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10007601 5α-hydroxy-6-keto Cholesterol
6-Oxo-3,5-diol; Cholestane-6-oxo-3β,5α-diol
(CAS 13027-33-3)
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Cholesterol is the most abundant neutral lipid present in the surfactant of the lung epithelial lining fluid. The double bond between carbons 5 and 6 of cholesterol is susceptible to attack by ozone within this surfactant environment. 5α-hydroxy-6-keto Cholesterol (6-oxo-3,5,-diol) is a major metabolite of cholesterol formed during exposure of lung epithelial cells to ozone, with formation of 5β,6β-epoxycholesterol as a predominant precursor.1 Exposure of C57BL/6J mice to 0.5-3 ppm ozone produced a dose-dependent formation of 6-oxo-3,5,-diol which was detectable in the bronchalveolar lavage fluid, lavaged cells, and lung homogenates.2 6-Oxo-3,5-diol is a potent inhibitor of cholesterol synthesis in human bronchial epithelial cells with an IC50 of 350 nM and exhibits significant cytotoxicity in the low µM range.1 Therefore, the toxic effects of ozone may be mediated by formation oxysterols of this type.
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1
Pulfer, M.K., Murphy, R.C. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. J Biol Chem 279(25) 26331-26338 (2004).
2
Pulfer, M.K., Taube, C., Gelfand, E., et al. Ozone exposure in vivo and formation of biologically active oxysterols in the lung. J Pharmacol Exp Ther 312(1) 256-264 (2005).
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Pricing updated 2010-03-14.
Prices are subject to change without notice.
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Stability of this item is suitable for room temperature overnight shipping. If shipment on ice is desired, it must be requested when the order is placed.
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