Tetraeicosahydroxyfullerene C60(ОН)24: optimized preparative synthesis, properties and applica-tions

Tetraeicosahydroxyfullerene C₆₀(OH)₂₄ has a wide range of unique and useful properties that allow it to be successfully used in a number of sectors of the national economy. Interest in this compound is due to its extremely high biological potential, which manifests itself in a potentiating effect against malignant neoplasms (when used together with cisplatin) and as an agent for the delivery of radioactive isotopes in radiation medicine. This paper presents a convenient and easily scalable procedure for the synthesis and purification of C₆₀(OH)₂₄ tetraeicosahydroxyfullerene by catalytic bromination of C₆₀ fullerene in liquid bromine in the presence of metallic iron. The technology of purification of the target product using ion exchange resins AB-17-8 and TOKEM-100 has been developed.

1. Orlova M.A., Trofimova T.P., Orlov A.P., Shatalov O.A., Napolov Yu.K., Svistunov A.A., Chekhonin V.P. Antitumor activity of fullerene derivatives and their possible use for target drug delivery. Onkogematologija = Oncohematology, 2013, no. 2, pp. 83−92. https://doi.org/10.17650/1818-8346-2013-8-2-83-92 (in Russian).

2. Dikusar E. A., Pushkarchuk A. L., Bezyazychnaya T. V., Kasandrovich E. G., Soldatov А. G., Kuten S. А., Stepin S. G., Nizovtsev A. P., Kilin S. Ya. Tetracosehydroxybuckminsterfullerenol is a reagent of the future. Chemical reagents, reagents and processes of small-scale chemistry. – Abstracts of the XXXI International scientific and technical conference “React-2018”. – October 2–4, 2018, Minsk, Belarus. Minsk: Belarusian Science, 2018, p. 22 (in Russian).

3. Piotrovskiy L. B., Kiselev O. I. Fullerenes in biology. St. Petersburg, Rostock, 2006. 335 p. (in Russian).

4. Đorđević A., Bogdanović G. Fullerenol: A new nanopharmaceutic? Archive of Oncology, 2008, vol. 16, no. 3–4, pp. 42–45. https://doi.org/10.2298/AOO0804042D

5. Panova G. G., Kanash E. V., Semenov K. N., Charykov N. A., Khomyakov Yu. V., Anikina L. M., Artem’eva A. M., Kornyukhin D. L., Vertebnyi V. E., Sinyavina N. G., Udalova O. R., Kulenova N. A., Blokhina S. Yu. Fullerene derivatives stimulate the production process, growth and resistance to oxidative stress in wheat and barley plants. Sel’skohozjajstvennaja biologija = Agricultural Biology, 2018, vol. 53, no. 1, pp. 38–49. doi: 10.15389/agrobiology.2018.1.38rus (in Russian).

6. Semenov K.N., Charykov N.A., Keskinov V.A. Fullerenol synthesis and identification. Рroperties of fullerenol water solutions. Journal of Chemical and Engineering Data, 2011, vol. 56, nn. 2, pp. 230–239. doi: https://pubs.acs.org/doi/10.1021/je100755v

7. Pushkarchuk A., Bezyazychnaya T., Potkin V., Dikusar E., Soldatov A., Kilin S., Nizovtsev A., Kuten S., Ermak D., Pushkarchuk V., Zhou H., Kulchitsky V. DFT Study of the Biological Activity of Fullerenol – Cisplatin Conjugate as an Antitumor Therapy Agent. Journal of Biomedical Research & Environmental Sciences, 2023, vol. 4, no. 2, pp. 179–183. doi: 10.37871/jbres1661

8. Dikusar E. A., Pushkarchuk A. L., Bezyazychnaya T. V., Akishina E. A., Soldatov А. G., Kuten S. А., Stepin S. G., Nizovtsev A. P., Kilin S. Ya., Potkin V. I. Quantum-chemical modeling of cortisone-fullerenol agents of cancer therapy. Vestsi Natsyyanal’nai akademii navuk Belarusi. Seryya khimichnykh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical Series, 2021, vol. 57, no. 4, pp. 400–407 (doi: https://doi.org/10.29235/1561-8331-2021-57-4-400-407 (in Russian).

9. Dikusar E. A., Pushkarchuk A. L., Bezyazychnaya T. V., Akishina E. A., Soldatov А. G., Kuten S. А., Stepin S. G., Nizovtsev A. P., Kilin S. Ya., Babichev L. F., Potkin V. I. Prospects for creating radon containing agents in radionuclide therapy. Vestnik farmacii = Pharmacy bulletin, 2021, no. 3 (93), pp. 64–72 (in Russian).

10. Dikusar E. A., Pushkarchuk A. L., Bezyazychnaya T. V., Akishina E. A., Soldatov А. G., Kuten S. А., Stepin S. G., Nizovtsev A. P., Kilin S. Ya., Kulchitsky V. A., Potkin V. I. Quantum-chemical modeling of doxorubicino-fullerenol agents of cancer therapy. Vestsi Natsyyanal’nai akademii navuk Belarusi. Seryya khimichnykh navuk = Proceedings of the National Academy of Sciences of Belarus. Сhemical series, 2022, vol. 58, no. 4, pp. 369–378 (in Russian).

11. Charkin O. P., Klimenko N. M., Wang Y.-S., Wang C.-C., Chen C.-H., Lin S. H. Theoretical and experimental study of fullerenol molecules and ions C60(OH)24-N (OL)N and C60(OH)24-N(OL)N L+ successively substituted by alkali metal atoms l (N = 1-24). Zhurnal neorganicheskoj himii = Russian journal of inorganic chemistry, 2011, vol. 56, no. 4, pp. 623–633 (in Russian).