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SML2076

Sigma-Aldrich

ONO-AE3-208

≥98% (HPLC)

Synonym(s):

4-(4-Cyano-2-(2-(4-fluoronaphthalen-1-yl)propanamido)phenyl)butanoic acid, 4-Cyano-2-[[2-(4-fluoro-1-naphthalenyl)-1-oxopropyl]amino]benzenebutanoic acid, AE3-208

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About This Item

Empirical Formula (Hill Notation):
C24H21FN2O3
CAS Number:
402473-54-5
Molecular Weight:
404.43
MDL number:
MFCD13184814
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

CC(C1=C(C=CC=C2)C2=C(F)C=C1)C(NC3=CC(C#N)=CC=C3CCCC(O)=O)=O

InChI

1S/C24H21FN2O3/c1-15(18-11-12-21(25)20-7-3-2-6-19(18)20)24(30)27-22-13-16(14-26)9-10-17(22)5-4-8-23(28)29/h2-3,6-7,9-13,15H,4-5,8H2,1H3,(H,27,30)(H,28,29)

InChI key

MTDIMKNAJUQTIO-UHFFFAOYSA-N

Biochem/physiol Actions

ONO-AE3-208 is an orally active prostaglandin E2 receptor 4 (EP4)-selective antagonist (Ki in nM = 1.3/EP4, 30/EP3, 790/FP and 2400/TP; Ki >10 μM for prostanoid receptors DP, EP1, EP2, IP). Both EP4-/- mice and ONO-AE3-208-treated wild-type mice (10 mg/kg/day in drinking water) are shown to develop severe symptoms (diarrhea, hemoccult, weight loss) in a murine model of DSS-induced colitis. ONO-AE3-208 is also reported to promote ductus arteriosus constriction among fetal and neonatal rats in vivo (10 mg/kg administered orogastrically). In addition, ONO-AE3-208 is demonstrated to effectively inhibit 1 ng/mL IL-1β-induced HUVEC migration in vitro (53% and 75% inhibition by 1 or 10 μM AE3-208, repectively) and block IL-1β (30 ng/Hydron pellet implant)-induced angionesis in mouse corneas in vivo (1 mg/kg/day p.o.).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Kenji Kabashima et al.
The Journal of clinical investigation, 109(7), 883-893 (2002-04-03)
We used mice deficient in each of the eight types and subtypes of prostanoid receptors and examined the roles of prostanoids in dextran sodium sulfate-induced (DSS-induced) colitis. Among the prostanoid receptor-deficient mice, only EP4-deficient mice and not mice deficient in
Kenta Watanabe et al.
Biochemical and biophysical research communications, 478(1), 154-161 (2016-07-28)
The metastasis of tumors to bone is known to be promoted by prostaglandin E2 (PGE2) produced by the tumor host stromal tissue. Although bone metastases frequently occur in prostate cancer patients, the significance of PGE2 in stromal responses to the
Mousumi Majumder et al.
Stem cells (Dayton, Ohio), 34(9), 2290-2305 (2016-06-15)
Cancer stem-like cells (SLC) resist conventional therapies, necessitating searches for SLC-specific targets. We established that cyclo-oxygenase(COX)-2 expression promotes human breast cancer progression by activation of the prostaglandin(PG)E-2 receptor EP4. Present study revealed that COX-2 induces SLCs by EP4-mediated NOTCH/WNT signaling.
Kazuo Momma et al.
Pediatric research, 58(5), 971-975 (2005-11-01)
Indomethacin is used to constrict the patent ductus arteriosus in premature infants. To clarify possible prostanoid receptor antagonists that can constrict the ductus, we studied in vivo constriction of the fetal and neonatal ductus arteriosus by AE3-208, a prostanoid EP4-receptor
Takashi Kuwano et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 18(2), 300-310 (2004-02-11)
Cyclooxygenase1 (COX1) and COX2 mediate the rate-limiting step in arachidonic acid metabolism. Expression of COX2 mRNA and protein is often enhanced in various human cell types by inflammatory cytokines such as interleukin-1beta (IL-1beta) and tumor necrosis factor alpha (TNFalpha). IL-1beta
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