Live-cell one- and two-photon uncaging of a far-red emitting acridinone fluorophore.
Total synthesis and photophysical properties of PENB-DDAO, a photoactivatable 1,3-dichloro-9,9-dimethyl-9H-acridin-2(7)-one (DDAO) derivative of a far-red emitting fluorophore, are described. The photoremovable group of the DDAO phenolic function comprises a donor/acceptor biphenyl platform which allows an efficient (> or = 95%) and rapid (< 15 micros time-range) release of the fluorescent signal and displays remarkable two-photon uncaging cross sections (delta(a) x Phi(u) = 3.7 GM at 740 nm). PENB-DDAO is cell permeable as demonstrated by the triggering of cytoplasmic red fluorescent signal in HeLa cells after one-photon irradiation (lambda(exc) around 360 nm) or by the generation of a red fluorescent signal in a delineated area of a single cell after two-photon photoactivation (lambda(exc) = 770 nm).
Laboratoire de Conception et Application de Molécules Bioactives, UMR 7199 CNRS, Faculté de Pharmacie, Université de Strasbourg, 74 Route du Rhin 67401 Illkirch Cédex, France.
David
D
Warther
Frédéric
F
Bolze
Jérémie
J
Léonard
Sylvestre
S
Gug
Alexandre
A
Specht
David
D
Puliti
Xiao-Hua
XH
Sun
Pascal
P
Kessler
Yves
Y
Lutz
Jean-Luc
JL
Vonesch
Barbara
B
Winsor
Jean-François
JF
Nicoud
Maurice
M
Goeldner
D000166:Acridines / Q000032:analysis* / Q000138:chemical synthesis / Q000378:metabolism; D002463:Cell Membrane Permeability; D005456:Fluorescent Dyes / Q000032:analysis* / Q000138:chemical synthesis / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D008856:Microscopy, Fluorescence / Q000379:methods*; D008958:Models, Molecular; D010777:Photochemistry
D000166:Acridines; D005456:Fluorescent Dyes