title: Synthesis and characterization of cell-permeable caged phosphates that can be photolyzed by visible light or 800 nm two-photon photolysis.
abstract: We report the synthesis and photolytic properties of caged inorganic phosphates (Pi compounds) based on the 2-(4'-{bis[2-(2-methoxyethoxy)ethyl]amino}-4-nitro-[1,1'-biphenyl]-3-yl)propan-1-ol (EANBP) and 7-(diethylamino)coumarin-4-yl]methyl (DEACM) protecting groups. The EANBP-Pi showed unprecedented photolysis efficiency at 405 nm, with 95 % release of free phosphate and a quantum yield of 0.28. Thanks to the high two-photon sensitivity of the EANBP chromophore, Pi release through two-photon photolysis is also possible, with an action cross section of 20.5 GM at 800 nm. Two bioactivatable acetoxymethyl protection groups were added to the "caged-Pi" compounds. The resulting triesters of phosphoric acid were able to diffuse through the cellular membranes of plant cells. Once inside a cell, the cleavage of these biocleavable motifs by intracellular esterases allows intracellular accumulation of EANBP-Pi. Bis(AM)-EANBP-Pi therefore represents a very attractive tool for study of the Pi signal transduction cascade in living cells.
authors.affiliation: Laboratoire de Conception et Application de Molécules Bioactives, UMR 7199, CNRS/UDS, Faculté de Pharmacie, 74 Route du Rhin, 67400 Illkirch (France); Current address: New York University Abu Dhabi, Abu Dhabi, P. O. BOX 129188 (United Arab Emirates).
authors.forename: Cyril
authors.initials: C
authors.lastname: Herbivo
authors.forename: Ziad
authors.initials: Z
authors.lastname: Omran
authors.forename: Julia
authors.initials: J
authors.lastname: Revol
authors.forename: Hélène
authors.initials: H
authors.lastname: Javot
authors.forename: Alexandre
authors.initials: A
authors.lastname: Specht
mesh_terms: D017360:Arabidopsis / Q000737:chemistry / Q000166:cytology / Q000254:growth & development; D002463:Cell Membrane Permeability; D002470:Cell Survival; D008027:Light; D015394:Molecular Structure; D010710:Phosphates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism / Q000528:radiation effects; D010782:Photolysis / Q000528:radiation effects*; D017785:Photons; D014466:Ultraviolet Rays
chemical_list: D010710:Phosphates
keywords: caged compounds; phosphate; photolysis; protecting groups; two-photon uncaging