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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Prostaglandin E2

Cayman Chemical Item Number 14010

PGE2; Dinoprostone (CAS 363-24-6)

Prostaglandin E2 (CAS 363-24-6)

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Description

PGE2 is one of the primary COX products of arachidonic acid and one of the most widely investigated prostaglandins. Its activity influences inflammation, fertility and parturition, gastric mucosal integrity, and immune modulation.1,2,3,4 The effects of PGE2 are transduced by at least four distinct receptors designated EP1, EP2, EP3, and EP4.5 Affinity constants (Kd) of PGE2 for these receptors range from 1-10 nM depending on the receptor subtype and tissue.

1 Willis, A.L., and Cornelsen, M. Repeated injection of prostaglandin E2 in rat paws induces chronic swelling and a marked decrease in pain threshold. Prostaglandins 3 353-357 (1973).

2 Jackson, G.M., Sharp, H.T., and Varner, M.W. Cervical ripening before induction of labor: A randomized trial of prostaglandin E2 gel versus low-dose oxytocin. Am J Obstet Gynecol 171 1092-1096 (1994).

3 Robert, A., Schultz, J.R., Nezamis, J.E., et al. Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16,16-dimethyl PGE2. Intravenous, oral and intrajejunal administration. Gastroenterology 70 359-370 (1976).

4 Arvind, P., Papavassiliou, E.D., Tsioulias, G.J., et al. Prostaglandin E2 down-regulates the expression of HLA-DR antigen in human colon adenocarcinoma cell lines. Biochemistry 34 5604-5609 (1995).

5 Coleman, R.A., Smith, W.L., and Narumiya, S. Classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol Rev 46 205-229 (1994).

Synonyms
  • PGE2
  • Dinoprostone
Formal Name 9-​oxo-​11α,​15S-​dihydroxy-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 363-24-6
Molecular Formula C20H32O5
Formula Weight 352.5
Formulation A crystalline solid
Purity ≥99%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCCC(O)​/C=C/[C@H]​1C(O)​CC(=O)​C1C/C=C\CCCC(=O)​O

Background Reading

Kuno, S., Ueno, R., Hayaishi, O., et al. Prostaglandin E2, a seminal constituent, facilitates the replication of acquired immune deficiency syndrome virus in vitro. Proc Natl Acad Sci USA 83 3487-3490 (1986).

Arvind, P., Papavassiliou, E.D., Tsioulias, G.J., et al. Prostaglandin E2 down-regulates the expression of HLA-DR antigen in human colon adenocarcinoma cell lines. Biochemistry 34 5604-5609 (1995).

Jackson, G.M., Sharp, H.T., and Varner, M.W. Cervical ripening before induction of labor: A randomized trial of prostaglandin E2 gel versus low-dose oxytocin. Am J Obstet Gynecol 171 1092-1096 (1994).

Schweer, H., and Fischer, S. Negative ion chemical ionization and collisionally activated decomposition mass spectra of O-2,3,4,5,6-pentafluorobenzyloxime derivatives of prostaglandins. Biol Mass Spectrom 23 47-56 (1994).

Takasuka, M., Kishi, M., and Yamakawa, M. FTIR spectral study of intramolecular hydrogen bonding in thromboxane A2 receptor agonist (U-46619), prostaglandin (PG)E2, PGD2, PGF, prostacyclin receptor agonist (carbacyclin), and their related compounds in dilute CCl4 solution: Structure-activity relationships. J Med Chem 37 47-56 (1994).

Weinreb, M., Suponitzky, I., and Keila, S. Systemic administration of an anabolic dose of PGE2 in young rats increases the osteogenic capacity of bone marrow. Bone 20 521-526 (1997).

Wijkander, J., O'Flaherty, J.T., Nixon, A.B., et al. 5-Lipoxygenase products modulate the activity of the 85-kDa phospholipase A2 in human neutrophils. J Biol Chem 270 26543-26549 (1995).

Stein, T.A., Angus, L., Borrero, E., et al. Picogram measurement of prostaglandin E2 synthesis by gastric mucosa by high-performance liquid chromatography. J Chromatogr 385 377-382 (1987).

Hayaishi, O. Sleep-wake regulation by prostaglandins D2 and E2. J Biol Chem 263 14593-14596 (1988).

Miledi, R., and Woodward, R.M. Membrane currents elicited by prostaglandins, atrial natriuretic factor and oxytocin in follicle-enclosed Xenopus oocytes. J Physiol 416 623-643 (1989).

Grundmann, H., Hähnle, U., Hegenscheid, B., et al. Inhibition of endotoxin-induced macrophage tumor necrosis factor expression by a prostacyclin analogue and its beneficial effect in experimental lipopolysaccharide intoxication. J Infect Dis 165 501-505 (1992).

Willis, A.L., and Cornelsen, M. Repeated injection of prostaglandin E2 in rat paws induces chronic swelling and a marked decrease in pain threshold. Prostaglandins 3 353-357 (1973).

Coleman, R.A., Smith, W.L., and Narumiya, S. Classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol Rev 46 205-229 (1994).

Robert, A., Schultz, J.R., Nezamis, J.E., et al. Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16,16-dimethyl PGE2. Intravenous, oral and intrajejunal administration. Gastroenterology 70 359-370 (1976).

Gobbetti, A., Zerani, M., and Bellini-Cardellini, L. A possible role of prostaglandin E2 in reproduction of the male water frog, in vivo and in vitro studies. Prostaglandins 44 277-289 (1992).

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Prostaglandin E2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $13.00 $0.00
5 mg $59.00 $0.00
10 mg $104.00 $0.00
50 mg $455.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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FAQs

What is the source of Cayman's Prostaglandin E2?

Cayman's Prostaglandin E2 is synthesized.

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What is the stability of a stock solution of Prostaglandin E2, prepared by dissolving the crystalline compound in an organic solvent such as ethanol?

The two year stability listed is only for the crystalline solid, not for a solution in an organic solvent. As solution in an organic solvent Prostaglandin E2 stored at - 20°C is likely to be good for several weeks.

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