Ruthenium tetrazene complexes bearing glucose moieties on their periphery: Synthesis, characterization, and in vitro cytotoxicity.

0533067 - ÚCHP 2021 RIV GB eng J - Journal Article
Hamala, Vojtěch - Martišová, A. - Červenková Šťastná, Lucie - Karban, Jindřich - Dančo, Andrej - Šimarek, Adam - Lamač, Martin - Horáček, Michal - Kolářová, T. - Hrstka, R. - Gyepes, Robert - Pinkas, Jiří
Ruthenium tetrazene complexes bearing glucose moieties on their periphery: Synthesis, characterization, and in vitro cytotoxicity.
Applied Organometallic Chemistry. Roč. 34, č. 11 (2020), č. článku e5896. ISSN 0268-2605. E-ISSN 1099-0739
R&D Projects: GA ČR(CZ) GA17-05838S
Institutional support: RVO:67985858 ; RVO:61388955
Keywords : anticancer activity * glucose derivatives * ruthenium complexes * tetrazene ligands
OECD category: Organic chemistry; Physical chemistry (UFCH-W)
Impact factor: 4.105, year: 2020
Method of publishing: Limited access

Ruthenium tetrazene complexes with general formula [Cp*RuCl(1,4-R2N4)] (Cp* = η5-C5Me5), where R = benzyl (1), 2-fluorobenzyl (2), β-D-glucopyr anosyl-unprotected (3a) and acyl-protected (3b–d), 2-acetamido-β-Dglucopyranosyl- 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).
Permanent Link: http://hdl.handle.net/11104/0311562