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Amino Derivatives of Natural Epoxyalantolactone: Synthesis and Cytotoxicity toward Tumor Cells

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Abstract

Reactions of natural epoxyalantolactone with primary and secondary amines, which lead to hydrated benzo[g]furo[4,3,2-cd]indolones and eudesmane-type amino derivatives, respectively, have been studied. Epoxyalantolactone conjugates have been synthesized with the involvement of pharmacophoric amines, and their cytotoxic activity toward some tumor cell lines has been tested. The involvement of the signaling pathway of protein p53 in the death of tumor cells, the contribution of oxidative stress, and the induction of apoptosis have been investigated in experiments in vitro.

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Abbreviations

ROS:

reactive oxygen species

NAC:

N-acetylcysteine

MTT:

3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

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Authors and Affiliations

  1. Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia

    S. A. Pukhov, S. V. Afanasyeva, L. V. Anikina, A. V. Semakov, E. S. Dubrovskaya & S. G. Klochkov

Authors
  1. S. A. Pukhov
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  2. S. V. Afanasyeva
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  3. L. V. Anikina
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  4. A. V. Semakov
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  5. E. S. Dubrovskaya
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  6. S. G. Klochkov
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Corresponding author

Correspondence to S. A. Pukhov.

Additional information

Original Russian Text © S.A. Pukhov, S.V. Afanasyeva, L.V. Anikina, A.V. Semakov, E.S. Dubrovskaya, S.G. Klochkov, 2018, published in Bioorganicheskaya Khimiya, 2018, Vol. 44, No. 5, pp. 560–569.

This article is published based on the report presented at the Third Russian Conference on Medicinal Chemistry, September 28– October 3, 2017, Kazan.

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Pukhov, S.A., Afanasyeva, S.V., Anikina, L.V. et al. Amino Derivatives of Natural Epoxyalantolactone: Synthesis and Cytotoxicity toward Tumor Cells. Russ J Bioorg Chem 44, 553–561 (2018). https://doi.org/10.1134/S1068162018040155

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  • DOI: https://doi.org/10.1134/S1068162018040155

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