New classes of carborane-appended 5-thio-D-glucopyranose derivatives

A series of carborane-appended 5-thio-D-glucopyranose (5-TDGP) derivatives containing one to two 5-TDGP moieties were synthesized via click cycloaddition reaction as well as following the traditional methods. Among the carboranyl-5-TDGP derivatives, the decapitated nido-carboranyl derivative 18 was...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2012-08, Vol.41 (29), p.8982-8988
Main Authors: Satapathy, Rashmirekha, Dash, Barada Prasanna, Bode, Barrie P, Byczynski, Emily A, Hosmane, Sumathy N, Bux, Sajit, Hosmane, Narayan S
Format: Article
Language:English
Subjects:
Boranes - chemistry
Cell Line, Tumor
Glucose - analogs & derivatives
Glucose - chemistry
Humans
Microscopy, Phase-Contrast
Temperature
Thioglucosides - chemistry
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Summary:A series of carborane-appended 5-thio-D-glucopyranose (5-TDGP) derivatives containing one to two 5-TDGP moieties were synthesized via click cycloaddition reaction as well as following the traditional methods. Among the carboranyl-5-TDGP derivatives, the decapitated nido-carboranyl derivative 18 was found to be highly water-soluble and therefore its preliminary biodistribution study was conducted. A comparative biological evaluation of 18 versus its carboranyl-D-glucopyranose analog 19 with human hepatocellular carcinoma cells (SK-Hep1) indicated 5-TDGP to be a better boron carrier than normal D-glucopyranose. The carboranyl-5-TDGP 18 showed a nearly two fold increase in cellular boron accumulation than carboranyl-D-glucopyranose analog 19 over a period of 2 h. The accumulation of both 18 and 19 was found to occur in a temperature dependent manner. The higher accumulation of 18 suggested excellent promise for it to be a candidate for further evaluation as a future BNCT agent.
ISSN:1477-9226
1477-9234
DOI:10.1039/c2dt30874f