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 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.

An α-benzithiazolyl 3-pyrrolyl BODIPY probe for ratiometric selective sensing of cyanide ions and bioimaging studies

“…3-Pyrrolyl BODIPY 1, in which the BF 2 -dipyrrin (BODIPY) unit (Scheme 1) has an additional pyrrole ring at the 3-position of BODIPY, is a highly useful fluorescent dye and absorbs and emits at higher wavelength with good quantum yield compared to BODIPY. 25 We [25][26][27][28] and others [29][30][31] have developed a much simpler and more rapid method to synthesize 3-pyrrolyl BODIPYs, which are now easily accessible. The appended pyrrole ring of 3pyrrolyl BODIPY is highly susceptible to functionalization and several functional groups such as -Br, -CHO, -NO 2 , -CCTMS, etc.…”

Synthesis and properties of covalently linked phenyl bridged 3-pyrrolyl BODIPY–BODIPY dyads

“…13 However, the synthesis of the BF 2 complex of a-pyrrolyl dipyrrin has not been thoroughly explored in previous studies due to the inaccessibility of a-pyrrolyl dipyrrin ligands. Recently, we [14][15][16][17][18][19][20][21] and others [22][23][24][25] developed a simple and facile synthetic route for BF 2 complexes of meso-aryl a-pyrrolyl dipyrrins 3a (Fig. 1).…”

α‐Acrylaldehyde 3‐Pyrrolyl BODIPY as a Specific Optical Sensor for Cysteine and Homocysteine

“…[1][2][3][4][5][6][7][8] This is because of their ease of synthesis, flexibility, and very attractive physicochemical properties, which can be tuned at will by suitable modifications. A few years back, we [9][10][11][12][13][14] and others [15][16][17][18][19] introduced a five membered pyrrole unit at the α-position of the BODIPY to form 3-pyrrolyl BODIPY 1. The pyrrolyl group at the α-position of BODIPY in 3-pyrrolyl BODIPY significantly alters the electronic properties as π-conjugation is extended and 3-pyrrolyl BODIPYs absorb and fluoresce at longer wavelength region with more quantum yields compared to BODIPYs.…”