Design and synthesis of photolabile caged cytokinin

Bioorg Med Chem Lett. 2012 Sep 1;22(17):5663-7. doi: 10.1016/j.bmcl.2012.06.090. Epub 2012 Jul 3.

Abstract

Cytokinins are phytohormones that regulate diverse developmental processes throughout the life of a plant. trans-Zeatin, kinetin, benzyladenine and dihydrozeatin are adenine-type cytokinins that are perceived by the AHK cytokinin receptors. Endogenous cytokinin levels are critical for regulating plant development. To manipulate intracellular cytokinin levels, caged cytokinins were designed on the basis of the crystal structure of the AHK4 cytokinin receptor. The caged cytokinin was photolyzed to release the cytokinin molecule inside the cells and induce cytokinin-responsive gene expression. The uncaging of intracellular caged cytokinins demonstrated that cytokinin-induced root growth inhibition can be manipulated with photo-irradiation. This caged cytokinin system could be a powerful tool for cytokinin biology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabidopsis / growth & development*
  • Arabidopsis / metabolism
  • Arabidopsis Proteins / metabolism*
  • Cytokinins / chemical synthesis
  • Cytokinins / chemistry*
  • Cytokinins / metabolism*
  • Models, Molecular
  • Photolysis
  • Plant Growth Regulators / chemical synthesis
  • Plant Growth Regulators / chemistry*
  • Plant Growth Regulators / metabolism*
  • Plant Roots / growth & development*
  • Plant Roots / metabolism
  • Protein Kinases / metabolism*
  • Receptors, Cell Surface / metabolism*

Substances

  • Arabidopsis Proteins
  • Cytokinins
  • Plant Growth Regulators
  • Receptors, Cell Surface
  • Protein Kinases
  • WOL protein, Arabidopsis