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BODIPY
DYES AND PIGMENTS · 2023 · IF 4.5

Triphenylamine-substituted BODIPY dye based photoinitiators for free radical and cationic photopolymerization under visible LED irradiation and application in 3D printing

Xianjun Zhao,Bo Hu,Qun Zhou,Yijie Yu,Erhong Hao,Xing Guo,Yangyang Xu,Changjiang Yu,Ke Sun,Jacques Lalevée

Until now the photopolymerization process is largely dependent on the hazardous UV or near UV light irradiation. Herein this work, a series of boron dipyrromethene (BODIPY) derivatives substituted by electron-donating triphenylamine moiety on different positions were introduced and investigated thoroughly. Markedly, their photoinitiation abilities under mild conditions, e.g. visible LEDs irradiation and room temperature, were examined for the first time. In combination with an iodonium salt and an amine as the co-initiators, these BODIPY dyes could form three-component photoinitiating systems (PISs) for the purpose to initiate both the free radical polymerization of acrylate monomers and cationic polymerization of epoxy monomers. Interestingly, under the irradiation of LED@405 nm, LED@530 nm or LED@660 nm, some of these BODIPYs-based PISs could conduct high monomeric conversion and rapid photopolymerization rates, as reflected by the relevant photopolymerization kinetics. Then the notable photochemical reactivity of these BODIPY dyes was examined by both steady state photolysis and fluorescence quenching experiments, and theoretical calculation was also performed on them in details. Finally, photocuring 3D printing technique was applied to the acrylate/epoxy mixture resin, as the result the BODIPYs-based PISs demonstrated great potential to fabricate truly three-dimensional objects in macroscopic scale with excellent spatial resolution.

CAS / MDL: 15625-89-5
研究领域: 材料科学 · 化学工程 · 光学工程
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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

A simple BODIPY-based fluorescent probe for sequential recognition of Cu2+ and GSH and its application on test strips and bioimaging in living cells

Mingya Wang,Shengling Li,Junli Shi,Yongzheng Liu,Duanlin Cao,Linxiu Zhao

A novel, highly sensitive “on-off-on” fluorescent probe ( E )- N ’-((1 H -imidazol-2-yl) methylene) -4-(5, 5-difluoro-1, 3, 7, 9-tetramethyl-5 H -4 λ 4 ,5 λ 4 -dipyrrolo [1, 2- c :2′, 1′- f ] [1,3,2] diazaborinin-10-yl) benzohydrazide ( BDB ) was developed in this study, and its structural and spectral properties were characterized by 13 C NMR, 1 H NMR, X-ray, ESI-MS, ultraviolet and fluorescence photometry. BDB could specifically and efficiently identify Cu 2+ among many other metal ions with a fluorescence quenching efficiency of 92.7% and a recognition limit of 0.65 μM in CH 3 CN/HEPES (7:3, v/v, pH = 7.23) buffer. The energy difference between BDB and BDB -Cu 2+ complex was calculated by DFT. The BDB -Cu 2+ complex could continuously identify GSH in the same system and show an obvious fluorescence enhancement response with a recovery efficiency of approximately 91% and a low recognition limit of 0.02 μM, which is significantly lower than the physiological concentration of GSH in living cells. The applicability of BDB is verified by the strip test. BDB can also be used to detect GSH in HeLa cells, which expand the application of fluorescent chemical sensors in biology.

研究领域: 分析化学 · 生物化学 · 材料科学 · 生物成像
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Biomaterials Science · 2016 ·Vol. 4 ·期 11 ·1638-1645 · IF 3.614

Near infrared imaging-guided photodynamic therapy under an extremely low energy of light by galactose targeted amphiphilic polypeptide micelle encapsulating BODIPY-Br2

