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 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.
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, USA.
Rashmirekha
R
Satapathy
Barada Prasanna
BP
Dash
Barrie P
BP
Bode
Emily A
EA
Byczynski
Sumathy N
SN
Hosmane
Sajit
S
Bux
Narayan S
NS
Hosmane
D001880:Boranes / Q000737:chemistry*; D045744:Cell Line, Tumor; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D006801:Humans; D008858:Microscopy, Phase-Contrast; D013696:Temperature; D013863:Thioglucosides / Q000737:chemistry*
D001880:Boranes; D013863:Thioglucosides; C575765:carboranyl-5-TDGP; C003002:5-thio-D-glucose; D005947:Glucose