Amides of moronic acid and morolic acid with the tripeptides MAG and GAM targeting antimicrobial, antiviral and cytotoxic effects

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F25%3A00616545" target="_blank" >RIV/61389030:_____/25:00616545 - isvavai.cz</a>

Alternative codes found

RIV/61388963:_____/25:00616545 RIV/61989592:15310/25:73628012 RIV/60461373:22330/25:43931019

Result on the web

<a href="https://doi.org/10.1039/d4md00742e" target="_blank" >https://doi.org/10.1039/d4md00742e</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d4md00742e" target="_blank" >10.1039/d4md00742e</a>

Result language

angličtina

Original language name

Amides of moronic acid and morolic acid with the tripeptides MAG and GAM targeting antimicrobial, antiviral and cytotoxic effects

Original language description

A series of amides of selected plant triterpenoids, moronic acid and morolic acid, with the tripeptides MAG and GAM, was designed and synthesized. Two required tripeptides 5 and 10 were synthesized by a step-wise chain elongation of the ethyl esters of either glycine or L-methionine at their N-terminus using Boc-protected amino acids in each step. The tripeptides 5 and 10 were used for the synthesis of 13-23, the derivatives of moronic acid (11) and morolic acid (12), to get a series of amide derivatives of the less frequently studied triterpenoids 11 and 12. The target compounds, and their intermediates, were subjected to an investigation of their antimicrobial, antiviral and cytotoxic activity. Selectivity of the pharmacological effects was found. Generally, the target compounds inhibited only the G(+) microorganisms. Compound 16 inhibited Staphylococcus aureus (I = 99.6%, c = 62.5 mu M) and Enterococcus faecalis (I = 85%, c = 250 mu M). Several compounds showed moderate antiviral effects, both anti-HIV-1, 19 (EC50 = 57.0 +/- 4.1 mu M, CC50 > 100 mu M), 20 (EC50 = 17.8 +/- 2.1 mu M, CC50 = 41.0 +/- 5.2 mu M) and 23 (EC50 = 12.6 +/- 0.82 mu M, CC50 = 38.0 +/- 4.2 mu M), and anti-HSV-1, 22 (EC50 = 27.7 +/- 3.5 mu M, CC50 > 100 mu M) and 23 (EC50 = 30.9 +/- 3.3 mu M, CC50 > 100 mu M). The target compounds showed no cytotoxicity in cancer cells, however, several of their intermediates were cytotoxic. Compound 21 showed cytotoxicity in HeLa (IC50 = 7.9 +/- 2.1 mu M), G-361 (IC50 = 8.0 +/- 0.6 mu M) and MCF7 (IC50 = 8.6 +/- 0.2 mu M) cancer cell lines, while being non-toxic in normal fibroblasts (BJ, IC50 > 50 mu M).

Czech name

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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

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2025

Confidentiality

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

Name of the periodical

RSC Medicinal Chemistry

ISSN

2632-8682

e-ISSN

2632-8682

Volume of the periodical

16

Issue of the periodical within the volume

2

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

801-811

UT code for WoS article

001353773700001

EID of the result in the Scopus database

2-s2.0-85208810916