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Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups

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journal contribution
posted on 06.02.2015, 00:00 authored by Christine Tran, Thibault Gallavardin, Morgane Petit, Riadh Slimi, Hamid Dhimane, Mireille Blanchard-Desce, Francine C. Acher, David Ogden, Peter I. Dalko
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).