Synthesis and photophysical properties of new fluorinated benzo[c]xanthenedyes as intracellular pH indicators

Citation
Jx. Liu et al., Synthesis and photophysical properties of new fluorinated benzo[c]xanthenedyes as intracellular pH indicators, BIOORG MED, 11(22), 2001, pp. 2903-2905
Citations number
26
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
11
Issue
22
Year of publication
2001
Pages
2903 - 2905
Database
ISI
SICI code
0960-894X(20011119)11:22<2903:SAPPON>2.0.ZU;2-4
Abstract
Two new fluorinated benzo[c]xanthene dyes were synthesized by reaction of f luorinated 1,6-dihydroxynaphthalenes with 2,4- (and 2,5)-dicarboxy-3'-dimet hylamino-2'-hydroxybenzophenone. The two critical fluorinated 1,6-dihydroxy naphthalene intermediates were prepared via a regioselective route. The flu orinated 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-de pendent dual-emission characteristics are well retained. Their cell-permeab le esters have been prepared for intracellular applications. (C) 2001 Elsev ier Science Ltd. All rights reserved.