Synthesis and Spectral Characteristics of BODIPY Dyes with Two or Three Dipyrrin Domains

Banakova, Elizaveta; Marfin, Yuriy S.; Molchanov, Evgeniy E.; Shipalova, Maria V.; Rumiantsev, Evgeniy; Fomina, N A

doi:10.1007/s10895-018-2308-2

Cited by 9 publications

(6 citation statements)

References 31 publications

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“…It can be said that the fluorescence spectrum of the studied photosensitizer without the presence of absorption and scattering components shows that the carbonyl group in the acetone solvent led to fluorescence at the wavelength of 564 nm, while the hydroxyl group in both methanol and ethanol solvents led to fluorescence at the wavelength of 600 nm. is is consistent with a study by Banakova et al of BODIPY derivatives, in which under the influence of different solvents, they noticed a wavelength shift in the fluorescence due to the change of the solvent [13]. In another study of BODIPY derivatives conducted by Donnelly et al, the fluorescence wavelength shifts depending on the nature of the solvent [26].…”

Section: Discussionsupporting

confidence: 92%

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Effect of Solvents on the Fluorescent Spectroscopy of BODIPY-520 Derivative

Kamel

El-Daher

Bachir

et al. 2022

Journal of Spectroscopy

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Photodynamic therapy (PDT) is a selective and minimally invasive technique for the treatment of tumors. It includes three components such as photosensitizer, light, and molecular oxygen. The purpose of this work is to investigate the effect of the solvents such as methanol, ethanol, acetone, and water on fluorescent spectroscopy produced by one of the BODIPY derivatives in turbid media. A 520 nm laser diode is used for exciting one of the BODIPY derivatives as a photosensitizer in tissue-like optical phantoms. Results show that the photosensitizer studied without absorption and scattering components in the methanol and ethanol solvent has a prominent fluorescence peak at 600 nm, whereas acetone solvent has a prominent fluorescence peak at 546 nm. Experimental results reveal that when absorption and scattering components are present in addition to the studied solvents, the characteristic fluorescence intensity peak is red-shifted to 678 nm.

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Section: Discussionsupporting

confidence: 92%

“…us, BODIPY derivatives have gained great interest due to their featured optical physical properties [13]. Moreover, the physical properties can be controlled by modifying the chemical composition of chromophore BODIPY; as a result, it covers a wide band of the absorption spectrum [14].…”

Section: Introductionmentioning

confidence: 99%

Effect of Solvents on the Fluorescent Spectroscopy of BODIPY-520 Derivative

Kamel

El-Daher

Bachir

et al. 2022

Journal of Spectroscopy

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“…Boron-dipyrromethene (BODIPY) as a fluorescent dye is widely used in PDT due to its efficient singlet oxygen yield and gentle synthesis process. 19 − 21 However, due to its poor biocompatibility, its application is limited. Thus, BODIPY-containing nano-photosensitizers have recently been designed and widely used.…”

Section: Introductionmentioning

confidence: 99%

“…To address this problem, chemo/photodynamic synergistic cancer therapy has been extensively studied for its multiple advantages in overcoming drug resistance and enhancing therapeutic efficacy. , Phototherapy, including photodynamic therapy (PDT) is a new method for the treatment of cancer. , It can trigger a series of photochemical and photobiological reactions under specific wavelength laser irradiation by a photosensitizer, the most important of which is the production of reactive oxygen species (ROS, such as singlet oxygen 1 O 2 , superoxide anion radical O 2 • – , and hydroxyl radical •HO), − thereby killing tumor cells. Boron-dipyrromethene (BODIPY) as a fluorescent dye is widely used in PDT due to its efficient singlet oxygen yield and gentle synthesis process. − However, due to its poor biocompatibility, its application is limited. Thus, BODIPY-containing nano-photosensitizers have recently been designed and widely used .…”

Section: Introductionmentioning

confidence: 99%

pH-Responsive Pluronic F127–Lenvatinib-Encapsulated Halogenated Boron-Dipyrromethene Nanoparticles for Combined Photodynamic Therapy and Chemotherapy of Liver Cancer

et al. 2021

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Combination therapy such as photodynamic therapy (PDT)-enhanced chemotherapy is regarded as a promising strategy for cancer treatment. Boron-dipyrromethene (BODIPY), as close relatives of porphyrins, was widely used in PDT. However, poor water solubility, rapid metabolism by the body and lack of targeting limits its clinical application. Lenvatinib, as the first-line drug for molecular-targeted therapy of liver cancer, restricted its clinical application for its side effects. Herein, to achieve the synergy between PDT and chemotherapy, we synthesized two halogenated BODIPY, BDPBr 2 and BDPCl 2 , which were prepared into self-assembly nanoparticles with lenvatinib, and were encapsulated with Pluronic F127 through the nanoprecipitation method, namely, LBPNPs (LBBr 2 NPs and LBCl 2 NPs). The fluorescence quantum yields of LBPNPs were 0.73 and 0.71, respectively. The calculated loading rates of lenvatinib for LBBr 2 NPs and LBCl 2 NPs were 11.8 and 10.2%, respectively. LBPNPs can be hydrolyzed under weakly acidic conditions (pH 5.0) to generate reactive oxygen species (ROS), and the release rate of lenvatinib reached 88.5 and 82.4%. Additionally, LBPNPs can be effectively taken up by Hep3B and Huh7 liver cancer cells, releasing halogenated BODIPY and lenvatinib in the acidic environment of tumor cells to enhance the targeting performance of chemotherapeutics. Compared with free lenvatinib and separate halogenated BODIPY, LBPNPs can inhibit tumor growth more effectively through pH-responsive chemo/photodynamic synergistic therapy and significantly promote the cascade of caspase apoptotic protease. This study shows that LBPNPs can be a promising nanotheranostic agent for synergetic chemo/photodynamic liver cancer therapy.

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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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Synthesis and Spectral Characteristics of BODIPY Dyes with Two or Three Dipyrrin Domains

Cited by 9 publications

References 31 publications

Effect of Solvents on the Fluorescent Spectroscopy of BODIPY-520 Derivative

Effect of Solvents on the Fluorescent Spectroscopy of BODIPY-520 Derivative

pH-Responsive Pluronic F127–Lenvatinib-Encapsulated Halogenated Boron-Dipyrromethene Nanoparticles for Combined Photodynamic Therapy and Chemotherapy of Liver Cancer

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

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