Cytotoxicity and Nanoassembly Characteristics of Aromatic Amides of Oleanolic Acid and Ursolic Acid
The result's identifiers
Result code in 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>
Alternative codes found
RIV/61389030:_____/25:00637360 RIV/61388963:_____/25:00637360 RIV/60461373:22330/25:43931556 RIV/61989592:15310/25:73631113
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Cytotoxicity and Nanoassembly Characteristics of Aromatic Amides of Oleanolic Acid and Ursolic Acid
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10404 - Polymer science
Result continuities
Project
<a href="/en/project/TN02000020" target="_blank" >TN02000020: Centre of Advanced Electron and Photonic Optics</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Omega
ISSN
2470-1343
e-ISSN
2470-1343
Volume of the periodical
10
Issue of the periodical within the volume
20
Country of publishing house
US - UNITED STATES
Number of pages
11
Pages from-to
20938-20948
UT code for WoS article
001485819600001
EID of the result in the Scopus database
2-s2.0-105004822981