Abstract
A highly selective NIR fluorescent turn-on probe for hydroxyl radical (·OH) has been built up using triphenylphosphine as a reactive-site for ·OH in an energy transfer cassette 2b consisting of 8-2′-(thiophen-2-yl) quinoline (TQ) as a donor and 3,5-diphenylphosphinostyryl-substituted BODIPY as an acceptor, which exhibits ca. 317 nm pseudo Stokes' shift due to efficient through-bond energy transfer (up to 169%). The triphenylphosphine substituent of 2b selectively oxidized by ·OH over the other reactive oxygen species (ROS) and the reactive nitrogen species (RNS) resulting in fluorescence enhancement in aqueous solution and in living cells.
Highlights
Free radicals that are natrually produced in vivo, by normal cellular metabolism or through disease process and xenobiotic activities, often cause many of the tissue changes associated with toxicities and disease processes (Dixon and Stockwell, 2014)
We report two near infrared (NIR) BODIPY probes using the triphenylphosphine as substituents at 3, 5-positions of the BODIPY core
Compounds 1a and 1b were synthesized in 65 and 39% yields according to a published procedure
Summary
Free radicals that are natrually produced in vivo, by normal cellular metabolism or through disease process and xenobiotic activities, often cause many of the tissue changes associated with toxicities and disease processes (Dixon and Stockwell, 2014). As the ESR measures the electron paramagnetic resonance spectrum of a spin adduct derivative after spin trapping, this method is insensitive and only qualitative estimates of ·OH (Valavanidis, 2000; Vidrio et al, 2008) Valavanidis to overcome these limitations, several fluorescent probes for ·OH have been developed. These probes include fluorescein with ·OH reactive-site (Zhang et al, 2016; Bai et al, 2017), cyanine dye based on a hybrid phenothiazine platform (Liu et al, 2016), a hybrid carbazole-cyanine dye (Zeng et al, 2017), fluorophore with nitroxide function group (Liras et al, 2016). The difference in lifetimes of ROS/RNS further increases the difficulty to design
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