Effects of quinones and nitroazoles on free-radical fragmentation of glycerol-1-phosphate and 1,2-dimyristoyl-glycero-3-phosphatidyl-glycerol

• Published in: Chemistry and physics of lipids Vol. 222; pp. 8 - 14
• Main Authors: Samovich, Svetlana N., Sladkova, Anastasia A., Sverdlov, Roman L., Edimecheva, Irina P., Shadyro, Oleg I.
• Format: Journal Article
• Language: English
• Published: Ireland Elsevier B.V 01-08-2019
• Subjects: Azoles; Azoles - chemistry; Free Radicals - chemical synthesis; Free Radicals - chemistry; Free-radical fragmentation; Glycerophosphates - chemistry; Inhibitors; Molecular Structure; Nitro Compounds - chemistry; Phosphatidylglycerols - chemistry; Quinones; Quinones - chemistry; Steady state radiolysis; Free-radical fragmentation; Quinones; Azoles; Steady state radiolysis; Inhibitors
• ISSN: 0009-3084; 1873-2941
• DOI: 10.1016/j.chemphyslip.2019.04.008

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•Quinones, including doxorubicin, and nitroazoles effectively inhibit free-radical dephosphorylation of glycerol-1-phosphate.•The test compounds block free-radical fragmentation of 1,2-dimyristoyl-glycero-3-phosphatidyl-glycerol.•Quinones and nitroazoles oxidize α-hydroxyl-containing carbon-centered radicals formed from the organic substrates.
Effects of quinones and azoles on the formation of steady-state radiolysis products in aqueous solutions of glycerol-1-phosphate and aqueous dispersions of 1,2-dimyristoyl-glycero-3-phosphatidyl-glycerol has been investigated. The data obtained by LC–MS-ESI and spectrophotometric measurements shows that the compounds having quinoid structures, including the antitumor agent doxorubicin, and azoles having nitro groups effectively inhibit free-radical fragmentation of glycerol-1-phosphate and 1,2-dimyristoyl-glycero-3-phosphatidyl-glycerol, decreasing the radiation-chemical yields of either inorganic phosphate or phosphatidic acid respectively. The observed effects of blocking free-radical processes are believed to be related to the ability of the tested compounds to oxidize α-hydroxyl-containing carbon-centered radicals of starting substrates, which give rise to fragmentation reaction. The possibility of using the discovered properties of quinones, doxorubicin and nitroazoles to provide practical solutions in oncological radiotherapy and pathophysiology is discussed.