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

Tran, Christine; Gallavardin, Thibault; Petit, Morgane; Slimi, Riadh; Dhimane, Hamid; Blanchard-Desce, Mireille; Acher, Francine C.; Ogden, David; Dalko, Peter I.

doi:10.1021/ol5035035.s001

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. 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 (δ_u = 2.0 GM) and good water solubility (c ≤ 50 mM, pH 7.4).