Your browser doesn't support javascript.
loading
Show: 20 | 50 | 100
Results 1 - 13 de 13
Filter
Add more filters










Publication year range
1.
Int J Mol Sci ; 24(2)2023 Jan 07.
Article in English | MEDLINE | ID: mdl-36674731

ABSTRACT

This research work is devoted to collecting a high-quality dataset of BODIPYs in a series of 10-30 solvents. In total, 115 individual compounds in 71 solvents are represented by 1698 arrays of the spectral and photophysical properties of the fluorophore. Each dye for a series of solvents is characterized by a calculated value of solvatochromic sensitivity according to a semiempirical approach applied to a series of solvents. The whole dataset is classified into 6 and 24 clusters of solvatochromic sensitivity, from high negative to high positive solvatochromism. The results of the analysis are visualized by the polarity mapping plots depicting, in terms of wavenumbers, the absorption versus emission, stokes shift versus - (absorption maxima + emission maxima), and quantum yield versus stokes shift. An analysis of the clusters combining several dyes in an individual series of solvents shows that dyes of a high solvatochromic sensitivity demonstrate regular behaviour of the corresponding plots suitable for polarity and viscosity mapping. The fluorophores collected in this study represent a high quality dataset of pattern dyes for analytical and bioanalytical applications. The developed tools could be applied for the analysis of the applicability domain of the fluorescent sensors.


Subject(s)
Boron Compounds , Fluorescent Dyes , Solvents
2.
Molecules ; 27(22)2022 Nov 16.
Article in English | MEDLINE | ID: mdl-36432012

ABSTRACT

A boron-dipyrromethene (BODIPY) derivative reactive towards amino groups of proteins (NHS-Ph-BODIPY) was synthesized. Spectroscopic and photophysical properties of amine-reactive NHS-Ph-BODIPY and its non-reactive precursor (COOH-Ph-BODIPY) in a number of organic solvents were investigated. Both fluorescent dyes were characterized by green absorption (521-532 nm) and fluorescence (538-552 nm) and medium molar absorption coefficients (46,500-118,500 M-1·cm-1) and fluorescence quantum yields (0.32 - 0.73). Solvent polarizability and dipolarity were found to play a crucial role in solvent effects on COOH-Ph-BODIPY and NHS-Ph-BODIPY absorption and emission bands maxima. Quantum-chemical calculations were used to show why solvent polarizability and dipolarity are important as well as to understand how the nature of the substituent affects spectroscopic properties of the fluorescent dyes. NHS-Ph-BODIPY was used for fluorescent labeling of a number of proteins. Conjugation of NHS-Ph-BODIPY with bovine serum albumin (BSA) resulted in bathochromic shifts of absorption and emission bands and noticeable fluorescence quenching (about 1.5 times). It was demonstrated that the sensitivity of BSA detection with NHS-Ph-BODIPY was up to eight times higher than with Coomassie brilliant blue while the sensitivity of PII-like protein PotN (PotN) detection with NHS-Ph-BODIPY and Coomassie brilliant blue was almost the same. On the basis of the molecular docking results, the most probable binding sites of NHS-Ph-BODIPY in BSA and PotN and the corresponding binding free energies were estimated.


Subject(s)
Boron , Fluorescent Dyes , Fluorescent Dyes/chemistry , Amines , Molecular Docking Simulation , Solvents/chemistry , Serum Albumin, Bovine
3.
Data Brief ; 43: 108464, 2022 Aug.
Article in English | MEDLINE | ID: mdl-35911627

ABSTRACT

The data presented here refer to the research article by Aleksei V. Solomonov, Yuriy S. Marfin, Alexander B. Tesler, Dmitry A. Merkushev, Elizaveta A. Bogatyreva, Elena V. Antina, Evgeniy V. Rumyantsev, and Ulyana Shimanovich "Spanning BODIPY fluorescence with self-assembled micellar clusters", Colloids and Surfaces B: Biointerfaces, 216, 2022, 112532. The present article provides details on optical characterization for a set of meso- and tetra-substituted boron-dipyrrin (BODIPY) complexes encapsulated inside of self-assembled Triton-X-based micellar coordination clusters (MCCs), based on Triton-X family surfactants. Changes in the optical properties of the BODIPY complexes upon interaction with bovine serum albumin, in a binary mixture of THF:H2O and titrated with Triton TX-114, were evaluated. The optical properties and the formation kinetics of the BODIPY-based MCCs and the BODIPY-supported micelle chelator aggregates (MCAs) are presented as well. The presented data provide additional insights into the structural and formation aspects of both the traditional and newly obtained micellar coordination clusters for their future optimization, control, and application. The synthetic procedures for the synthesis of a set of meso- and tetra-substituted BODIPY complexes and their optical properties in different media are also presented. The research is related to the paper (Solomonov et al., 2022).

