Abstract
Unsaturated nitro fatty acids (NO2-FAs) constitute a category of molecules that may be formed endogenously by the reaction of unsaturated fatty acids (UFAs) with secondary species of nitrogen monoxide and nitrite anions. The warhead of NO2-FAs is a nitroalkene moiety, which is a potent Michael acceptor and can undergo nucleophilic attack from thiol groups of biologically relevant proteins, showcasing the value of these molecules regarding their therapeutic potential against many diseases. In general, NO2-FAs inhibit nuclear factorκ-B (NF-κB), and simultaneously they activate nuclear factor (erythroid derived)-like 2 (Nrf2), which activates an antioxidant signaling pathway. NO2-FAs can be synthesized not only endogenously in the organism, but in a synthetic laboratory as well, either by a step-by-step synthesis or by a direct nitration of UFAs. The step-by-step synthesis requires specific precursor compounds and is in position to afford the desired NO2-FAs with a certain position of the nitro group. On the contrary, the direct nitration of UFAs is not a selective methodology; thus, it affords a mixture of all possible nitro isomers.
Highlights
CenterDrug Design and Discovery, National and Kapodistrian University of Athens, Center of Excellence
Nitro fatty acids (NO2-FAs) is a class of compounds that are endogenously formedNitro fatty acids (NO2 -FAs) is a class of compounds that are endogenously formed by the reaction of unsaturated fatty acids (UFAs) [oleic (OA), linoleic (LA), etc.] with secby the reaction of unsaturated fatty acids (UFAs)[oleic (OA), linoleic (LA), etc.] with ondary products of nitrogen monoxide (NO.) and. nitrite anions (NO2−) (Scheme1), resultsecondary products of nitrogen monoxide (NO ) and nitrite anions (NO2 − ) (Scheme 1), ing in the formation of a reactive nitroalkene moiety [1,2,3]
Another very important metabolic pathway for the regulation of inflammation is induced by cycloxygenase-2 (COX-2)-derived prostaglandins (PGs) and by the synthesis of leukotrienes (LTs), which are dependent on LO [45]
Summary
Drug Design and Discovery, National and Kapodistrian University of Athens, Center of Excellence.
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