SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2019
·
IF 2.931
Chunmei Huang,Ying Qian
A near-infrared turn-on two-photon fluorescent probe ST-BODIPY for glutathione-specific detection was designed and synthesized by attaching triphenylamine to BODIPY skeleton through the Knoevenagel condensation to prolong the maximum emission wavelength to the NIR region. And 2,4-dinitrobenzenesulfonyl group (DNBS), as the fluorescence quencher and thiol recognition moiety, was modified in 8 position of BODIPY. In the presence of GSH, the probe afforded an “off-on” signal response with a significant NIR fluorescence enhancement centered at 719 nm accompanying by quantum yield increased to 0.44, which was ascribed to the glutathione-induced S N Ar (aromatic substitution) reaction. Surprisingly, we found that the probe could discriminate GSH from other biothiols including Cys and Hcy upon the addition of intracellular concentrations of them. Time-dependence also demonstrated that the probe could distinguish GSH from Cys and Hcy under physiological environment. The limit of detection (LOD) for GSH was calculated as 25.46 nM from the titration experiments, which is lower than most previously reported GSH-selective probes. Under the Ti:sapphire pulsed laser's 800 nm irradiation, ST-BODIPY toward GSH generated an “off-on” signal response with a significant enhancement of fluorescence emission at 719 nm after treatment with GSH. Besides, the 2PA cross section value (σ 2 ) was calculated to be 410 GM, suggesting that it could not only function well as an excellent two-photon fluorescent probe for the detection of intracellular GSH, but also be applied for two-photon imaging with high sensitivity in living cells. Moreover, ST-BODIPY probe has been successfully employed for monitoring exogenous and endogenous GSH in MCF-7 cells with satisfying results, perhaps it was feasible for detecting abnormal contents of GSH in a biological system and accomplishing the goal of maintaining normal human activities.
研究领域:
生物化学
·
医学影像学
·
分析化学
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF COLLOID AND INTERFACE SCIENCE
·
2021
·
IF 8.128
Huiping Dang,Youliang Tian,Quan Cheng,Changchang Teng,Kai Xie,Lifeng Yan
It is essential to develop novel multifunctional and easily synthesized stable NIR-II fluorescent probes to guide photothermal therapy for tumors. Here, we propose a new strategy to construct boron dipyrromethene (BODIPY) J-aggregates by intermolecular hydrogen bonding (H-bond) and π-π stacking interactions to achieve fluorescence emission in the second near-infrared window (NIR-II, 1000–1700 nm). A novel meso -benzamide galactose hexanoate-BODIPY (Gal-OH-BDP) amphiphilic small molecular dye was synthesized and it formed nanoparticles spontaneously in aqueous solution with a maximum emission wavelength near 1060 nm, which works as a smart nanomedicine for targeting NIR-II imaging-guided photothermal therapy (PTT) of hepatocellular carcinoma. Galactose not only provided hydrogen bonds to regulate the aggregation pattern of the molecules but also effectively targeted hepatocellular carcinoma cells and promoted the formation of well-dispersed nanoparticles of dye molecules due to their hydrophilicity . Moreover, due to high photothermal conversion efficiency (PCE = 55%), Gal-OH-BDP NPs achieve galactose-targeted NIR-II imaging and PTT, which is important for the precise diagnosis and treatment of tumors ( Scheme 1 ). In the present research work, H-bond was introduced for the first time into BODIPY for building J-aggregates to achieve the NIR-II fluorescence.
研究领域:
生物医学工程
·
肿瘤学
·
纳米医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
RSC Advances
·
2017
·Vol. 7
·期 54
·33975-33985
·
IF 3.108
Junxu Liao,Hongbin Zhao,Yongjun Xu,Weinan Zhou,Fei Peng,Yong Wang,Yutang Fang
Four new donor–π–acceptor (D–π–A) structured organic sensitizers (CB1-4), with N-octyl or N-methoxyphenyl carbazole connected to a 2-cyanoacrylate BODIPY module through their 2 or 3-positions, were designed and synthesized for application in dye-sensitized solar cells (DSSCs). The photophysical and electrochemical properties were systematically studied and their performances as sensitizers in DSSCs were comparatively investigated. The structure–property relationship suggests that the electron-donating ability and substitution positions of the donor have a significant effect on these dyes' electronic and photovoltaic properties. Electron-rich N-methoxyphenyl carbazole as a donor and substitution at the 2-position shows a positive influence on the efficiency of DSSCs. Consequently, CB4, with the combination of these advantages, presents the broadest (300–650 nm) and strongest absorption profile with a high extinction coefficient (1.71 × 105 M−1 cm−1) and the best photovoltaic performance with a short circuit photocurrent density of 10.20 mA cm−2, an open circuit voltage of 600 mV, and a fill factor of 0.7, corresponding to a fairly good overall conversion efficiency of 4.28% under AM 1.5 irradiation (100 mW cm−2).