4.
Colloids Surf B Biointerfaces ; 216: 112532, 2022 Aug.
Article in English | MEDLINE | ID: mdl-35525227

ABSTRACT

BODIPY dyes possess favorable optical properties for a variety of applications including in vivo and in vitro diagnostics. However, their utilization might be limited by their water insolubility and incompatibility with chemical modifications, resulting in low aggregation stability. Here, we outline the route for addressing this issue. We have demonstrated two approaches, based on dye entrapment in micellar coordination clusters (MCCs); this provides a general solution for water solubility as well as aggregation stability of the seven BODIPY derivatives. These derivatives have various bulky aromatic substituents in the 2,3,5,6- and meso-positions and can rotate relative to a dipyrrin core, which also provides molecular rotor properties. The molecular structural features and the presence of aromatic groups allows BODIPY dyes to be used as "supporting molecules", thus promoting micelle-micelle interaction and micellar network stabilization. In the second approach, self-micellization, following BODIPY use, leads to MCC formation without the use of any mediators, including chelators and/or metal ions. In both approaches, BODIPY exhibits an excellent optical response, at a concentration beyond its solubilization limit in aqueous media and without undesired crystallization. The suggested approaches represent systems used to encapsulate BODIPY in a capsule-based surfactant environment, enabling one to track the aggregation of BODIPY; these approaches represent an alternative system to study and apply BODIPY's molecular rotor properties. The stabilized compounds, i.e., the BODIPY-loaded MCCs, provide a unique feature of permeability to hydrophilic ligand-switching proteins such as BSA; they exhibit a bright "turn-on" fluorescence signal within the clusters via macromolecular complexation, thus expanding the possibilities of water-soluble BODIPY-loaded MCCs utilization for functional indicators.


Subject(s)
Fluorescent Dyes , Micelles , Boron Compounds/chemistry , Fluorescence , Fluorescent Dyes/chemistry , Water/chemistry
5.
Spectrochim Acta A Mol Biomol Spectrosc ; 255: 119683, 2021 Jul 05.
Article in English | MEDLINE | ID: mdl-33799189

ABSTRACT

A simple semiempiric phenomenological approach is developed for quantifying the solvent effect on the absorption and emission properties of BODIPYs. It is based on a new rule describing the linear relationship between the difference (Stokes shift) and the sum (double Gibbs free energy of electron transfer) for absorption and emission wavenumbers derived from a combination of solvent functions of Liptay theory. This rule is correspondent to changes of dipole moments in the ground and excited states. High reliability and advantages of the developed approach in comparison with traditional methods of the analysis of the solvatochromism based on Dimroth-Reichard and Lippert-Mataga solvent scales are illustrated for selected BODIPYs exhibiting positive, negative, and near-zero solvatochromism.

6.
Molecules ; 25(22)2020 Nov 17.
Article in English | MEDLINE | ID: mdl-33212835

ABSTRACT

A comprehensive study of the molecular structure of aza-BODIPY and its derivatives, obtained by introduction of one or more substituents, was carried out. We considered the changes in the characteristics of the electronic and geometric structure of the unsubstituted aza-BODIPY introducing the following substituents into the dipyrrin core; phenyl, 2-thiophenyl, 2-furanyl, 3-pyridinyl, 4-pyridinyl, 2-pyridinyl, and ethyl groups. The ground-state geometries of the unsubstituted Aza-BODIPY and 27 derivatives were computed at the PBE/6-31G(d) and CAM-B3LYP/6-31+G(d,p) levels of theory. The time-dependent density-functional theory (TDDFT) together with FC vibronic couplings was used to investigate their absorption and emission spectra.


