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

Christine Tran (1) , Thibault Gallavardin (1) , Morgane Petit (1) , Riadh Slimi (2) , Hamid Dhimane (1) , Mireille Blanchard-Desce , Francine C. Acher (1) , David Ogden (3) , Peter Dalko (1)

1 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques
2 UTCBS - UM 4 (UMR 8258 / U1022) - Unité de Technologies Chimiques et Biologiques pour la Santé
3 LPC - UMR 8118 - Laboratoire de physiologie cérébrale

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).

Domaines: Chimie; Chimie organique

Christine Tran, Thibault Gallavardin, Morgane Petit, Riadh Slimi, Hamid Dhimane, et al.. Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups. Organic Letters, 2015, 17 (3), pp.402-405. ⟨10.1021/ol5035035⟩. ⟨hal-02383361⟩