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BODIPY
MATERIALS CHEMISTRY AND PHYSICS · 2022 · IF 4.778

Water soluble chitosan-amino acid-BODIPY fluorescent probes for selective and sensitive detection of Hg2+/Hg+ ions

Jiao He,Congwei Li,Xinjian Cheng

Three chitosan-BODIPY probes were prepared in this work. The water solubility of original chitosan has been improved. Water soluble fluorescent probes were obtained. They also exhibited good sensing ability to Hg 2+ /Hg + ions. Firstly, through the amidation reaction, arginine, cysteine, and tryptophan were grafted respectively onto chitosan chains. And then chitosan-BODIPY probes were produced by means of Schiff base formation reaction. By this way, the high structural regularity of chitosan polymer chains was changed with introducing amino acids and fluorescent groups. It also endowed fluorescence sensing ability. They could recognize Hg 2+ /Hg + ions with the interaction of C N groups. It could selectively recognize Hg 2+ /Hg + in aqueous solution, the detection limits reached 0.747μM/0.783 μM. Moreover, by the introduction of hydrophilic groups, the contact angle of modified chitosan film was improved as well. It realized performance transformation from the hydrophobic to hydrophilic. The viscoelasticity , thermal, rheological properties and fluorescence properties of the hydrogels were investigated. C N groups not only acted as a binding site to coordinate with heavy metals, but also could enhance the water solubility of the fluorescent chitosan.

研究领域: 生物化学 · 材料科学 · 环境科学
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SENSORS AND ACTUATORS B-CHEMICAL · 2017 · IF 5.401

A highly specific BODIPY-based fluorescent probe for the detection of nerve-agent simulants

Zhengliang Lu,Wenlong Fan,Xiaomin Shi,Cory A. Black,Chunhua Fan,Fangfang Wang

Nerve agents such as Sarin, Soman and Tabun are all very toxic organophosphorus (OP) compounds capable of being used as chemical weapons. Unfortunately, the ability to rapidly sense OPCs is still an ongoing challenging. In this report, we designed and synthesized a fast-response fluorescent probe ( 1 ) for the detection of OP nerve agent simulants with high selectivity and sensitivity. The probe contains an electron donor-to-acceptor system in which a BODIPY moiety acts as a reporter group and the hydroxyl group as a reaction site for nerve agent simulants. The electron deficient nitrile group was introduced to lower the background fluorescence of the probe. A significant enhancement of fluorescence intensities at 531   nm was observed upon gradual addition of nerve agent simulants on excitation at 480   nm. The emission intensity rapidly reached its maximum within only 540   s on adding 6 equiv. of nerve agent simulants with a quantum yield of the reaction product of 0.808, 81-fold larger than the probe itself (Ф   =   0.01). A color change in following a paper test experiment verified its portable application.

研究领域: 化学 · 生物医学工程
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EUROPEAN POLYMER JOURNAL · 2021 · IF 4.598

Fully-water-soluble BODIPY containing fluorescent polymers prepared by RAFT method for the detection of Fe3+ ions

Suyan He,Li Xiao,Luminita Marin,Yike Bai,Xinjian Cheng

The development of water-soluble polymer dyes is of great practical and scientific significance. In this article, small fluorescent molecule boron-dipyrromethene (BODIPY) bearing C=C bond was synthesized first. And then, via Suzuki reaction, recognition groups were introduced into the 2, 6 positions of BODIPY. Thus polymerizable fluorescent monomers were prepared. Finally, methacrylic acid (MAA) was copolymerized with the as-prepared small molecular fluorescent monomers via reversible addition-fragmentation chain transfer (RAFT) polymerization methodology. Four fully-water-soluble polymer sensors with BODIPY moieties in the end of the polymer chain were obtained eventually. In the presence of long PMAA chain, and by the assistance of it, BODIPY could be dissolved totally in water. These polymer sensors exhibited sensitive and selective recognition ability to Fe 3+ . Even the content rate of BODIPY was as low as 0.5% of the polymer (calculated from element analysis), the detection limit could reach 1.2 μM. The sensors with two recognition groups in one BODIPY unit were more sensitive than that with one recognition groups in each BODIPY unit. The sensing mechanism was investigated as well. By endowing the water solubility to organic sensors, the application scope could be greatly enlarged in sensing metal ions in aqueous environments. This work provides a method to develop water soluble high performance polymer sensors.

