Triterpenoid-PEG Ribbons Targeting Selectivity in Pharmacological Effects

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F21%3A43922244" target="_blank" >RIV/60461373:22330/21:43922244 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61389030:_____/21:00549087 RIV/61388963:_____/21:00549087 RIV/61989592:15310/21:73610839

Výsledek na webu

<a href="https://www.mdpi.com/2227-9059/9/8/951" target="_blank" >https://www.mdpi.com/2227-9059/9/8/951</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/biomedicines9080951" target="_blank" >10.3390/biomedicines9080951</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Triterpenoid-PEG Ribbons Targeting Selectivity in Pharmacological Effects

Popis výsledku v původním jazyce

(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. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Název v anglickém jazyce

Triterpenoid-PEG Ribbons Targeting Selectivity in Pharmacological Effects

Popis výsledku anglicky

(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. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10609 - Biochemical research methods

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Biomedicines

ISSN

2227-9059

e-ISSN

—

Svazek periodika

9

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

14

Strana od-do

—

Kód UT WoS článku

000688878800001

EID výsledku v databázi Scopus

2-s2.0-85112313481