE2) signaling in the angiogenic feedback of endothelial cells to hypoxia
  • as an EP2 antagonist to study its effects on tumor angiogenesis in human prostate cancer cell lines
  • as an EP2 antagonist to analyze its effects on overexpression of amyloid precursor protein (APP)

Biochem/physiol Actions

AH6809 plays a role in antagonizing the proliferation of non-small cell lung cancer cell lines.
DP/EP prostanoid receptor antagonist; has the highest affinity for DP receptors, but also acts as a weak antagonist at murine EP1 and EP2 prostanoid receptors.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Amy M Pooler et al.
Neuroscience letters, 362(2), 127-130 (2004-06-15)
We investigated the effects of prostaglandin E2 (PGE2) on amyloid precursor protein (APP) expression in cultured rat microglia. PGE2 treatment significantly increased the expression of APP holoprotein and was associated with an elevation in cyclic AMP (cAMP). Direct activation of
Shalini Jain et al.
Cancer research, 68(19), 7750-7759 (2008-10-03)
In cancer management, the cyclooxygenase (COX)-targeted approach has shown great promise in anticancer therapeutics. However, the use of COX-2 inhibitors has side effects and health hazards; thus, targeting its major metabolite prostaglandin E(2) (PGE(2))-mediated signaling pathway might be a rational
Sarah A Maher et al.
American journal of respiratory and critical care medicine, 180(10), 923-928 (2009-09-05)
A significant population of patients with severe asthma and chronic obstructive pulmonary disease is less responsive to beta(2)-adrenoceptor agonists and corticosteroids, and there are possible safety issues concerning long-term use of these drugs. Inhaled prostaglandin E(2) (PGE(2)) is antiinflammatory and
F Stanisçuaski et al.
Journal of insect physiology, 56(9), 1078-1086 (2010-03-13)
Urease isoforms from jack bean seeds are toxic to insects, and this entomotoxic effect is mostly due to the release of a peptide by insect digestive enzymes. We previously demonstrated that jack bean urease (JBU) has antidiuretic effects on Rhodnius
Hiroyuki Isshiki et al.
Biochemical and biophysical research communications, 489(3), 305-311 (2017-06-01)
Methods for the artificial three-dimensional (3D) culture of mouse and human small-intestinal and large-intestinal stem cells have been established with CD24 Using various tissue homogenates, we investigated the colonic organoid forming capacity under the TMDU protocol immediately adjacent to Ootani's

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