Nanomolar affinity, iminosugar-based chemical probes for specific labeling of lysosomal glucocerebrosidase

Three different photoprobes were synthesized to label β-glucosidases; one probe was based on glucose, two probes on the iminosugar deoxynojirimycin. The affinity of the probes for three different β-glucosidases was determined. Furthermore, their labeling efficiencies, binding specificities through c...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2010, Vol.18 (1), p.267-273
Main Authors: Scherpenzeel, Monique van, van den Berg, Richard J.B.H.N., Donker-Koopman, Wilma E., Liskamp, Rob M.J., Aerts, Johannes M.F.G., Overkleeft, Herman S., Pieters, Roland J.
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Bacteria - chemistry
Biological and medical sciences
Enzymes and enzyme inhibitors
Fundamental and applied biological sciences. Psychology
Glucose - chemistry
Glucose - metabolism
Glucosidases
Glucosylceramidase - analysis
Glucosylceramidase - chemistry
Glucosylceramidase - metabolism
HeLa Cells
Humans
Hydrolases
Imino Sugars - chemistry
Imino Sugars - metabolism
Lysosomes - enzymology
Photochemistry
Photolabeling
Protein Binding
Proteomics probes
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Summary:Three different photoprobes were synthesized to label β-glucosidases; one probe was based on glucose, two probes on the iminosugar deoxynojirimycin. The affinity of the probes for three different β-glucosidases was determined. Furthermore, their labeling efficiencies, binding specificities through competition with deoxynojirimycin, and binding specificities in the presence of cell lysate, were evaluated. Especially one showed very high affinity towards non-lysosomal glucoceramidase (IC 50 = 20 nM).
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2009.10.060