Subject(s)
Boron Compounds/chemistry , Coloring Agents/chemistry , Electrons , Infrared Rays , Models, Molecular , Quantum Theory , Spectrum Analysis , Computer Simulation , Molecular Conformation , Rotation , Thermodynamics , Vibration
7.
J Fluoresc ; 30(6): 1611-1621, 2020 Dec.
Article in English | MEDLINE | ID: mdl-32965594

ABSTRACT

Despite significant progress in understanding of dye aggregation, there are still processes that need to be further explored and which can significantly affect aggregation. In this work it was shown that the aggregation of dyes is influenced not only by dye concentration, but also by solvent polarity. It was found that nature, positions and number of fluorescent peaks may be controlled by simultaneous varying of both water fraction and dye concentration. This effect is most pronounced for molecular rotors, which aggregates' geometry may be stabilized in different separate states depending on the aggregation degree. The concentration effect plays a significant role in dye aggregation and should be considered in new studies in order to prevent misinterpretation or to obtain new results in fields of molecular sensing or fine-tuning of fluorescence color. In this paper aggregation caused spectral changes are discussed in line with the dye structure preorganization as the strategy for the fine tuning of practically valuable spectral characteristics.

8.
Molecules ; 25(17)2020 Aug 21.
Article in English | MEDLINE | ID: mdl-32825590

ABSTRACT

The design of cargo carriers with high biocompatibility, unique morphological characteristics, and capability of strong bonding of fluorescent dye is highly important for the development of a platform for smart imaging and diagnostics. In this paper, BODIPY-doped silica nanoparticles were prepared through a "one-pot" soft-template method using a sol-gel process. Several sol-gel precursors have been used in sol-gel synthesis in the presence of soft-template to obtain the silica-based materials with the most appropriate morphological features for the immobilization of BODIPY molecules. Obtained silica particles have been shown to be non-cytotoxic and can be effectively internalized into the cervical cancer cell line (HeLa). The described method of synthesis allows us to obtain silica-based carriers with an immobilized fluorescent dye that provide the possibility for real-time imaging and detection of these carriers.


Subject(s)
Boron Compounds/chemistry , Boron/chemistry , Dimethylamines/chemistry , Nanoparticles/administration & dosage , Silicon Dioxide/chemistry , Uterine Cervical Neoplasms/drug therapy , Cell Survival , Female , HeLa Cells , Humans , Nanoparticles/chemistry , Phase Transition , Uterine Cervical Neoplasms/metabolism
9.
Data Brief ; 25: 104052, 2019 Aug.
Article in English | MEDLINE | ID: mdl-31198832

ABSTRACT

The data presented here refer to a research article entitled "Self-Assembled Micellar Clusters Based on Triton-X-family Surfactants for Enhanced Solubilization, Encapsulation, Proteins Permeability Control, and Anticancer Drug Delivery" Solomonov et al., 2019. The present article provides the General Procedure for clusterization of Triton-X-based micelles and the effect of (i) metal ion, surfactant, and chelator concentration on the developed clusters formation, (ii) surfactant-chelator relation change, (iii) metal ion-micelles concertation ratio variation, (iv) metal ion replacement, (v) solvent replacement, (vi) kinetics of clusters formation, (vii) hydrophobic fluorescent dye (Coumarin 6) solubilization in aqueous MCs media, (viii) novel anticancer peptidyl drug synthesis and characterization and (ix) the viability of HeLa cells with and without the presence of drug-free Triton-X-based family MCs. These data provide additional insights useful for understanding all aspects of the micellar clusters formation, optimization, and control.

10.
Mater Sci Eng C Mater Biol Appl ; 99: 794-804, 2019 Jun.
Article in English | MEDLINE | ID: mdl-30889754

ABSTRACT

Non-ionic surfactants have raised a considerable interest for solubilization, encapsulation, permeabilization and controlled release of various compounds due to their unique physicochemical properties. Nevertheless, it is still challenging to create convenient self-assembled multifunctional materials with high solubilization and encapsulation capacities by preserving their advanced capabilities to protect loaded cargos without altering their characteristics. In this work, we present an extended concept of micellar clusters (MCs) formation based on partial entrapment and stabilization of chelate ligands by hydrophobic forces found on the non-ionic surfactant micelle interface of the Triton-X family (TX-100/TX-114), followed by subsequent complexation of the preformed structures either by metal ions or a supporting chelator. The formation aspects, inner structure and the role of external factors such as the addition of competitive ligands have been extensively studied. MCs loaded by hydrophobic fluorescent compounds with high encapsulation efficiency demonstrate an excellent optical response in aqueous media without crystallization as well as sufficient increase in solubility of toxic hydrophobic compounds such as bilirubin (>50 times compared to pure surfactants). Furthermore, Triton-X-based MCs provide a unique feature of selective permeability to hydrophilic ligand-switching proteins such as UnaG and BSA demonstrating bright "turn-on" fluorescence signal either inside the cluster or on its interface via complexation. The proposed strategies allowed us to successfully encapsulate and visualize a newly synthesized, highly hydrophobic anticancer PTR-58-CLB-CAMP peptide drug, while MCs loaded by the drug exhibit a considerable antitumor activity against HeLa cells.


