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Journal article

A Bioorthogonal Chemical Reporter of Viral Infection.

  • Neef AB Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland) http://www.bioorganic-chemistry.com.
  • Pernot L Pharmaceutical Biochemistry, University of Geneva (Switzerland).
  • Schreier VN Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland) http://www.bioorganic-chemistry.com.
  • Scapozza L Pharmaceutical Biochemistry, University of Geneva (Switzerland).
  • Luedtke NW Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich (Switzerland) http://www.bioorganic-chemistry.com. nathan.luedtke@chem.uzh.ch.
  • 2015-05-15
Published in:
  • Angewandte Chemie (International ed. in English). - 2015
bioorthogonal chemistry
chemical reporters
click chemistry
nucleosides
viruses
Animals
Azides
Catalytic Domain
Chlorocebus aethiops
Click Chemistry
Fluorescent Dyes
Halogenation
HeLa Cells
Herpes Simplex
Herpesvirus 1, Human
Humans
Microscopy, Fluorescence
Models, Molecular
Staining and Labeling
Thymidine Kinase
Uridine
Vero Cells
English Pathogen-selective labeling was achieved by using the novel gemcitabine metabolite analogue 2'-deoxy-2',2'-difluoro-5-ethynyluridine (dF-EdU) and click chemistry. Cells infected with Herpes Simplex Virus-1 (HSV-1), but not uninfected cells, exhibit nuclear staining upon the addition of dF-EdU and a fluorescent azide. The incorporation of the dF-EdU into DNA depends on its phosphorylation by a herpes virus thymidine kinase (TK). Crystallographic analyses revealed how dF-EdU is well accommodated in the active site of HSV-1 TK, but steric clashes prevent dF-EdU from binding human TK. These results provide the first example of pathogen-enzyme-dependent incorporation and labeling of bioorthogonal functional groups in human cells.
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  • English
Open access status
green
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https://sonar.ch/global/documents/258835
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