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Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif
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SYSNO ASEP 0583649 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif Author(s) Hamala, Vojtěch (UCHP-M) RID, SAI, ORCID
Ondrášková, K. (CZ)
Červenková Šťastná, Lucie (UCHP-M) RID, ORCID, SAI
Krčil, Aleš (UCHP-M)
Müllerová, Monika (UCHP-M) RID, ORCID, SAI
Kurfiřt, Martin (UCHP-M) RID, ORCID, SAI
Hiršová, Kateřina (UCHP-M)
Holčáková, J. (CZ)
Gyepes, R. (CZ)
Císařová, I. (CZ)
Bernášková, Jana (UCHP-M) RID, SAI
Hrstka, R. (CZ)
Karban, Jindřich (UCHP-M) RID, ORCID, SAIArticle number e7399 Source Title Applied Organometallic Chemistry. - : Wiley - ISSN 0268-2605
Roč. 38, č. 5 (2024)Number of pages 15 s. Language eng - English Country US - United States Keywords antitumor ; cytotoxicity ; ferrocene ; apoptosis OECD category Inorganic and nuclear chemistry R&D Projects LTC20052 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UCHP-M - RVO:67985858 UT WOS 001173816400001 EID SCOPUS 85186554432 DOI 10.1002/aoc.7399 Annotation Acylated N-acetyl hexosamine hemiacetals are known for their cytotoxicity. We have previously reported that cytotoxicity can be increased by replacing
one 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.Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2025 Electronic address https://onlinelibrary.wiley.com/doi/10.1002/aoc.7399
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