Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging

Abigail E. Reese; Charles Lochenie; Ailsa Geddis; Luana A. Machado; Marcos C. de Souza; Flávia F. C. Marques; Carlos A. de Simone; Marcos M. Gouvêa; Leandro F. Pedrosa; Eufrânio N. da Silva Júnior; Marc Vendrell

doi:10.3390/chemosensors10010019

Chemosensors (Jan 2022)

Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging

Abigail E. Reese,
Charles Lochenie,
Ailsa Geddis,
Luana A. Machado,
Marcos C. de Souza,
Flávia F. C. Marques,
Carlos A. de Simone,
Marcos M. Gouvêa,
Leandro F. Pedrosa,
Eufrânio N. da Silva Júnior,
Marc Vendrell

Affiliations

Abigail E. Reese: UoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UK
Charles Lochenie: UoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UK
Ailsa Geddis: UoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UK
Luana A. Machado: Institute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, Brazil
Marcos C. de Souza: Institute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, Brazil
Flávia F. C. Marques: Institute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, Brazil
Carlos A. de Simone: Institute of Physics, University of São Paulo, São Carlos 13560-160, SP, Brazil
Marcos M. Gouvêa: Institute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, Brazil
Leandro F. Pedrosa: Institute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, Brazil
Eufrânio N. da Silva Júnior: Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, Belo Horizonte 31270-901, MG, Brazil
Marc Vendrell: UoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UK

DOI: https://doi.org/10.3390/chemosensors10010019
Journal volume & issue: Vol. 10, no. 1
p. 19

Abstract

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Five new disubstituted 2,6-thioaryl-BODIPY dyes were synthesized via selective aromatic electrophilic substitution from commercially available thiophenols. The analysis of the photophysical properties via absorption and emission spectroscopy showed unusually large Stokes shifts for BODIPY fluorophores (70–100 nm), which makes them suitable probes for bioimaging. Selected compounds were evaluated for labelling primary immune cells as well as different cancer cell lines using confocal fluorescence microscopy.

Published in Chemosensors

ISSN: 2227-9040 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry: Biochemistry
Website: http://www.mdpi.com/journal/chemosensors

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