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Article

Triterpenoid–PEG Ribbons Targeting Selectivity in Pharmacological Effects

1
Department of Chemistry of Natural Compounds, University of Chemistry and Technology in Prague, Technická 5, 16628 Prague 6, Czech Republic
2
Isotope Laboratory, Institute of Experimental Botany of the Czech Academy of Sciences, Vídeňská 1083, 14220 Prague 4, Czech Republic
3
Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technická 5, 16628 Prague 6, Czech Republic
4
Department of Experimental Biology, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic
5
Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 16610 Prague 6, Czech Republic
6
Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71, pr. Oktyabrya, 450054 Ufa, Russia
*
Author to whom correspondence should be addressed.
Z.Ö., U.B. and M.Č. contributed equally.
L.R., cytotoxicity screening tests; M.Z. and B.L., antiviral tests.
Academic Editor: Jun Lu
Biomedicines 2021, 9(8), 951; https://doi.org/10.3390/biomedicines9080951
Received: 18 June 2021 / Revised: 29 July 2021 / Accepted: 30 July 2021 / Published: 3 August 2021
(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. View Full-Text
Keywords: triterpenoid; molecular ribbon; Huisgen 1,3-dipolar cycloaddition; amide bond; multifunctional PEG3 derivative; antimicrobial activity; anti-HIV activity; cytotoxicity; supramolecular self-assembly triterpenoid; molecular ribbon; Huisgen 1,3-dipolar cycloaddition; amide bond; multifunctional PEG3 derivative; antimicrobial activity; anti-HIV activity; cytotoxicity; supramolecular self-assembly
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MDPI and ACS Style

Özdemir, Z.; Bildziukevich, U.; Čapková, M.; Lovecká, P.; Rárová, L.; Šaman, D.; Zgarbová, M.; Lapuníková, B.; Weber, J.; Kazakova, O.; Wimmer, Z. Triterpenoid–PEG Ribbons Targeting Selectivity in Pharmacological Effects. Biomedicines 2021, 9, 951. https://doi.org/10.3390/biomedicines9080951

AMA Style

Özdemir Z, Bildziukevich U, Čapková M, Lovecká P, Rárová L, Šaman D, Zgarbová M, Lapuníková B, Weber J, Kazakova O, Wimmer Z. Triterpenoid–PEG Ribbons Targeting Selectivity in Pharmacological Effects. Biomedicines. 2021; 9(8):951. https://doi.org/10.3390/biomedicines9080951

Chicago/Turabian Style

Özdemir, Zulal, Uladzimir Bildziukevich, Martina Čapková, Petra Lovecká, Lucie Rárová, David Šaman, Michala Zgarbová, Barbora Lapuníková, Jan Weber, Oxana Kazakova, and Zdeněk Wimmer. 2021. "Triterpenoid–PEG Ribbons Targeting Selectivity in Pharmacological Effects" Biomedicines 9, no. 8: 951. https://doi.org/10.3390/biomedicines9080951

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