Le Liu,Zheng Ruan,Tuanwei Li,Pan Yuan,Lifeng Yan

Near infrared (NIR) imaging-guided photodynamic therapy (PDT) is attractive, especially the utilization of one dye as both a photosensitizer and fluorescent probe, and the as-synthesized BODIPY-Br2 molecule is a candidate. Here, a galactose targeted amphiphilic copolymer of a polypeptide was synthesized and its micelles work as nanocarriers for BODIPY for targeting the NIR imaging-guided PDT of hepatoma cancer cells. At the same time, BODIPY could light up the cytoplasm for real-time imaging and kill cancer cells when the light was switched on. In vitro tests performed on both HepG2 and HeLa cells confirmed that the as-prepared PMAGP-POEGMA-PLys-B micelles showed efficient cell suppression of the cells with galactose receptors in the presence of light under an extremely low energy density (6.5 J cm−2). This protocol highlights the potential of polypeptides as biodegradable carriers for NIR image-guided and confined targeting photodynamic therapy.

研究领域: 生物医学工程 · 肿瘤学 · 材料科学
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DYES AND PIGMENTS · 2021 · IF 4.889

A multifunctional BODIPY based fluorescent probe for hydrogen sulfide detection and photodynamic anticancer therapy in HCT116 colon cancer cell

Yun-Yun Quan,Lanlan Fan,Hongyan Shen,Binbin Wu,Shanshan Kong,Yanshu Luo,Zu-Sheng Huang,Xiaoxia Ye

Development of multifunctional probes that can be simultaneously utilized for both efficient hydrogen sulfide detection and photodynamic therapy in cancer cells is in high demand but remains worldwide challenge. Herein, a fluorescent probe DB2T based on a BODIPY structure for H 2 S fluorescence “turn-on” detection together with light sensitive anticancer capacity has been designed and synthesized. The probe DB2T features high selectivity towards H 2 S, excellent low detection limit (6.39 nM), and good biocompatibility . Importantly, the probe DB2T has been satisfactorily applied in fluorescence imaging of exogenous H 2 S in zebrafish, and successfully employed in fluorescence imaging of endogenous H 2 S in HCT116 cell and tumor tissues. Moreover, evaluation of the phototherapy effect demonstrates that the probe DB2T performs well as a photosensitizer for photodynamic ablation of HCT116 cancer cells upon white light irradiation. This work should facilitate significant advances in rational design of fluorescence systems for H 2 S detection and even in the diagnosis and treatment of H 2 S related diseases.

研究领域: 生物化学 · 肿瘤学 · 药物开发
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Journal of Materials Chemistry B · 2024 · IF 6.1

Heavy-Atom-Free BODIPY Dendrimer: Utilizing the Spin-Vibronic Coupling Mechanism for Two-Photon Photodynamic Therapy in Zebrafish

Lingfeng Wang,Ying Qian

In this paper, the heavy-atom-free BODIPY dendrimer TM4-BDP was synthesized for the near-infrared photodynamic therapy, which was composed of the triphenylamine-BODIPY dimer and four 1-(2-morpholinoethyl)-1H-indole-3-ethenyl groups. The TM4-BDP could achieve the near-infrared photodynamic therapy through two different photosensitive pathway, which include the one-photon excitation at 660 nm and two-photon excitation at 1000 nm. In the one-photon excitation pathway, the TM4-BDP could generate singlet oxygen and superoxide radical under 660 nm illumination. In addition, the one-photon PDT experiment in human nasopharyngeal carcinoma (CNE-2) cells also indicated that the TM4-BDP could specific accumulate in lysosomes and shown great cell phototoxicity with the IC50 at 22.1μM. In the two-photon excitation pathway, the two-photon absorption cross section at 1030 nm of TM4-BDP was determined as 383 GM, which make it could generate the reactive oxygen species (ROS) under 1000 nm femtosecond laser excitation. Moreover, the two-photon PDT experiment in zebrafish also indicated the TM4-BDP could be used for the two-photon fluorescence imaging and the two-photon induced ROS generation in biological environment. Besides that, in the ROS generation mechanism aspect, the TM4-BDP employ the novel spin-vibronic coupling intersystem crossing (SV-ISC) process for the mechanism of ROS generation and the femtosecond transient absorption spectra indicated that this novel SV-ISC mechanism was closely related with its’ lifetime of charge transfer state. These above experiments of TM4-BDP demonstrate that the dendrimer design was an effective strategy for constructing heavy-atom-free NIR BODIPY photosensitizers and lay the foundation for the two-photon photodynamic therapy in the future clinical trails.

