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BODIPY
Journal of Innovative Optical Health Sciences · 2022 · IF 2.396

A novel BODIPY-based nano-photosensitizer with aggregation-induced emission for cancer photodynamic therapy

Yuting Zhang,Guojing Li,Jiong Li,Ming Wu,Xiaolong Liu,Jingfeng Liu

The discovery of aggregation-induced emission (AIE) effect provides opportunities for the rapid development of fluorescence imaging-guided photodynamic therapy (PDT). In this work, a boron dipyrromethene (BODIPY)-based photosensitizer (ET-BDP-O) with AIE characteristics was developed, in which the two linear arms of BODIPY group were linked with triphenylamine to form an electron Donor–Acceptor–Donor (D–A–D) architecture while side chain was equipped with triethylene glycol group. ET-BDP-O was able to directly self-assemble into nanoparticles (NPs) without supplement of any other matrices or stabilizers due to its amphiphilic property. The as-prepared ET-BDP-O NPs had an excellent colloid stability with the size of 125 nm. Benefiting from the AIE property, ET-BDP-O NPs could generate strong fluorescence and reactive oxygen species under light-emitting diode light irradiation (60 mW/cm 2 ) 2) . After internalized in cancer cells, ET-BDP-O NPs were able to emit bright red fluorescence signal for bioimaging. In addition, the cell viability assay demonstrated that the ET-BDP-O NPs exhibited excellent photo-cytotoxicity against cancer cells, while negligible cytotoxicity under dark environment. Thus, ET-BDP-O NPs might be regarded as a promising photosensitizer for fluorescence imaging-guided PDT in future.

✓ 已验证 DOI 高影响因子
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DYES AND PIGMENTS · 2026 · IF 3.9

Orderly self-assembly promoting the photodynamic properties of BODIPY-based hydrogen-bonded organic frameworks

Qian Liu,Hean Zhang,Lu Han,Chuang Yao,Jun Zhang,Qianling Cui,Lidong Li

A BODIPY-based H 4 BP-HOF is constructed from non-orthogonal dimers. • Differing from monomers and random aggregates, its ordered structure enhances the ROS generation efficiency. • This H 4 BP-HOF displays excellent photodynamic antibacterial activity, advancing novel photosensitizer design. Hydrogen-bonded organic frameworks (HOFs), which are assembled by organic building blocks mainly via hydrogen bonds in a controlled manner, provide an ideal platform for modulating the optical properties of conjugated fluorophores. Herein, a non-orthogonal boron dipyrromethene (BODIPY) dimer-based fluorophore carrying four carboxylic acid groups (H 4 BP) was synthesized and used to construct HOF nanosheets via H-bonding and π-π stacking effects. The orderly self-assembly structure in H 4 BP-HOF considerably improved the light-triggered reactive oxygen species (ROS) generation efficiency, which was much higher than that of H 4 BP monomers and randomly aggregated particles (H 4 BP-P). Under white light irradiation, H 4 BP-HOF efficiently generated singlet oxygen ( 1 O 2 ) and hydroxyl radical (•OH), and displayed a promising photodynamic antibacterial activity toward Escherichia coli . This work provides a novel BODIPY-based HOF material and a promising strategy to fabricate heavy-atom-free photosensitizers for ROS-related applications like photocatalysis and photodynamic therapy. Download: Download high-res image (235KB) Download: Download full-size image

✓ 已验证 产品关联 DOI 高影响因子
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ACS Applied Bio Materials · 2023 · IF 4.7

BODIPY-Based Multifunctional Nanoparticles for Dual Mode Imaging-Guided Tumor Photothermal and Photodynamic Therapy

Zhongyan Chen,Yuncong Chen,Yunjian Xu,Xiangchao Shi,Zhong Han,Yang Bai,Hongbao Fang,Weijiang He,Zijian Guo

