Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells

J Am Chem Soc. 2013 Nov 13;135(45):16766-9. doi: 10.1021/ja407867a. Epub 2013 Oct 31.

Abstract

The tetrazole-based photoclick chemistry has provided a powerful tool to image proteins in live cells. To extend photoclick chemistry to living organisms with improved spatiotemporal control, here we report the design of naphthalene-based tetrazoles that can be efficiently activated by two-photon excitation with a 700 nm femtosecond pulsed laser. A water-soluble, cell-permeable naphthalene-based tetrazole was identified that reacts with acrylamide with the effective two-photon cross-section for the cycloaddition reaction determined to be 3.8 GM. Furthermore, the use of this naphthalene-tetrazole for real-time, spatially controlled imaging of microtubules in live mammalian cells via the fluorogenic, two-photon-triggered photoclick chemistry was demonstrated.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • CHO Cells
  • Cell Survival
  • Click Chemistry
  • Cricetulus
  • Fluorescent Dyes / chemistry*
  • Microscopy, Fluorescence
  • Microtubules / ultrastructure*
  • Models, Molecular
  • Naphthalenes / chemistry*
  • Optical Imaging
  • Photons
  • Tetrazoles / chemistry*

Substances

  • Fluorescent Dyes
  • Naphthalenes
  • Tetrazoles
  • naphthalene
  • 1H-tetrazole