Electrochemical study of the free form of anti-tumor antibiotic doxorubicin and encapsulated in a biocompatible copolymer of N-vinyl pyrrolidone with (di)methacrylates

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Abstract

A comparative study of the electrochemical behavior of various forms of the antitumor antibiotic doxorubicin (DOX) - free and encapsulated in micelle-like nanoparticles of the biocompatible amphiphilic copolymer N-vinylpyrrolidone (VP) — methacrylic acid — triethylene glycol dimethacrylate (TEGDM) — in aqueous neutral buffer solutions on a glassy carbon electrode was carried out. The hydrodynamic radii of the Rh copolymer and DOX polymer nanostructures were determined using the dynamic light scattering method. It was demonstrated using cyclic and square wave voltammetry the presence of two main redox transitions for both forms of DOX at pH 7.24: irreversible oxidation/reduction in the potential range from 0.2 to 0.6 V and reversible reduction/reoxidation — from −0.4 to −0.7 V (saturated Ag/AgCl reference electrode), and their redox potentials were determined. The difference in the potentials of the corresponding peaks of both redox transitions does not exceed several tens (20–30) mV, while the oxidation of the encapsulated form is easier than the free one, and reduction is somewhat more difficult. Analysis of the dependence of the reduction current of both forms of DOX on the rate of potential sweep shows that electron transfer to a molecule of free DOX is largely determined by the rate of accumulation of the reagent in the adsorption layer, and the encapsulated form is characterized by mixed adsorption-diffusion control. Based on voltammetric data and the results of quantum chemical modeling, it was concluded that a hydrogen bond is formed between the oxygen-containing groups of the monomer units of the copolymer and the H-atoms OH and NH2 groups of DOX. The bond energies in the structures considered are calculated and it is shown that their values are close to classical ones if the carbonyl group of the lactam ring of VP in the encapsulating polymer is an electron donor, and the hydrogens OH and NH2 groups of DOX are acceptors. At the same time, the bonds formed with the participation of the oxygen atom of the ester group of the TEGDM unit are extremely weak.

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V. A. Kurmaz

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS

Author for correspondence.
Email: kurmaz@icp.ac.ru
Russian Federation, Chernogolovka

D. V. Konev

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS

Email: dkfrvzh@yandex.ru
Russian Federation, Chernogolovka

S. V. Kurmaz

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS

Email: kurmaz@icp.ac.ru
Russian Federation, Chernogolovka

N. S. Emelyanova

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS

Email: kurmaz@icp.ac.ru
Russian Federation, Chernogolovka

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Supplementary files

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2. Scheme 1. General mechanism of electroreduction of quinones in protic media (stages a, c, c’, d, e) and aprotic media (stages a, b, f).

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3. Scheme 2. General mechanism of electrooxidation of hydroquinones in aprotic media.

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4. Fig. 1. Structural formula of doxorubicin.

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5. Scheme 3. General mechanism of EV and EO DOX in protogenic environments.

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6. Fig. 2. Comparison of the CVA background curves obtained at v = 0.1 V/s in an aqueous phosphate buffer solution with pH 7.24: 1 — buffer solution; 2 — buffer solution + 0.3 mg/ml TP; 3 — buffer solution + 0.3 mg/ml TP + 8.5×10–4 M lactose.

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7. Fig. 3. Distribution of light scattering intensity by particle sizes in aqueous buffer solutions of VP-MAC-DMTEG terpolymer (1, 2) and TP-DOX polymer composition (3). Concentrations of TP are 1 (1) and 3.5 mg/ml (2), and of TP-DOX polymer composition (3) is 1 mg/ml, 25°C. pH 7.2–7.4 with additions of NaCl (137 mM) and KCl (2.68 mM).

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8. Fig. 4. CVA curves of DOX (a) and TP-DOX (b) in an aqueous phosphate buffer solution (pH 7.24) at the GC electrode in the I, E coordinates at scan rates v = 0.01–2 V/s. DOX concentration is 4.0×10−5 (a) and 1.4×10−5 M (b); (c), (d) — curves of Fig. (a) and (b) in the I/v, E coordinates. 1st scan.

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9. Fig. 5. CVA curves of DOX (1) and TP-DOX (2) from Fig. 4a, 4b. v = 0.1 V/s.

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10. Fig. 6. CVA curves of DOX (a) and TP-DOX structure (b) in the region of cathodic potentials in an aqueous phosphate buffer solution (pH 7.24) on a GC electrode in the I, E coordinates at scan rates v of 0.01–2 V/s. DOX concentration 3.9×10−5 (a) and 3.5×10−5 M (b); (c), (d) — curves of Fig. (a) and (b) in the I/v, E coordinates. 1st scan.

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11. Fig. 7. QVVA DOX (a) and TP-DOX structures (c), obtained at different frequencies and reduced to 1 (b, d). DOX concentration 3.9×10−5 (a) and 3.5×10−5 M (c).

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12. Fig. 8. (a) Dependences of the heights of the ipc1 cathodic peaks on the sweep rate (log ipc1, log v) for different concentrations of DOX: 1.43×10−5 (1), 3.5×10−6 (2), and 3.9×10−5 M (3), and TP-DOX 3.5×10−5 M (4); (b) dependences of the heights of the cathodic ipc1 (1, 3) and anodic ipa1 (2, 4) peaks on the sweep rate (log ipc1, ipa1, lg v) for 3.5×10−6 M DOX (1, ​​2) and 3.5×10−5 M TP-DOX (3, 4). Numbers near the graphs are the slopes. The capacitive current has been subtracted.

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13. Fig. 9. CVA curves of DOX (a), (b) and TP-DOX (c), (d) in the region of anodic potentials in an aqueous phosphate buffer solution (pH 7.24) at the GC electrode in the I, E coordinates at scan rates v of 0.01–2 V/s. DOX concentration 3.9×10−5 (a) and 3.5×10−5 M (b); (c), (d) — curves of Fig. (a) and (b) in the I/v, E coordinates. 1st scan.

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