Russ. J. Bioorganic Chem., 1997, 23(3):190-198

Artificially functionalized polyenoic fatty acids as new lipid bioregulators

Dopamine, histamine, serotonin, and serotonin analogs were acylated with arachidonic and eicosapentaenoic acids, and the reaction products were named as artificially functionalized fatty acids (AFFA). The amides of arachidonic acid with serotonin, dopamine, and histamine were found to inhibit human platelet aggregation induced by ADP, arachidonic acid and adrenaline. Amides of arachidonic and eicosapentaenoic acids with serotonin and dopamine protect sea urchin early embryos against cytotoxic action of serotonin and histamine antagonists. These effects are not connected with the possible hydrolytic cleavage of AFFA to their constituent polyenoic fatty acids and amines. Arachidonic acid dopaminamide was shown to be a substrate of soybean 15-lipoxygenase, whereas the arachidonic acid amides with serotonin and its derivatives were resistant to this enzyme. Moreover, arachidonic acid serotoninamide turned out to be an irreversible lipoxygenase inhibitor. Considerable amount of hydroxyl radicals (fluorescent assay) were found for the first time to accompany lipoxygenase oxidation of linoleic acid; arachidonic acid serotoninamide blocked this process completely. Therefore, it was concluded that AFFA possess specific biological activity and can be considered as a novel group of lipid bioregulators. © 1997 MAEe cyrillic signK Hayκa/Interperiodica Publishing.

Bezuglov VV, Manevich Y, Archakov AV, Bobrov MY, Kuklev DV, Petrukhina GN, Makarov VA, Buznikov GA

IBCH: 6185
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