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A1221

Sigma-Aldrich

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:
33458-93-4
Molecular Weight:
298.29
MDL number:
MFCD08056083
UNSPSC Code:
12352200
PubChem Substance ID:
329770690
NACRES:
NA.77

Quality Level

100

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)

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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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 M Dickerson et al.
Endocrinology, 152(2), 581-594 (2010-12-31)
In mammals, sexual differentiation of the hypothalamus occurs during prenatal and early postnatal development due in large part to sex differences in hormones. These early organizational processes are critically important for the attainment and maintenance of adult reproductive functions. We
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
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
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