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11β-Prostaglandin F2α-d4

Cayman Chemical Item Number 10008989

11β-Prostaglandin F2α-d4

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Description

11β-Prostaglandin F2α-d4 (11β-PGF2α-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 11β-PGF2α by GC- or LC-mass spectrometry. 11β-PGF2α is the primary plasma metabolite of PGD2 in vivo.1 Normal human urinary excretion of 11β-PGF2α is about 54 ng/mmol creatinine, which is increased nearly 3-fold upon allergen-induced bronchoconstriction in asthmatics.2 It is equipotent to PGF2α in inducing human bronchial smooth muscle contractions and inhibition of adipose differentiation.3,4 11β-PGF2α inhibits ADP or thrombin-induced human platelet aggregation at concentrations of 0.14 to 2.8 µM.5

1 Liston, T.E., and Roberts, L.J. Transformation of prostaglandin D2 to 9α,11β-(15S)-trihydroxy-prosta-(5Z,13E)-dien-1-oic acid (9α,11β-prostaglandin F2): A unique biologically active prostaglandin produced enzymatically in vivo in humans. Proc Natl Acad Sci USA 82 6030-6034 (1985).

2 O'Sullivan, S., Dahlén, B., Dahlén, S., et al. Increased urinary excretion of the prostaglandin D2 metabolite 9α,11β-prostaglandin F2 after aspirin challenge supports mast cell activation in aspirin-induced airway obstruction. J Allergy Clin Immunol 98 421-432 (1996).

3 Coleman, R.A., and Sheldrick, R.L.G. Prostanoid-induced contraction of human bronchial smooth muscle is mediated by TP-receptors. Br J Pharmacol 96 688-692 (1989).

4 Lepak, N.M., and Serrero, G. Inhibition of adipose differentiation by 9α, 11β-prostaglandins F2α. Prostaglandins 46 511-517 (1993).

5 Pugliese, G., Spokas, E.G., Marcinkiewicz, E., et al. Hepatic transformation of prostaglandin D2 to a new prostanoid, 9α,11β-prostaglandin F2, that inhibits platelet aggregation and constricts blood vessels. J Biol Chem 260 14621-14625 (1985).

Formal Name 9α,​11β.,​15S-​trihydroxy-​prosta-​5Z,​13E-​dien-​1-​oic-​3,​3,​4,​4-​d4 acid
Molecular Formula C20H34D4O5
Formula Weight 362.5
Formulation A solution in ethanol
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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O[C@@H]​1[C@H]​(/C=C/[C@@H]​(O)​CCCCC)​[C@@H]​(C/C=C\C([2H]​)​([2H]​)​C([2H]​)​([2H]​)​CC(O)​=O)​[C@@H]​(O)​C1

Background Reading

Liston, T.E., and Roberts, L.J. Transformation of prostaglandin D2 to 9α,11β-(15S)-trihydroxy-prosta-(5Z,13E)-dien-1-oic acid (9α,11β-prostaglandin F2): A unique biologically active prostaglandin produced enzymatically in vivo in humans. Proc Natl Acad Sci USA 82 6030-6034 (1985).

Pugliese, G., Spokas, E.G., Marcinkiewicz, E., et al. Hepatic transformation of prostaglandin D2 to a new prostanoid, 9α,11β-prostaglandin F2, that inhibits platelet aggregation and constricts blood vessels. J Biol Chem 260 14621-14625 (1985).

Lepak, N.M., and Serrero, G. Inhibition of adipose differentiation by 9α, 11β-prostaglandins F2α. Prostaglandins 46 511-517 (1993).

O'Sullivan, S., Dahlén, B., Dahlén, S., et al. Increased urinary excretion of the prostaglandin D2 metabolite 9α,11β-prostaglandin F2 after aspirin challenge supports mast cell activation in aspirin-induced airway obstruction. J Allergy Clin Immunol 98 421-432 (1996).

Coleman, R.A., and Sheldrick, R.L.G. Prostanoid-induced contraction of human bronchial smooth muscle is mediated by TP-receptors. Br J Pharmacol 96 688-692 (1989).

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Size Price Quantity Subtotal
50 µg $65.00 $0.00
100 µg $124.00 $0.00
500 µg $293.00 $0.00
5 mg $3,900.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-05-25. 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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11β-Prostaglandin F2α EIA Kit
Prostaglandin F2α
Prostaglandin F2α-d4
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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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