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Unoprostone

Names

[ CAS No. ]:
120373-36-6

[ Name ]:
Unoprostone

[Synonym ]:
[1R-[1a(Z),2b,3a,5a]]-7-[3,5-Dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoic acid
13,14-Dihydro-15-keto-20-ethyl-PGF2a
Unoprostone
13,14-DIHYDRO-15-KETO-20-ETHYL PROSTAGLANDIN F2ALPHA
Unii-6X4F561V3w
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoic acid
9ALPHA,11ALPHA-DIHYDROXY-15-OXO-20A,20B-DIHOMOPROST-5-EN-1-OIC ACID

Biological Activity

[Description]:

Unoprostone, a prostaglandin F2α analogs (PGAs), activates BK channels to reduce oxidative stress- and light-induced retinal cell death, and phagocytotic dysfunction. Unoprostone reduces intraocular pressure and is used topically for glaucoma or ocular hypertension[1].

[Related Catalog]:

Research Areas >> Neurological Disease
Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

[In Vitro]

Pretreatment with Unoprostone (0.01, 0.1, 1 μM; 1 h before H2O2 treatment) protects against H2O2-induced cell death in a concentration-dependent manner and the effect is significant at 0.1 μM and 1 μM concentrations[1]. Pretreatment with Unoprostone at concentrations of 0.1 to 3 μM protects against light-induced cell death in a concentration-dependent manner; the effect is significant at the 1 and 3 μM concentrations. Unoprostone reduces the morphological change, and it significantly inhibits the low mitochondrial membrane potential and cell death induced by light irradiation[1]. Unoprostone has prostaglandin F2α receptors (FP) binding affinity with a Ki of 3.86 μM[2]. Cell Viability Assay[1] Cell Line: H2O2-induced photoreceptor cell Concentration: 0.01, 0.1, 1 μM Incubation Time: 1 hour before H2O2 treatment Result: Protected against H2O2-induced cell death in a concentration-dependent manner.

[In Vivo]

Unoprostone (0.06%, 0.12%; topical instillation; 3 µl) reduces mouse intraocular pressure (IOP) in a dose-dependent manner[3]. Animal Model: Male mice (6 weeks old)[3] Dosage: 0.06%, 0.12% Administration: Topical instillation; 3 µl Result: Reduced mouse IOP in a dose-dependent manner.

[References]

[1]. Tsuruma K, et al. Unoprostone reduces oxidative stress- and light-induced retinal cell death, and phagocytoticdysfunction, by activating BK channels. Mol Vis. 2011;17:3556-65. Epub 2011 Dec 30.

[2]. Kelly CR, et al. Real-time intracellular Ca2+ mobilization by travoprost acid, bimatoprost, unoprostone, and otheranalogs via endogenous mouse, rat, and cloned human FP prostaglandin receptors. J Pharmacol Exp Ther. 2003 Jan;304(1):238-45.

[3]. Ota T, et al. The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4159-63.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
562.9±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C22H38O5

[ Molecular Weight ]:
382.534

[ Flash Point ]:
308.3±23.8 °C

[ Exact Mass ]:
382.271912

[ PSA ]:
94.83000

[ LogP ]:
3.19

[ Vapour Pressure ]:
0.0±3.5 mmHg at 25°C

[ Index of Refraction ]:
1.509

Related Compounds