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Cyclopropyl Substituents Transform the Viscosity-Sensitive BODIPY Molecular Rotor into a Temperature Sensor

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Aurimas Vyšniauskas, Bethan Cornell, Peter S. Sherin, Karolina Maleckaite, Marketa Kubankova, Maria Angeles Izquierdo, Thanh Truc Vu, Yulia A. Volkova, Ekaterina M. Budynina, Carla Molteni, Marina K. Kuimova

Original languageEnglish
Pages (from-to)2158-2167
Number of pages10
JournalACS Sensors
Volume6
Issue number6
Early online date1 Jun 2021
DOIs
Accepted/In press14 May 2021
E-pub ahead of print1 Jun 2021
Published25 Jun 2021

Bibliographical note

Funding Information: A.V. is thankful to the Research Council of Lithuania for a grant no. S-MIP-19-6. B.C. and C.M. thank the U.K. Engineering and Physical Science Research Council for computational support through the UKCP consortium (EP/P022472/1) and the Materials and Molecular Modelling Hub (partially funded by EP/P020194/1). This work was partially supported by the European Commission in the form of Marie Curie individual Fellowships to T.T.V., P.S.S. and M.A.I., M.K. was supported by an EPSRC Doctoral Prize fellowship. M.K.K. is grateful to the EPSRC for a Career Acceleration Fellowship (EP/I003983/1). Publisher Copyright: © 2021 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

King's Authors

Abstract

A quantitative fluorescent probe that responds to changes in temperature is highly desirable for studies of biological environments, particularly in cellulo. Here, we report new cell-permeable fluorescence probes based on the BODIPY moiety that respond to environmental temperature. The new probes were developed on the basis of a well-established BODIPY-based viscosity probe by functionalization with cyclopropyl substituents at α and β positions of the BODIPY core. In contrast to the parent BODIPY fluorophore, α-cyclopropyl-substituted fluorophore displays temperature-dependent time-resolved fluorescence decays showing greatly diminished viscosity dependence, making it an attractive sensor to be used with fluorescence lifetime imaging microscopy (FLIM). We performed theoretical calculations that help rationalize the effect of the cyclopropyl substituents on the photophysical behavior of the new BODIPYs. In summary, we designed an attractive new quantitative FLIM-based temperature probe that can be used for temperature sensing in live cells.

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