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Novel oleanolic acid-tryptamine and-fluorotryptamine amides: From adaptogens to agents targeting in vitro cell apoptosis
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SYSNO ASEP 0551814 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Novel oleanolic acid-tryptamine and-fluorotryptamine amides: From adaptogens to agents targeting in vitro cell apoptosis Author(s) Bildziukevich, Uladzimir (UEB-Q) RID, ORCID
Kvasnicová, Marie (UEB-Q) ORCID
Šaman, David (UOCHB-X) RID, ORCID
Rárová, L. (CZ)
Wimmer, Zdeněk (UEB-Q) RID, ORCIDNumber of authors 5 Article number 2082 Source Title Plants. - : MDPI
Roč. 10, č. 10 (2021)Number of pages 15 s. Language eng - English Country CH - Switzerland Keywords Adaptogen ; Apoptosis ; Caspase ; Cytotoxicity ; Fluorotryptamine ; Oleanolic acid ; Psychotropic drug ; Tryptamine OECD category Organic chemistry R&D Projects FV10599 GA MPO - Ministry of Industry and Trade (MPO) FV30300 GA MPO - Ministry of Industry and Trade (MPO) EF16_019/0000738 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 ; UEB-Q - RVO:61389030 UT WOS 000713037700001 EID SCOPUS 85116072656 DOI 10.3390/plants10102082 Annotation 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. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2022 Electronic address http://doi.org/10.3390/plants10102082
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