✓ 已验证
DOI
高影响因子
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2016
·
IF 2.653
Jian Pan,Junchao Xu,Youlai Zhang,Liang Wang,Caiqin Qin,Lintao Zeng,Yue Zhang
A novel fluorescent probe for H 2 S was developed based on a far-red emitting indole-BODIPY, which was decorated with morpholine and 2,4-dinitrobenzenesulfonyl (DNBS) group. This probe showed rapid response (t 1/2 = 3 min), high selectivity and sensitivity for H 2 S with significant colorimetric and fluorescence OFF–ON signals, which was triggered by cleavage of 2,4-dinitrobenzenesulfonyl group. This probe could quantitatively detect the concentrations of H 2 S ranging from 0 to 60 μM, and the detection of limit was found to be as low as 26 nM. Cell imaging results indicated that the probe could detect and visualize H 2 S in the living cells.
研究领域:
生物化学
·
医学检测
·
细胞生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
DYES AND PIGMENTS
·
2025
·
IF 4.2
Xiaoxue Mo,Yuexin Lv,Jiayu Lu,Yajing Hou,Hua Qian,Cheng Wang,Huaizhen He
MAS-related G protein-coupled receptor X2 (MRGPRX2) is a key target receptor and an important drug target for triggering pseudo-allergic reactions. Studying its ligands will help to understand the mechanism of pseudo-allergic reactions and discover anti-allergic drugs. Small-molecule fluorescent probes are widely used to study the localization of G protein-coupled receptors (GPCRs) on the cell membrane, the transport and internalization of GPCRs, and the interaction between receptors and ligands due to their high selectivity, sensitivity and safety. MRGPRX2 is one of GPCRs with an active hydrophobic ligand binding domain, so designing small-molecule fluorescent probes with environmental sensitivity is very important for the study of MRGPRX2 ligands and the visualization of this receptor. In this study, we selected the agonist of MRGPRX2 ( R )-ZINC-3573 as the recognition group and used different fluorophore skeleton structures as the luminescent group to synthesize a series of small-molecule fluorescent probes targeting MRGPRX2. Among them, PoX2-B with BODIPY FL as the fluorescent group had good photostability and environmentally sensitive properties to the hydrophobic ligand binding domain of MRGPRX2, and could be used for living cell imaging. Furthermore, PoX2-B could specifically recognize MRGPRX2, and it was expected to be used to screen effective ligands of MRGPRX2 in the future, so as to play a role in the development of anti-allergy drugs and the pathogenesis of allergic diseases.
研究领域:
药理学
·
生物化学
·
分子生物学
✓ 已验证
DOI
高影响因子
Journal of Innovative Optical Health Sciences
·
2025
·
IF 2.2
Haitao Liao,Qingxuan Meng,Yuhao Li,Senqiang Zhu,Rui Liu,Hongjun Zhu
Optical imaging in vivo holds significant implications for disease diagnosis, and nanoprobes with near-infrared (NIR) emission leverage the deep tissue penetration and high spatiotemporal resolution provided by NIR light, demonstrating considerable application potential. This study presents the design and synthesis of three nitrogen-doped boron–dipyrrin (Aza-BODIPY) molecules: Aza–BDP–OCH 3 , Aza–BDP–OH, and Aza–BDP-I. Leveraging the strong electron-accepting properties of the Aza-BODIPY core, we developed a donor–acceptor–donor (D-A-D) structure for Aza–BDP–OCH 3 through modifications with triphenylamine and methoxy groups, resulting in NIR fluorescence. Aza–BDP–OH was obtained via demethylation using boron tribromide, whereas Aza–BDP-I was synthesized by introducing iodine into Aza–BDP–OCH 3 . These three molecules self-assemble with the amphiphilic polymer PMHC 1 8 -mPEG to form nanoparticles (NPs), yielding optical nanoprobes. The resulting NPs exhibit NIR emission, good water solubility, and biocompatibility. At a concentration of 100 μ g ⋅ mL − 1 , these NPs demonstrate low biological toxicity, highlighting their potential for biological applications. Following tail vein injection, Aza–BDP-I NPs accumulate in tumors and effectively illuminate them via the enhanced permeability and retention (EPR) effect. Furthermore, these organic NPs were metabolized by the liver. Therefore, Aza-BODIPY-based NIR fluorescent NPs offer a promising platform for the development of in vivo optical nanoprobes.