Multifunctional nanoparticles integrating accurate multi-diagnosis and efficient therapy hold great prospects in tumor theranostics. However, it is still a challenging task to develop multifunctional nanoparticles for imaging-guided effective eradication of tumors. Herein, we developed a near-infrared (NIR) organic agent Aza/I-BDP by coupling 2,6-diiodo-dipyrromethene (2,6-diiodo-BODIPY) with aza-boron-dipyrromethene (Aza-BODIPY). Through encapsulating with an amphiphilic biocompatible copolymer DSPE-mPEG5000, well-distributed Aza/I-BDP nanoparticles (NPs) were developed, which exhibited high 1O2 generation, high photothermal conversion efficiency, and excellent photo-stability. Notably, coassembly of Aza/I-BDP and DSPE-mPEG5000 effectively inhibits H-aggregation of Aza/I-BDP in aqueous solution and enhances the brightness simultaneously up to 31-fold. More importantly, in vivo experiments demonstrated that Aza/I-BDP NPs might be used for NIR fluorescent and photoacoustic imaging-guided photodynamic and photothermal therapy.

研究领域: 纳米医学 · 癌症诊疗 · 光动力治疗 · 光热治疗 · 分子成像
✓ 已验证 DOI 高影响因子
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JOURNAL OF PORPHYRINS AND PHTHALOCYANINES · 2024 ·Vol. 28 ·期 03 ·166-172 · IF 0.9

Novel naphthalimide bridged zinc porphyrin/BODIPY nanomaterials with D-A structure for photodynamic therapy

Min Cui,Sijie Zhu,Mengmeng Xiong,Huijie Zuo,Xiang Li,Kai Wang,Jun Jiang

As a non-invasive cancer therapy method, photodynamic therapy (PDT) shows tremendous promise in clinical cancer treatment. Light-activated singlet oxygen production of photosensitizers (PSs) is the prerequisite for cancer PDT, and the use of organic photosensitizers is always limited by visible light-based activation, hydrophilicity, biocompatibility, selectivity and quantum yield of singlet oxygen. Currently, both zinc porphyrin- and BODIPY-based structures have been widely used in the development of PDT PSs. Here, we developed a novel naphthalimide bridged zinc porphyrin/BODIPY molecule ( Por-BDP-1 ) with two poly(ethylene glycol) (PEG) chains, in which D-A structure was constructed between the naphthalimide group and porphyrin group. After self-assembly into nanoparticles, Por-BDP-1 NPs (Diameter: 122.4 nm) could quench fluorescence in 600–700 nm, bind with calf thymus-DNA, and produce singlet oxygen during light-irradiation (laser: 680 nm, 1.0 W/cm 2 ) . In addition, Por-BDP-1 NPs effectively killed HeLa cells with a IC 5 0 value = 44.8 μg/mL and showed a lower dark toxicity under the same conditions. All our results demonstrated that our naphthalimide bridged zinc porphyrin/BODIPY nano-photosensitizer is a promising nanoagent for PDT in the clinic.

研究领域: 材料科学 · 纳米医学 · 光动力治疗 · 有机化学 · 生物医学工程
✓ 已验证 DOI 高影响因子
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ACS Applied Materials & Interfaces · 2020 · IF 8.758

Aza-BODIPY Probe-Decorated Mesoporous Black TiO2 Nanoplatform for the Highly Efficient Synergistic Phototherapy