研究领域: 材料科学 · 化学传感器 · 分析化学
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MOLECULES · 2018 ·Vol. 23 ·期 7 ·1594 · IF 3.098

Application of the Fluorescent Dye BODIPY in the Study of Lipid Dynamics of the Rice Blast Fungus Magnaporthe oryzae

Jiaoyu Wang,Xiaoyu Guo,Ling Li,Haiping Qiu,Zhen Zhang,Yanli Wang,Guochang Sun

Rice blast is one of the most serious diseases affecting rice yield which is caused byMagnaporthe oryzae, a model organism for studies on plant pathogenic fungi. Lipids stored inM. oryzaecells have been shown to be crucial for the development of appressorium turgor and the ability of the pathogen to cause infection. Nile red staining is a common method to study lipid dynamics in phytopathogenic fungi. However, the disadvantages of this dye include its wide spectrum, poor water solubility, and susceptibility to quenching. Boron dipyrromethene (BODIPY) is a new type of fluorescent dye that has a different emission wavelength to that of Nile red as well as many desirable spectral and chemical properties. In this study, we used BODIPY to stain the lipids inM. oryzaecells to seek a possible substitute to Nile red in the study of lipid dynamics in plant pathogenic fungi. Our data showed that through simple and routine procedures, BODIPY was able to distinctly label lipids in the cells of mycelia and conidia. The positions of lipids labeled by BODIPY were essentially identical to those labeled by Nile red, but with more clear fluorescence labelling, lower background, and higher specificity. The use of BODIPY to stain germinatingM. oryzaeconidia allowed the lipid dynamics to be clearly tracked during this process. We also achieved double and multiple fluorescent staining conidia by combining BODIPY with the red fluorescent protein mCherry and other fluorescent dyes, such as Calcofluor white and DAPI, in conidia, mycelia, and sexual structures ofM. oryzae. These results indicate that BODIPY is an ideal fluorescent dye for staining fungal lipids and provide a method for the study of the lipid dynamics and lipid metabolism in plant pathogenic fungi.Keywords:Magnaporthe oryzae;lipid dynamics;BODIPY;fluorescent staining

研究领域: 植物病理学 · 真菌学
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MICROPOROUS AND MESOPOROUS MATERIALS · 2020 · IF 4.551

Reduction responsive BODIPY decorated mesoporous silica nanoscale platforms for photodynamic therapy

Yu Zhu,Nan Song,Li Chen,Zhigang Xie

In this work, we decorated the surface hydroxyl of mesoporous silica nanoparticles (MSNs-OH) by using iodine BODIPY containing disulfide bond and carboxyl group (I 2 BDP–SS–COOH) for photodynamic therapy. To improve the water solubility, the MSNs were further PEGylated by PEG–SS–COOH to prepare MSNs-I 2 BDP-PEG. The particle size and stability of MSNs-I 2 BDP-PEG were characterized by the transmission electron microscopy (TEM) and dynamic light scattering (DLS). The confocal laser imaging and cells cytotoxicity experiments indicated that MSNs-I 2 BDP-PEG could be endocytosed well, and the intracellular higher concentrations of glutathione in tumor cells could stimulate the cleavage of disulfide bonds to release BODIPY for photodynamic therapy. This work highlights the great potential of post-modificating silica nanoparticles as multifunctional materials in biomedical fields.

