Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups Christine Tran Thibault Gallavardin Morgane Petit Riadh Slimi Hamid Dhimane Mireille Blanchard-Desce Francine C. Acher David Ogden Peter I. Dalko 10.1021/ol5035035.s001 https://acs.figshare.com/articles/journal_contribution/Two_Photon_Caging_Groups_Effect_of_Position_Isomery_on_the_Photorelease_Properties_of_Aminoquinoline_Derived_Photolabile_Protecting_Groups/2208730 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 (δ<sub>u</sub> = 2.0 GM) and good water solubility (<i>c</i> ≤ 50 mM, pH 7.4). 2015-02-06 00:00:00 photolysi water solubility section EWG GM