Synthesis and cytotoxicity of the conjugates of diterpenoid isosteviol and N-acetyl-D-glucosamine

Garifullin, Bulat F.; Strobykina, Irina Yu.; Khabibulina, Leysan R.; Sapunova, Anastasiya S.; Voloshina, Aleksandra D.; Sharipova, Radmila R.; Khairutdinov, Bulat I.; Zuev, Yuriy F.; Kataev, Vladimir E.

doi:10.6084/m9.figshare.9519971.v1

gnpl_a_1650355_sm5179.pdf (3.67 MB)

Synthesis and cytotoxicity of the conjugates of diterpenoid isosteviol and N-acetyl-D-glucosamine

journal contribution

posted on 2019-08-12, 09:14 authored by Bulat F. Garifullin, Irina Yu. Strobykina, Leysan R. Khabibulina, Anastasiya S. Sapunova, Aleksandra D. Voloshina, Radmila R. Sharipova, Bulat I. Khairutdinov, Yuriy F. Zuev, Vladimir E. Kataev

A series of conjugates of diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) and N-acetyl-D-glucosamine was synthesised and their cytotoxicity against several human cancer cell lines (M-Hela, MCF-7, Hep G2, Panc-1, PC-3), as well as normal human cell lines (WI-38, Chang liver) was assayed. Most of the conjugates were found to be cytotoxic against the mentioned cancer cell lines in the range of IC₅₀ values 13–89 µM. Two lead compounds 14a and 14b showed selective cytotoxicity against M-Hela (IC₅₀ 13 and 14 µM) that was two times as high as the cytotoxicity of the anti-cancer drug Tamoxifen in control (IC₅₀ 28 µM). It was found that cytotoxic activity of the lead compounds against M-Hela cells is due to induction of apoptosis.