研究领域: 纳米医学 · 生物材料学 · 肿瘤治疗学
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COMPOSITES PART B-ENGINEERING · 2021 · IF 9.078

BODIPY coated on MXene nanosheets for improving mechanical and fire safety properties of ABS resin

San-E Zhu,Fen-Dou Wang,Jun-Jie Liu,Li-Li Wang,Cheng Wang,Anthony Chun Yin Yuen,Timothy Bo Yuan Chen,Imrana I. Kabir,Guan Heng Yeoh,Hong-Dian Lu,Wei Yang

Acrylonitrile-butadiene-styrene (ABS) resin is a commonly used engineering thermoplastic . Nevertheless, the fire toxicity hazards (HCN, NO x , NH 3 and CO) generated from the combustion of ABS remains a major concern, especially in building fire scenarios. To address this issue, boron dipyrromethene (BODIPY) modified MXene (Ti 3 C 2 T x ) nanosheets were prepared and utilized as a flame retardant for ABS. The loading of 0.5 wt% BODIPY-MXene resulted in the uniform dispersion in ABS. Accordingly, the tensile strength , Young's modulus and elongation at break of ABS/BODIPY-MXene0.5 were improved by 27.8%, 18.6% and 17.9% respectively compared to neat ABS, suggesting the enhanced mechanical properties . The limiting oxygen index (LOI) value was increased from 19.5% for neat ABS to 21.5% and 23.5% for ABS/BODIPY-MXene0.5 and ABS/BODIPY-MXene2.0 benefitted from the rapid carbonization . The cone calorimeter coupled with FTIR analysis showed that the reductions in peak heat release rate (−24.5%), peak smoke production rate (−18.4%), peak concentration of HCN (−33.5%), NO (−22.0%), N 2 O (−46.6%), NH 3 (−76.0%) and CO (−28.8%) were achieved by incorporating 0.5 wt% BODIPY-MXene to ABS in comparison with pure ABS. The improved fire safety properties were primarily attributed to the excellent barrier, free radical capture, and catalytic carbonization effect of BODIPY-MXene nanosheets within ABS matrix.

CAS / MDL: 7789-24-4
研究领域: 材料科学 · 高分子化学 · 消防安全
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ORGANIC & BIOMOLECULAR CHEMISTRY · 2019 ·Vol. 17 ·期 34 ·8001-8007 · IF 3.49

A novel BODIPY-based photosensitizer with pH-active singlet oxygen generation for photodynamic therapy in lysosomes

Chengjun Wang,Ying Qian

A novel photosensitizer BDPI-lyso has been developed for photodynamic therapy (PDT). The photosensitizer BDPI-lyso showed a high singlet oxygen quantum yield (ΦΔ = 0.95) and low fluorescence quantum yield (ΦF = 0.05) in EtOH. Different singlet oxygen quantum yields were found in acidic solution (pH = 5, ΦΔ = 0.51) and in neutral solution (pH = 7, ΦΔ = 0.38). DFT and TD-DFT calculations of BDPI-lyso and its protonated product BDPI-lysoH+ indicated that the S1/T3 transition was responsible for the intersystem crossing (ISC) enhancement which would promote the production of singlet oxygen. The negligible dark cytotoxicity toward the hepatoma cell line Bel-7402 was confirmed by MTT assay, AO/EB dual staining, and cell images. Upon exposure to a low dose of light illumination, the disruption of the cell plasma membrane and the calculated half-maximal inhibitory concentration (IC50) of 0.4 μM showed a high phototoxicity of the photosensitizer BDPI-lyso. The light-induced intracellular ROS generation was verified as the PDT mechanism of BDPI-lyso. Colocalization experiments of LysoTracker Green and BDPI-lyso in the dark indicated the good lysosome-targeting ability of BDPI-lyso. The images of cells costained with LysoTracker Green and BDPI-lyso, and the appearance of intracellular and extracellular blebs with green fluorescence after light illumination revealed the light-induced dysfunction of lysosomes and cell apoptosis.

