OXIDIZED DERIVATIVES OF THIAMINE: FORMATION, PROPERTIES, BIOLOGICAL ROLE
Yu. M. Parkhomenko1, I. I. Stepuro2, G. V. Donchenko1, V. I. Stsiapura3
The data available in literature about formation, properties, possible biological role and practical application of the oxidized derivatives of В1 vitamin (thiamine) is first generalized and analysed in the review. It is known that at the values of рН > 7.0 the molecule of thiamine is able to undergo two-phase reaction of opening of thiazole ring with formation of anion of thiol form of thiamine and unstable tricyclic form. In the presence of oxidants in an alkaline environment a thiol form of thiamine is oxidized to thiamine disulfide, tricyclic form – to thiochrome. Oxidative transformation of thiamine molecule is promoted by phenoxyl radicals, their level can be substantially increased in animal tissues at oxidizing stress of different origin when the level of reactive forms of oxygen sharply increases and content of hemoproteins oxoferryl forms is raised. The analysis of literature data gives grounds to assume that thiamine and its hydrophobic metabolite – thiochrome – under certain conditions can perform an important antioxidant function in protection of cell structures against damaging action of peroxinitrite, nitrogen dioxide, peroxide. The presence of oxidized metabolites of thiamine and its phosphates in the cells of animals, even in minor quantities, is an established fact and, consequently, there is a possibility, that they can interact specifically with cellular structures or proteins to effect cellular processes in certain conditions.
Key words: thiamine, thiamine disulfide, disulfide of thiamine diphosphate, thiol and tricyclic forms of thiamine, thiochrome, phenoxyl radicals, hemoproteins oxoferryl forms.
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