Ning Liu,Ming Zhu,Niu Niu,Jia Ren,Na Yang,Cong Yu

As an important noninvasive tumor treatment method, phototherapy has drawn extensive research interest. However, the requirements of separate excitation wavelengths, high degree of electron–hole recombination, and low reactive oxygen species (ROS) production capability are still the major barriers. This work reports the construction of a novel nanoplatform: design and synthesis of an aza-BODIPY (AB) probe-decorated mesoporous black titanium dioxide (TiO2) (MT) nanoparticles (NPs) for enhanced photodynamic therapy and photothermal therapy under single-wavelength near-infrared (NIR) laser irradiation for the first time. AB probe-decorated MT NPs (abbreviated as MTAB) were synthesized through the Al reduction of mesoporous anatase TiO2 NPs and subsequent adsorption of the AB probe. The mesoporous structure of MT ensured AB loading capacity and avoided the complicated modification and synthesis processes. Heterogeneous MTAB, which possessed staggered energy levels, were assessed for their capability for effective separation of photogenerated electrons and holes for the first time. Upon NIR laser light irradiation, MTAB exhibited sufficient ROS generation, resulting in distinct tumor cell killing and tumor tissue elimination. This unique heterogeneous nanoplatform with staggered energy levels provides a new strategy to enhance ROS generation and improve the therapeutic efficacy.

CAS / MDL: 5471-63-6
研究领域: 肿瘤治疗 · 纳米医学 · 光化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Nano Research · 2021 ·Vol. 15 ·期 1 ·716-727 · IF 8.897

Aza-BODIPY-based phototheranostic nanoagent for tissue oxygen auto-adaptive photodynamic/photothermal complementary therapy

Zhao Meijiao,Zeng Qin,Li Xipeng,Xing Da,Zhang Tao

Tumor oxygen spatial heterogeneity is a critical challenge for the photodynamic inhibition of solid tumors. Development of an intelligent nanoagent to initiate optimal therapeutics according to the localized oxygen levels is an effective settlement. Herein, we report an activatable nanoagent (BDP-Oxide nanoparticles (NPs)) to enable the oxygen auto-adaptive photodynamic/photothermal complementary treatment. Upon the nanoagent accumulated in the tumor region, the low extracellular pH could trigger the disassociation of the nanoagent to release the phototheranostic agent, BDP-Oxide, which will subsequently afford the fluorescence imaging-guided photodynamic oxidation after it gets into the outer oxygen-rich tumors. Along with the penetration deepening in the solid tumor, furthermore, BDP-Oxide could be reduced into BDP by the cytochrome P450 (CYP450) enzymes activated in the low oxygen tension regions of inner hypoxic tumors, which will switch on the photothermal and photoacoustic effects. Overall, the BDP-Oxide NPs-enabled photodynamic/photothermal complementary therapy significantly suppressed the solid tumor growth (inhibition rate of 94.8%). This work proposes an intelligent platform to address the oxygen partial pressure for the optimization of cancer phototherapeutics.

✓ 已验证 产品关联 DOI 高影响因子
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ANALYST · 2014 ·Vol. 140 ·期 2 ·574-581 · IF 3.906

A rapid response “Turn-On” fluorescent probe for nitroreductase detection and its application in hypoxic tumor cell imaging

Jian Xu,Shaobo Sun,Qian Li,Ying Yue,Yingdong Li,Shijun Shao

A novel “Turn-On” fluorescent probe, quaternarized 4-pyridinyl-substituted BODIPY dye by incorporating a 5-nitrofuran moiety, was developed and applied for imaging the hypoxic status of tumor cells by the indirect detection of nitroreductase. The design was based on a nitroreductase-catalyzed reduction of the nitrofuran moiety in the presence of reduced nicotinamide adenine dinucleotide (NADH) as an electron donor and followed by the 1,6-rearrangement-elimination and the release of free 4-pyridinyl-substituted BODIPY dye 2. This probe displayed desired properties such as high specificity, “Turn-On” fluorescence response with suitable sensitivity, appreciable water solubility and rapid response time (within 5 min). Moreover, as a biocompatible molecule, the probe has been successfully applied for imaging the hypoxic status of tumor cells (e.g. A549 cells) and especially used for real-time determination of nitroreductase produced by Escherichia coli. Therefore, we hope to apply this novel method in the biomedical research fields for the imaging of disease-relevant hypoxia and detection of pathogenic microorganisms.