研究领域: 生物化学 · 医学 · 药物化学
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RSC Advances · 2019 ·Vol. 9 ·期 59 ·34652-34657 · IF 3.049

A chemosensor with a paddle structure based on a BODIPY chromophore for sequential recognition of Cu2+ and HSO3−

Shengling Li,Duanlin Cao,Zhiyong Hu,Zhichun Li,Xianjiao Meng,Xinghua Han,Wenbing Ma

In this study, a highly selective chemosensor ML based on a BODIPY fluorescent chromophore was synthesized for sequential recognition of Cu2+ and HSO3− in a CH3OH/H2O (99 : 1 v/v) system, which contained three recognition sites and its structure characterized by 1H NMR, 13C NMR and ESI-HR-MS. The sensor ML showed an obvious “on–off” fluorescence quenching response toward Cu2+ and the ML-Cu2+ complex showed an “off–on” fluorescence enhancement response toward HSO3−. The detection limit of the sensor ML was 0.36 μM to Cu2+ and 1.4 μM to HSO3−. In addition, the sensor ML showed a 1 : 3 binding stoichiometry to Cu2+ and the recovery rate of ML-Cu2+ complex identifying HSO3− could be over 70%. Sensor ML showed remarkable detection ability in a pH range of 4–8.

研究领域: 分析化学 · 生物化学
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BIOMACROMOLECULES · 2017 · IF 5.246

A Water-Soluble Galactose-Decorated Cationic Photodynamic Therapy Agent Based on BODIPY to Selectively Eliminate Biofilm

Xiaomei Dai,Xuelei Chen,Yu Zhao,Yunjian Yu,Xiaosong Wei,Xinge Zhang,Chaoxing Li

A multitude of serious chronic infections are involved in bacterial biofilms that are difficult to eradicate. Here, a water-soluble galactose-functionalized cationic 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based photodynamic therapy agent was synthesized for selectively eliminating the bacterial biofilm. These conjugates can capture bacteria to form aggregations through electrostatic interaction and then generate a large number of reactive oxygen species (ROS) under visible light irradiation to kill the bacteria without the emergence of bacterial resistance. Simultaneously, this agent could effectively inhibit and eradicate both Gram-positive and Gram-negative bacterial biofilms. The in-depth analysis of the antimicrobial mechanism confirmed that the conjugates can quickly bind on the bacterial surface, irreversibly disrupt the bacterial membrane, and distinctly inhibit intracellular enzyme activity, ultimately leading to the bacterial death. Importantly, these conjugates are highly selective toward bacterial cells over mammalian cells as well as no cytotoxicity to A549 cells and no discernible hemolytic activity. Collectively, this water-soluble galactose-decorated cationic BODIPY-based photodynamic therapy agent design provides promising insights for the development of therapy for antibiotic-resistant bacteria.

研究领域: 微生物学 · 药理学
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ACS Applied Materials & Interfaces · 2016 · IF 7.145

pH-Triggered Polypeptides Nanoparticles for Efficient BODIPY Imaging-Guided Near Infrared Photodynamic Therapy

Le Liu,Liyi Fu,Titao Jing,Zheng Ruan,Lifeng Yan

An efficient pH-responsive multifunctional polypeptide micelle for simultaneous imaging and in vitro photodynamic therapy (PDT) has been prepared. The goal here is to detect and treat cancer cells by near-infrared fluorescence (NIRF) imaging and PDT synchronously. A photosensitizer BODIPY-Br2 with efficient singlet oxygen generation was synthesized at first which owns both seductive abilities in fluorescence emission and reactive oxygen species (ROS) generation under light irradiation. Then, amphiphilic copolymer micelles pH-triggered disassembly were synthesized from N-carboxyanhydride (NCA) monomer via a ring-opening polymerization and click reaction for the loading of BODIPY-Br2 by hydrophobic interaction, and the driving force is the protonation of the diisopropylethylamine groups conjugated to the polypeptide side chains. In vitro tests performed on HepG2 cancer cells confirm that the cell suppression rate was improved by more than 40% in the presence of light in the presence of an extremely low energy density (12 J/cm2) with very low concentration of 5.4 μM photosensitizer. At the same time, the internalization of the nanoparticles by cells can also be traced by NIRF imaging, indicating that the NIR nanoparticles presented imaging guided photodynamic therapy properties. It provides the potential of using polypeptide as a biodegradable carrier for NIR image-guided photodynamic therapy.

