Journal
BIOCONJUGATE CHEMISTRY
Volume 21, Issue 7, Pages 1280-1287Publisher
AMER CHEMICAL SOC
DOI: 10.1021/bc100079n
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Funding
- Consejo Superior de Investigaciones Cientificas [PIF06-045]
- Spanish Ministry of Science [BFU2007-63287, BFU2007-62062, CTQ2006-01123, CTQ2009-13705]
- Generalitat de Catalunya [2009/SGR/208]
- Instituto de Salud Carlos III [CB06_01_0019]
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Oligonueleotide conjugates carrying carbohydrates at the 5'-end have been prepared. Glucose, fucose, and saccharides containing glucose at the nonreducing end were attached to DNA strands using the classical phosphoramidite chemistry. Two types of spacers and a dendron scaffold helped to obtain a diversity of sugar presentations in the DNA conjugates. Cellular surface adsorption and cellular uptake of carbohydrate oligonucicotide antisense sequences were measured using flow cytotnetric analysis. Conjugates with the glucose moiety linked through long spacers (15 to 18 atom distances) were internalized better than those with short linkers (4 atom distance) and than DNA control strands without sugar modification. Conjugates with tetravalent presentation of glucose did not improve cell uptake.
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