研究领域: 光动力疗法 · 纳米技术 · 生物医学工程 · 材料科学 · 光学 · 药物化学 · 分子生物学 · 细胞生物学 · 斑马鱼研究
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FOOD CHEMISTRY · 2023 · IF 8.8

Fabrication of BODIPY/polyvinyl alcohol/alkaline lignin antibacterial composite films for food packing

Yanchao Liu,Min Zheng

Foodborne pathogens seriously endanger people's health and cause significant economic losses. Therefore, it is of great significance to design potent packaging materials with the function of alleviating food spoiling and extending shelf life. Here, three BODIPY derivatives (named as N-BDPI, B-BDPI and P-BDPI) were synthesized by substituting the 8-position of BODIPY with naphthalene, biphenyl and pyridine groups, respectively, and their photophysical properties as well as antibacterial capacities were characterized. The results demonstrated that N-BDPI had the best singlet oxygen generation ability and could completely kill S. aureus under light irradiation with the minimum inhibitory concentration of only 50 nmol/L. In addition, 1.0% [email protected] /AL composite film was fabricated by doping N-BDPI into polyvinyl alcohol (PVA) and alkaline lignin (AL) exhibited high antibacterial activity on Gram-positive bacteria. The coating of strawberries with 1.0% [email protected] /AL film not only effectively inhibited the mildew of strawberries, but also extended their shelf life.

CAS / MDL: 121-44-8
研究领域: 材料科学 · 食品科学 · 生物技术 · 化学
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Materials Science & Engineering C-Materials for Biological Applications · 2018 · IF 5.08

Reduction-sensitive polypeptide nanogel conjugated BODIPY-Br for NIR imaging-guided chem/photodynamic therapy at low light and drug dose

Le Liu,Tuanwei Li,Zheng Ruan,Pan Yuan,Lifeng Yan

A heavy atoms modified reaction-active photosensitizer NHS-BODIPY-Br possessing efficient near infrared (NIR) fluorescence emission and singlet oxygen generation properties has been synthesized, which can be used for synchronous NIR imaging and photodynamic therapy (PDT). A reduction-sensitive PEGylated polypeptide nanogel was prepared by ring-opening polymerization (ROP) of l -cystine- N -carboxy anhydride. Poly (ethylene glycol) methyl ether was used as initiator and hydrophilic segment, the as-prepared nanogel was conjugated with the NHS-BODIPY-Br molecule by chemical linkage, and it can be directly used as a macrophotosentizer for NIR imaging-guided PDT. In addition, the nanogel also showed good encapsulating ability for doxorubicin (DOX). In the presence of glutathione (10 mM), the obtained NIR nanogel showed obvious reduction-induced drug release behavior. In vitro tests on internalization of the NIR nanogel by HepG2 cells indicated its efficiency in detecting cancer cells. Meanwhile, MTT assays performed on HepG2 cells confirmed that the cancer cells growth could be obviously suppressed (almost all cells) when exposed to an extremely low energy light (25 mW/cm 2 , 10–15 J/cm 2 ) and low dose of DOX (3–5 μg/ml), indicates an efficient NIR image-guided chem/photodynamic therapy.

研究领域: 生物材料 · 肿瘤学 · 药剂学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF CONTROLLED RELEASE · 2024 · IF 10.5

Engineered manganese-BODIPY coordinated nanoadjuvants for enhanced NIR-II photo-metalloimmunotherapy

Yushi Zhang,Xuya Yu,Lingpeng Luo,Yigang Xu,Hanjie Zhang,Zhuo Mao,Yuqin Zhang,Cuihong Yang,Lu Wang,Pengcheng Zhang,Sitong Li,Meitong Ou,Ran Luo,Dunwan Zhu,Wen Li,Lin Mei

