Novel Oleanolic Acid-Tryptamine and -Fluorotryptamine Amides: From Adaptogens to Agents Targeting In Vitro Cell Apoptosis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F21%3A43922165" target="_blank" >RIV/60461373:22330/21:43922165 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61389030:_____/21:00551814

Výsledek na webu

<a href="https://www.mdpi.com/2223-7747/10/10/2082" target="_blank" >https://www.mdpi.com/2223-7747/10/10/2082</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/plants10102082" target="_blank" >10.3390/plants10102082</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Novel Oleanolic Acid-Tryptamine and -Fluorotryptamine Amides: From Adaptogens to Agents Targeting In Vitro Cell Apoptosis

Popis výsledku v původním jazyce

Background: Oleanolic acid is a natural plant adaptogen, and tryptamine is a natural psychoactive drug. To compare their effects of with the effect of their derivatives, tryptamine and fluorotryptamine amides of oleanolic acid were designed and synthesized. Methods: The target amides were investigated for their pharmacological effect, and basic supramolecular self-assembly characteristics. Four human cancer cell lines were involved in the screening tests performed by standard methods. Results: The ability to display cytotoxicity and to cause selective cell apoptosis in human cervical carcinoma and in human malignant melanoma was seen with the three most active compounds of the prepared series of compounds. Tryptamine amide of (3 beta)-3-(acetyloxy)olean-12-en-28-oic acid (3a) exhibited cytotoxicity in HeLa cancer cell lines (IC50 = 8.7 &amp; PLUSMN; 0.4 mu M) and in G-361 cancer cell lines (IC50 = 9.0 &amp; PLUSMN; 0.4 mu M). Fluorotryptamine amides of (3 beta)-3-(acetyloxy)olean-12-en-28-oic acid (compounds 3b and 3c) showed cytotoxicity in the HeLa cancer cell line (IC50 = 6.7 &amp; PLUSMN; 0.4 mu M and 12.2 &amp; PLUSMN; 4.7 mu M, respectively). The fluorotryptamine amide of oleanolic acid (compound 4c) displayed cytotoxicity in the MCF7 cancer cell line (IC50 = 13.5 &amp; PLUSMN; 3.3 mu M). Based on the preliminary UV spectra measured in methanol/water mixtures, the compounds 3a-3c were also found to self-assemble into supramolecular systems. Conclusions: An effect of the fluorine atom present in the molecules on self-assembly was observed with 3b. Enhanced cytotoxicity has been achieved in 3a-4c in comparison with the effect of the parent oleanolic acid (1) and tryptamine. The compounds 3a-3c showed a strong induction of apoptosis in HeLa and G-361 cells after 24 h.

Název v anglickém jazyce

Novel Oleanolic Acid-Tryptamine and -Fluorotryptamine Amides: From Adaptogens to Agents Targeting In Vitro Cell Apoptosis

Popis výsledku anglicky

Background: Oleanolic acid is a natural plant adaptogen, and tryptamine is a natural psychoactive drug. To compare their effects of with the effect of their derivatives, tryptamine and fluorotryptamine amides of oleanolic acid were designed and synthesized. Methods: The target amides were investigated for their pharmacological effect, and basic supramolecular self-assembly characteristics. Four human cancer cell lines were involved in the screening tests performed by standard methods. Results: The ability to display cytotoxicity and to cause selective cell apoptosis in human cervical carcinoma and in human malignant melanoma was seen with the three most active compounds of the prepared series of compounds. Tryptamine amide of (3 beta)-3-(acetyloxy)olean-12-en-28-oic acid (3a) exhibited cytotoxicity in HeLa cancer cell lines (IC50 = 8.7 &amp; PLUSMN; 0.4 mu M) and in G-361 cancer cell lines (IC50 = 9.0 &amp; PLUSMN; 0.4 mu M). Fluorotryptamine amides of (3 beta)-3-(acetyloxy)olean-12-en-28-oic acid (compounds 3b and 3c) showed cytotoxicity in the HeLa cancer cell line (IC50 = 6.7 &amp; PLUSMN; 0.4 mu M and 12.2 &amp; PLUSMN; 4.7 mu M, respectively). The fluorotryptamine amide of oleanolic acid (compound 4c) displayed cytotoxicity in the MCF7 cancer cell line (IC50 = 13.5 &amp; PLUSMN; 3.3 mu M). Based on the preliminary UV spectra measured in methanol/water mixtures, the compounds 3a-3c were also found to self-assemble into supramolecular systems. Conclusions: An effect of the fluorine atom present in the molecules on self-assembly was observed with 3b. Enhanced cytotoxicity has been achieved in 3a-4c in comparison with the effect of the parent oleanolic acid (1) and tryptamine. The compounds 3a-3c showed a strong induction of apoptosis in HeLa and G-361 cells after 24 h.

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

2021

Kód důvěrnosti údajů

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

Název periodika

Plants

ISSN

2223-7747

e-ISSN

—

Svazek periodika

10

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

15

Strana od-do

"nestrankovano"

Kód UT WoS článku

000713037700001

EID výsledku v databázi Scopus

2-s2.0-85116072656