16,16-dimethyl Prostaglandin E2
Item № 14750
CAS № 39746-25-3
Purity ≥98%
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1 mg $69.00 $0.00
5 mg $328.00 $0.00
10 mg $621.00 $0.00

Pricing updated 2015-09-03. Prices are subject to change without notice.

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Description
Synonyms
  • 16,16-dimethyl PGE2

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

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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 ≥98%
Formulation A solution in methyl acetate
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 ​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

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
Stability 1 year
Product Downloads & Resources
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Download Product Insert 120 Kb PDF

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Additional Information

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References & Background Reading
Product Description References

1. Ohno, H., Morikawa, Y., and Hirata, F. Studies on 15-hydroxyprostaglandin dehydrogenase with various prostaglandin analogues. J Biochem 84 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 70 359-370 (1976).

3. 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).

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).

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