Immunotherapy, a pivotal and promising approach for tumor treatment, has demonstrated prominent clinical efficacy. However, its effectiveness is often impeded by insufficient antitumor immune responses attributed to the immunosuppressive tumor microenvironment (TME). The combination of immune activation through the stimulator of interferon genes (STING) pathway and phototherapy holds great potential for surmounting this challenge in advanced tumor immunotherapy. Herein, a novel manganese-boosted NIR-II photo-metalloimmunotherapy is proposed to synergistically enhance antitumour efficacy by fabricating Mn 2+ -BODIPY-based coordinated photo-immune nanoadjuvants (BMR), modified with tumor-targeted peptide cRGD. The obtained BMR could effectively deliver Mn 2+ to tumor sites, and immunogenic cell death (ICD) was evoked by localized photothermal ablation of tumors using NIR-II laser irradiation. Simultaneously, pH-responsive release of Mn 2+ would trigger the activation of STING pathway to promote the production of type I interferons (I-IFNs), significantly facilitating the maturation of dendritic cells (DCs) and polarization of macrophages to M1 phenotypes. Furthermore, by synergistically initiating systematic and robust antitumour immune responses, the BMR-mediated NIR-II photo-metalloimmunotherapy achieved remarkable therapeutic efficacy against both primary and lung metastasis of B16F10 tumors. Overall, in light of the versatile functionalities and synthetic flexibility of coordinated nanoadjuvants, formulated with photofunctional ligands and diverse metal ions, this work provides new insights into the design of metal coordination nanomedicine for effective antitumor photo-metalloimmunotherapy.

研究领域: 癌症治疗 · 纳米技术 · 免疫学 · 光疗 · 材料科学
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RSC Advances · 2018 ·Vol. 8 ·期 36 ·20087-20094 · IF 2.936

A novel amphiphilic fluorescent probe BODIPY–O-CMC–cRGD as a biomarker and nanoparticle vector

Tingting Zhu,Ji Xiong,Zhongbo Xue,Yu Su,Fengnan Sun,Ran Chai,Jialiang Xu,Yaqing Feng,Shuxian Meng

Fluorescent probes have been demonstrated to be promising candidates as biomarkers and biological carriers. Our study focuses on the development of a novel amphiphilic fluorescent probe with good photostability, high water solubility, excellent specificity and promising loading capability for tumor diagnosis and treatment. At first, BODIPY dye and O-carboxymethyl chitosan were prepared via a chemical reaction. Then, the prepared BODIPY dye and cRGD were bonded to O-carboxymethyl chitosan successively via an acylation reaction. Finally, we obtained the desired amphiphilic fluorescent probe: BODIPY–O-CMC–cRGD, which was based on the fluorescence resonance energy transfer (FRET) principle for selective visualization of tumors in vitro. Through a series of experiments, we found that this fluorescent probe possessed better fluorescence characteristics and tumor targeting properties. Simultaneously, by self-assembly, the amphiphilic probe encapsulated the other flexible structure of BODIPY2 and the rigid structure of porphyrin, which formed distinct nanoparticles with different particle sizes. Hence, we could observe different phagocytosis processes of the two nanoparticles in the tumor cells via the fluorescence of dyes by confocal laser scanning microscopy. Therefore, the results suggest that the fluorescent probe has advantages in tumor detection, and the constructed tumor-specific nanoparticles show high clinical potential to be utilized not only in visual and precise diagnosis but also in excellent drug delivery for tumor treatment. Henceforth, we will prepare new targeted and visualized pharmaceuticals by replacing BODIPY2 and porphyrin with antineoplastic drugs for future tumor treatment.

研究领域: 生物医学工程 · 药学 · 分子生物学 · 癌症研究
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Journal of Materials Chemistry B · 2018 ·Vol. 6 ·期 5 ·753-762 · IF 4.776

PEG conjugated BODIPY-Br2 as macro-photosensitizer for efficient imaging-guided photodynamic therapy

