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Enhancing effect of cystamine in its amides with betulinic acid as antimicrobial and antitumor agent in vitro

U. Bildziukevich, L. Rárová, L. Janovská, D. Šaman, Z. Wimmer,

. 2019 ; 148 (-) : 91-98. [pub] 20190422

Language English Country United States

Document type Journal Article, Research Support, Non-U.S. Gov't

Persistent link   https://www.medvik.cz/link/bmc20023802

Amides of betulinic acid with cystamine were synthesized to investigate their antimicrobial and antitumor activity, and their influence on the cell cycle and cell apoptosis. The former target amide (6) displayed cytotoxicity in CEM cell line after 72 h of treatment (IC50 = 3.0 ± 0.7 μM; TI = 20), and induced apoptosis by caspase-3/7 activation in CEM cells. The latter target amide (9) displayed antimicrobial activity against Streptococcus mutans (MIC 3.125 μM; MBC 3.125 μM) and Bacillus cereus (MIC 25 μM; MBC 25 μM). The achieved results demonstrate enhancing of their biological activity over that of the parent compounds. However, two intermediate compounds (2 and 7) displayed either considerable cytotoxicity (2; 7.5 ± 0.8 μM; TI = 10, against G361) or antimicrobial activity (7; both against Actinomyces odontolycus and Clostridium perfrigens with MIC 12.5 µM and MBC 12.5 µM). The experimental data were compared with the in silico calculated physico-chemical and ADME parameters of the target compounds, including successful intermediates.

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$a Enhancing effect of cystamine in its amides with betulinic acid as antimicrobial and antitumor agent in vitro / $c U. Bildziukevich, L. Rárová, L. Janovská, D. Šaman, Z. Wimmer,
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$a Amides of betulinic acid with cystamine were synthesized to investigate their antimicrobial and antitumor activity, and their influence on the cell cycle and cell apoptosis. The former target amide (6) displayed cytotoxicity in CEM cell line after 72 h of treatment (IC50 = 3.0 ± 0.7 μM; TI = 20), and induced apoptosis by caspase-3/7 activation in CEM cells. The latter target amide (9) displayed antimicrobial activity against Streptococcus mutans (MIC 3.125 μM; MBC 3.125 μM) and Bacillus cereus (MIC 25 μM; MBC 25 μM). The achieved results demonstrate enhancing of their biological activity over that of the parent compounds. However, two intermediate compounds (2 and 7) displayed either considerable cytotoxicity (2; 7.5 ± 0.8 μM; TI = 10, against G361) or antimicrobial activity (7; both against Actinomyces odontolycus and Clostridium perfrigens with MIC 12.5 µM and MBC 12.5 µM). The experimental data were compared with the in silico calculated physico-chemical and ADME parameters of the target compounds, including successful intermediates.
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$a Rárová, Lucie $u Palacký University, Centre of the Region Haná for Biotechnological and Agricultural Research, Department of Chemical Biology and Genetics, Šlechtitelů 27, 783 71 Olomouc, Czech Republic.
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$a Janovská, Lucie $u Palacký University, Department of Microbiology, Faculty of Medicine and Dentistry, Hněvotínská 3, 775 15 Olomouc, Czech Republic; Palacký University & Institute of Experimental Botany AS CR, Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Šlechtitelů 27, 783 71 Olomouc, Czech Republic.
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$a Šaman, David $u Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo náměstí 2, 166 10 Prague 6, Czech Republic.
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$a Wimmer, Zdeněk $u University of Chemistry and Technology, Department of Chemistry of Natural Compounds, Technická 5, 166 28 Prague 6, Czech Republic; Institute of Experimental Botany AS CR, v.v.i., Isotope Laboratory, Vídeňská 1083, 142 20 Prague 4, Czech Republic. Electronic address: wimmerz@vscht.cz.
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