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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F20%3A43923763" target="_blank" >RIV/60461373:22310/20:43923763 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/67985858:_____/20:00533067 RIV/61388955:_____/20:00533067 RIV/00209805:_____/20:00078468 RIV/00216208:11310/20:10420989

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/10.1002/aoc.5896" target="_blank" >https://onlinelibrary.wiley.com/doi/10.1002/aoc.5896</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/aoc.5896" target="_blank" >10.1002/aoc.5896</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

Ruthenium tetrazene complexes with general formula [Cp*RuCl(1,4-R2N4)] (Cp* = η5-C5Me5), 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). © 2020 John Wiley &amp; Sons, Ltd.

Název v anglickém jazyce

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

Popis výsledku anglicky

Ruthenium tetrazene complexes with general formula [Cp*RuCl(1,4-R2N4)] (Cp* = η5-C5Me5), 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). © 2020 John Wiley &amp; Sons, Ltd.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Applied Organometallic Chemistry

ISSN

0268-2605

e-ISSN

—

Svazek periodika

34

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

12

Strana od-do

—

Kód UT WoS článku

000544622600001

EID výsledku v databázi Scopus

2-s2.0-85087296067