PUBLICATION
Biocompatible Copper(I) Catalysts for in Vivo Imaging of Glycans
- Authors
- Soriano Del Amo, D., Wang, W., Jiang, H., Besanceney, C., Yan, A.C., Levy, M., Liu, Y., Marlow, F.L., and Wu, P.
- ID
- ZDB-PUB-101115-14
- Date
- 2010
- Source
- Journal of the American Chemical Society 132(47): 16893-16899 (Journal)
- Registered Authors
- Marlow, Florence
- Keywords
- none
- MeSH Terms
-
- Alkynes/chemistry
- Animals
- Azides/chemistry
- Biocompatible Materials/chemistry*
- Biocompatible Materials/toxicity
- Blastula/metabolism
- Catalysis
- Cell Line
- Cell Survival
- Click Chemistry
- Copper/chemistry*
- Embryonic Development
- Fucose/metabolism
- Humans
- Microinjections
- Molecular Imaging/methods*
- Polysaccharides/metabolism*
- Time Factors
- Triazoles/chemistry
- Zebrafish/embryology
- PubMed
- 21062072 Full text @ J. Am. Chem. Soc.
Citation
Soriano Del Amo, D., Wang, W., Jiang, H., Besanceney, C., Yan, A.C., Levy, M., Liu, Y., Marlow, F.L., and Wu, P. (2010) Biocompatible Copper(I) Catalysts for in Vivo Imaging of Glycans. Journal of the American Chemical Society. 132(47):16893-16899.
Abstract
The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is the standard method for bioorthogonal conjugation. However, current Cu(I) catalyst formulations are toxic, hindering their use in living systems. Here we report that BTTES, a tris(triazolylmethyl)amine-based ligand for Cu(I), promotes the cycloaddition reaction rapidly in living systems without apparent toxicity. This catalyst allows, for the first time, noninvasive imaging of fucosylated glycans during zebrafish early embryogenesis. We microinjected embryos with alkyne-bearing GDP-fucose at the one-cell stage and detected the metabolically incorporated unnatural sugars using the biocompatible click chemistry. Labeled glycans could be imaged in the enveloping layer of zebrafish embryos between blastula and early larval stages. This new method paves the way for rapid, noninvasive imaging of biomolecules in living organisms.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping