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Triterpenoid–peg ribbons targeting selectivity in pharmacological effects
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SYSNO ASEP 0549087 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Triterpenoid–peg ribbons targeting selectivity in pharmacological effects Author(s) Özdemir, Zülal (UEB-Q) ORCID
Bildziukevich, Uladzimir (UEB-Q) RID, ORCID
Čapková, M. (CZ)
Lovecká, P. (CZ)
Rárová, L. (CZ)
Šaman, David (UOCHB-X) RID, ORCID
Zgarbová, Michala (UOCHB-X) ORCID
Lapuníková, Barbora (UOCHB-X)
Weber, Jan (UOCHB-X) RID, ORCID
Kazakova, O. (GB)
Wimmer, Zdeněk (UEB-Q) RID, ORCIDNumber of authors 11 Article number 951 Source Title Biomedicines. - : MDPI
Roč. 9, č. 8 (2021)Number of pages 14 s. Language eng - English Country CH - Switzerland Keywords Amide bond ; Antimicrobial activity ; Anti‐HIV activity ; Cytotoxicity ; Huisgen 1,3‐dipolar cycloaddition ; Molecular ribbon ; Multifunctional PEG3 derivative ; Supramolecular self‐assembly ; Triterpenoid OECD category Biochemical research methods R&D Projects FV30300 GA MPO - Ministry of Industry and Trade (MPO) EF16_019/0000738 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UEB-Q - RVO:61389030 ; UOCHB-X - RVO:61388963 UT WOS 000688878800001 EID SCOPUS 85112313481 DOI https://doi.org/10.3390/biomedicines9080951 Annotation (1) Background: To compare the effect of selected triterpenoids with their structurally resembling derivatives, designing of the molecular ribbons was targeted to develop compounds with selectivity in their pharmacological effects. (2) Methods: In the synthetic procedures, Huisgen 1,3‐ dipolar cycloaddition was applied as a key synthetic step for introducing a 1,2,3‐triazole ring as a part of a junction unit in the molecular ribbons. (3) Results: The antimicrobial activity, antiviral activity, and cytotoxicity of the prepared compounds were studied. Most of the molecular ribbons showed antimicrobial activity, especially on Staphylococcus aureus, Pseudomonas aeruginosa, and Enterococcus faecalis, with a 50–90% inhibition effect (c = 25 μg∙mL−1). No target compound was effective against HSV‐1, but 8a displayed activity against HIV‐1 (EC50 = 50.6 ± 7.8 μM). Cytotoxicity was tested on several cancer cell lines, and 6d showed cytotoxicity in the malignant melanoma cancer cell line (G‐361, IC50 = 20.0 ± 0.6 μM). Physicochemical characteristics of the prepared compounds were investigated, namely a formation of supramolecular gels and a self‐assembly potential in general, with positive results achieved with several target compounds. (4) Conclusions: Several compounds of a series of triterpenoid molecular ribbons showed better pharmacological profiles than the parent compounds and displayed certain selectivity in their effects. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2022 Electronic address http://doi.org/10.3390/biomedicines9080951
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