Российская академия наук


MULTIFUNCTIONAL Antioxidants based on derivatives of NITROBENZOFUROxANs



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MULTIFUNCTIONAL Antioxidants based on derivatives of NITROBENZOFUROxANs

Chugunova E.A.1, Neganova M.E.2, Timasheva R.E.3, Serkov I.V.2, Proshin A.N.2,

Gibadullina E.M.1, Shevtsova E.F.2, Burilov A.R.1

1 State Budgetary-Funded Institution of Science A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russia; 2State Budgetary-Funded Institution of Science Institute of Physiologically Active Compounds of Russian Academy of Science, Chernogolovka, Russia; 3The Kazan National Research Technological University, Kazan, Russia; chugunova.ea @ gmail.com
There are numerous data showing the role of oxidative stress in the development of pathological conditions accompanying various diseases, including neurodegenerative ones. In the modern industry of drugs antioxidants are used as a means of prevention and treatment of diseases that are directly associated with the development of oxidative cascade. It is known that under conditions of oxidative stress, NO can act as an antioxidant, able to suppress free radical lipid. Nitrogen monoxide (NO) has a pronounced effect on the cardiovascular system and has cytotoxic, immune-modulatory and neurotransmitter action. As it is impossible to include NO into the molecule of an organic compound, its "hidden" forms are used, such as benzofuroxan that can spontaneously emit it in the body. Promising platforms are 4,6-dichloro-5-nitrobenzofuroxan and 7-chloro-4,6-dinitrobenzofuroxan, based on which, thanks to the presence in the molecule of readily movable chlorine atoms, the possibility of synthesizing a variety of new NO-donor antioxidants appears.

As a result of the directed chemical synthesis a series of new derivatives of (di) nitrobenzofuroxans containing fragments of amino acids and nitroaminoalcohols was obtained.

At the initial stage of studying the biological activity of these compounds, substances with antioxidant properties were researched. Model of lipid peroxidation (LPO) initiated with Fe3+ ions in rat brain homogenates was chosen. The accumulation of malondialdehyde at 530-620 nm was determined spectrophotometrically. The most active of the derivative series in this test was the 6-chloro-5-nitro-4-[(2-(nitroxy) ethyl)amino]benzofuroxan compound. It inhibited lipid peroxidation by 54,2 ± 2,3% at the concentration of 0,1 mM.

Thus, the introduction of an additional molecule of benzofuroxan with NO-donor group in the form of nitroaminoalcohol enhan fragment increases the antioxidant action of this compound.



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