%0 Journal Article
%A Tran, Christine
%A Gallavardin, Thibault
%A Petit, Morgane
%A Slimi, Riadh
%A Dhimane, Hamid
%A Blanchard-Desce, Mireille
%A Acher, Francine C.
%A Ogden, David
%A Dalko, Peter I.
%D 2015
%T Two-Photon “Caging” Groups: Effect of
Position Isomery on the Photorelease Properties of Aminoquinoline-Derived
Photolabile Protecting Groups
%U 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
%R 10.1021/ol5035035.s001
%2 https://ndownloader.figshare.com/files/3844261
%K photolysi
%K water solubility
%K section
%K EWG
%K GM
%X 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).
%I ACS Publications