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<p>The interactions of dsDNA with alpha-lipoic acid (ALA, α-lipoic acid) and ALA embedded into phospholipid nanoparticles (ALA-NPhs) were studied electrochemically by square-wave voltammetry technique. Screen-printed electrodes (SPE) modified with a freshly prepared water dispersion of single-walled carbon nanotubes (SPE/CNT), were used for the quantitative electrochemical analysis of ALA and ALANPhs. SPE/CNTs effectively registered direct electrochemical oxidation of guanine, adenine, and thymine heterocyclic bases of dsDNA, and their changes in the presence of ALA or ALA-NPhs. The electrochemical oxidation signal of adenine was chosen as the most pronounced detecting signal registered in the presence of ALA or ALA-NPhs. From the obtained experimental data on the decrease in the amplitude of the adenine oxidation currents, the electrochemical coefficient of the toxic effect was calculated as the ratio of the unbound dsDNA signal to the dsDNA signal in the presence of ALA or ALA-NPhs. Binding constants (Kb) of the DNA–drug complexes were calculated in accordance with the decline of adenine oxidation signals. Based on our experiments, we have proven that incorporating ALA–Loaded into Phospholipid Nanoparticles (ALA-NPhs) changes the moderately toxic effect of lipoic acid on DNA to a non-toxic effect. The calculated Kb = 2.30 M<sup>− 1</sup> value for DNA–ALA-NPhs complex also confirmed this suggestion. The Kb of the DNA–ALA complex is about 1.45 × 10<sup>3</sup> M<sup>− 1</sup> and reflects non-covalent interaction with DNA through hydrogen bonding within the minor groove.</p>

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Comparative Analysis of Physicochemical and Biochemical Properties of Lipoic acid and its Phospholipid Composition

  • 期刊论文

  • 发表日期：

    2026年7月14日

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  • Lyubov E. Agafonova,
  • Yulia A. Tereshkina,
  • Nadezhda V. Pyndyk,
  • Tatiana V. Bondarenko,
  • Elena G. Tikhonova,
  • Yulia A. Romashova,
  • Alexander I. Archakov,
  • Victoria V. Shumyantseva

摘要

The interactions of dsDNA with alpha-lipoic acid (ALA, α-lipoic acid) and ALA embedded into phospholipid nanoparticles (ALA-NPhs) were studied electrochemically by square-wave voltammetry technique. Screen-printed electrodes (SPE) modified with a freshly prepared water dispersion of single-walled carbon nanotubes (SPE/CNT), were used for the quantitative electrochemical analysis of ALA and ALANPhs. SPE/CNTs effectively registered direct electrochemical oxidation of guanine, adenine, and thymine heterocyclic bases of dsDNA, and their changes in the presence of ALA or ALA-NPhs. The electrochemical oxidation signal of adenine was chosen as the most pronounced detecting signal registered in the presence of ALA or ALA-NPhs. From the obtained experimental data on the decrease in the amplitude of the adenine oxidation currents, the electrochemical coefficient of the toxic effect was calculated as the ratio of the unbound dsDNA signal to the dsDNA signal in the presence of ALA or ALA-NPhs. Binding constants (Kb) of the DNA–drug complexes were calculated in accordance with the decline of adenine oxidation signals. Based on our experiments, we have proven that incorporating ALA–Loaded into Phospholipid Nanoparticles (ALA-NPhs) changes the moderately toxic effect of lipoic acid on DNA to a non-toxic effect. The calculated Kb = 2.30 M− 1 value for DNA–ALA-NPhs complex also confirmed this suggestion. The Kb of the DNA–ALA complex is about 1.45 × 103 M− 1 and reflects non-covalent interaction with DNA through hydrogen bonding within the minor groove.