ol5035035_si_001.pdf (4.59 MB)
Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups
journal contribution
posted on 2015-02-06, 00:00 authored by Christine Tran, Thibault Gallavardin, Morgane Petit, Riadh Slimi, Hamid Dhimane, Mireille Blanchard-Desce, Francine C. Acher, David Ogden, Peter I. DalkoHigh
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).