A1221
AH6809
≥98%, crystalline solid or supercooled liquid
Synonym(s):
6-Isopropoxy-9-oxoxanthene-2-carboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C17H14O5
CAS Number:
Molecular Weight:
298.29
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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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
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
Certificates of Analysis (COA)
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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
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
Marchessini Casibang et al.
Lung cancer (Amsterdam, Netherlands), 36(1), 33-42 (2002-03-14)
The effects of prostaglandin (PG)E2 on lung cancer cells were investigated. 3H-PGE2 bound with high affinity to membranes derived from small cell lung cancer (SCLC) and non-SCLC (NSCLC) cell lines. Using NSCLC NCI-H1299 membranes, specific 3H-PGE2 binding to NCI-H1299 membranes
P Li et al.
Neuroscience, 164(3), 948-962 (2009-08-29)
This study aimed to investigate the effect of hypoxia on the expression of cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2), microsomal prostaglandin-E synthase (mPGES-1), E-prostanoid receptor 2 (EP2) in microglia; and the roles of EP2-cyclic adenosine monophosphate (cAMP) signaling pathway in the prostaglandin
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