title: Two-photon "caging" groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups.
abstract: 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).
authors.affiliation: Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR8601-CNRS, Université Paris Descartes , 45, rue des Saints-Pères, 75270, Paris Cedex 06, France.
authors.forename: Christine
authors.initials: C
authors.lastname: Tran
authors.forename: Thibault
authors.initials: T
authors.lastname: Gallavardin
authors.forename: Morgane
authors.initials: M
authors.lastname: Petit
authors.forename: Riadh
authors.initials: R
authors.lastname: Slimi
authors.forename: Hamid
authors.initials: H
authors.lastname: Dhimane
authors.forename: Mireille
authors.initials: M
authors.lastname: Blanchard-Desce
authors.forename: Francine C
authors.initials: FC
authors.lastname: Acher
authors.forename: David
authors.initials: D
authors.lastname: Ogden
authors.forename: Peter I
authors.initials: PI
authors.lastname: Dalko
mesh_terms: D000634:Aminoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D010782:Photolysis; D017785:Photons; D012995:Solubility
chemical_list: C000596452:8-dimethylaminoquinoline; D000634:Aminoquinolines