Two-photon "caging" groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups

Org Lett. 2015 Feb 6;17(3):402-5. doi: 10.1021/ol5035035. Epub 2015 Jan 27.


High two-photon photolysis cross sections and water solubility of probes are important to avoid toxicity in biomedical applications of photolysis. Systematic variation of the position of a carboxyl electron-withdrawing group (EWG) on photolysis of 8-dimethylaminoquinoline protecting groups identified the C5-substituted isomer as a privileged dipole. The 5-benzoyl-8-DMAQ substitution yields a caging group with an enhanced two-photon uncaging cross section (δu = 2.0 GM) and good water solubility (c ≤ 50 mM, pH 7.4).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoquinolines / chemistry*
  • Molecular Structure
  • Photolysis*
  • Photons*
  • Solubility


  • 8-dimethylaminoquinoline
  • Aminoquinolines