A multiple acetal chalcone-BODIPY-based fluorescence: synthesis, physical property, and biological studies

Wang, Yuling; Xiao, Fuyan; Shao, Tingyu; Hu, Kaibo; Lian, Guangchang; Feng, Jiankang; Chen, Hao; Jin, Guofan

doi:10.1007/s00216-021-03208-8

Cited by 16 publications

(4 citation statements)

References 43 publications

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“…Acrylic resin has been the subject of substantial study and application, particularly in the field of pharmacy ( Wang et al, 2021 ; Xu et al, 2021 ). For many medications, insoluble coating technology offers a practical solution.…”

Section: Introductionmentioning

confidence: 99%

A porous form Coomassie brilliant blue G250-isorhamnetin fluorescent composite coated with acrylic resin for tumor cell imaging

Hu,

Teng,

et al. 2023

Front. Chem.

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Four distinct fluorescence complexes, the fluorescent complex-1 (FC-1), fluorescent complex-2 (FC-2), fluorescent complex third (FC-3) and fluorescent complex fourth (FC-4), were created using isorhamnetin and Coomassie brilliant blue G250 as raw materials. The issue of isorhamnetin’s low solubility has been resolved, and isorhamnetin-coomassie brilliant blue G250 now has better biocompatibility. Four different forms of fluorescence compounds’ ultraviolet absorption spectra were identified. It was discovered that FC-2, FC-3, and FC-4, respectively, had double peaks at 483–620 nm. FC-4 had the highest ultraviolet absorption intensity, whereas FC-1 exhibited the most consistent and longest wavelength of ultraviolet absorption. Transmission electron microscopy revealed that the acrylic resin evenly disseminated the Coomassie brilliant blue G250-isorhamnetin complex in an amorphous flocculent form. Human prostate cancer cells (PC3) and human cervical cancer cells (HeLa) were investigated in the (Cell Counting Kit-8) CCK8 experiment under 10 different concentration circumstances, and the proliferation impact was 64.30% and 68.06%, respectively. Shown the complex’s strong anti-tumor properties and minimal cytotoxicity. Through in vitro imaging of tumor cells, it was found that FC-1’s fluorescent complex has high selectivity and can accurately infiltrate tumor cells, proving that it is biocompatible. The design not only addresses the issue of isorhamnein-Coomassie Bright Blue G250’s bioavailability, but it also has an effective visual fluorescence targeting effect.

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Section: Introductionmentioning

confidence: 99%

A porous form Coomassie brilliant blue G250-isorhamnetin fluorescent composite coated with acrylic resin for tumor cell imaging

Hu,

Teng,

et al. 2023

Front. Chem.

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“…The introduction of a hydrophilic component into the carborane structure can greatly improve water solubility and thus simplify drug administration in vivo [22][23][24][25]. To improve the drug solubility, make the drug reach the target site smoothly, and observe the drug distribution in the cell, we designed a simple, efficient fluorescent molecular probe to make the intracellular visualization [26,27]. At the same time, P-CBMA was used as a water-soluble intermediate carrier to improve water solubility and biocompatibility.…”

Section: Introductionmentioning

confidence: 99%

Water-soluble BODIPY-nido-carborane nanoparticles applied to biocompatibility tumor cell imaging

Dai

Lian

et al. 2022

Photochem Photobiol Sci

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In this article, o-carborane has a high boron content, high hydrophobicity, and good chemical stability. It has been widely used in the fields of biology and medicine, especially in the application of boron neutron capture therapy (BNCT). However, o-carborane is a fat-soluble compound, its hydrophobicity is too strong, and its bioavailability is poor. This project aims to improve the water solubility of o-carborane drugs, so that the drugs can reach specific sites. For this reason, this article provides a one-pot reaction for the synthesis of water-soluble boron-containing drugs. 2-Chloro-1-(difluoroboranyl)-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(phenyl) methyl)-1H-pyrrole and ethylenediamine are used as raw materials to synthesize fluorescent molecular probe BODIPY-NH 2 , and the fluorescent molecular probe is reacted with P-CBMA (poly(carboxybetaine methacrylate)) to produce a water-soluble gel polymer. Water-soluble o-carborane polymers were synthesized by hydrogen bonding of the polymers with bis(4-azaspiro[3.4]octan-4-ium)-nido-ortho-carborane and bis(5azaspiro[4.5]decan-5-ium)-nido-ortho-caborane. The two polymers were characterized and the results showed that the maximum UV absorption wavelength of the two boron polymers in different polar solutions was 530-540 nm. In the fluorescence spectrum, the maximum emission wavelengths of the two boron polymers are concentrated between 550 and 560 nm. Through electron microscopy imaging, the fluoroboron pyrrole polymers wrap the boron clusters to form a spherical stacked. Through fluorescent cell imaging, both boron polymers can enter target cells.

