Enhancing effect of cystamine in its amides with betulinic acid as antimicrobial and antitumor agent in vitro
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
31022408
DOI
10.1016/j.steroids.2019.04.004
PII: S0039-128X(19)30069-8
Knihovny.cz E-resources
- Keywords
- Antimicrobial activity, Apoptosis, Betulinic acid, Cystamine, Cytotoxicity,
- MeSH
- Actinomyces drug effects MeSH
- Amides chemistry pharmacology MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Apoptosis drug effects MeSH
- Bacillus cereus drug effects MeSH
- Clostridium drug effects MeSH
- Cystamine chemistry pharmacology MeSH
- Cells, Cultured MeSH
- Betulinic Acid MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Molecular Conformation MeSH
- Pentacyclic Triterpenes MeSH
- Cell Proliferation drug effects MeSH
- Antineoplastic Agents chemical synthesis chemistry pharmacology MeSH
- Drug Screening Assays, Antitumor MeSH
- Streptococcus mutans drug effects MeSH
- Triterpenes chemistry pharmacology MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Amides MeSH
- Anti-Bacterial Agents MeSH
- Cystamine MeSH
- Betulinic Acid MeSH
- Pentacyclic Triterpenes MeSH
- Antineoplastic Agents MeSH
- Triterpenes MeSH
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.
References provided by Crossref.org
Terpenes and Terpenoids Conjugated with BODIPYs: An Overview of Biological and Chemical Properties
Synthesis and Pharmacological Effects of Diosgenin-Betulinic Acid Conjugates
