Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging
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 fluorophor...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | Chemosensors |
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| Online Access: | https://www.mdpi.com/2227-9040/10/1/19 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Abigail E. Reese |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T01:43:27Z |
| format | Article |
| id | doaj.art-8dfeb160bd3644399b293b60d58d1f49 |
| institution | Directory Open Access Journal |
| issn | 2227-9040 |
| language | English |
| last_indexed | 2024-03-10T01:43:27Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemosensors |
| spelling | doaj.art-8dfeb160bd3644399b293b60d58d1f492023-11-23T13:19:56ZengMDPI AGChemosensors2227-90402022-01-011011910.3390/chemosensors10010019Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell ImagingAbigail E. Reese0Charles Lochenie1Ailsa Geddis2Luana A. Machado3Marcos C. de Souza4Flávia F. C. Marques5Carlos A. de Simone6Marcos M. Gouvêa7Leandro F. Pedrosa8Eufrânio N. da Silva Júnior9Marc Vendrell10UoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UKUoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UKUoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UKInstitute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, BrazilInstitute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, BrazilInstitute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, BrazilInstitute of Physics, University of São Paulo, São Carlos 13560-160, SP, BrazilInstitute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, BrazilInstitute of Chemistry, Fluminense Federal University, Niterói 24020-141, RJ, BrazilInstitute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, Belo Horizonte 31270-901, MG, BrazilUoE Centre for Inflammation Research, The University of Edinburgh, Edinburgh EH16 4TJ, UKFive 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.https://www.mdpi.com/2227-9040/10/1/19fluorophoresprobesmicroscopycytometrylabelling |
| spellingShingle | 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 Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging Chemosensors fluorophores probes microscopy cytometry labelling |
| title | Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging |
| title_full | Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging |
| title_fullStr | Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging |
| title_full_unstemmed | Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging |
| title_short | Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging |
| title_sort | rational design and synthesis of large stokes shift 2 6 sulphur disubstituted bodipys for cell imaging |
| topic | fluorophores probes microscopy cytometry labelling |
| url | https://www.mdpi.com/2227-9040/10/1/19 |
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