9-Nitrooleate-d₁₇

9-Nitrooleate-d₁₇ is intended for use as an internal standard for the quantification of 9-nitrooleate (Item No. 10012554) by GC- or LC-MS. Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate (LNO₂; Item No. 10037), 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 (Item No. 10008043) (OA-NO₂; used for the mixture of isomers), which are formed by nitration of oleic acid (Item No. 90260) 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

WARNING This product is not for human or veterinary use.

1. Lim, D.G., Sweeney, S., Bloodsworth, A., et al. Nitrolinoleate, a nitric oxide-derived mediator of cell function: Synthesis, characterization, and vasomotor activity. Proc. Natl. Acad. Sci. USA 99(25), 15941-15946 (2002).

2. Schopfer, F.J., Lin, Y., Baker, P.R.S., et al. Nitrolinoleic acid: An endogenous peroxisome proliferator-activated receptor γ ligand. Proc. Natl. Acad. Sci. USA 102(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 vasorelaxation. Free Radic. Biol. Med. 39(4), 532-539 (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 quantitation. Proc. Natl. Acad. Sci. USA 101(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 ligands. The Journal of Biological Chemisty 280(51), 42464-42475 (2005).