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<p>A new method for the synthesis of pyridoxine salts with dicarboxylic acids was proposed. The specific features of the synthesis include the preliminary generation of free pyridoxine from the hydrochloride form by treatment with a solution of triethylamine in chloroform and conduction of the reaction of pyridoxine with dicarboxylic acid in a specially selected solvent mixture. The combination of pyridoxine as a known antioxidant and fumarate as an activator of the transcription factor Nrf2 in one molecule gave rise to a unique structure, bis[3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridinium] fumarate (DPNF). <i>In vitro</i> experiments showed the ability of this compound to bind superoxide, suppress lipid peroxidation processes, and behave as a mitochondrial cytoprotective agent and Nrf2 activator. The results of the study can be used to develop a new type of drugs based on activators of the transcription factor Nrf2 to protect cells and tissues from oxidative damage.</p>

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Synthesis and biological activity of bis[3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridinium] fumarate as a new activator of the transcription factor Nrf2

  • 期刊论文

  • 发表日期：

    2025年3月1日

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  • A. A. Balakina,
  • V. I. Amozova,
  • T. S. Stupina,
  • V. A. Mumyatova,
  • A. D. Podgurskaya,
  • S. Ya. Gadomsky

摘要

A new method for the synthesis of pyridoxine salts with dicarboxylic acids was proposed. The specific features of the synthesis include the preliminary generation of free pyridoxine from the hydrochloride form by treatment with a solution of triethylamine in chloroform and conduction of the reaction of pyridoxine with dicarboxylic acid in a specially selected solvent mixture. The combination of pyridoxine as a known antioxidant and fumarate as an activator of the transcription factor Nrf2 in one molecule gave rise to a unique structure, bis[3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridinium] fumarate (DPNF). In vitro experiments showed the ability of this compound to bind superoxide, suppress lipid peroxidation processes, and behave as a mitochondrial cytoprotective agent and Nrf2 activator. The results of the study can be used to develop a new type of drugs based on activators of the transcription factor Nrf2 to protect cells and tissues from oxidative damage.