9-Nitrooleate-d17

9-Nitrooleate-d₁₇ contains 17 deuterium atoms at the 11, 11, 12, 12, 13, 13, 14, 14, 15, 15, 16, 16, 17, 17, 18, 18, and 18 positions. It is intended for use as an internal standard for the quantification of 9-nitrooleate by GC- or LC-mass spectrometry. Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate , cholesteryl nitrolinoleate, and nitrohydroxylinoleate, represent a new class of endogenous lipid-derived signalling molecules. LNO₂ isomers serve as potent endogenous ligands for PPARγ and can also decompose or be metabolized to release nitric oxide.^1,2,3,4 9-Nitrooleate is one of two regioisomers of nitrooleate, the other being 10-nitrooleate (OA-NO₂; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions in vivo.⁵ Peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of H₂O₂ and nitrite, all mediate the nitration of oleic acid. OA-NO₂ is found in human plasma as the free acid and esterified in phospholipids at concentrations of 619 ± 52 nM and 302 ± 369 nM, respectively. OA-NO₂ activates PPARγ approximately 7-fold at a concentration of 1 µM and effectively promotes differentiation 3T3-L1 preadipocytes to adipocytes at 3 µM.⁵

1.Lim, D.G., Sweeney, S., Bloodsworth, A., et al.Nitrolinoleate, a nitric oxide-derived mediator of cell function: Synthesis, characterization, and vasomotor activityProceedings of the National Academy of Sciences of the United States of America99(25)15941-15946(2002) 2.Schopfer, F.J., Lin, Y., Baker, P.R.S., et al.Nitrolinoleic acid: An endogenous peroxisome proliferator-activated receptor g ligandProceedings of the National Academy of Sciences of the United States of America102(7)2340-2345(2005) 3.Lima, E.S., Bonini, M.G., Augusto, O., et al.Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxationFree Radical Biology & Medicine39532-539(2005) 4.Baker, P.R.S., Schopfer, F.J., Sweeney, S., et al.Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitationProceedings of the National Academy of Sciences of the United States of America101(32)11577-11582(2004) 5.Baker, P.R., Lin, Y., Schopfer, F.J., et al.Fatty acid transduction of nitric oxide signaling. Multiple nitrated unsaturated acid derivatives exist in human blood and urine serve as endogenous peroxisome proliferator-activated receptor ligandsThe Journal of Biological Chemisty280(51)42464-42475(2005)