Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Synthesis, Optical Properties, Preliminary Antimycobacterial Evaluation and Docking Studies of Trifluoroacetylated 3-Pyrrolyl Boron-Dipyrromethene. / Horetski, Matvey; Gorlova, Anna; Płocińska, Renata и др.
в: ChemistrySelect, Том 7, № 22, e202200506, 13.06.2022.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Synthesis, Optical Properties, Preliminary Antimycobacterial Evaluation and Docking Studies of Trifluoroacetylated 3-Pyrrolyl Boron-Dipyrromethene
AU - Horetski, Matvey
AU - Gorlova, Anna
AU - Płocińska, Renata
AU - Brzostek, Anna
AU - Faletrov, Yaroslav
AU - Dziadek, Jarosław
AU - Shkumatov, Vladimir
N1 - Funding Information: This work was supported by grant from the Ministry of Education of the Republic of Belarus N 736/41. The computations were carried out at the Novosibirsk State University Supercomputer center. Publisher Copyright: © 2022 Wiley-VCH GmbH.
PY - 2022/6/13
Y1 - 2022/6/13
N2 - 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 of 2 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.
AB - 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 of 2 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.
KW - Acylation
KW - Antibiotics
KW - Density functional calculations
KW - Fluorescence
KW - Molecular modeling
UR - http://www.scopus.com/inward/record.url?scp=85132006752&partnerID=8YFLogxK
U2 - 10.1002/slct.202200506
DO - 10.1002/slct.202200506
M3 - Article
AN - SCOPUS:85132006752
VL - 7
JO - ChemistrySelect
JF - ChemistrySelect
SN - 2365-6549
IS - 22
M1 - e202200506
ER -
ID: 36433824