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(±)9,10-DiHOME-d4 contains four deuterium atoms at the 9, 10, 12, and 13 positions. It is intended for use as an internal standard for the quantification of (±)9,10-DiHOME by GC- or LC-mass spectrometry (MS). Leukotoxin is the 9(10) epoxide of linoleic acid, generated by neutrophils during the oxidative burst.1,2,3 This unstable compound is rapidly degraded by epoxide hydrolases to form the diol, 9,10-DiHOME.4 Mitochondrial dysfunction, vasodilation, and apoptosis are features of leukotoxin toxicity. In renal proximal tubular cells, the diol hydrolysis products of leukotoxin, such as 9,10-DiHOME, have been directly implicated as the cytotoxic agent responsible for cell death.5
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1
Hayakawa, M., Sugiyama, S., Takamura, T., et al. Neutrophils biosynthesize leukotoxin, 9,10-epoxy-12-octadecenoate. Biochem Biophys Res Commun 137 424-430 (1986).
2
Ishizaki, T., Takahashi, H., Ozawa, T., et al. Leukotoxin, 9,10-epoxy-12-octadecenoate causes pulmonary vasodilation in rats. J Am Physiol Soc 1040 L123-L128 (1995).
3
Ozawa, T., Hayakawa, M., Takamura, T., et al. Biosynthesis of leukotoxin, 9,10-epoxy-12 octadecenoate, by leukocytes in lung lavages of rat after exposure to hyperoxia. Biochem Biophys Res Commun 134 1071-1078 (1986).
4
Greene, J.F., Williamson, K.C., Newman, J.W., et al. Metabolism of monoepoxides of methyl linoleate: Bioactivation and detoxification. Arch Biochem Biophys 376 420-432 (2000).
5
Moran, J.H., Weise, R., Schnellmann, R.G., et al. Cytotoxicity of linoleic acid diols to renal proximal tubular cells. Toxicol Appl Pharmacol 146 53-59 (1997).
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