Biocompatible copper(I) catalysts for in vivo imaging of glycans

David Soriano Del Amo, Wei Wang, Hao Jiang, Christen Besanceney, Amy C. Yan, Matthew Levy, Yi Liu, Florence L. Marlow, Peng Wu

Research output: Contribution to journalArticle

231 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)16893-16899
Number of pages7
JournalJournal of the American Chemical Society
Volume132
Issue number47
DOIs
StatePublished - Dec 1 2010

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Alkynes
Cycloaddition
Cycloaddition Reaction
Zebrafish
Polysaccharides
Copper
Guanosine Diphosphate Fucose
Bearings (structural)
Embryonic Structures
Click Chemistry
Blastula
Imaging techniques
Catalysts
Azides
Poisons
Biomolecules
Sugars
Embryonic Development
Amines
Toxicity

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Soriano Del Amo, D., Wang, W., Jiang, H., Besanceney, C., Yan, A. C., Levy, M., ... Wu, P. (2010). Biocompatible copper(I) catalysts for in vivo imaging of glycans. Journal of the American Chemical Society, 132(47), 16893-16899. https://doi.org/10.1021/ja106553e

Biocompatible copper(I) catalysts for in vivo imaging of glycans. / Soriano Del Amo, David; Wang, Wei; Jiang, Hao; Besanceney, Christen; Yan, Amy C.; Levy, Matthew; Liu, Yi; Marlow, Florence L.; Wu, Peng.

In: Journal of the American Chemical Society, Vol. 132, No. 47, 01.12.2010, p. 16893-16899.

Research output: Contribution to journalArticle

Soriano Del Amo, D, Wang, W, Jiang, H, Besanceney, C, Yan, AC, Levy, M, Liu, Y, Marlow, FL & Wu, P 2010, 'Biocompatible copper(I) catalysts for in vivo imaging of glycans', Journal of the American Chemical Society, vol. 132, no. 47, pp. 16893-16899. https://doi.org/10.1021/ja106553e
Soriano Del Amo D, Wang W, Jiang H, Besanceney C, Yan AC, Levy M et al. Biocompatible copper(I) catalysts for in vivo imaging of glycans. Journal of the American Chemical Society. 2010 Dec 1;132(47):16893-16899. https://doi.org/10.1021/ja106553e
Soriano Del Amo, David ; Wang, Wei ; Jiang, Hao ; Besanceney, Christen ; Yan, Amy C. ; Levy, Matthew ; Liu, Yi ; Marlow, Florence L. ; Wu, Peng. / Biocompatible copper(I) catalysts for in vivo imaging of glycans. In: Journal of the American Chemical Society. 2010 ; Vol. 132, No. 47. pp. 16893-16899.
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