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“…Optical imaging technology ( Zhang et al, 2015 ; Zhou et al, 2016 ; Du et al, 2019 ) based on fluorescent probe is considered as a potential technology for tumor diagnosis by the academic circles because of its advantages of non-invasive and sensitivity ( Guo et al, 2018 ; Karan et al, 2021 ; Barth et al, 2022 ). Boron-dipyrromethene (BODIPY) dye ( Labra-Vazquez et al, 2020 ; Xiao et al, 2020 ; Qiao et al, 2021 ; Vales et al, 2021 ; Wen et al, 2021 ; Wang et al, 2021 ) has many advantages, such as good light stability ( Kyeong et al, 2018 ; Haldar et al, 2020 ), large molar extinction coefficient ( Che et al, 2020 ; Pfeifer et al, 2020 ), stable spectral properties ( Zlatic et al, 2020 ), and narrow spectral half-peak ( Zhu et al, 2019 ; Song et al, 2020 ). Since it came out, it has attracted the attention of scholars from various circles.…”

Section: Introductionmentioning

confidence: 99%

“…Since it came out, it has attracted the attention of scholars from various circles. In particular, as a widely used biological imaging reagent, the development of organic dyes (including BODIPY) with strong absorption and fluorescence bands in the near infrared (NIR) region has attracted great attention, so that it has the advantages of strong anti-interference ability, and clear and accurate imaging, making it have great potential in the field of optical imaging ( Li et al, 2019 ; Wang et al, 2020 ; Wang et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Symmetry dual functional pyrimidine-BODIPY probes for imaging targeting and activity study

Liu²,

Wang³

et al. 2022

Front. Chem.

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Nondestructive diagnosis of tumor has always been the goal of scientists. Fluorescent dyes have become the rising star in the field of cancer diagnosis because of their excellent characteristics. Therefore, in this work, fluorescence probes d-Y-B and dO-Y-B with anti-tumor activity were constructed by introducing pyrimidine groups with high anti-tumor activity using fluorescence dye BODIPY as parent nucleus. The modified BODIPY group in the structure had the advantage of fluorescent dye, ensuring the strong fluorescence and photosensitivity of the target compound. That ethylenediamine acts as a bridge with two -NH- groups to increase molecular hydrogen bonding, and can bind firmly to multiple proteins. Co-localization of the target compounds d-Y-B and dO-Y-B with the hoechst dye for labeling living cells showed that these compounds had high biocompatibility and photostability for localization to HeLa cells. In vivo imaging in mice can realize specific localization and real-time visualization of tumor cells. The results of cytotoxicity experiments in vitro and computer software simulating molecular docking confirmed the potential of the target compounds as an anticancer agents. The bifunctional probe realized visualization of cancer cells in mice, and can kill cancer cells by anti-proliferation, which may provide a direction for future anticancer drug development.

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A multiple acetal chalcone-BODIPY-based fluorescence: synthesis, physical property, and biological studies

Cited by 16 publications

References 43 publications

A porous form Coomassie brilliant blue G250-isorhamnetin fluorescent composite coated with acrylic resin for tumor cell imaging

A porous form Coomassie brilliant blue G250-isorhamnetin fluorescent composite coated with acrylic resin for tumor cell imaging

Water-soluble BODIPY-nido-carborane nanoparticles applied to biocompatibility tumor cell imaging

Symmetry dual functional pyrimidine-BODIPY probes for imaging targeting and activity study

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