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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

15(R)-Prostaglandin F2α

Cayman Chemical Item Number 16740

15-epi PGF2α (CAS 37658-84-7)

15(R)-Prostaglandin F2α (CAS 37658-84-7)

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Description

15(R)-PGF2α is the C-15 epimer of the naturally occurring mammalian autacoid PGF2α. It has only 25% of the potency of PGF2α in hamster antifertility studies,1 which may be due to reduced affinity for FP receptors. Compared to PGF2α, 15(R)-PGF2α has a binding affinity of 6.7% to ovine luteal cell receptors.2 Similarly, the binding affinity to rat vascular smooth muscle cells is negligible as compared to PGF2α.3

1 Miller, W.L., and Sutton, M.J. Relative biological activity of certain prostaglandins and their enantiomers. Prostaglandins 11 77-84 (1976).

2 Balapure, A.K., Rexroad, C.E., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem Pharmacol 38 2375-2381 (1989).

3 Hanasaki, K., Kishi, M., and Arita, H. Phorbol ester-induced expression of the common, low-affinity binding site for primary prostanoids in vascular smooth muscle cells. J Biol Chem 265 4871-4875 (1990).

Synonyms
  • 15-epi PGF2α
Formal Name 9α,​11α,​15R-​trihydroxy-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 37658-84-7
Molecular Formula C20H34O5
Formula Weight 354.5
Formulation A solution in methyl acetate
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCC[C@@H]​(O)​/C=C/[C@H]​1C(O)​CC(O)​C1C/C=C\CCCC(=O)​O

Background Reading

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

Andersen, N.H., Imamoto, S., Subramanian, N., et al. Molecular basis for prostaglandin potency. III. Tests of the significance of the 'hairpin conformation' in biorecognition phenomena. Prostaglandins 22 841-856 (1981).

Miller, W.L., and Sutton, M.J. Relative biological activity of certain prostaglandins and their enantiomers. Prostaglandins 11 77-84 (1976).

Andersen, N.H., and Lin, B. 500-MHz proton NMR studies of the medium-dependent conformational preference of prostaglandin F2α analogues. Biochemistry 24 2338-2347 (1985).

Hanasaki, K., Kishi, M., and Arita, H. Phorbol ester-induced expression of the common, low-affinity binding site for primary prostanoids in vascular smooth muscle cells. J Biol Chem 265 4871-4875 (1990).

Balapure, A.K., Rexroad, C.E., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem Pharmacol 38 2375-2381 (1989).

Sun, F.F., Armour, S.B., Bockstanz, V.R., et al. Studies on 15-hydroxyprostaglandin dehydrogenase from monkey lung. Adv Prostaglandin Thromboxane Res 1 163-169 (1976).

Andersen, N.H., and Leovey, E.M.K. Identification and quantitative determination of prostaglandins by high pressure liquid chromatography. Prostaglandins 6 361-374 (1974).

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15(R)-Prostaglandin F2α is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $60.00 $0.00
5 mg $270.00 $0.00
10 mg $480.00 $0.00
50 mg $2,100.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Prostaglandin F2α

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