(±)9(10)-EpOME-d4 (Synonyms: (±)9,10EODEd4, Leukotoxind4)

(±)9,10-EpOME-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 latanoprost by GC- or LC-mass spectrometry (MS). (±)9(10)-EpOME is the 9,10-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst.¹ It has been recovered from the lungs of hyperoxic rats and from humans with acute respiratory distress syndrome.² Mitochondrial dysfunction is the main feature of (±)9(10)-EpOME cytotoxicity, which may be due to the diol metabolites as well as the parent epoxide.^3,4

1.Hayakawa, M., Sugiyama, S., Takamura, T., et al.Neutrophils biosynthesize leukotoxin, 9,10-epoxy-12-octadecenoateBiochem. Biophys. Res. Commun.137(1)424-430(1986) 2.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 hyperoxiaBiochem. Biophys. Res. Commun.134(3)1071-1078(1986) 3.Kosaka, K., Suzuki, K., Hayakawa, M., et al.Leukotoxin, a linoleate epoxide: Its implication in the late death of patients with extensive burnsMol. Cell. Biochem.139(2)141-148(1994) 4.Moran, J.H., Weise, R., Schnellmann, R.G., et al.Cytotoxicity of linoleic acid diols to renal proximal tubular cellsToxicol. Appl. Pharmacol.146(1)53-59(1997)