研究领域:
生物医学成像
·
纳米技术
·
有机化学
·
分子探针
·
癌症诊断
✓ 已验证
产品关联
DOI
高影响因子
Polymer Chemistry
·
2024
·Vol. 15
·期 47
·4875-4887
·
IF 4.1
Yangyang Xu,Wenlong Tang,Hui Deng,Jianjun Zhang,Zhongquan Zhu,Changjiang Yu,Haiguang Zhu,Ke Sun,Jiazhu Li,Jacques Lalevée
Polymerization reactions induced by light are gaining increasing importance in the field of polymer synthesis; however, effective photopolymerization under visible light emitting diodes (LEDs), as opposed to UV light, remains limited and warrants further research and development. In this work, a family of bisbenzothieno[b]-fused boron dipyrromethene (BODIPY) derivatives, which have not been previously tested for photopolymerization, were designed. They contain seven fused aromatic rings with broad absorption properties and were introduced with amine and iodonium salt to form three-component photoinitiating systems (PISs) for the first time. Remarkably, under visible light irradiation, e.g. LED@405 nm and LED@660 nm, these PISs were able to initiate the free radical polymerization of acrylate monomers and cationic polymerization of epoxy monomers at room temperature, displaying different photopolymerization kinetics. This excellent initiation ability at both ends of the visible spectrum (i.e. the highest and lowest photon energy) indicated a remarkable panchromatic initiation ability. The exceptional photochemical reactivity of these BODIPY dyes and the underlying photoinitiation mechanisms of the PISs were thoroughly investigated through steady-state photolysis, fluorescence quenching experiments, and theoretical calculations. Finally, three-dimensional patterns with excellent spatial resolution were successfully printed using the BODIPY dye with the highest photoinitiation efficiency via direct laser writing, highlighting its significant potential for 3D printing applications.
研究领域:
材料科学
·
化学
✓ 已验证
产品关联
DOI
高影响因子
RSC Advances
·
2024
·Vol. 14
·期 39
·28957-28964
·
IF 3.9
Lu Yang,Yanglin Jiang,Ailin Sun,Mingqing Chen,Qiwei Li,Peng Wang,Jianping Zhang
Two styryl BODIPY derivatives, BOH and BOE, with different hydrophilic properties, were investigated for their reaction mechanisms in lipid bilayers against aqueous ClO−, by both experimental and theoretical methods. Density functional theory (DFT) calculations confirmed their identical conformations in solution. Fluorescence spectra and high-resolution mass spectra corroborated the central vinyl group as a common antioxidation moiety against ClO− oxidation. In giant unilamellar vesicles (GUVs), distinct reaction kinetics with ClO− suggested that BOE provided superior protective effects compared to BOH on lipids. Molecular dynamics simulations indicated that the lipophilic octyloxy group in BOE led to its deeper localization within the lipid phase, bringing it closer to the corresponding lipid target group. This study establishes the two styryl BODIPYs as promising fluorescent probes for detecting aqueous ClO− in lipid-water polyphasic systems.
研究领域:
生物化学
·
分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF COLLOID AND INTERFACE SCIENCE
·
2025
·
IF 9.7
Junyang Liu,Yanan Wang,Mengping Wang,Xinyi Dong,Xinxin Liu,Mengqi Li,Guangjiu Zhao
The photoelectric properties of perovskite quantum dots make them have great potential in photocatalytic antibacterial applications. However, commonly used long-chain ligands are not conducive to the transfer of photogenerated charge carriers in perovskite quantum dots. In this work, we used short chain ligands with higher conjugated systems (BODIPY-OH) for surface regulated synthesis of MAPbBr 3 quantum dots (BDP/QDs). We found that there is a photogenerated carrier transfer process between BODIPY-OH and MAPbBr 3 quantum dots. BODIPY-OH can effectively separate the photogenerated carriers in MAPbBr 3 quantum dots. Due to this property, BDP/QDs have great application prospects in the field of photocatalysis. Using the specific chemical trapping techniques, we show that the binding of BODIPY-OH successfully enhances the singlet oxygen generation ability of MAPbBr 3 quantum dots through the process of photogenerated carrier transfer. Based on the excellent waterproof performance of SiO 2 , we further improved the water stability of BDP/QDs using SiO 2 (SiO 2 @BDP/QDs). The photogenerated singlet oxygen generated by SiO 2 @BDP/QDs has an effective antibacterial effect on Escherichia coli. This work provides new ideas and understanding for designing halide perovskite photocatalytic antibacterial materials for efficient antibacterial effects.