研究领域: 生物医学工程 · 癌症治疗 · 材料科学
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Journal of Materials Chemistry B · 2016 ·Vol. 4 ·期 47 ·7549-7559 · IF 4.872

A novel triphenylamine-BODIPY dendron: click synthesis, near-infrared emission and a multi-channel chemodosimeter for Hg2+ and Fe3+

Bao-xing Shen,Ying Qian

A novel triphenylamine-BODIPY based Schiff base fluorescent probe (TPA-BODIPY-OH) with an emission in the near-infrared (NIR) region was designed and prepared by click reaction. TPA-BODIPY-OH showed three emission bands at 510 nm, 598 nm and 670 nm, and can detect Fe3+ and Hg2+ ions with remarkable fluorescence enhancement in THF/H2O (v/v, 1 : 1, buffered with 10 mM HEPES pH = 7.4) based on the hydrolysis reaction of the –CN bond, and naked eye detection was realized with an obvious color change. The stoichiometry between the probe and ions was deduced from a Job's plot, which is 1 : 3 for TPA-BODIPY-OH/Fe3+ and 1 : 2 for TPA-BODIPY-OH/Hg2+, respectively. The dissociation constant value was found to be 1.35 × 10−16 M for TPA-BODIPY-OH/Fe3+ and 2.06 × 10−11 M for TPA-BODIPY-OH/Hg2+. The low detection limit was calculated from the titration results with the values of 5.15 × 10−7 M for TPA-BODIPY-OH/Fe3+ and 6.81 × 10−7 M for TPA-BODIPY-OH/Hg2+, respectively. In order to investigate the biological applications of TPA-BODIPY-OH, a living cell imaging experiment was carried out. The results demonstrate that TPA-BODIPY-OH can be successfully applied as a bioimaging agent in living cells. In addition, amino-group-functionalized silica fluorescent nanoparticles (FNPs) encapsulating the TPA-BODIPY-OH dyes were prepared and characterized by transmission electron microscopy. TPA-BODIPY-OH/SiO2 nanoparticles exhibit good dispersibility, and the quantum yield of FNPs at 657 nm was 42.3%.

CAS / MDL: 577-11-7 78-08-0
研究领域: 化学 · 生物成像 · 材料科学
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DYES AND PIGMENTS · 2019 · IF 4.018

Novel BODIPY-based fluorescent probes with large Stokes shift for imaging hydrogen sulfide

Xiao-Yan Zhu,Hao Wu,Xiao-Feng Guo,Hong Wang

Hydrogen sulfide has important biomedical significance because it plays a regulatory role in a variety of physiological processes. In our previous work, we investigated the effect of substituents on Stokes shift of BODIPY and found that methoxy groups on phenyl substituents at 3,5-positions could expand the Stokes shift of BODIPY-based probes. In this study, taking hydrogen sulfide (H 2 S) as analyte, we designed and synthesized 4,4-difluoro-8-{4-(2,4-dinitrophenoxy)phenyl}-3,5-bis(2,4-dimethoxyphenyl)-4-bora-3a,4a-diaza- s -indancene (DMOEPB) and 4,4-difluoro-8-(4-nitrophenyl)-3,5-bis(2,4-dimethoxyphenyl)-4-bora-3a,4a-diaza- s -indancene (DMONPB) according to the same strategy. As expected, Stokes shifts of 49 nm and 51 nm were obtained respectively, which demonstrate the feasibility of the strategy in the synthesis of other fluorescent probes for the detection of small biomolecules . DMONPB can react with H 2 S to form the derivative with a fluorescence quantum yield of 0.13. An excellent linear relationship was observed in the range of H 2 S concentrations from 0 μM to 800 μM and the detection limit was 1.3 μM. Furthermore, it can be successfully applied to imaging of H 2 S in cells and tissues. For DMOEPB, the presence of m -dinitrophenyl did not cause the expected fluorescence quenching, which makes it impossible to perform bioimaging . We speculate that the strong electron-withdrawing property of nitro group is obviously weaker when the two benzene rings are separated at 8-position and are not conjugated with the fluorophore . It provides experience and lessons for designing the same type of turn-on probe.

研究领域: 分析化学 · 生物化学 · 生物医学工程
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