Electrochemical studies of the interaction of rifampicin and nanosome/rifampicin with dsDNA

Victoria V Shumyantseva; Tatiana V Bulko; Elena G Tikhonova; Maxim A Sanzhakov; Alexey V Kuzikov; Rami A Masamrekh; Dmitry V Pergushov; Felix H Schacher; Larisa V Sigolaeva

doi:10.1016/j.bioelechem.2020.107736

Electrochemical studies of the interaction of rifampicin and nanosome/rifampicin with dsDNA

Bioelectrochemistry. 2021 Aug:140:107736. doi: 10.1016/j.bioelechem.2020.107736. Epub 2020 Dec 29.

Authors

Victoria V Shumyantseva¹, Tatiana V Bulko², Elena G Tikhonova³, Maxim A Sanzhakov³, Alexey V Kuzikov⁴, Rami A Masamrekh⁴, Dmitry V Pergushov⁵, Felix H Schacher⁶, Larisa V Sigolaeva²

Affiliations

¹ Institute of Biomedical Chemistry, Pogodinskaya Street 10, 119121 Moscow, Russia; Pirogov Russian National Research Medical University, Ostrovitianov Street 1, 117997 Moscow, Russia; Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russia. Electronic address: viktoria.shumyantseva@ibmc.msk.ru.
² Institute of Biomedical Chemistry, Pogodinskaya Street 10, 119121 Moscow, Russia; Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russia.
³ Institute of Biomedical Chemistry, Pogodinskaya Street 10, 119121 Moscow, Russia.
⁴ Institute of Biomedical Chemistry, Pogodinskaya Street 10, 119121 Moscow, Russia; Pirogov Russian National Research Medical University, Ostrovitianov Street 1, 117997 Moscow, Russia; Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russia.
⁵ Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russia.
⁶ Institute of Organic Chemistry and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, D-07743 Jena, Germany; Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena, D-07743 Jena, Germany; Center for Energy and Environmental Chemistry (CEEC), Friedrich-Schiller-University Jena, D-07743 Jena, Germany.

PMID: 33494014
DOI: 10.1016/j.bioelechem.2020.107736

Abstract

The interactions of dsDNA with rifampicin (RF) or with rifampicin after encapsulation in phospholipid micelles (nanosome/rifampicin) (NRF) were studied electrochemically. Screen-printed electrodes (SPEs) modified by stable dispersions of multi-wolled carbon nanotubes (MWCNTs) in aqueous solution of poly(1,2-butadiene)-block-poly(2-(dimethylamino)ethyl methacrylate) (PB₂₉₀-b-PDMAEMA₂₄₀) diblock copolymer were used for quantitative electrochemical investigation of direct electrochemical oxidation of guanine at E = 0.591 V (vs. Ag/AgCl) and adenine at E = 0.874 V (vs. Ag/AgCl) of dsDNA and its change in the presence of RF or NRF. Due to RF or NRF interaction with dsDNA, the differential pulse voltammetry (DPV) peak currents of guanine and adenine decreased and the peak potentials shifted to more positive values with increasing drug concentration (RF or NRF). Binding constants (K_b) of complexes RF-dsDNA and NRF-dsDNA were calculated based on adenine and guanine oxidation signals. The K_b values for RF-dsDNA were 1.48 × 10⁴ M^-1/8.56 × 10⁴ M^-1, while for NRF-dsDNA were 2.51 × 10⁴ M^-1/1.78 × 10³ M^-1 (based on adenine or guanine oxidation signals, respectively). The values of K_b revealed intercalation mode of interaction with dsDNA for RF and mixed type of interaction (intercalation and electrostatic mode) for NRF. The estimated values of ΔG (Gibbs free energy) of the complex formation confirmed that drug-dsDNA interactions are spontaneous and favourable reactions.

Keywords: Amphiphilic diblock copolymer; Antibiotic; DNA; Electrochemical biosensor; Phospholipid nanoparticles; Rifampicin.

MeSH terms

Antibiotics, Antitubercular / administration & dosage
Antibiotics, Antitubercular / pharmacology*
DNA / metabolism*
Electrochemical Techniques
Micelles
Models, Molecular
Nanocapsules / chemistry*
Phospholipids / chemistry
Rifampin / administration & dosage
Rifampin / pharmacology*

Substances

Antibiotics, Antitubercular
Micelles
Nanocapsules
Phospholipids
DNA
Rifampin