Novel oleanolic acid-tryptamine and-fluorotryptamine amides: From adaptogens to agents targeting in vitro cell apoptosis

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F21%3A00551814" target="_blank" >RIV/61389030:_____/21:00551814 - isvavai.cz</a>

Alternative codes found

RIV/61388963:_____/21:00551814 RIV/60461373:22330/21:43922165 RIV/61989592:15310/21:73610737

Result on the web

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

DOI - Digital Object Identifier

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

Result language

angličtina

Original language name

Novel oleanolic acid-tryptamine and-fluorotryptamine amides: From adaptogens to agents targeting in vitro cell apoptosis

Original language description

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 (3β)-3-(acetyloxy)olean-12-en-28-oic acid (3a) exhibited cytotoxicity in HeLa cancer cell lines (IC50 = 8.7 ± 0.4 µM) and in G-361 cancer cell lines (IC50 = 9.0 ± 0.4 µM). Fluorotryptamine amides of (3β)-3-(acetyloxy)olean-12-en-28-oic acid (compounds 3b and 3c) showed cytotoxicity in the HeLa cancer cell line (IC50 = 6.7 ± 0.4 µM and 12.2 ± 4.7 µM, respectively). The fluorotryptamine amide of oleanolic acid (compound 4c) displayed cytotoxicity in the MCF7 cancer cell line (IC50 = 13.5 ± 3.3 µM). 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.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

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

Publication year

2021

Confidentiality

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

Name of the periodical

Plants

ISSN

2223-7747

e-ISSN

2223-7747

Volume of the periodical

10

Issue of the periodical within the volume

10

Country of publishing house

CH - SWITZERLAND

Number of pages

15

Pages from-to

2082

UT code for WoS article

000713037700001

EID of the result in the Scopus database

2-s2.0-85116072656