Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties

Aseeva, Natalia V.; Danilenko, Nadezhda V.; Plotnikov, Evgenii V.; Korotkova, Elena I.; Lipskikh, Olga I.; Solomonenko, Anna N.; Erkovich, Alina V.; Eskova, Daria D.; Khlebnikov, Andrei I.

doi:10.3390/ijms252212245

Open AccessArticle

Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties

by

Natalia V. Aseeva

^1,*,

Nadezhda V. Danilenko

²,

Evgenii V. Plotnikov

³

,

Elena I. Korotkova

¹

,

Olga I. Lipskikh

¹

,

Anna N. Solomonenko

¹,

Alina V. Erkovich

¹

,

Daria D. Eskova

³

and

Andrei I. Khlebnikov

^2,*

¹

Engineering School of Natural Resources, Department of Chemical Engineering, National Research Tomsk Polytechnic University, Lenin Avenue, 30, Tomsk 634034, Russia

²

The School of Advanced Manufacturing Technologies, National Research Tomsk Polytechnic University, Lenin Avenue, 30, Tomsk 634034, Russia

³

Research School of Chemistry & Applied Biomedical Sciences, National Research Tomsk Polytechnic University, Lenin Avenue, 30, Tomsk 634034, Russia

^*

Authors to whom correspondence should be addressed.

Int. J. Mol. Sci. 2024, 25(22), 12245; https://doi.org/10.3390/ijms252212245

Submission received: 14 October 2024 / Revised: 4 November 2024 / Accepted: 6 November 2024 / Published: 14 November 2024

(This article belongs to the Section Physical Chemistry and Chemical Physics)

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Abstract

This study presents the synthesis of new fluorosulfate derivatives of 1,4-naphthoquinone by the SuFEx reaction. Anticancer properties of obtained compounds were studied on PC-3 (prostate adenocarcinoma), SKOV-3 (ovarian cancer), MCF-7 (breast cancer), and Jurkat cell lines. All the studied compounds showed higher cytotoxic effects than Cisplatin. The DFT method was applied to determine the electronic structure characteristics of 1,4-naphthoquinone derivatives associated with cytotoxicity. A method of determination of 2,3-dichloro-1,4-naphthoquinone (NQ), 3-chloro-2-((4-hydroxyphenylamino)-1,4-naphthoquinone (NQ1), and 4-((3-chloro-1,4-naphthoquinon-2-yl)amino)phenyl fluorosulfate (NQS) in a pharmaceutical substance using an impregnated graphite electrode (IMGE) was developed. The morphology of the IMGE surface was studied using scanning electron microscopy (SEM). The electrochemical behavior of NQ, NQ1, and NQS was studied by cyclic voltammetry (CV) in 0.1 M NaClO₄ (96% ethanol solution) at pH 4.0 in a potential range from −1 to +1.2 V. Electrochemical redox mechanisms for the investigated compounds were proposed based on the determining main features of the electrochemical processes. Calibration curves were obtained by linear scan voltammetry in the first derivative mode (LSVFD) with the detection limit (LOD) 7.2 × 10⁻⁶ mol·L⁻¹ for NQ, 8 × 10⁻⁷ mol·L⁻¹ for NQ1, and 8.6 × 10⁻⁸ mol·L⁻¹ for NQS, respectively.

Keywords: 1,4-naphthoquinone fluorosulfate derivatives; SuFEx reaction; anticancer properties; impregnated graphite electrode; voltammetry

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MDPI and ACS Style

Aseeva, N.V.; Danilenko, N.V.; Plotnikov, E.V.; Korotkova, E.I.; Lipskikh, O.I.; Solomonenko, A.N.; Erkovich, A.V.; Eskova, D.D.; Khlebnikov, A.I. Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties. Int. J. Mol. Sci. 2024, 25, 12245. https://doi.org/10.3390/ijms252212245

AMA Style

Aseeva NV, Danilenko NV, Plotnikov EV, Korotkova EI, Lipskikh OI, Solomonenko AN, Erkovich AV, Eskova DD, Khlebnikov AI. Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties. International Journal of Molecular Sciences. 2024; 25(22):12245. https://doi.org/10.3390/ijms252212245

Chicago/Turabian Style

Aseeva, Natalia V., Nadezhda V. Danilenko, Evgenii V. Plotnikov, Elena I. Korotkova, Olga I. Lipskikh, Anna N. Solomonenko, Alina V. Erkovich, Daria D. Eskova, and Andrei I. Khlebnikov. 2024. "Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties" International Journal of Molecular Sciences 25, no. 22: 12245. https://doi.org/10.3390/ijms252212245

APA Style

Aseeva, N. V., Danilenko, N. V., Plotnikov, E. V., Korotkova, E. I., Lipskikh, O. I., Solomonenko, A. N., Erkovich, A. V., Eskova, D. D., & Khlebnikov, A. I. (2024). Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties. International Journal of Molecular Sciences, 25(22), 12245. https://doi.org/10.3390/ijms252212245

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Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties

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