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Ruthenium tetrazene complexes bearing glucose moieties on their periphery: Synthesis, characterization, and in vitro cytotoxicity
Author(s) -
Hamala Vojtěch,
Martišová Andrea,
Červenková Šťastná Lucie,
Karban Jindřich,
Dančo Andrej,
Šimarek Adam,
Lamač Martin,
Horáček Michal,
Kolářová Tamara,
Hrstka Roman,
Gyepes Róbert,
Pinkas Jiří
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5896
Subject(s) - chemistry , cytotoxicity , electrospray ionization , ruthenium , cisplatin , stereochemistry , in vitro , apoptosis , cell culture , mass spectrometry , biochemistry , chromatography , medicine , surgery , chemotherapy , biology , genetics , catalysis
Ruthenium tetrazene complexes with general formula [Cp*RuCl(1,4‐R 2 N 4 )] (Cp* = η 5 ‐C 5 Me 5 ), where R = benzyl ( 1 ), 2‐fluorobenzyl ( 2 ), β ‐ d ‐glucopyranosyl‐unprotected ( 3a ) and acyl‐protected ( 3b – d ), 2‐acetamido‐ β ‐ d ‐glucopyranosyl‐unprotected ( 4a ) and acyl‐protected ( 4b – d ), propyl‐ β ‐ d ‐glucopyranoside‐unprotected ( 5a ), and O ‐acetylated ( 5b ), were synthesized and characterized using nuclear magnetic resonance and electrospray ionization–mass spectrometry. In addition, the molecular structure of 3b was determined using X‐ray crystallography. The cytotoxicity of complexes against ovarian (A2780, SK‐OV‐3) and breast (MDA‐MB‐231) cancer cell lines and noncancerous cell line HEK‐293 was evaluated and compared to cisplatin activity. The carbohydrate‐modified complexes bearing acyl‐protecting groups exhibited higher efficacy (in low micromolar range) than unprotected ones, where the most active 4d was superior to cisplatin up to five times against all investigated cancer cell lines; however, no significant selectivity was achieved. The complex induced apoptotic cell death at low micromolar concentrations (0.5 μM for A2780 and HEK293; 2 μM for SK‐OV‐3 and MDA‐MB‐231).