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Isopropyl unoprostone

Names

[ CAS No. ]:
120373-24-2

[ Name ]:
Isopropyl unoprostone

[Synonym ]:
MFCD00886951
Unoprostone Isopropyl
Isopropyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoate
5-Heptenoic acid, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-, 1-methylethyl ester, (5Z)-
Unoprostone Isopropyl Ester
Isopropyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate (non-preferred name)
Isopropyl unoprostone

Biological Activity

[Description]:

Isopropyl unoprostone (Unoprostone isopropyl ester), an analogue of a prostaglandin metabolite, is a potent large conductance Ca2+-activated K+ (BK) channels activator. Isopropyl unoprostone has antiglaucoma effects, lowering intraocular pressure (IOP) by increasing aqueous humour outflow. Isopropyl unoprostone can improve retinal sensitivity and the protection of central retinal sensitivity[1][2].

[Related Catalog]:

Research Areas >> Others
Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

[Target]

BK channels[1]


[In Vitro]

Isopropyl unoprostone (0.01-1 μM; 24 h) protects against H2O2-induced 661W cell death[2]. Isopropyl unoprostone (0.1-3 μM; 24 h) reduced the morphological change of 661W cells and protects against light-induced cell death[2]. Isopropyl unoprostone (0.001-1 μM; 48 h) suppresses light-induced phagocytotic dysfunction in ARPE-19 cells[2]. Apoptosis Analysis[2] Cell Line: 661W (treated with Isopropyl unoprostone for 1 h, then added H2O2) Concentration: 0.01, 0.1 and 1 μM Incubation Time: 24 h Result: Protected against H2O2-induced cell death in a concentration-dependent manner. Apoptosis Analysis[2] Cell Line: 661W (treated with Isopropyl unoprostone for 1 h, then exposed to 2,500 lux of white fluorescent light) Concentration: 0.1, 1 and 3 μM Incubation Time: 24 h Result: Protected against light-induced cell death in a concentration-dependent manner, and the effect was significant at the 1 and 3 μM concentrations; reduced the morphological change (the transition to a rounder shape) which is potentially indicative of a pre-apoptotic stage.

[References]

[1]. Haria M, et al. Unoprostone (isopropyl unoprostone). Drugs Aging. 1996 Sep;9(3):213-8; discussion 219-20. 

[2]. Tsuruma K, et al. Unoprostone reduces oxidative stress- and light-induced retinal cell death, and phagocytotic dysfunction, by activating BK channels. Mol Vis. 2011;17:3556-65.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
546.3±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C25H44O5

[ Molecular Weight ]:
424.614

[ Flash Point ]:
172.2±22.2 °C

[ Exact Mass ]:
424.318878

[ PSA ]:
83.83000

[ LogP ]:
4.63

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.492

[ Storage condition ]:
-20°C Freezer

MSDS


Related Compounds