title: Synthesis, cell-surface binding, and cellular uptake of fluorescently labeled glucose-DNA conjugates with different carbohydrate presentation.
abstract: Oligonucleotide 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 oligonucleotide antisense sequences were measured using flow cytometric 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.
authors.affiliation: Unidad de Biofisica, Centro Mixto CSIC-UPV/EHU, Universidad del Pais Vasco, 48080 Bilbao, Spain.
authors.forename: Begoña
authors.initials: B
authors.lastname: Ugarte-Uribe
authors.forename: Sonia
authors.initials: S
authors.lastname: Pérez-Rentero
authors.forename: Ricardo
authors.initials: R
authors.lastname: Lucas
authors.forename: Anna
authors.initials: A
authors.lastname: Aviñó
authors.forename: José J
authors.initials: JJ
authors.lastname: Reina
authors.forename: Itziar
authors.initials: I
authors.lastname: Alkorta
authors.forename: Ramón
authors.initials: R
authors.lastname: Eritja
authors.forename: Juan C
authors.initials: JC
authors.lastname: Morales
mesh_terms: D000327:Adsorption; D001665:Binding Sites; D001692:Biological Transport; D002462:Cell Membrane / Q000378:metabolism*; D002478:Cells, Cultured; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D005434:Flow Cytometry; D005456:Fluorescent Dyes / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry / Q000378:metabolism*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D006367:HeLa Cells; D006801:Humans; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005456:Fluorescent Dyes; D006001:Glycoconjugates; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D004247:DNA; D005947:Glucose