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Molecules 2016, 21(6), 709; doi:10.3390/molecules21060709

A Deoxyuridine-Based Far-Red Emitting Viscosity Sensor

1
Department of Chemistry, University of Central Florida, P.O. Box 162366, Orlando, FL 32816, USA
2
Institute of Physics, National Academy of Sciences of Ukraine, Prospect Nauki, 46, Kiev-28 03028, Ukraine
3
School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
4
College of Science and Liberal Arts, New Jersey Institute of Technology, University Heights, Newark, NJ 07102, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Zhen Cheng
Received: 13 April 2016 / Revised: 20 May 2016 / Accepted: 24 May 2016 / Published: 30 May 2016
(This article belongs to the Special Issue Molecular Imaging Probes)
View Full-Text   |   Download PDF [2304 KB, uploaded 30 May 2016]   |  

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. View Full-Text
Keywords: microviscosity sensor; far-red fluorescent probe; bioimaging; nucleosides; Sonogashira coupling; molecular rotor microviscosity sensor; far-red fluorescent probe; bioimaging; nucleosides; Sonogashira coupling; molecular rotor
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wang, M.; Zhang, Y.; Yue, X.; Yao, S.; Bondar, M.V.; Belfield, K.D. A Deoxyuridine-Based Far-Red Emitting Viscosity Sensor. Molecules 2016, 21, 709.

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