Nano-assembly of cytotoxic amides of moronic and morolic acid

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F23%3A43927403" target="_blank" >RIV/60461373:22330/23:43927403 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61389030:_____/23:00576382 RIV/61389013:_____/23:00576382 RIV/61388963:_____/23:00576382 RIV/61989592:15310/23:73620293

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2023/SM/D3SM01035J" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2023/SM/D3SM01035J</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d3sm01035j" target="_blank" >10.1039/d3sm01035j</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Nano-assembly of cytotoxic amides of moronic and morolic acid

Popis výsledku v původním jazyce

Moronic acid and morolic acid, less frequently studied plant triterpenoids, were subjected to derivation with several structural modifiers, namely, piperazine-, pyrazine-, 1H-indole- and l-methionine-based compounds. Derivation was targeted to design and prepare novel compounds capable of nano-assembling and/or displaying cytotoxicity. Formation of nanostructures has been proven for several novel target compounds that formed different types of nanostructures, either in chloroform or in water. Isometric nanoparticles with broad size distributions (12 and 25), distorted single sheets (23) or very large thin warped films (13) were formed in chloroform solutions. Sheet-like nanostructures (12 and 23), and sphere-like nanostructures (hydrogen bonding connected nanoparticles; 3, 5, 13, 21 and 25) were formed in water suspensions. Cytotoxicity was also investigated and compared with that of the parent triterpenoids, showing enhanced effect of 18 that was the most successful derivative of the prepared series with sufficient balance between its cytotoxicity in CEM (IC50 = 11.7 +/- 2.4 mu M), HeLa (IC50 = 9.0 +/- 0.7 mu M) and G-361 (IC50 = 10.6 +/- 5.5 mu M) cancer cell lines, and toxicity in BJ (IC50 = 43.3 +/- 1.5 mu M). The calculated selectivity index values for 18 are SI = 3.9 (CEM), 4.8 (HeLa) and 4.4 (G-361). Additional compounds displaying cytotoxicity were 5, 7, 9 and 15, all of them showed comparable cytotoxicity with 18, in the investigated cancer cell lines; however, they were more toxic in BJ than 18.Moronic acid and morolic acid, less frequently studied plant triterpenoids, were subjected to derivation with several structural modifiers, namely, piperazine-, pyrazine-, 1H-indole- and l-methionine-based compounds.

Název v anglickém jazyce

Nano-assembly of cytotoxic amides of moronic and morolic acid

Popis výsledku anglicky

Moronic acid and morolic acid, less frequently studied plant triterpenoids, were subjected to derivation with several structural modifiers, namely, piperazine-, pyrazine-, 1H-indole- and l-methionine-based compounds. Derivation was targeted to design and prepare novel compounds capable of nano-assembling and/or displaying cytotoxicity. Formation of nanostructures has been proven for several novel target compounds that formed different types of nanostructures, either in chloroform or in water. Isometric nanoparticles with broad size distributions (12 and 25), distorted single sheets (23) or very large thin warped films (13) were formed in chloroform solutions. Sheet-like nanostructures (12 and 23), and sphere-like nanostructures (hydrogen bonding connected nanoparticles; 3, 5, 13, 21 and 25) were formed in water suspensions. Cytotoxicity was also investigated and compared with that of the parent triterpenoids, showing enhanced effect of 18 that was the most successful derivative of the prepared series with sufficient balance between its cytotoxicity in CEM (IC50 = 11.7 +/- 2.4 mu M), HeLa (IC50 = 9.0 +/- 0.7 mu M) and G-361 (IC50 = 10.6 +/- 5.5 mu M) cancer cell lines, and toxicity in BJ (IC50 = 43.3 +/- 1.5 mu M). The calculated selectivity index values for 18 are SI = 3.9 (CEM), 4.8 (HeLa) and 4.4 (G-361). Additional compounds displaying cytotoxicity were 5, 7, 9 and 15, all of them showed comparable cytotoxicity with 18, in the investigated cancer cell lines; however, they were more toxic in BJ than 18.Moronic acid and morolic acid, less frequently studied plant triterpenoids, were subjected to derivation with several structural modifiers, namely, piperazine-, pyrazine-, 1H-indole- and l-methionine-based compounds.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

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

2023

Kód důvěrnosti údajů

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

Název periodika

SOFT MATTER

ISSN

1744-683X

e-ISSN

1744-6848

Svazek periodika

19

Číslo periodika v rámci svazku

39

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

7625-7634

Kód UT WoS článku

001077878500001

EID výsledku v databázi Scopus

2-s2.0-85173979917