Pentamethinium salts as ligands for cancer: Sulfated polysaccharide co-receptors as possible therapeutic target.
Animals
Antineoplastic Agents
/ chemical synthesis
Apoptosis
/ drug effects
Benzothiazoles
/ chemical synthesis
CHO Cells
Cell Line, Tumor
Cricetulus
Drug Design
Glycosaminoglycans
/ metabolism
Humans
Hydrophobic and Hydrophilic Interactions
Indoles
/ chemical synthesis
Ligands
Molecular Structure
Pyridinium Compounds
/ chemical synthesis
Sulfuric Acid Esters
/ metabolism
Anticancer activity
Cytotoxicity
Fluorescent cyanine
Pentamethinium salt
Recognition
Sulfated polysaccharides
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
02 2019
02 2019
Historique:
received:
07
09
2017
revised:
02
02
2018
accepted:
10
02
2018
pubmed:
3
10
2018
medline:
4
9
2019
entrez:
2
10
2018
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 30273836
pii: S0045-2068(17)30693-4
doi: 10.1016/j.bioorg.2018.02.011
pii:
doi:
Substances chimiques
Antineoplastic Agents
0
Benzothiazoles
0
Glycosaminoglycans
0
Indoles
0
Ligands
0
Pyridinium Compounds
0
Sulfuric Acid Esters
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Video-Audio Media
Langues
eng
Sous-ensembles de citation
IM
Pagination
74-85Informations de copyright
Copyright © 2018. Published by Elsevier Inc.