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Synthesis and study of the structure—antitumor activity relationship of new pyridoxine-containing structural analogs of saccharumoside-B

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Abstract

We synthesized a number of new derivatives of phenolic glycoside saccharumoside-B based on pyridoxine and 3-hydroxy-2-methylpyridine and studied their cytotoxicity in vitro against three normal (HEK-293, Chang Liver, MSC) and nine tumor (MCF-7, MDA-MB-231, A-498, SNB-19, M-14, NCI-H322M, HCT-115, HCT-116, PC-3) human cell lines compared with camptothecin, doxorubicin, and saccharumoside-B. The effect of the peripheral fragments of phenolic glycoside on the target activity was studied and the structure—antitumor activity relationship was established. A new efficient approach to the synthesis of saccharumoside-B was proposed.

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Authors and Affiliations

  1. Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    M. V. Pugachev, M. N. Agafonova, Yu. V. Badeev, E. I. Romanova, T. V. Nikishova, K. V. Balakin & Yu. G. Shtyrlin

  2. Zavoisky Physical-Technical Institute — Subdivision of Federal Research Center, Kazan Scientific Center of the Russian Academy of Sciences, 10/7 ul. Sibirskiy trakt, 420029, Kazan, Russian Federation

    O. I. Gnezdilov

Authors
  1. M. V. Pugachev
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  2. M. N. Agafonova
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  3. O. I. Gnezdilov
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  4. Yu. V. Badeev
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  5. E. I. Romanova
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  6. T. V. Nikishova
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  7. K. V. Balakin
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  8. Yu. G. Shtyrlin
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Corresponding author

Correspondence to Yu. G. Shtyrlin.

Additional information

The work was financially supported by the Grant from the President of the Russian Federation (MK-73.2020.3) and the subsidy allocated to the Kazan Federal University for the Project part of the Russian state assignment in Scientific area (Project No. 0671-2020-0053). Gnezdilov O. I. performed NMR measurements within the framework of the Russian state assignment for FRC KazSC RAS.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2416–2425, November, 2022.

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Pugachev, M.V., Agafonova, M.N., Gnezdilov, O.I. et al. Synthesis and study of the structure—antitumor activity relationship of new pyridoxine-containing structural analogs of saccharumoside-B. Russ Chem Bull 71, 2416–2425 (2022). https://doi.org/10.1007/s11172-022-3669-x

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  • DOI: https://doi.org/10.1007/s11172-022-3669-x

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