Synthesis, Optical Properties, Preliminary Antimycobacterial Evaluation and Docking Studies of Trifluoroacetylated 3‐Pyrrolyl Boron‐Dipyrromethene
Abstract The article provides the route to trifluoroacetylated fluorescent boron dipyrromethene dye (2). The compound performs intensive absorption and emission bands in near‐red wavelength region. Photophysical properties of2 are investigated in different solvents. A notable increase of fluorescence quantum yield after trifluoroacetyl group insertion connected with a change in intramolecular interactions parameters. The role of molecular geometry aspects in observed photophysical properties and molecular fragments rotation energy barriers are explained by quantum‐mechanical calculations.2 performs considerable antimycobacterial activity. According to molecular docking simulations,2 is capable of affinity binding in the active sites of mycobacterial MycP1 and MycP3 serine proteases. The geometries of final ligand‐protein complexes show the possibility of protein active site covalent modification at the serine residue of the catalytic triad. At lower concentrations,2 can act as a fluorescent dye for microscopy analysis and corresponding staining patterns are shown for Mycobacterium smegmatis and Staphylococcus aureus cells..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:7 |
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| Enthalten in: |
ChemistrySelect - 7(2022), 22 |
| Beteiligte Personen: |
Horetski, Matvey [VerfasserIn] |
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| Anmerkungen: |
© 2022 Wiley‐VCH GmbH |
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| Umfang: |
7 |
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| doi: |
10.1002/slct.202200506 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Abstract The article provides the route to trifluoroacetylated fluorescent boron dipyrromethene dye (2). The compound performs intensive absorption and emission bands in near‐red wavelength region. Photophysical properties of2 are investigated in different solvents. A notable increase of fluorescence quantum yield after trifluoroacetyl group insertion connected with a change in intramolecular interactions parameters. The role of molecular geometry aspects in observed photophysical properties and molecular fragments rotation energy barriers are explained by quantum‐mechanical calculations.2 performs considerable antimycobacterial activity. According to molecular docking simulations,2 is capable of affinity binding in the active sites of mycobacterial MycP1 and MycP3 serine proteases. The geometries of final ligand‐protein complexes show the possibility of protein active site covalent modification at the serine residue of the catalytic triad. At lower concentrations,2 can act as a fluorescent dye for microscopy analysis and corresponding staining patterns are shown for Mycobacterium smegmatis and Staphylococcus aureus cells. | ||
| 700 | 1 | |a Gorlova, Anna |4 aut | |
| 700 | 1 | |a Płocińska, Renata |4 aut | |
| 700 | 1 | |a Brzostek, Anna |4 aut | |
| 700 | 1 | |a Faletrov, Yaroslav |4 aut | |
| 700 | 1 | |a Dziadek, Jarosław |4 aut | |
| 700 | 1 | |a Shkumatov, Vladimir |4 aut | |
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