Amphiphilic derivatives of (3β,17β)-3-hydroxyandrost-5-ene-17-carboxylic acid
Language English Country United States Media print-electronic
Document type Journal Article
PubMed
29100780
DOI
10.1016/j.steroids.2017.10.011
PII: S0039-128X(17)30191-5
Knihovny.cz E-resources
- Keywords
- Amphiphile, Antimicrobial activity, Cytotoxicity, Diamine, Polyamine, Steroid,
- MeSH
- Androstenes chemical synthesis chemistry pharmacology MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Escherichia coli drug effects pathogenicity MeSH
- Carboxylic Acids chemical synthesis chemistry pharmacology MeSH
- Microbial Sensitivity Tests MeSH
- Polyamines chemical synthesis chemistry pharmacology MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Androstenes MeSH
- Anti-Bacterial Agents MeSH
- Carboxylic Acids MeSH
- Polyamines MeSH
A series of amphiphilic derivatives of (3β,17β)-3-hydroxyandrost-5-ene-17-carboxylic acid (1) with the polyamine spermine and three other diamines, 1,2-diaminoethane, piperazine and cadaverine, were synthesized and their antimicrobial activity and cytotoxicity were investigated. Among the target compounds, several ones showed antimicrobial activity on Gram positive and Gram negative microorganisms. The most active compounds were 20 (Streptococcus mutans CCM 7409, 3.125 µM), 16 (Streptococcus mutans CCM 7409, 12.5 µM) and 10d (Escherichia coli CCM 3954, 12.5 µM). In addition, compounds 5d, 10d, 13 and 20 displayed cytotoxicity on CEM (12.1 ± 2.1 µM, 7.6 ± 1.0 µM, 19.0 ± 0.4 µM and 5.9 ± 0.7 µM, respectively). Two additional compounds displayed medium cytotoxicity on CEM, 5a (34.6 ± 5.2 µM) and 5c (37.7 ± 5.9 µM). The compound 13 and 20 displayed high toxicity also on normal fibroblasts.
References provided by Crossref.org
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