16,16-Dimethyl-prostaglandin E2 A PGE2 analog that is resistant to metabolism

16,16-Dimethyl-prostaglandin E2 (CAS 39746-25-3)

16,16-Dimethyl-prostaglandin E2 | CAS 39746-25-3 is rated 5.0 out of 5 by 1.
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Synonym: 16,16-dimethyl PGE2;9-oxo-11α,15R-dihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid
Application: A PGE2 analog that is resistant to metabolism
CAS Number: 39746-25-3
Purity: ≥98%
Molecular Weight: 380.52
Molecular Formula: C22H36O5
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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16,16-Dimethyl-prostaglandin E2 is an antisecretory, antiulcer Prostaglandin E2 (PGE2; sc-201225) analog with potent cytoprotective activity that binds to PGDH (prostaglandin dehydrogenase or HPGD), but is resistant to metabolism, thereby inhibiting the enzyme. This enhanced resistance to metabolism imparts a higher duration of activity than Prostaglandin E2 (sc-201225), but the methylations do not severely affect the binding affinity for all four EP receptors (EP1,2,3, and 4). PGE2 is the most physiologically abundant eiconasoid regulating many biological functions and since this product has nearly identical binding affinities, it also has numerous and similar physiological functions. 16,16-Dimethyl-prostaglandin E2 is an inhibitor of PGDH and an activator of EP2.


References

1. Robert, A., et al., 1976. Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16, 16-dimethyl PGE2. Intravenous, oral and intrajejunal administration. Gastroenterology. 70(3): 359-70. PMID: 174967
2. Ohno, H., et al., 1978. Studies on 15-hydroxyprostaglandin dehydrogenase with various prostaglandin analogues. Journal of biochemistry. 84(6): 1485-94. PMID: 216666
3. Coleman, R A., et al., 1994. International Union of Pharmacology classification of prostanoid receptors: properties, distribution, and structure of the receptors and their subtypes. Pharmacological reviews. 46(2): 205-29. PMID: 7938166
4. Bhattacherjee, P., et al., 1996. Identification of prostanoid receptors in rabbit non-pigmented ciliary epithelial cells. Experimental eye research. 62(5): 491-8. PMID: 8759517
5. Failla, Marco., et al., 2009. 16,16-Dimethyl prostaglandin E2 efficacy on prevention and protection from bleomycin-induced lung injury and fibrosis. American journal of respiratory cell and molecular biology. 41(1): 50-8. PMID: 19059888

Usage :
To change solvent evaporate the supplied solution under a gentle stream of inert gas and immediately redissolve in new solvent that has been purged with inert gas. For aqueous solutions either dilute a minimal amount of organic solution or directly dissolve the neat oil. Use aqueous solutions within 12 hours or preparation.
Formulation :
Solution in methyl acetate
Appearance :
Solution
Physical State :
Liquid
Solubility :
Soluble in ethanol (~100 mg/ml), DMSO (~100 mg/ml), methyl acetate, DMF (~100 mg/ml), and PBS (~5 mg/ml,pH 7.2).
Storage :
Store at -80° C
Boiling Point :
57° C
Refractive Index :
n20D 1.55
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
RTECS :
UK7894000
PubChem CID :
5283066
MDL Number :
MFCD00151141
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

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Certificate of Analysis

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What is the half-life of this compound in mice? Many texts site the extended half-life relative to PGE2 itself, but I am having trouble pinning down an exact value. Thank you.

Asked by: Jrysndrs
Thank you for your question. Literature states that this compound has a prolonged half-life in vivo due to its resistance to metabolism by 15-hydroxy PGDH. We could not find an exact half-life, however the following publication states that the mouse was dosed with the compound 2 days prior to tumor excision. Bennett, A., et al. "Treatment of mouse carcinoma in vivo with a prostaglandin E2 analogue and indomethacin." British journal of cancer 52.2 (1985): 245.
Answered by: Technical Support
Date published: 2017-09-11

Is there any dmPGE2 as GMP grade?

Asked by: OscarQB
Thank you for your question. Unfortunately we are not able to provide that information. Our compounds are not pharmaceutical grade and not manufactured under GMP guidelines, and should be used for research use only.
Answered by: Tech Service
Date published: 2017-04-27
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Rated 5 out of 5 by from Speth Speth, JM. et al. (PubMed 24167196) found that ex vivo pulse treatment with 16,16-Dimethyl-prostaglandin E2, enhances the function of hematopoietic stem and progenitor cells. -SCBT Publication Review
Date published: 2015-07-09
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