Studies on phenyl glycosides as inhibitors of D-glucose uptake by Rhesus monkey kidney cells.

Some analogs of phenyl 6-halogeno-6-deoxy-beta-D-glucopyranosides have been found to be inhibitors of glucose uptake by Rhesus monkey kidney cells (LLCMK2 cells). The structures of the glycone and aglycone parts were both found to contribute to the inhibitory activity. Introduction of alkyl groups into the phenyl residue caused appreciable enhancement of the inhibition. p-(sec-Butyl)phenyl-6-chloro-6-deoxy-beta-D-glucopyranoside, which is the most potent inhibitor in this series, showed competitive and reversible inhibition. As a result of this study, we prepared p-azidophenyl-6-chloro-6-deoxy-beta-D-glucopyranoside as a possible compound for photoaffinity labeling of the glucose uptake site in animal cells.