A competitive 15-hydroxy PGDH inhibitor
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16,16-dimethyl Prostaglandin E2

Item No. 14750

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-oxo-11α,15R-dihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid
CAS Number
39746-25-3
Synonyms
  • 16,16-dimethyl PGE2
Molecular Formula
C22H36O5
Formula Weight
380.5
Purity
≥95%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/ml (from PGE2)DMSO: >100 mg/ml (from PGE2)Ethanol: >100 mg/ml (from PGE2)PBS pH 7.2: >5 mg/ml (from PGE2)
SMILES
O=C1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)C(C)(C)CCCC)[C@H](O)C1
InChi Code
InChI=1S/C22H36O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h6,8,12-13,16-17,19-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)/b8-6-,13-12+/t16-,17-,19-,20-/m1/s1
InChi Key
QAOBBBBDJSWHMU-WMBBNPMCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $120

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    5 mg

    $570

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    10 mg

    $1,080

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    Product Description

    16,16-dimethyl PGE2 is a competitive inhibitor of 15-hydroxy PGDH, but it is not a substrate for the enzyme.1 Because of its resistance to metabolism by 15-hydroxy PGDH, it has a prolonged half-life in vivo. 16,16-dimethyl PGE2 acts as an agonist on most EP receptor subtypes, and has been used experimentally to induce cervical ripening, uterine contraction, and prevent ulceration of the gastric mucosa in rats and dogs.2,3 The Kd for activation of isolated EP2 receptors is about 1 nM.3 16,16-dimethyl PGE2 can be used to preserve the self-renewal properties while preventing the differentiation of hematopoietic stem cells during expansion in culture.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ohno, H., Morikawa, Y., and Hirata, F. Studies on 15-hydroxyprostaglandin dehydrogenase with various prostaglandin analogues. J. Biochem. 84(6), 1485-1494 (1978).

    2. 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(3), 359-370 (1976).

    3. Coleman, R.A., Smith, W.L., and Narumiya, S. International Union of Pharmacology classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol. Rev. 46(2), 205-229 (1994).

    4. Hagedorn, E.J., Durand, E.M., Fast, E.M., et al. Getting more for your marrow: Boosting hematopoietic stem cell numbers with PGE2. Exp. Cell Res. (2014).

    5. Genovese, P., Schiroli, G., Escobar, G., et al. Targeted genome editing in human repopulating haematopoietic stem cells. Nature 510(7504), 235-240 (2014).

    Product Citations

    Roulis, M., Kaklamanos, A., Schernthanner, M., et al. Paracrine orchestration of intestinal tumorigenesis by a mesenchymal niche. Nature 580(7804), 524-529 (2020).

    Roulis, M., Nikolaou, C., Kotsaki, E., et al. Intestinal myofibroblast-specific Tpl2-Cox-2-PGE2 pathway links innate sensing to epithelial homeostasis. Proc. Natl. Acad. Sci. USA 111(43), E4658-E4667 (2014).