Subject(s)
Antineoplastic Agents/pharmacology , Drug Delivery Systems , Micelles , Polyethylene Glycols/chemistry , Surface-Active Agents/chemistry , Chelating Agents/chemistry , Electrolytes/chemistry , Fluorescent Dyes/chemistry , HeLa Cells , Humans , Hydrophobic and Hydrophilic Interactions , Ions , Iron/analysis , Kinetics , Ligands , Particle Size , Permeability , Solubility , Solutions , Solvents/chemistry , Temperature
11.
Curr Med Chem ; 24(25): 2745-2772, 2017.
Article in English | MEDLINE | ID: mdl-28571557

ABSTRACT

BACKGROUND: The group of fluorophores on boron dipyrrin platform (4,4- difluoro-4-bora3a,4a-diaza-s-indacene, also known as BODIPY) has attracted much attention in the field of molecular sensorics, including sensing of biomolecules and bioprocesses. Structural diversity of existing BODIPY with ample opportunities of directed modification of compounds makes this class of fluorophores attractive for medical and biological purposes. The recent progress in the design and functionalization of BODIPY allows using them for modification of drug micro- and nanocarriers in order to improve their therapeutic effect in cancer treatment. At the same time, integration of BODIPY into drug carriers provides the possibility of in vitro and in vivo real time imaging of used drug carriers. The high fluorescent intensity and low toxicity of BODIPY granted for conjugation with different biomolecules. RESULTS: The present review focuses on the recent advances for application of individual BODIPY in medical diagnostics, antimicrobial activity, as well as establishing the role of BODIPY in labeling of biomolecules (e.g. proteins, hormones and DNA). Also the review highlights the potential of BODIPY in functionalization of drug micro- and nanocarriers in order to achieve better therapeutic efficiency compared with non-modified materials. The advantages derived from the use of BODIPY for preparation and modification of drug carriers are critically evaluated and potential for future challenges, especially concerning the design of innovative multi-functional BODIPY-based nanocarriers, is discussed in detail using representative examples from literature. CONCLUSION: Our objective was to show that BODIPY are powerful tools for bioimaging, labeling of biomolecules and construction of new multifunctional drug carriers.


Subject(s)
Boron Compounds/analysis , Boron Compounds/chemistry , Drug Carriers/analysis , Drug Carriers/chemistry , Neoplasms/diagnosis , Neoplasms/drug therapy , Humans
12.
J Fluoresc ; 26(6): 1975-1985, 2016 Nov.
Article in English | MEDLINE | ID: mdl-27492609

ABSTRACT

Four boron-dipyrrine (BODIPY) based dyes with π-extended substituents in 8-position of dipyrrin ligand have been synthesized and characterized. Photophysical properties of the obtained compounds have been investigated in different individual solvents. Deposits of solvent polarity and viscosity were evaluated. BODIPY with 8-biphenyl substituent was found to be the fluorescent molecular rotor in contrast to more extended substituents. The complex nature of solvent-solute interactions leads to the poor applicability of standard multiparameter approaches to BODIPY solvatochromic properties. Fluorescence intensity was found to increase in case of solvent polarity growth, it is not typical for BODIPY. Taking that into account the BODIPY with π-extended substituents could be used for fluorescence viscosity measurements, and as the fluorescent media polarity indicators in analytical chemistry and biochemistry.

13.
J Fluoresc ; 25(5): 1517-26, 2015 Sep.
Article in English | MEDLINE | ID: mdl-26280106

ABSTRACT

Three boron-dipyrrine (BODIPY) based dyes with bulky substituents in 8-position of dipyrrin ligand have been synthesized and characterized. Photophysical properties of the obtained compounds have been investigated in different individual solvents and solvent mixtures. Investigated compounds was found to be intensive fluorescent molecular rotors. The influence of different solvent parameters and the substituent nature on rotor characteristics have been observed and discussed. Minor changes in the nature of 8-substituent does not influence the spectral properties, but the presence of nitrogen donor atom in the phenyl substituent could be used for the sensing of the donor-acceptor interactions with solvent or dissolved compounds. The new approach of spectral properties correlation with solvent parameters was proposed, the viscosity parameter should be taken into account in case of BODIPYs with bulky substituents. The intensity of fluorescence molecular rotor properties decrease gradually with the viscosity increase above 1 cP.

SELECTION OF CITATIONS
SEARCH DETAIL
...