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Prostaglandin E2-d4

Cayman Chemical Item Number 314010

Dinoprostone-d4; PGE2-d4

Prostaglandin E2-d4

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Description

Prostaglandin E2-d4 (PGE2-d4) contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of PGE2 by GC- or LC-mass spectrometry. PGE2 is one of the primary cyclooxygenase 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 The 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
  • Dinoprostone-d4
  • PGE2-d4
Formal Name 9-​oxo-​11α,​15S-​dihydroxy-​prosta-​5Z,​13E-​dien-​1-​oic-​3,​3,​4,​4-​d4 acid
Molecular Formula C20H28D4O5
Formula Weight 356.5
Formulation A solution in methyl acetate
Purity ≥99% deuterated forms (d1-d4)
Stability 1 year
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

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).

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).

Praticò, D., and Fitzgerald, G.A. Generation of 8-epiprostaglandin F2α by human monocytes. Discriminate production by reactive oxygen species and prostaglandin endoperoxide synthase-2. J Biol Chem 271 8919-8924 (1996).

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).

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Size Price Quantity Subtotal
50 µg $46.00 $0.00
100 µg $87.00 $0.00
500 µg $368.00 $0.00
5 mg $2,760.00 $0.00
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Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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