9(10)-Nitrooleate

9(10)-Nitrooleate is a mixture of the nitroalkene endogenous lipid signaling molecules 9-nitrooleate. 9(10)-Nitrooleate is formed by nitration of oleic acid by peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of hydrogen peroxide (H₂O₂) and nitrite.¹ It induces transactivation of peroxisome proliferator-activated receptor γ (PPARγ) or nuclear factor erythroid 2-related factor 2 (Nrf2) in reporter assays using MCF-7 cells when used at concentrations greater than or equal to 0.3 and greater than or equal to 3 ?M, respectively.² 9(10)-Nitrooleate also induces transactivation of PPARγ, PPARδ, or PPARα in reporter assays using CV-1 cells in a concentration-dependent manner.¹ It induces adipogenesis in 3T3-L1 preadipocytes and glucose uptake in differentiated 3T3-L1 adipocytes when used at a concentration of 3 ?M. In vivo, 9(10)-nitrooleate (500 ?g/kg every six hours for 24 hours) decreases ischemia-induced increases in plasma levels of blood urea nitrogen, creatinine, and TNF-α and kidney levels of myeloperoxidase (Mpo) and IL-1β and reduces tubular necrosis and tubule dilation in a mouse model of renal ischemia-reperfusion injury.³

References:
[1]. 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 ligandsJ. Biol. Chem.280(51)42464-42475(2005).
[2]. Bates, D.J.P., Smitherman, P.K., Townsend, A.L., et al.Nitroalkene fatty acids mediate activation of Nrf2/ARE-dependent and PPARγ-dependent transcription by distinct signaling pathways and with significantly different potenciesBiochemistry50(36)7765-7773(2011).
[3]. Liu, H., Jia, Z., Soodvilai, S., et al.Nitro-oleic acid protects the mouse kidney from ischemia and reperfusion injuryAm. J. Physiol. Renal. Physiol.295(4)F942-F949(2008).