ONO-AE3-208
ONO-AE3-208 Basic information
- Product Name:
- ONO-AE3-208
- Synonyms:
-
- 4-Cyano-2-[[2-(4-fluoro-1-naphthalenyl)-1-oxopropyl]amino]Benzenebutanoic acid
- ONO-AE3-208
- AE 3-208
- AE 3-208;ONO AE3 208
- ONO-AE3-208;AE 3-208;ONO AE3 208
- Benzenebutanoic acid, 4-cyano-2-[[2-(4-fluoro-1-naphthalenyl)-1-oxopropyl]amino]-
- 4-(4-cyano-2-(2-(4-fluoronaphthalen-1-yl)propanamido)phenyl)butanoic acid
- 4-{4-Cyano-2-[2-(4-fluoro-naphthalen-1-yl)-propionylamino]-phenyl}-butyric acid
- CAS:
- 402473-54-5
- MF:
- C24H21FN2O3
- MW:
- 404.43
- Mol File:
- 402473-54-5.mol
ONO-AE3-208 Chemical Properties
- Boiling point:
- 662.4±55.0 °C(Predicted)
- Density
- 1.30
- storage temp.
- -20°C
- solubility
- ≥40.4 mg/mL in DMSO with gentle warming; insoluble in H2O; ≥8.1 mg/mL in EtOH with gentle warming and ultrasonic
- pka
- 4.69±0.10(Predicted)
- form
- powder
- color
- white to beige
- InChI
- 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)
- InChIKey
- MTDIMKNAJUQTIO-UHFFFAOYSA-N
- SMILES
- C1(CCCC(O)=O)=CC=C(C#N)C=C1NC(=O)C(C1=C2C(C=CC=C2)=C(F)C=C1)C
ONO-AE3-208 Usage And Synthesis
Uses
ONO AE3 208 is a prostaglandin E receptor EP4 antagonist, which inhibits breast cancer metastasis.
Biological Activity
ono-ae3-208 is an antagonist of ep4 [1].ep4 is one of the prostaglandin e2 receptors and is associated with inflammatory disease and cancer such as prostate cancer. as an antagonist of ep4, ono-ae3-208 is expected to be a potential therapy for prostate cancer. in vitro assays show that ono-ae3-208 can suppress the migration and invasion of prostate cancer cells. 10μm of ono-ae3-208 decreases wound healing proportion of pc3 and lncap cell lines in wound-healing assay. and in transwell invasion assay, ono-ae3-208 inhibits cell invasion even at concentration of 0.1μm. ono-ae3-208 is also reported to suppress bone metastasis in vivo [1].since activation of e2 can increase the expression of matrix metalloproteinase (mmp) and release inflammatory cytokines, and then exacerbates abdominal aortic aneurism (aaa) formation, ono-ae3-208 is also used in the studies of aaa formation. it has been proved that ono-ae3-208 can cause the elastic fiber degradation and inhibit aaa formation in vivo in a dose-dependent manner [2].
in vivo
ONO-AE3-208 surpresses the in vivo bone metastasis of PC3 cells in mice[2]. The photon tumor burdens are significantly increased in a time-dependent manner in the control group in comparison with those in the ONO-AE3-208-treated group. The rate of metastasis formation is significantly higher in the former than in the latter. The median time of metastasis formation is 29 d in the ONO-AE3-208-treated animals as compared with 21 d in the controls[4].
IC 50
FP: 790 nM (Ki); TP Receptor: 2400 nM (Ki); EP4: 1.3 nM (Ki); EP3: 30 nM (Ki)
storage
Store at -20°C
References
[1] song xu, zhengyu zhang, osamu ogawa,takeshi yoshikawa, hiromasa sakamoto, noboru shibasaki, akayuki goto, liming wang, naoki terada. an ep4 antagonist ono-ae3-208 suppresses cell invasion, migration and metastasis of prostate cancer. cell biochem biophys. 2014, april.
[2] utako yokoyama, ryo ishiwata, mei-hua jin, yuko kato, orie suzuki, huiling jin, yasuhiro ichikawa, syun kumagaya, yuzo katayama, takayuki fujita, satoshi okumura, motohiko sato, yukihiko sugimoto, hiroki aoki, shinichi suzuki, munetaka masuda, susumu minamisawa, yoshihiro ishikawa. inhibition of ep4 signaling attenuates aortic aneurysm formation. plos one. 2012, may. 7, 5, e36724.
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