Synthesis and photophysical properties of new fluorinated benzo[c]xanthene dyes as intracellular pH indicators.
Two new fluorinated benzo[c]xanthene dyes were synthesized by reaction of fluorinated 1,6-dihydroxynaphthalenes with 2,4- (and 2,5)-dicarboxy-3'-dimethylamino-2'-hydroxybenzophenone. The two critical fluorinated 1,6-dihydroxynaphthalene intermediates were prepared via a regioselective route. The fluorinated benzo[c]xanthene dyes exhibit desired lower pK(a) values (6.4 and 7.2, respectively) than their parent compound (pK(a)=7.5) while the pH-dependent dual-emission characteristics are well retained. Their cell-permeable esters have been prepared for intracellular applications.
Liu
J
J
Molecular Probes, Inc., 4849 Pitchford Avenue, Eugene, OR 97402, USA. jixiangliu@probes.com
Diwu
Z
Z
Leung
W Y
WY
D001578:Benzopyrans; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013057:Spectrum Analysis; D014966:Xanthenes / Q000737:chemistry*
D001578:Benzopyrans; D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D009284:Naphthols; C063917:SNARF dye; D014966:Xanthenes