title: A Deoxyuridine-Based Far-Red Emitting Viscosity Sensor.
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.
authors.affiliation: Department of Chemistry, University of Central Florida, P.O. Box 162366, Orlando, FL 32816, USA. wmyround@knights.ucf.edu.
authors.forename: Mengyuan
authors.initials: M
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Central Florida, P.O. Box 162366, Orlando, FL 32816, USA. zhangyuanwei2008@hotmail.com.
authors.forename: Yuanwei
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of Central Florida, P.O. Box 162366, Orlando, FL 32816, USA. xyue@sbpdiscovery.org.
authors.forename: Xiling
authors.initials: X
authors.lastname: Yue
authors.affiliation: Department of Chemistry, University of Central Florida, P.O. Box 162366, Orlando, FL 32816, USA. sheng.yao@ucf.edu.
authors.forename: Sheng
authors.initials: S
authors.lastname: Yao
authors.affiliation: Institute of Physics, National Academy of Sciences of Ukraine, Prospect Nauki, 46, Kiev-28 03028, Ukraine. mike_bondar@hotmail.com.
authors.forename: Mykhailo V
authors.initials: MV
authors.lastname: Bondar
authors.affiliation: School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China. belfield@njit.edu.|College of Science and Liberal Arts, New Jersey Institute of Technology, University Heights, Newark, NJ 07102, USA. belfield@njit.edu.
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Belfield
mesh_terms: D016475:3T3 Cells; D000818:Animals; D015374:Biosensing Techniques; D058948:Cell Tracking / Q000379:methods; D003857:Deoxyuridine / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes; D005990:Glycerol / Q000737:chemistry; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D051379:Mice; D015394:Molecular Structure; D012996:Solutions; D013696:Temperature; D014783:Viscosity
chemical_list: D005456:Fluorescent Dyes; D012996:Solutions; D005990:Glycerol; D003857:Deoxyuridine; D000432:Methanol
keywords: Sonogashira coupling; bioimaging; far-red fluorescent probe; microviscosity sensor; molecular rotor; nucleosides