Cytotoxicity and Nanoassembly Characteristics of Aromatic Amides of Oleanolic Acid and Ursolic Acid

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F25%3A00637360" target="_blank" >RIV/61389013:_____/25:00637360 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61389030:_____/25:00637360 RIV/61388963:_____/25:00637360 RIV/60461373:22330/25:43931556 RIV/61989592:15310/25:73631113

Výsledek na webu

<a href="https://doi.org/10.1021/acsomega.5c02760" target="_blank" >https://doi.org/10.1021/acsomega.5c02760</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acsomega.5c02760" target="_blank" >10.1021/acsomega.5c02760</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Cytotoxicity and Nanoassembly Characteristics of Aromatic Amides of Oleanolic Acid and Ursolic Acid

Popis výsledku v původním jazyce

A series of more than 20 new amides of oleanolic acid and ursolic acid with selected aromatic amines were synthesized, and the structures of all compounds were analyzed and elucidated. Moreover, the compounds were subjected to the cytotoxicity assays in four cancer cell lines (CCRF-CEM, MCF7, HeLa, and G-361), using normal human fibroblasts (BJ) as reference cells for determining the toxicity of the investigated compounds. The 1,10-phenanthroline derivatives 4a, 4b, 5a, and 5b showed the highest cytotoxicity in all four cancer cell lines, but they were comparably toxic in human fibroblasts. The most promising results were achieved with 14a and 14b showing high cytotoxicity in the cancer cell lines and no toxicity in human fibroblasts. They were subjected to the investigation of the in vitro cell apoptosis, resulting in a confirmation of activation of apoptotic pathways in the CCRF-CEM cell line. The structure-activity relationships were documented by the cytotoxicity of 14a vs. 16a, and of 14b vs 16b, showing reverse effects in CCRF-CEM and MCF7 cancer cell lines. To investigate nanoassembly, initial screening of the target compounds by ultraviolet (UV) spectrometry was performed. Compounds 9b, 13b, 16b, and 17b, soluble both in methanol and in water, were selected for a more detailed investigation by transmission electron microscopy (TEM) microscopy and were found to form spherical nanoassemblies, frequently interconnected in small agglomerates and/or loose networks, while the other target compounds of this series showed no nanoassembling based on the TEM imaging. For each investigated compound, the nanoassemblies formed in methanol were substantially bigger than those formed in water.

Název v anglickém jazyce

Cytotoxicity and Nanoassembly Characteristics of Aromatic Amides of Oleanolic Acid and Ursolic Acid

Popis výsledku anglicky

A series of more than 20 new amides of oleanolic acid and ursolic acid with selected aromatic amines were synthesized, and the structures of all compounds were analyzed and elucidated. Moreover, the compounds were subjected to the cytotoxicity assays in four cancer cell lines (CCRF-CEM, MCF7, HeLa, and G-361), using normal human fibroblasts (BJ) as reference cells for determining the toxicity of the investigated compounds. The 1,10-phenanthroline derivatives 4a, 4b, 5a, and 5b showed the highest cytotoxicity in all four cancer cell lines, but they were comparably toxic in human fibroblasts. The most promising results were achieved with 14a and 14b showing high cytotoxicity in the cancer cell lines and no toxicity in human fibroblasts. They were subjected to the investigation of the in vitro cell apoptosis, resulting in a confirmation of activation of apoptotic pathways in the CCRF-CEM cell line. The structure-activity relationships were documented by the cytotoxicity of 14a vs. 16a, and of 14b vs 16b, showing reverse effects in CCRF-CEM and MCF7 cancer cell lines. To investigate nanoassembly, initial screening of the target compounds by ultraviolet (UV) spectrometry was performed. Compounds 9b, 13b, 16b, and 17b, soluble both in methanol and in water, were selected for a more detailed investigation by transmission electron microscopy (TEM) microscopy and were found to form spherical nanoassemblies, frequently interconnected in small agglomerates and/or loose networks, while the other target compounds of this series showed no nanoassembling based on the TEM imaging. For each investigated compound, the nanoassemblies formed in methanol were substantially bigger than those formed in water.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10404 - Polymer science

Projekt

<a href="/cs/project/TN02000020" target="_blank" >TN02000020: Centrum pokročilé elektronové a fotonové optiky</a><br>

Návaznosti

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

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

ACS Omega

ISSN

2470-1343

e-ISSN

2470-1343

Svazek periodika

10

Číslo periodika v rámci svazku

20

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

11

Strana od-do

20938-20948

Kód UT WoS článku

001485819600001

EID výsledku v databázi Scopus

2-s2.0-105004822981