研究领域: 生物化学 · 医学影像 · 肿瘤学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF ORGANIC CHEMISTRY · 2024 · IF 3.3

Unsymmetrical Benzothieno-Fused BODIPYs as Efficient NIR Heavy-Atom-Free Photosensitizers

Xiaofan Fu,Yingxiu Man,Changjiang Yu,Yingzhu Sun,Erhong Hao,Qinghua Wu,Anzhi Hu,Guangyao Li,Chang-Cheng Wang,Jiazhu Li

Heavy-atom-free photosensitizers are potentially suitable for use in photodynamic therapy (PDT). In this contribution, a new family of unsymmetrical benzothieno-fused BODIPYs with reactive oxygen efficiency up to 50% in air-saturated toluene was reported. Their efficient intersystem crossing (ISC) resulted in the generation of both 1O2 and O2–• under irradiation. More importantly, the PDT efficacy of a respective 4-methoxystyryl-modified benzothieno-fused BODIPY in living cells exhibited an extremely high phototoxicity with an ultralow IC50 value of 2.78 nM. The results revealed that the incorporation of an electron-donating group at the α-position of the unsymmetrical benzothieno-fused BODIPY platform might be an effective approach for developing long-wavelength absorbing heavy-atom-free photosensitizers for precision cancer therapy.

CAS / MDL: rp173719
研究领域: 药物化学 · 肿瘤学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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NEW JOURNAL OF CHEMISTRY · 2021 ·Vol. 45 ·期 48 ·22888-22901 · IF 3.591

Fluorescent multi-component polymer sensors for the sensitive and selective detection of Hg2+/Hg+ ions via dual mode fluorescence and colorimetry

Kaiqi Liu,Luminita Marin,Li Xiao,Xinjian Cheng

Multi-component polymers (MCPs) incorporate multiple components into the main chain or pendant group and have special functions. In this work, the small-molecule fluorescent boron-dipyrromethene (BODIPY), with ester groups and/or alkoxyl long chains, was synthesized first. Then, this small-molecule BODIPY and the components containing CC bonds (HD and PD) were reacted via the Heck coupling reaction to obtain macromolecular probes that perform different functions. With the help of ester groups and alkoxyl “tail”, polymers MCP1 and MCP2 were soluble in a variety of water-miscible organic solvents. Moreover, MCP3 and MCP4 were completely soluble in water. These macromolecular probes showed sensitive and selective recognition toward Hg2+/Hg+ because of the introduced components (HD and PD) containing CC bonds. After binding to Hg2+/Hg+, MCP1 and MCP2 demonstrated fluorescence quenching and color changes, which allowed the dual-channel specific detection of Hg2+/Hg+. Compared with the probes containing HD, the probes containing PD showed higher sensitivity, and the good recognition ability caused the detection limit to be as low as 0.32 μM, which may be due to the “molecular wire” mechanism. The small-molecule components with different functional groups were polymerized into fluorescent polymer materials. This methodology endows the polymer probe with good solubility and high sensitivity, and the as-prepared polymers could sense metal ions in aqueous environments.

研究领域: 分析化学 · 材料科学
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ANALYST · 2021 ·Vol. 146 ·期 9 ·2974-2982 · IF 4.616

A turn-on homodimer fluorescent probe based on homo-FRET for the sensing of biothiols in lysosome: a trial of a new turn-on strategy

