Copper Catalysis in Living Systems and In Situ Drug Synthesis

Jessica Clavadetscher, Scott Hoffmann, Annamaria Lilienkampf, Logan Mackay, Muhammad Rahimi Usop, Sebastien A. Rider, John J. Mullins, Mark Bradley

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

The copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction has proven to be a pivotal advance in chemical ligation strategies with applications ranging from polymer fabrication to bioconjugation. However, application in vivo has been limited by the inherent toxicity of the copper catalyst. Herein, we report the application of heterogeneous copper catalysts in azide–alkyne cycloaddition processes in biological systems ranging from cells to zebrafish, with reactions spanning from fluorophore activation to the first reported in situ generation of a triazole-containing anticancer agent from two benign components, opening up many new avenues of exploration for CuAAC chemistry.

Original languageEnglish
Pages (from-to)15662-15666
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number50
DOIs
Publication statusPublished - 2016

Fingerprint

Catalysis
Copper
Cycloaddition
Pharmaceutical Preparations
Catalysts
Triazoles
Fluorophores
Biological systems
Antineoplastic Agents
Toxicity
Polymers
Chemical activation
Fabrication

Keywords

  • bioorthogonal chemistry
  • copper
  • heterogeneous catalysis
  • prodrugs

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Clavadetscher, J., Hoffmann, S., Lilienkampf, A., Mackay, L., Usop, M. R., Rider, S. A., ... Bradley, M. (2016). Copper Catalysis in Living Systems and In Situ Drug Synthesis. Angewandte Chemie - International Edition, 55(50), 15662-15666. https://doi.org/10.1002/anie.201609837

Copper Catalysis in Living Systems and In Situ Drug Synthesis. / Clavadetscher, Jessica; Hoffmann, Scott; Lilienkampf, Annamaria; Mackay, Logan; Usop, Muhammad Rahimi; Rider, Sebastien A.; Mullins, John J.; Bradley, Mark.

In: Angewandte Chemie - International Edition, Vol. 55, No. 50, 2016, p. 15662-15666.

Research output: Contribution to journalArticle

Clavadetscher, J, Hoffmann, S, Lilienkampf, A, Mackay, L, Usop, MR, Rider, SA, Mullins, JJ & Bradley, M 2016, 'Copper Catalysis in Living Systems and In Situ Drug Synthesis', Angewandte Chemie - International Edition, vol. 55, no. 50, pp. 15662-15666. https://doi.org/10.1002/anie.201609837
Clavadetscher, Jessica ; Hoffmann, Scott ; Lilienkampf, Annamaria ; Mackay, Logan ; Usop, Muhammad Rahimi ; Rider, Sebastien A. ; Mullins, John J. ; Bradley, Mark. / Copper Catalysis in Living Systems and In Situ Drug Synthesis. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 50. pp. 15662-15666.
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