Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif
The result's identifiers
Result code in 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>
Alternative codes found
RIV/00216224:14310/24:00136214 RIV/00209805:_____/24:00079691 RIV/00216208:11310/24:10480939
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10402 - Inorganic and nuclear chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Applied Organometallic Chemistry
ISSN
0268-2605
e-ISSN
1099-0739
Volume of the periodical
38
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
15
Pages from-to
e7399
UT code for WoS article
001173816400001
EID of the result in the Scopus database
2-s2.0-85186554432