13,14-dihydro-16,16-difluoro Prostaglandin D2

13,14-dihydro-16,16-difluoro Prostaglandin D₂ Exclusive

Cayman Chemical Item Number 13612

13,14-dihydro-16,16-difluoro PGD₂

Description

Prostaglandin D₂ (PGD₂) plays important roles in vascular smooth muscle relaxation, the inhibition of platelet aggregation, and anaphylaxis. 13,14-dihydro-16,16-difluoro PGD₂ is an analog of PGD₂. While its biological activities have not been evaluated, it should be noted that the addition of two electron-withdrawing fluorine atoms has been used to stabilize prostanoids and significantly delay degradation in vivo.¹ Importantly, 13,14-dihydro PGE₁ has activity that is comparable to that of PGE₁, suggesting that this analog of PGD₂ could be biologically active.^2,3

1 Hatano, Y., Kohli, J.D., Goldberg, L.I., et al. Vascular relaxing activity and stability studies of 10,10-difluoro-13,14-dehydroprostacyclin. Proc Natl Acad Sci USA 77(11) 6846-6850 (1980).

2 Änggård, E. The biological activities of three metabolites of prostaglandin E₁. Acta Physiol Scand 66 509-510 (1966).

3 Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E₁ and E₂ in man. J Biol Chem 246 6713-6721 (1971).

Synonyms

13,14-dihydro-16,16-difluoro PGD2

Formal Name

9a,15S-dihydroxy-11-oxo-16,16-difluoro-prosta-5Z-en-1-oic acid

Molecular Formula

C₂₀H₃₂F₂O₅

Formula Weight

390.5

Formulation

A solution in methyl acetate

Purity

≥95%

Stability

1 year

Storage

-20°C

Shipping

Wet ice in continental US; may vary elsewhere

SMILES

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O=C1[C@H](CC[C@@H](O)C(F)(F)CCCC)[C@@H](C/C=C\CCCC(O)=O)[C@@H](O)C1

Background Reading

Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E₁ and E₂ in man. J Biol Chem 246 6713-6721 (1971).

Hatano, Y., Kohli, J.D., Goldberg, L.I., et al. Vascular relaxing activity and stability studies of 10,10-difluoro-13,14-dehydroprostacyclin. Proc Natl Acad Sci USA 77(11) 6846-6850 (1980).

Änggård, E. The biological activities of three metabolites of prostaglandin E₁. Acta Physiol Scand 66 509-510 (1966).

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100 µg 
$29.00

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500 µg 
$131.00

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1 mg 
$232.00

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5 mg 
$1,015.00

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13,14-dihydro-16,16-difluoro Prostaglandin D₂ Exclusive