Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F24%3A00583649" target="_blank" >RIV/67985858:_____/24:00583649 - isvavai.cz</a>
Nalezeny alternativní kódy
RIV/00216224:14310/24:00136214 RIV/00209805:_____/24:00079691 RIV/00216208:11310/24:10480939
Výsledek na webu
<a href="https://onlinelibrary.wiley.com/doi/10.1002/aoc.7399" target="_blank" >https://onlinelibrary.wiley.com/doi/10.1002/aoc.7399</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/aoc.7399" target="_blank" >10.1002/aoc.7399</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif
Popis výsledku v původním jazyce
Acylated N-acetyl hexosamine hemiacetals are known for their cytotoxicity. We have previously reported that cytotoxicity can be increased by replacingnone or more acyloxy groups with fluorine. Herein, we present the synthesis of 4,6-difluorinated D-gluco- and 4-fluorinated D-galacto-configured hexosaminederived glycoconjugates with organoruthenium or ferrocene complexes and their in vitro cytotoxicity against three cancer cell lines (A2780, SK-OV-3, and MDA-MB-231) and one noncancerous cell line (HEK-293). The attachment of the organometallic moiety at the 2-position significantly enhanced the cytotoxicity, especially against triple-negative MDA-MB-231 and the cisplatin resistant SK-OV-3 cancer cells. We observed a clear significance of an unprotected and acetyl protected anomeric hydroxyl for the cytotoxicity. Glycoconjugates with a non-hydrolysable organic or organometallic group at the anomeric position were generally nontoxic. A more detailed analysis revealed that, in particular, complexes with the ruthenium tetrazene complex induced apoptosis in both SK-OV-3 and MDA-MB-231 cells, as demonstrated by western blot analysis and Annexin V-FITC/PI staining. The structures of the two most cytotoxic organoruthenium and ferrocene glycoconjugates were confirmed by X-ray diffraction analysis.
Název v anglickém jazyce
Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif
Popis výsledku anglicky
Acylated N-acetyl hexosamine hemiacetals are known for their cytotoxicity. We have previously reported that cytotoxicity can be increased by replacingnone or more acyloxy groups with fluorine. Herein, we present the synthesis of 4,6-difluorinated D-gluco- and 4-fluorinated D-galacto-configured hexosaminederived glycoconjugates with organoruthenium or ferrocene complexes and their in vitro cytotoxicity against three cancer cell lines (A2780, SK-OV-3, and MDA-MB-231) and one noncancerous cell line (HEK-293). The attachment of the organometallic moiety at the 2-position significantly enhanced the cytotoxicity, especially against triple-negative MDA-MB-231 and the cisplatin resistant SK-OV-3 cancer cells. We observed a clear significance of an unprotected and acetyl protected anomeric hydroxyl for the cytotoxicity. Glycoconjugates with a non-hydrolysable organic or organometallic group at the anomeric position were generally nontoxic. A more detailed analysis revealed that, in particular, complexes with the ruthenium tetrazene complex induced apoptosis in both SK-OV-3 and MDA-MB-231 cells, as demonstrated by western blot analysis and Annexin V-FITC/PI staining. The structures of the two most cytotoxic organoruthenium and ferrocene glycoconjugates were confirmed by X-ray diffraction analysis.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10402 - Inorganic and nuclear chemistry
Návaznosti výsledku
Projekt
Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.
Návaznosti
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Ostatní
Rok uplatnění
2024
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Applied Organometallic Chemistry
ISSN
0268-2605
e-ISSN
1099-0739
Svazek periodika
38
Číslo periodika v rámci svazku
5
Stát vydavatele periodika
US - Spojené státy americké
Počet stran výsledku
15
Strana od-do
e7399
Kód UT WoS článku
001173816400001
EID výsledku v databázi Scopus
2-s2.0-85186554432