188199-02-2Relevant academic research and scientific papers
Hexose keto-C-glycoside conjugates: Design, synthesis, cytotoxicity, and evaluation of their affinity for the glucose transporter glut-1
Uriel, Clara,Egron, Marie-Jose,Santarromana, Monique,Scherman, Daniel,Antonakis, Kostas,Herscovici, Jean
, p. 2081 - 2090 (2007/10/03)
The design, synthesis, cytotoxicity, and biological evaluation of carbohydrate/C-glycoside conjugates are described. The design concept is predicted on the idea that physiological barriers like the blood brain barrier could be crossed selectively by using glucose or glucose derivative/drug conjugates. The study demonstrates that, (1) carbohydrates and C-glycosides can be bonded at nonanomeric positions by the reaction of carbohydrate triflates with C-glycoside alkoxydes in the presence of DMPU; (2) there is a structure-activity relationship between the cytotoxicity of the conjugate and the nature of the carbohydrate residue; and (3) peracetylated hexose keto-C-glycoside conjugates are the most cytotoxic keto-glycosides.
