Aggregation behavior and spectroscopic properties of red-emitting distyryl-BODIPY in aqueous solution, Langmuir-Schaefer films and Pluoronic® F127 micelles.

Red-emitting distyryl substituted BODIPY dyes are among the most promising luminophors for bioimaging and optics applications. However, the practical application of BODIPYs is limited due to their high hydrophobicity and tendency to aggregate in aqueous organic solutions and solid phase. In this article, we propose an elegant solution to this problem. To this end, we carried out the detailed experimental and quantum-chemical study of the structural and spectral features of BF2-ms-phenyl-5,5'-bis(4-dimethylaminostyryl)-3,3'-dimethyl-2,2'-dipyrromethene (distyryl-BDP). The particular attention was paid to analysis of high sensitivity of the distyryl-BDP spectral characteristics to the solvent properties, and also the aggregation behavior features both in water-organic media and in mono- and multilayer Langmuir-Schaefer films. We selected the best conditions to obtain the hydrophilic micellar structures of distyryl-BDP with Pluronic® F127 having a high efficiency of dye solubilization. This method increasing the solubility improves the distyryl-BDP transport efficiency in physiological aqueous media. The aqueous solutions of distyryl-BDP-Pl micelles show the intense fluorescence in the phototherapy window region (λfl = 739 nm).

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment.

Fluorescent dyes absorbing and emitting in the visible and near-IR regions are promising for the development of fluorescent probes for labeling and bio-visualization of body cells. The ability to absorb and emit in the long-wavelength region increases the efficiency of recording the spectral signals of the probes due to the higher permeability of the skin layers. Compared to other fluorescent dyes, BODIPYs are attractive due to their excellent photophysical properties-narrow absorption and emission, intense fluorescence, simple signal modulation for the practical applications. As part of conjugates with biomolecules, BODIPY could act as a biomarker, but as therapeutic agent, which allows solving several problems at once-labeling or bioimaging and treatment based on the suppression of pathogenic microflora and cancer cells, which provides a huge potential for practical application of BODIPY conjugates in medicine. The review is devoted to the discussion of the recent, promising directions of BODIPY application in the field of conjugation with biomolecules. The first direction is associated with the development of BODIPY conjugates with drugs, including compounds of platinum, paclitaxel, chlorambucil, isoxazole, capsaicin, etc. The second direction is devoted to the labeling of vitamins, hormones, lipids, and other biomolecules to control the processes of their transport, localization in target cells, and metabolism. Within the framework of the third direction, the problem of obtaining functional optically active materials by conjugating BODIPY with other colored and fluorescent particles, in particular, phthalocyanines, is being solved.

A New «off-on¼ Fluorescence Zinc Ion Sensors Based on Iodo- and Bromosubstituted Dipyrromethenes.

Monoiodo- and dibromsubstituted dipyrromethenes HL1 - HL3 were described as a highly sensitive and selective «Off-On¼ fluorescent chemosensor for Zn2+ based on the chelation-enhanced fluorescence (CHEF) effect. Сoordination reactions of HL1 - HL3 with Zn2+ cations are accompanied by a significant (124 to 215-fold) increase in fluorescence intensity against the background of other metal ions in the binary propanol-1/cyclohexane mixture (1:30). The fluorometric detection limit of Zn2+ ions using HL1 - HL3 sensors is from 3.0∙10-8 to 3.3·10-9 mol/L. The presence of Na+, K+, Ca2+, Mg2+, Mn2+, Ni2+, Co2+, Pb2+ cations does not interfere with the detection of Zn2+. Complexation reactions are accompanied by a visual change in the color of the solution from yellow-orange to pink-raspberry so that the HL1 - HL3 ligands can also be used as a «naked-eye¼ indicators of the presence of Zn2+ ions.

Spectroscopic and In Vitro Investigations of Boron(III) Complex with Meso-4-Methoxycarbonylpropylsubstituted Dipyrromethene for Fluorescence Bioimaging Applications.

This study focuses on the behavior of a new fluorescent marker for labeling individual biomolecules and staining cell organelles developed on a meso-substituted BODIPY platform. Boron(III) complex with meso-4-methoxycarbonylpropylsubstituted 3,3',5,5'-tetramethyl-2,2'-dipyrromethene has been synthesized and identified via visible, UV-, NMR- and MS-spectra X-ray. The behavior of fluorophore in solutions has been studied with various experimental techniques. It has been found that luminophore exhibits a high quantum yield (almost ~100-75%) in the blue-green region (513-520 nm) and has high photostability. In addition, biological analysis indicates that the fluorophore exhibits a tendency to effectively penetrate into cell membranes. On the other hand, the proposed BODIPY can be used to study the significant differences among a large number of pathogens of mycotic infections, as well as to visualize structural changes in the plasma membrane, which is necessary for the clearance of mammalian cells undergoing apoptotic cell death.