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Molecular complexes of triterpene glycosides with 5-fluorouracil sodium salt: spectral characterization and cytotoxic activity

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Abstract

Interactions of the triterpene glycosides α-hederin (1), hederasaponin C (2), and glycyrrhizic acid (GC) monoammonium salt with 5-fluorouracil (5FU) sodium salt were studied by electronic, IR, and NMR spectroscopy. The complete assignment of signals in the 13C and 19F NMR spectra in DMSO-d6 for individual compounds and their complexes in equimolar ratios was performed. The obtained spectral data indicate the formation of complexes. The in vitro cytotoxicity of the synthesized complexes was evaluated in cancer cell lines (SH-SY5Y, MCF-7, HepG2) and conditionally normal cells (HEK293). The complexes 2—5FU and GC—5FU were found to have high activity only against the SH-SY5Y neuroblastoma cell line. Compared to glycoside 1, the complex 1—5FU exhibited more pronounced activity and high selectivity against the SH-SY5Y human neuroblastoma cell line and the MCF-7 breast ductal adenocarcinoma cell line comparable with the corresponding characteristics of the reference compound doxorubicin.

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Funding

The study was performed within the framework of the state assignment for the Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences on the theme “Synthesis of biologically active compounds based on natural products. Development of environmentally benign materials and processes” (No. 122031400260-7).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Centre, Russian Academy of Sciences, 69 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    N. N. Gibadullina, L. V. Spirikhin & V. A. Dokichev

  2. Sevastopol State University, 33 ul. Universitetskaya, 299053, Sevastopol, Russian Federation

    L. A. Yakovishin

  3. V. I. Vernadsky Crimean Federal University, 4 prosp. Vernadskogo, 295007, Simferopol, Russian Federation

    V. I. Grishkovets

  4. Institute of Biochemistry and Genetics, Ufa Federal Research Centre, Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    V. A. Vakhitov & D. V. Ishmetova

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  1. N. N. Gibadullina
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  2. L. A. Yakovishin
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  3. V. I. Grishkovets
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  4. L. V. Spirikhin
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  5. V. A. Vakhitov
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  6. D. V. Ishmetova
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  7. V. A. Dokichev
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Correspondence to N. N. Gibadullina.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 1, pp., January, 2024.

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Gibadullina, N.N., Yakovishin, L.A., Grishkovets, V.I. et al. Molecular complexes of triterpene glycosides with 5-fluorouracil sodium salt: spectral characterization and cytotoxic activity. Russ Chem Bull 73, 179–188 (2024). https://doi.org/10.1007/s11172-024-4130-0

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  • DOI: https://doi.org/10.1007/s11172-024-4130-0

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