DDAO Controlled Synthesis of Organo-Modified Silica Nanoparticles with Encapsulated Fluorescent Boron Dipyrrins and Study of Their Uptake by Cancerous Cells

Goncharenko, Alexander A.; Tarasyuk, Ilya A.; Marfin, Yuriy S.; Grzhegorzhevskii, K. V.; Muslimov, Аlbert R.; Bondarenko, A. B.; Lebedev, Maxim D.; Kuzmin, Ilya; Вашурин, А. С.; Lepik, Kirill V.; Timin, Alexander S.; Rumyantsev, E. V.

doi:10.3390/molecules25173802

Cited by 11 publications

(4 citation statements)

References 56 publications

(78 reference statements)

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“…Due to the low solubility of the studied compounds in water, this solvent was not included. The use of compounds in biosensorics will require DMSO as a co-solvent or the immobilization of aza-BODIPYs into micelles and/or functional materials [12,48]. Compared to classic BODIPYs, the aza-BODIPY 1-3's electronic transitions were observed in the red and near-infrared (NIR) regions.…”

Section: Resultsmentioning

confidence: 99%

“…They can also be used in the design of biomimetic materials [5][6][7] or smart materials [8][9][10][11], allowing one to explore and adapt their properties for a specific task. Spectral techniques allow one to track the localization of functional molecules [12], determining the characteristics of their molecular environment [13] and, in some cases, detailing the mechanisms of the processes occurring in the organism [14]. At the same time, the use of fluorophores requires, as a rule, fine-tuning of their spectral and photophysical characteristics [4,15].…”

Section: Introductionmentioning

confidence: 99%

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Design of Promising aza-BODIPYs for Bioimaging and Sensing

Merkushev

Vodyanova

Telegin

et al. 2022

Designs

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The obtainment of new luminophores for molecular sensorics of biosystems is becoming one of the urgent tasks in the field of chemical synthesis. The solution to each practical problem imposes its own limitations in the design of new structures with practically useful properties. The relationship between the structure and spectral properties is still to be unveiled. Three aza-BODIPY complexes with substituents of different natures were studied using time-resolved and steady-state fluorescence and absorption spectroscopy. The solvatochromic properties of aza-BODIPYs were studied with the use of a combined polyparametric approach and analysis by chemoinformatics methods for the first time. It was found that red shift of aza-BODIPY dyes was due to the increase of their structural lability. Predictive and experimental methods showed that the investigated aza-BODIPYs exhibited a positive solvatochromic effect, in contrast to classic BODIPYs (bearing C in the meso-position of the dipyrromethene core), which represents the negative solvatochromic properties. Spectral maxima in the area of the therapeutic window, low and predictable solvatochromism, and the ability to fine-tune the spectral characteristics make the investigated aza-BODIPYs promising scaffolds for the construction of bioengineering devices. Generalizations on the aza-BODIPYs’ design patterns were made in accordance with further bioimaging applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design of Promising aza-BODIPYs for Bioimaging and Sensing

Merkushev

Vodyanova

Telegin

et al. 2022

Designs

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“…The novelty of the discussed process of obtaining silica particles consists in carrying out all stages in one reaction medium (one-pot) and using a surfactant-dodecyldimethylamine N-oxide [57][58][59].…”

Section: Introductionmentioning

confidence: 99%

Sol-Gel Synthesis of Organically Modified Silica Particles as Efficient Palladium Catalyst Supports to Perform Hydrogenation Process

et al. 2021

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Modern approaches to the production of new materials require the improvement of synthesis techniques towards simplifying the processes of their preparation and reducing the number of stages. Thus, in this study, one-stage synthesis of organomodified silica materials is developed using a special surfactant—dodecyldimethylamin N-oxide (DDAO). The peculiarity of this approach is that there is no need for heat treatment of the material, since DDAO is removed by washing in alcohol. Amino-, mercapto-, methyl-, and phenyl-modified silicas were synthesized using this method. The SEM images showed the morphology of all the obtained materials is close, all particles are spherical, and the diameter of individual particles is about 500 nm. Palladium particles were precipitated on these supports, then the experiments were carried out to study the catalytic activity of these materials in a model reaction of nitroaniline reduction. The phenyl modified matrix-based materials showed very low activity. This is due to the fact that the support and the substrate contain aromatic fragments, thus, hydrophobic interactions arise between them, which complicates the diffusion of the products. The leader is a matrix with an amino fragment, which is associated with its electron-donor effect. The XPS method revealed the amount of fixed palladium, as well as the binding energy shifts, which are 0.68 eV for 5% Pd/SiO2–C6H5; 0.56 eV for 5% Pd/SiO2–C3H6–NH2; 0.26 eV for 5% Pd/SiO2–CH3; and 0.13 eV for 5% Pd/SiO2.

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“…На схеме 3 представлены синтезированные нами флуоресцентные красители на основе BODIPY, которые можно разделить на четыре группы в зависимости от особенностей их химического строения: борфторидные комплексы дипиррина с заместителями различной природы в α-, β-, β'-и/или μ-положениях дипирринового остова BODIPY1-20 [48][49][50][51][52][53][54][55][56][57][58][59][60][61][62][63], их димерные и тримерные производные BODIPY21-24 [64], а также соединение с расширенной π-системой BODIPY25 [65], и кроме того, аза-замещенные борфторидные комплексы дипиррина с заместителями различной природы в α-, β-и/или β'-положениях дипирринового остова аза-BODIPY26-30 [60,61,66,67].…”

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Chemistry of Liquid Systems and Functional Materials Based on Coordination Compounds of Linear and Cyclic Polypyrroles

2023

Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.

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The review presents a generalization of research on the chemistry of solutions and materials based on linear and cyclic polypyrrole compounds carried out at the Department of Inorganic Chemistry of the Ivanovo State University of Chemistry and Technology. The review focuses on key areas related to synthetic approaches to the preparation of boron complexes with pyrrole derivatives, as well as complexes of a wide range of metals of the periodic system with substituted derivatives of the phthalocyanine ligand. Spectroscopic, luminescent, acid-base properties of synthesized compounds and their practical application in sensor systems are considered separately. In addition, the possibilities of obtaining hybrid and functional materials, including derivatives of borondipyrrins and tetrapyrrole macroheterocyclic compounds, which have increased catalytic and biological activity in liquid-phase processes are shown. For citation: Vashurin A.S., Bobrov A.V., Botnar A.A., Bychkova A.N., Gornukhina O.V., Grechin O.V., Erzunov D.A., Kovanova M.A., Ksenofontova K.V., Kuznetsov V.V., Lefedova O.V., Latypova A.R., Litova N.A., Marfin Yu.S., Pukhovskaya S.G., Tarasyuk I.A., Tikhomirova T.V., Rumyantsev E.V., Usoltsev S.D., Filippov D.V. Chemistry of liquid systems and functional materials based on coordination compounds of linear and cyclic polypyrroles. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2023. V. 66. N 7. P. 76-97. DOI: 10.6060/ivkkt.20236607. 6840j.

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DDAO Controlled Synthesis of Organo-Modified Silica Nanoparticles with Encapsulated Fluorescent Boron Dipyrrins and Study of Their Uptake by Cancerous Cells

Cited by 11 publications

References 56 publications

Design of Promising aza-BODIPYs for Bioimaging and Sensing

Design of Promising aza-BODIPYs for Bioimaging and Sensing

Sol-Gel Synthesis of Organically Modified Silica Particles as Efficient Palladium Catalyst Supports to Perform Hydrogenation Process

Chemistry of Liquid Systems and Functional Materials Based on Coordination Compounds of Linear and Cyclic Polypyrroles

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