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ChemicalBook--->CAS DataBase List--->1628759-75-0

1628759-75-0

1628759-75-0 Structure

1628759-75-0 Structure
IdentificationBack Directory
[Name]

KMN-80
[CAS]

1628759-75-0
[Synonyms]

KMN-80
KMN80,KMN 80
CBIUADIJQPJQEZ-VIDOSBHOSA-N
1-Pyrrolidineheptanoic acid, 2-[(1E,3S,4S)-3-hydroxy-4-methyl-1-nonen-6-yn-1-yl]-5-oxo-, (2R)-
[Molecular Formula]

C21H33NO4
[MDL Number]

MFCD34469274
[MOL File]

1628759-75-0.mol
[Molecular Weight]

363.49
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

DMF: 20 mg/ml; DMSO: 15 mg/ml; Ethanol: 25 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
[form ]

A crystalline solid
Hazard InformationBack Directory
[Description]

The prostaglandin E receptor 4 (EP4) is one of four G protein-coupled receptors that mediate the actions of prostaglandin E2 (PGE2; ). Binding of PGE2 to the EP4 receptor causes an increase in intracellular cyclic AMP, which plays important roles in bone formation and resorption, cancer, and atherosclerosis.1,2,3,4 KMN-80 is a substituted γ-lactam (pyrrolidinone) derivative of PGE1 that acts as a selective and potent agonist of EP4 with an IC50 value of 3 nM (IC50 = 1.4 μM for EP3 and > 10 μM for all other prostanoid receptors).5 In functional assays it has been shown to stimulate secreted alkaline phosphatase gene reporter activity in EP4-transfected HEK293 cells with an EC50 value of 0.19 nM, demonstrating >5,000 and 50,000-fold selectivity against EP2 and TP, respectively.5 KMN-80 can induce the differentiation of bone marrow stem cells from both young and aged rats into osteoblasts in vitro (EC50s = 20 and 153 nM, respectively) and exhibits favorable tolerability up to at least 10 μM, whereas the EP4 agonist L-902,688 is highly cytotoxic at similar concentrations in these cells.6 KMN-80 has been used to repair calvarial defects in an in vivo rat craniomaxillofacial reconstruction model (rate of reduction in defect size equivalent to BMP-2 treated rats) and to promote bone formation in a rat incisor tooth socket model.6
[storage]

Store at -20°C
[References]

1. Li, M., Thompson, D.D., and Paralkar, V.M. Prostaglandin E2 receptors in bone formation Int. Orthop. 31(6),767-772(2007).
2. Hawcroft, G., Ko, C.W.S., and Hull, M.A. Prostaglandin E2-EP4 receptor signalling promotes tumorigenic behaviour of HT-29 human colorectal cancer cells Oncogene 26(21),3006-3019(2007).
3. Babaev, V.R., Chew, J.D., Ding, L., et al. Macrophage EP4 deficiency increases apoptosis and suppresses early atherosclerosis Cell Metab. 8(6),492-501(2008).
4. Konya, V., Marsche, G., Schuligoi, R., et al. E-type prostanoid receptor 4 (EP4) in disease and therapy Pharmacol. Ther. 138(3),485-502(2013).
5. Barrett, S.D., Ciske, F.L., Endres, G.W., et al. Novel Potent Lactam Acetylene EP4 Agonists Stimulate Alkaline Phosphatase Production and Differentiation in Bone Marrow Cells ,(2014).
6. O'Malley, J., Uzieblo, A., Germain, B.D., et al. Development of a novel prostaglandin EP4 agonist which stimulates local bone formation in vivo ,(2014).
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