A Deoxyuridine-Based Far-Red Emitting Viscosity Sensor
Keywords
Bioimaging; Far-red fluorescent probe; Microviscosity sensor; Molecular rotor; Nucleosides; Sonogashira coupling
Abstract
A novel deoxyuridine (dU) benzothiazolium (BZ) derivative, referred to as dU-BZ, is reported that was synthesized via Sonogashira coupling reaction methodology. The deoxyuridine building block was introduced to enhance hydrophilicity, while an alkynylated benzothiazolium dye was incorporated for long wavelength absorption to reduce potential phototoxicity that is characteristic of using UV light to excite common fluorphores, better discriminate from native autofluorescence, and potentially facilitate deep tissue imaging. An impressive 30-fold enhancement of fluorescence intensity of dU-BZ was achieved upon increasing viscosity. Fluorescence quantum yields in 99% glycerol/1% methanol (v/v) solution as a function of temperature (293-343 K), together with viscosity-dependent fluorescence lifetimes and radiative and non-radiative rate constants in glycerol/methanol solutions (ranging from 4.8 to 950 cP) were determined. Both fluorescence quantum yields and lifetimes increased with increased viscosity, consistent with results predicted by theory. This suggests that the newly-designed compound, dU-BZ, is capable of functioning as a probe of local microviscosity, an aspect examined by in vitro bioimaging experiments.
Publication Date
6-1-2016
Publication Title
Molecules
Volume
21
Issue
6
Document Type
Article
Personal Identifier
scopus
DOI Link
https://doi.org/10.3390/molecules21060709
Copyright Status
Unknown
Socpus ID
84976539705 (Scopus)
Source API URL
https://api.elsevier.com/content/abstract/scopus_id/84976539705
STARS Citation
Wang, Mengyuan; Zhang, Yuanwei; Yue, Xiling; Yao, Sheng; and Bondar, Mykhailo V., "A Deoxyuridine-Based Far-Red Emitting Viscosity Sensor" (2016). Scopus Export 2015-2019. 2395.
https://stars.library.ucf.edu/scopus2015/2395