Electrochemical analysis of the interaction between DNA and abiraterone D4A metabolite

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The electroanalytical characteristics of double-stranded DNA (dsDNA) and the complex of dsDNA with the anticancer drug metabolite, abiraterone D4A, in the concentration range of 25–200 μM were investigated using differential pulse voltammetry. The effect of D4A on dsDNA was detected by changes in the intensity of the electrochemical oxidation of the heterocyclic bases guanine, adenine, and thymine. This investigation used screen-printed electrodes modified with carbon nanotubes. Binding constants (Kb) for guanine, adenine, and thymine in the dsDNA/D4A complexes were calculated to be 1.1 × 104, 5.5 × 103, and 2.5 × 103 M–1, respectively. The DNA-mediated electrochemical coefficients of the toxic effect were calculated as the ratio of the signal intensities of guanine and adenine in the presence of D4A compared to those without the drug (T, %). Based on an analysis of electrochemical parameters and binding constant values, an assumption was made regarding the mechanism of the interaction between D4A and DNA, predominantly through electrostatic interactions and the formation of hydrogen bonds with the minor groove. Conclusions about the mechanism of the interaction of the abiraterone D4A metabolite with the dsDNA minor groove, obtained by electrochemical methods, were supported by the molecular simulation of the DNA/D4A complex.

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作者简介

V. Shumyantseva

Orekhovich Research Institute of Biomedical Chemistry; Russian National Research Medical University

编辑信件的主要联系方式.
Email: viktoria.shumyantseva@ibmc.msk.ru

Faculty of Medicine and Biology

俄罗斯联邦, 119121, Moscow; 117321, Moscow

A. Berezhnova

Orekhovich Research Institute of Biomedical Chemistry

Email: viktoria.shumyantseva@ibmc.msk.ru
俄罗斯联邦, 119121, Moscow

L. Agafonova

Orekhovich Research Institute of Biomedical Chemistry

Email: viktoria.shumyantseva@ibmc.msk.ru
俄罗斯联邦, 119121, Moscow

T. Bulko

Orekhovich Research Institute of Biomedical Chemistry

Email: viktoria.shumyantseva@ibmc.msk.ru
俄罗斯联邦, 119121, Moscow

A. Veselovsky

Orekhovich Research Institute of Biomedical Chemistry; Russian National Research Medical University

Email: viktoria.shumyantseva@ibmc.msk.ru

Faculty of Medicine and Biology

俄罗斯联邦, 119121, Moscow; 117321, Moscow

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2. Scheme 1. Oxidation of abiraterone by 3b-hydroxysteroid dehydrogenase (3b-HSD) to form a 3-keto-Δ4-derivative of abiraterone (a metabolite of abiraterone D4A) [20, 23, 24].

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3. Fig. 1. Methods of studying DNA/drug complexes.

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4. Fig. 2. (a) Differential pulse voltammograms of PGE/CNT/D4A with a metabolite concentration of 100 microns in the potential range 0.2–1.2 V. (b) Cyclic voltammograms of PGE/CNT/D4A in the potential range 0.2–1.2 V.

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5. 3. (a) Differential pulse voltammograms of PGE/UN, GE/UND/D4 A and GE/UND/dsDNA (1.5 mg/ml)/D4 A (100 microns) with different incubation time of the complex. The dependence of the intensity of electrooxidation signals during the interaction of the D4A metabolite with DNA on the incubation time for: (b) guanine, (c) adenine, and (d) thymine.

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6. Fig. 4. (a) Differential pulse voltammograms of PGE/UN, GE/UND/DNA and PEG/UNT/DNA (1.5 mg/ml) / D4A with different concentrations of the drug. The dependences of the values of dsDNA electrooxidation potentials for (b) guanine and adenine, (c) thymine on concentrations of 0-200 microns of the metabolite abiraterone D4A.

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7. 5. The effect of therapeutic concentrations (0-200 microns) of the metabolite abiraterone D4A on the intensity of dsDNA electrooxidation (1.5 mg/ml) of (a) guanine, (b) adenine, and (c) thymine.

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8. 6. The dependence of log(1/[D4A]) on log[IDNA/D4A/(IDNA –IDNA/D4A)] for determining the binding constants for (a) guanine, (b) adenine, and (c) thymine.

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9. 7. Models of (a) abiraterone and (b) D4A complexes with DNA. The yellow dotted lines show hydrogen bonds.

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