Pentamethinium salts as ligands for cancer: Sulfated polysaccharide co-receptors as possible therapeutic target
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't, Video-Audio Media
PubMed
30273836
DOI
10.1016/j.bioorg.2018.02.011
PII: S0045-2068(17)30693-4
Knihovny.cz E-resources
- Keywords
- Anticancer activity, Cytotoxicity, Fluorescent cyanine, Pentamethinium salt, Recognition, Sulfated polysaccharides,
- MeSH
- Antineoplastic Agents chemical synthesis chemistry metabolism pharmacology MeSH
- Apoptosis drug effects MeSH
- Benzothiazoles chemical synthesis chemistry metabolism pharmacology MeSH
- CHO Cells MeSH
- Cricetulus MeSH
- Sulfuric Acid Esters metabolism MeSH
- Glycosaminoglycans metabolism MeSH
- Hydrophobic and Hydrophilic Interactions MeSH
- Indoles chemical synthesis chemistry metabolism pharmacology MeSH
- Humans MeSH
- Ligands MeSH
- Molecular Structure MeSH
- Cell Line, Tumor MeSH
- Pyridinium Compounds chemical synthesis chemistry metabolism pharmacology MeSH
- Drug Design MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Animals MeSH
- Publication type
- Video-Audio Media MeSH
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antineoplastic Agents MeSH
- Benzothiazoles MeSH
- Sulfuric Acid Esters MeSH
- Glycosaminoglycans MeSH
- Indoles MeSH
- Ligands MeSH
- Pyridinium Compounds MeSH
A series of pentamethinium salts with benzothiazolium and indolium side units comprising one or two positive charges were designed and synthesized to determine the relationships among the molecular structure, charge density, affinity to sulfated polysaccharides, and biological activity. Firstly, it was found that the affinity of the pentamethinium salts to sulfated polysaccharides correlated with their biological activity. Secondly, the side heteroaromates displayed a strong effect on the cytotoxicity and selectivity towards cancer cells. Finally, doubly charged pentamethinium salts possessing benzothiazolium side units exhibited remarkably high efficacy against a taxol-resistant cancer cell line.
1st Faculty of Medicine Charles University Prague Kateřinská 32 121 08 Prague 2 Czech Republic
Institute of Molecular and Translational Medicine Hněvotínská 5 779 00 Olomouc Czech Republic
University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic
References provided by Crossref.org
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