Spermine amides of selected triterpenoid acids: dynamic supramolecular system formation influences the cytotoxicity of the drugs

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F20%3A73604375" target="_blank" >RIV/61989592:15310/20:73604375 - isvavai.cz</a>

Result on the web

<a href="https://pubs.rsc.org/en/content/articlehtml/2020/tb/c9tb01957j" target="_blank" >https://pubs.rsc.org/en/content/articlehtml/2020/tb/c9tb01957j</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c9tb01957j" target="_blank" >10.1039/c9tb01957j</a>

Result language

angličtina

Original language name

Spermine amides of selected triterpenoid acids: dynamic supramolecular system formation influences the cytotoxicity of the drugs

Original language description

Cancer is a global disease of great importance, and the need for novel cytotoxic drugs is still eminent. A series of spermine amides of several selected triterpene acids (betulonic, heterobetulonic, oleanolic, ursolic and platanic acid) have been synthesized to search for new cytotoxic and antimicrobial agents. The compounds have also been subjected to the investigation of their physico-chemical characteristics (ability to self-assemble), and to an in silico comparative calculation of their physico-chemical and ADME parameters. In the in vitro screening tests with several target compounds (8a–8c and 11c), their cytotoxicity changed with prolonged time, which appeared to be a result of formation of dynamic supramolecular networks. This phenomenon is important in investigation of the effect of self-assembly on biological activity. The most important compounds in this series were spermine derivatives of heterobetulonic acid (3b) and ursolic acid (8b), showing cytotoxicity &lt;5 μM and &lt;10 μM, respectively, on all tested cancer cell lines. Comparable cytotoxicity was also displayed by 13b, formerly a model compound prepared for testing of the synthetic procedures, the 1,2-diaminoethane derivative. The target compounds 3b and 8b displayed antimicrobial activity on Staphylococcus aureus, Streptococcus mutans and Listeria monocytogenes at a concentration 6.25 μM. Supramolecular characteristics of several compounds were documented by the TEM and SEM micrographs showing fibrous, partially helical, networks, and UV measurements showing changes in the intensity of UV signals, also indicating formation of supramolecular systems.

Czech name

—

Czech description

—

Type

J_SC - Article in a specialist periodical, which is included in the SCOPUS database

CEP classification

—

OECD FORD branch

30107 - Medicinal chemistry

Project

<a href="/en/project/EF16_019%2F0000868" target="_blank" >EF16_019/0000868: Molecular, cellular and clinical approach to healthy ageing</a><br>

Continuities

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

Publication year

2020

Confidentiality

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

Name of the periodical

Journal of Materials Chemistry B

ISSN

2050-7518

e-ISSN

—

Volume of the periodical

8

Issue of the periodical within the volume

3

Country of publishing house

GB - UNITED KINGDOM

Number of pages

8

Pages from-to

484-491

UT code for WoS article

000508846000011

EID of the result in the Scopus database

2-s2.0-85078549580