Zheng Ruan,Yangyang Zhao,Pan Yuan,Le Liu,Yucai Wang,Lifeng Yan

Drug-free biocompatible nanoparticles with photosensitizers as both diagnostic and therapy agents represent an emerging approach for imaging-guided photodynamic therapy (PDT). Here, a NSH-active boron-dipyrromethene (BODIPY) derivative with a bromine substituted (BODIPY-Br2, for simplicity, BDP-Br) photosensitizer was synthesized; it showed a high ability of generating reactive oxygen species (ROS) upon irradiation for PDT and near infrared fluorescence imaging ability. Then, a simple PEGylated BDP-Br (PEG-BDP) as a kind of macro photosensitizer was prepared which showed superior cellular uptake ability, high efficiency of imaging, and curing with PDT therapy in vitro and in vivo. After administration with a 4T1 orthotopic tumor model, the resultant PEG-BDP showed prolonged blood circulation and preferential tumor accumulation compared with free BDP-Br molecules. Once accumulated in tumor tissues, therapeutic effects of PEG-BDP could significantly suppress primary tumor growth and has no evident side effects at a weak irradiation energy as low as 35 mW cm−2 for 20 minutes. The designation of this simple structure macro photosensitizer agent provides new avenues for efficient imaging-guided cancer PDT.

CAS / MDL: 1122-58-3 25952-53-8
研究领域: 癌症研究 · 药学科学 · 分子影像 · 纳米医学 · 诊疗一体化
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2025 · IF 3.8

Real-time monitoring of cell membrane viscosity in a 3D hydrogel cultivation microenvironment using BODIPY-based fluorescent probe

Shi Junli,Chong Hui,Yang Xiaofei,Zhong Guangjie,Wu Shengnan,Gu Zehao,Tao Qi,Wang Dong-An,Xue Huaiguo,Yang Yi,Yao Hang

This study reports a viscosity-responsive fluorescent probe, BODIPY-C, designed to measure viscosity in a 3D live-cell hydrogel microenvironment using a fluorescence lifetime-based method. This method enables real-time monitoring of cell membrane viscosity changes through the fluorescent lifetime signals of the probe. Functionally, the BODIPY-C exhibits microviscosity sensitivity; the non-toxic probe enables long-term tracking with high sensitivity ( R 2  = 0.99). Structurally, the BODIPY-C features polymerizable vinyl groups that facilitate covalent conjugation to hydrogel networks via UV-initiated polymerization. This design synergistically integrates the molecular specificity of BODIPY-C-based viscosity sensing with the mechanobiology of covalent hydrogel networks. Notably, softer 3D hydrogel microenvironments extend the probe’s fluorescence lifetime due to restricted molecular motion from differential elastic collisions between polymer chains. The covalent anchoring of BODIPY-C within hydrogel networks enables in situ monitoring of viscosity dynamics in encapsulated cells, establishing a promising platform for investigating mechanobiological processes. Graphical abstract

研究领域: 生物化学 · 生物物理 · 细胞生物学 · 材料科学 · 分析化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

Building Rhodamine-BODIPY fluorescent platform using Click reaction: Naked-eye visible and multi-channel chemodosimeter for detection of Fe3+ and Hg2+

Bao-xing Shen,Ying Qian

A novel ratiometric fluorescent probe RhB-BODIPY-OH based on Rhodamine and boron dipyrromethene (BODIPY) platform for sensing Fe 3+ and Hg 2+ ions was synthesized by Click reaction. RhB-BODIPY-OH dendron was a hybrid fluorescent probe with reaction-based as well as lock/key-based detection sites, which contains four recognition positions including Schiff base C N functionality, triazole–triazole linker and the spirocyclic ring of the Rhodamine unit. Naked eye detection was realized with the obvious color change. In addition, low detection limit was calculated from titration results with the value were 7.74 × 10 −8  M for RhB-BODIPY-OH/Hg 2+ as well as 3.91 × 10 −7  M for RhB-BODIPY-OH/Fe 3+ , separately. The probe is highly sensitive, the detection time is less than 2s. On top of that, living cell imaging experiment was carried out, which demonstrated that RhB-BODIPY-OH is a good bioimaging agent in living cells. Eventually, amino-group-functionalized silica fluorescent nanoparticles (FNPs) encapsulating the RhB-BODIPY-OH dyes were prepared and characterized by transmission electron microscopy.

研究领域: 化学 · 生物医学工程 · 分析化学
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