研究领域:
材料科学
·
光催化
·
生物医学工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Materials Today Chemistry
·
2024
·
IF 6.7
Huishuang Zhang,Qilong Sha,Guojing Li,Liwei Xiong,Ming Luo,Fengshou Wu
Cancer is one of the major diseases that threaten human being's health and life. Recently, phototherapy has gained great attention due to the advantages of high selectivity and low toxicity. Nonetheless, the development a single photosensitizer capable of simultaneously achieving photothermal and photodynamic effects remains a great challenge. Aza-boron-dipyrromethene (aza-BODIPY) dyes have been widely studied in biomedical area for their significant absorption in the near infrared region and high fluorescence quantum yield . In this contribution, three aza-BODIPY molecules (TAS-BP, TES-BP and TESO-BP) that conjugated with triphenylamine (TPA) or tetraphenylethylene (TPE) were designed and synthesized. The presence of donor-acceptor-donor pairs within compounds enables the intermolecular electron transfer , leading to the augmentation of near-infrared (NIR) absorbance and the generation of non-radiative heat. The nanoparticles were prepared via the assembly of the related organic compounds with amphiphilic polymer (DSPE-PEG 2000 ), which were named as TAS-BP NPs, TES-BP NPs and TESO-BP NPs, respectively. Importantly, three nanoparticles can generate heat and reactive oxygen species (ROS) simultaneously induced by a single laser (808 nm). The photothermal conversion efficiency of TAS-BP NPs, TES-BP NPs and TESO-BP NPs were determined to be 64.5%, 65.7%, and 53.6%, respectively. Furthermore, the cellular experiments demonstrated the good biocompatibility and outstanding photocytotoxicity of three nanoparticles , and the TES-BP NPs exhibited the highest photodynamic/photothermal synergistic effect. Thus, the as-prepared organic nanomaterials were demonstrated as potential candidates for cancer treatment through phototherapy.
研究领域:
生物医学
·
肿瘤学
·
材料科学
✓ 已验证
DOI
高影响因子
TETRAHEDRON
·
2014
·
IF 2.817
Junchao Xu,Leiming Zhu,Qiusheng Wang,Lintao Zeng,Xichao Hu,Boqiao Fu,Zhe Sun
A series of meso -C 6 F 5 BODIYs have been successfully synthesized and characterized. Some of them displayed excellent spectroscopic properties, such as relatively large Stokes shift , high fluorescence quantum yield , far-red or near infrared region (NIR) emission, and good photostability. In particular, the dye functionalized with oligo(ethylene glycol) ether-phenyl groups at the 3,5-position of BODIPY core became water-soluble and its emission located in the NIR region with large Stokes shift. Time-dependent density functional theory calculations were conducted to understand the structure–optical properties relationship. Furthermore, cell staining tests demonstrated that the meso -C 6 F 5 BODPY derivative with oligo(ethylene glycol) ether-phenyl group was membrane permeable and selectively stained cytosol in living cells.
研究领域:
化学
·
生物医学工程
·
细胞生物学
✓ 已验证
产品关联
DOI
高影响因子
ANALYTICA CHIMICA ACTA
·
2022
·
IF 6.911
Jin-Ye Lu,Qiu-Yun Chen,Su-Ci Meng,Chang-Jian Feng
Phthalates can penetrate the environment and enrich various aquatic organisms through the food chain, which is involved in promoting the growth of breast cancer. It is of current interest to develop new sensors for phthalates. We herein reported a hydrogen-bond competing fluorescent sensor, BANP, for the detection of dibutyl phthalate (DBP). The BANP compound was synthesized by assembling andrographolide (Andro), nitro- and cyano-substituted BODIPY dye (BCN), and polyethylene glycol derivatives (DSPE-mPEG5000). BANP was found to be a turn-on fluorescent probe for DBP in water with a detection limit of 0.13 μg/g; the DBP-water system acts as a hydrogen bond switch to turn on the fluorescence. And BANP fluorescently detected DBP in contaminated fish meat. Moreover, BANP sensed the DBP-induced growth of human breast cancer MCF-7 cells, and the release of Andro in the DBP-cultivated cancer cells inhibited the proliferation of the MCF-7 cells. Taken together, BANP is a DBP-responsive probe for sensitive DBP detection in water, cells, and fish meats. The BANP sensor may be used in both in vitro fluorescence and cellular imaging analyses. Our results show that guest-induced reassembly brings forth significant fluorescence change, which is a promising way of designing new fluorescent probes for the analysis of phthalates in the environment and food.
研究领域:
分析化学
·
环境科学
·
生物医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）