Abstract
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.
Keywords:
Anticancer activity; Cytotoxicity; Fluorescent cyanine; Pentamethinium salt; Recognition; Sulfated polysaccharides.
Copyright © 2018. Published by Elsevier Inc.
Publication types
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Research Support, Non-U.S. Gov't
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Video-Audio Media
MeSH terms
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Animals
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / metabolism
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Antineoplastic Agents / pharmacology*
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Apoptosis / drug effects
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Benzothiazoles / chemical synthesis
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Benzothiazoles / chemistry
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Benzothiazoles / metabolism
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Benzothiazoles / pharmacology
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CHO Cells
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Cell Line, Tumor
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Cricetulus
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Drug Design
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Glycosaminoglycans / metabolism*
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Humans
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Hydrophobic and Hydrophilic Interactions
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Indoles / chemical synthesis
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Indoles / chemistry
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Indoles / metabolism
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Indoles / pharmacology*
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Ligands
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Molecular Structure
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Pyridinium Compounds / chemical synthesis
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Pyridinium Compounds / chemistry
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Pyridinium Compounds / metabolism
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Pyridinium Compounds / pharmacology*
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Sulfuric Acid Esters / metabolism
Substances
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Antineoplastic Agents
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Benzothiazoles
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Glycosaminoglycans
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Indoles
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Ligands
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Pyridinium Compounds
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Sulfuric Acid Esters