Tetrazine-Responsive Self-immolative Linkers

Chembiochem. 2017 Jan 3;18(1):91-95. doi: 10.1002/cbic.201600560. Epub 2016 Dec 16.

Abstract

Molecules that undergo activation or modulation following the addition of benign external small-molecule chemical stimuli have numerous applications. Here, we report the highly efficient "decaging" of a variety of moieties by activation of a "self-immolative" linker, by application of water-soluble and stable tetrazine, including the controlled delivery of doxorubicin in a cellular context.

Keywords: Diels-Alder reaction; doxorubicin; nanoparticles; prodrugs; tetrazine.

MeSH terms

  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cycloaddition Reaction
  • Doxorubicin / chemistry
  • Doxorubicin / metabolism
  • Doxorubicin / toxicity
  • Drug Carriers / chemistry*
  • Drug Liberation
  • HEK293 Cells
  • Heterocyclic Compounds, 1-Ring / chemistry*
  • Humans
  • Nanoparticles / chemistry
  • Polyethylene Glycols / chemistry

Substances

  • Drug Carriers
  • Heterocyclic Compounds, 1-Ring
  • Polyethylene Glycols
  • Doxorubicin