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Synthesis and Cytotoxic Activity of the Conjugate of an Oxygenated Betulinic Acid Analog with the Delocalized Lipophilic Cationic Compound F16

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Chemistry of Natural Compounds Aims and scope

A new lupane triterpenoid containing a 1α,2β,3β-triacetoxy-functionalized ring A was synthesized from betulinic acid. Its conjugate with the membrane-penetrating cationic compound F16 was prepared. The conjugate exhibited significantly more pronounced antitumor activity than betulinic acid (betulinic acid IC50 34.5 μM, conjugate IC50 6.3 μM) in studies of the cytotoxic activity against H1299 and A549 lung adenocarcinoma cells but did not show selectivity between tumor cells and noncancer murine embryonic fibroblasts (MEFs).

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Acknowledgment

The research was supported by Russian Science Foundation Grant No. 23-23-00098, https://rscf.ru/project/23-23-00098/. Structural studies of synthesized compounds were performed at the Agidel Center for Common Use, UFRC, RAS.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 Prosp. Oktyabrya, Ufa, 450075, Russia

    A. Yu. Spivak, E. V. Davletshin, D. A. Nedopekina & R. R. Khalitova

  2. V. A. Almazov National Medical Research Centre, Ministry of Health of the Russian Federation, 12 Mayakovsky St, St. Petersburg, 191014, Russia

    Yu. P. Belsky

  3. Institute of Cytology, Russian Academy of Sciences, 4 Tikhoretskii Prosp., St. Petersburg, 194064, Russia

    O. Yu. Shuvalov

Authors
  1. A. Yu. Spivak
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  2. E. V. Davletshin
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  3. D. A. Nedopekina
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  4. R. R. Khalitova
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  5. Yu. P. Belsky
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  6. O. Yu. Shuvalov
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Corresponding author

Correspondence to A. Yu. Spivak.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2023, pp. 730–735.

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Spivak, A.Y., Davletshin, E.V., Nedopekina, D.A. et al. Synthesis and Cytotoxic Activity of the Conjugate of an Oxygenated Betulinic Acid Analog with the Delocalized Lipophilic Cationic Compound F16. Chem Nat Compd 59, 865–871 (2023). https://doi.org/10.1007/s10600-023-04137-x

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  • DOI: https://doi.org/10.1007/s10600-023-04137-x

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