Ying-Jie Tang,Wen-Le Fang,Kui Ren,Xiao-Feng Guo,Hong Wang

Fluorescence resonance energy transfer (FRET) is often applied to construct fluorescent probes for acquiring high selectivity and sensitivity. According to the FRET theory, a homodimer composed of two identical fluorophores with a small Stokes shift has only weak fluorescence due to homo-FRET between fluorophores, and the fluorescence could be recovered after the destruction of the homodimer. In this study, we designed and synthesized a homodimer fluorescent probe, namely 1,3,5,7-tetramethyl-8-(4′-phenylthiophenol)-boron difluoride-dipyrrole methane dimer (D-TMSPB), based on this turn-on strategy. In D-TMSPB, the disulfide moiety was selected as the response moiety of biothiols, and BODIPY fluorophore was chosen as both donor and acceptor in FRET due to the ultra-small Stokes shifts and obvious overlap of its excitation/emission peak. D-TMSPB exhibited only weak fluorescence. After selective reaction with biothiols, FRET was destroyed and the derivative exhibited strong fluorescence at 514 nm with the limit of detection of about 0.15 μM for GSH. Notably, the derivative of biothiols shows remarkable fluorescence only in acidic conditions, which accords with the internal environment of lysosome. Thus, D-TMSPB was applied to image the biothiols of lysosome in living cells. The turn-on fluorescence of D-TMSPB indicated that homo-FRET is a practical strategy to design turn-on fluorescent probes, particularly for the sensing mechanism based on leaving groups.

研究领域: 生物化学 · 细胞生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Cells · 2023 ·Vol. 12 ·期 19 ·2351 · IF 6

Red-Light-Activatable AND-Gated Antitumor Immunosuppressant

Ziqi Zhou,Yan Zhang,Simin Xia,Xi Chen

Immunosuppressants are emerging as promising candidates for cancer therapy with lower cytotoxicity compared to traditional chemotherapy drugs; yet, the intrinsic side effects such as immunosuppression remain a critical concern. Herein, we introduce a photoactivatable antitumor immunosuppressant called dmBODIPY-FTY720 (BF) that shows no cytotoxicity but can be temporally and locally activated by deep-red light illumination to induce tumor cell apoptosis. To further reduce potential side effects, we integrate BF with another classic photosensitizer called methylene blue (MB) that is activated under the same wavelength of deep-red light (>650 nm) and successfully establish a red-light-activatable AND Boolean logic gate through a mechanism that we found to be synergetic apoptotic induction. At further decreased dosages, deep-red light illumination does not induce cell death in the presence of either BF or MB, but significant cancer cell death is triggered in the presence of both drugs. Therefore, the dosage of BF is further reduced, which will be highly beneficial to minimize any potential side effects of BF. This AND-gated strategy has been successfully applied in vivo for effective suppression of hepatocarcinoma tumors in living mice.Keywords:antitumor immunosuppressant;FTY720;logic gate;BODIPY photocage;red light;photodynamic therapy

CAS / MDL: 162359-56-0
研究领域: 癌症治疗 · 药理学 · 光化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Frontiers in Chemistry · 2021 · IF 5.221

A Labeling Strategy for Living Specimens in Long-Term/Super-Resolution Fluorescence Imaging

Han Yubing,Zhang Zhimin,Liu Wenjie,Yao Yuanfa,Xu Yingke,Liu Xu,Kuang Cuifang,Hao Xiang

Despite the urgent need to image living specimens for cutting-edge biological research, most existing fluorescent labeling methods suffer from either poor optical properties or complicated operations required to realize cell-permeability and specificity. In this study, we introduce a method to overcome these limits—taking advantage of the intrinsic affinity of bright and photostable fluorophores, no matter if they are supposed to be live-cell incompatible or not. Incubated with living cells and tissues in particular conditions (concentration and temperature), some Atto and BODIPY dyes show live-cell labeling capability for specific organelles without physical cell-penetration or chemical modifications. Notably, by using Atto 647N as a live-cell mitochondrial marker, we obtain 2.5-time enhancement of brightness and photostability compared with the most commonly used SiR dye in long-term imaging. Our strategy has expanded the scientist's toolbox for understanding the dynamics and interactions of subcellular structures in living specimens.

研究领域: 分子生物学 · 细胞生物学 · 生物物理学 · 成像科学
✓ 已验证 DOI PubMed 高影响因子
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