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