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Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity

The pharmacological effects of the presence of a sugar moiety, 1,2,3-triazole ring and silyl groups in the structure of biologically active compounds have been extensively studied in drug design and medicinal chemistry. These components can be useful tools to tailoring the bioavailability of target...

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Autores principales: Żurawska, Katarzyna, Burdalska, Daria, Skonieczna, Magdalena, Byczek-Wyrostek, Anna, Dawicka, Anahit, Kasprzycka, Anna, Walczak, Krzysztof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10143444/
https://www.ncbi.nlm.nih.gov/pubmed/37111282
http://dx.doi.org/10.3390/ph16040525
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author Żurawska, Katarzyna
Burdalska, Daria
Skonieczna, Magdalena
Byczek-Wyrostek, Anna
Dawicka, Anahit
Kasprzycka, Anna
Walczak, Krzysztof
author_facet Żurawska, Katarzyna
Burdalska, Daria
Skonieczna, Magdalena
Byczek-Wyrostek, Anna
Dawicka, Anahit
Kasprzycka, Anna
Walczak, Krzysztof
author_sort Żurawska, Katarzyna
collection PubMed
description The pharmacological effects of the presence of a sugar moiety, 1,2,3-triazole ring and silyl groups in the structure of biologically active compounds have been extensively studied in drug design and medicinal chemistry. These components can be useful tools to tailoring the bioavailability of target molecules. Herein we present the study on the impact of the sugar substituent structure and triisopropylsilyl group presence on the anticancer activity of mucochloric acid (MCA) derivatives containing the furan-2(5H)-one or 2H-pyrrol-2-one core. The obtained results clearly indicated that tested compounds caused a significant decrease in cell viability of HCT116 and MCF-7 cell lines. MCF-7 cells indicate serious resistance toward investigated compounds in comparison with HCT116 cell line, it suggests that estrogen-dependent breast cancer cells are significantly less sensitive to the tested derivatives. Depending on the structure of the sugar, the type and site of connection with the furanone or 2H-pyrrol-2-one derivative and the presence of the silyl group, the selectivity of the compound towards cancer cells can be controlled. The obtained results may have an impact on the design of new furanone-based anticancer compounds.
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spelling pubmed-101434442023-04-29 Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity Żurawska, Katarzyna Burdalska, Daria Skonieczna, Magdalena Byczek-Wyrostek, Anna Dawicka, Anahit Kasprzycka, Anna Walczak, Krzysztof Pharmaceuticals (Basel) Article The pharmacological effects of the presence of a sugar moiety, 1,2,3-triazole ring and silyl groups in the structure of biologically active compounds have been extensively studied in drug design and medicinal chemistry. These components can be useful tools to tailoring the bioavailability of target molecules. Herein we present the study on the impact of the sugar substituent structure and triisopropylsilyl group presence on the anticancer activity of mucochloric acid (MCA) derivatives containing the furan-2(5H)-one or 2H-pyrrol-2-one core. The obtained results clearly indicated that tested compounds caused a significant decrease in cell viability of HCT116 and MCF-7 cell lines. MCF-7 cells indicate serious resistance toward investigated compounds in comparison with HCT116 cell line, it suggests that estrogen-dependent breast cancer cells are significantly less sensitive to the tested derivatives. Depending on the structure of the sugar, the type and site of connection with the furanone or 2H-pyrrol-2-one derivative and the presence of the silyl group, the selectivity of the compound towards cancer cells can be controlled. The obtained results may have an impact on the design of new furanone-based anticancer compounds. MDPI 2023-03-31 /pmc/articles/PMC10143444/ /pubmed/37111282 http://dx.doi.org/10.3390/ph16040525 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Żurawska, Katarzyna
Burdalska, Daria
Skonieczna, Magdalena
Byczek-Wyrostek, Anna
Dawicka, Anahit
Kasprzycka, Anna
Walczak, Krzysztof
Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity
title Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity
title_full Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity
title_fullStr Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity
title_full_unstemmed Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity
title_short Glycoconjugates of Mucochloric Acid—Synthesis and Biological Activity
title_sort glycoconjugates of mucochloric acid—synthesis and biological activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10143444/
https://www.ncbi.nlm.nih.gov/pubmed/37111282
http://dx.doi.org/10.3390/ph16040525
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