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JOURNAL OF MEDICINAL CHEMISTRY · 2025 · IF 6.8

A Water-Soluble Aggregation-Induced Emission Photosensitizer with Intrinsic Antibacterial Activity as an Antiplanktonic and Antibiofilm Therapeutic Agent

Cheung-Hin Hung,Ka Hin Chan,Wai-Po Kong,Ruo-Lan Du,Kang Ding,Zhiguang Liang,Yong Wang,Kwok-Yin Wong

Photosensitizers (PSs) with aggregation-induced emission (AIE) properties have gained popularity for treating bacterial infections. However, most AIE PSs have a poor water solubility and low selectivity, limiting their applications in biological systems. Herein, we report a water-soluble and bacteria-targeting AIE PS that exhibits minimum cytotoxicity toward human cells with and without light irradiation. Acting as a narrow-spectrum antibacterial agent without light irradiation, TPA-1 eradicates planktonic Staphylococcus aureus and inhibits biofilm formation by targeting the S. aureus membrane, inhibiting the supercoiling activity of S. aureus DNA gyrase, and causing the downregulation of multiple essential proteins. Upon light irradiation, TPA-1 generates reactive oxygen species (ROS) that cause membrane damage, resulting in excellent antiplanktonic and antibiofilm activities against S. aureus and Pseudomonas aeruginosa, significantly reducing the number of viable bacteria in biofilms and promoting wound healing in vivo.

CAS / MDL: 10294-33-4 72287-26-4
研究领域: 微生物学 · 药理学 · 光动力治疗
✓ 已验证 产品关联 DOI PubMed 高影响因子
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DYES AND PIGMENTS · 2017 · IF 3.473

Synthesis of water-soluble and thermoresponsive phthalocyanine ended block copolymers as potential photosensitizer

YanHui Li,Dehai Zhao,Yanwei Li,Yongzhe Liu,Qian Duan,Toyoji Kakuchi

A novel zinc(II) tetraaminophthalocyanine ended block copolymer methoxypolyethylene glycol- b -poly(N-isopropylacrylamide) (MPEG- b -PNIPAAM-ZnTAPc) had been synthesized through an easy way. First, the diblock copolymers MPEG- b -PNIPAAM were synthesized by atom transfer radical polymerization (ATRP) and functionalized with one molecule of maleic anhydride (MA) by ATRP, and then reacted with ZnTAPc to form a water-soluble and thermoresponsive photosensitizer . The lower critical solution temperatures for the copolymers can be easily controlled by changing the ratio of MPEG and PNIPAAM. In aqueous solution, the thermosensitive copolymers will self-assemble into micelles and characterized by dynamic light scattering and transmission electron microscopy , and the sizes of micelles will increase with temperature increasing. In the micelles, ZnTAPc will aggregate to induce fluorescence quenching. As a photosensitizer, MPEG- b -PNIPAAM-MA-ZnTAPc can generated singlet oxygen species with good quantum yields (Φ Δ  = 0.23), which were believed to be the major reactive oxygen species. And the copolymer had low dark cytotoxicity and high phototoxicity based on MTT assay, so the MPEG- b -PNIPAAM-ZnTAPc will used in the field of photodynamic therapy and photocatalytic oxidation .

研究领域: 材料科学 · 生物医学工程 · 药学
✓ 已验证 DOI 高影响因子
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ANALYTICAL CHEMISTRY · 2020 · IF 6.785

Electrochemically Lighting Up Luminophores at Similar Low Triggering Potentials with Mechanistic Insights

Li Fu,Bin Zhang,Kena Fu,Xuwen Gao,Guizheng Zou

Electrochemiluminescence (ECL) with high electrode compatibility and less electrochemical interference has conventionally been envisioned by lowering the oxidative potential of luminophores and/or screening luminophores with a low oxidative potential. Herein, an alternative was developed by employing the environmental-friendly carbohydrazide as a coreactant, which enabled serial luminophores with oxidative-reduction ECL at one similar low triggering potential around 0.55 V versus Ag/AgCl, including Ru(bpy)32+ as well as CdTe, CdSe, CuInS2/ZnS, and Au nanocrystals. Because the eight-electron releasing process of carbohydrazide was electrochemically triggered at ∼0.25 V versus Ag/AgCl, the radicals generated via electrochemical oxidation of carbohydrazide could reduce the luminophores at a much lower potential than those of traditional coreactants. All the luminophore/carbohydrazide systems exhibited one ECL process around 0.55 V, which was about 0.65 V lower than that of a traditional Ru(bpy)32+/tri-n-propylamine system (typically around +1.2 V), and even lower than the oxidative potential of some luminophores. The ECL of the luminophore/carbohydrazide system was spectrally close to that of the corresponding luminophore/tri-n-propylamine system; the maximum emission wavelength of the low triggering potential ECL could shift from 540 to 783 nm via the selection of luminophores in this case. The coreactant screening strategy would be a favorable addition to the expected luminophore screening strategy for achieving enhanced ECL performance. This work created an avenue toward a deeper understanding of the ECL mechanism.

研究领域: 分析化学 · 电化学 · 材料科学
✓ 已验证 DOI 高影响因子
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DYES AND PIGMENTS · 2024 · IF 4.1

Molecular Engineering of membrane structure targeted photosensitizers for antitumor photodynamic therapy

Xiaojuan Wang,Xin Liu,Wei Lu,Yuheng Ma,Xue Wang,Lufei Xiao,Zhangjun Hu,Zhengjie Liu,Yingzhong Zhu,Lin Kong

Photodynamic therapy (PDT) has been used to cure special diseases or the diseases that localized at special sites in comparison with conventional therapy, due to its high spatiotemporal selectivity, non-invasion, low drug resistance. However, vast majority of photosensitizers (PSs) still suffer from several limitations including poor aqueous solubility and poor photostability. Here, we used two strategies, promoting the intramolecular charge transfer and terminal modification, to overcome these limitations and enhance therapeutic effects. Three membrane-structure targeted molecules, 3CN-Np, 3CN–OH, and 3CN-QA, were designed and synthesized, which exhibited high extinction coefficient, excellent photostability and reactive oxygen species (ROS) productive capacity. In cell imaging, the designing molecules would stain endoplasmic reticulum for 3CN-Np and 3CN–OH, and cell membrane for 3CN-QA, respectively. Afterwards, we used white light (25 mW/cm 2 ) to irradiate the probe cultured cells for 20 min, the ratio of the dead and live cells was 3.0 for 3CN-Np, 3.5 for 3CN–OH, and 3.7 for 3CN-QA. Based on the high cell apoptosis in vitro under a white-light, 3CN–OH was selected to inhibited tumor growth in vivo, and the tumor volume was reduced to 45 % with non-toxicity to vitals. The study provided new sights in developing PSs with high water-solubility, photostability, and ROS generating ability in white-light mediating PDT system.

研究领域: 分子工程学 · 肿瘤学 · 药理学
✓ 已验证 DOI 高影响因子
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JOURNAL OF CATALYSIS · 2018 · IF 6.759

Functionalizing carbon nitride with heavy atom-free spin converters for enhanced 1O2 generation

Wenting Wu,Congcong Han,Qinhua Zhang,Qinggang Zhang,Zhongtao Li,David J. Gosztola,Gary P. Wiederrecht,Mingbo Wu

Carbon nitride as a metal-free conjugated polymer exhibits an intriguing prospect for the design of advanced photosensitizers for singlet oxygen ( 1 O 2 ) generation. However, the intersystem crossing (ISC) process is quite insufficient in carbon nitride, limiting the 1 O 2 generation. Here, we report a facile and general strategy to confined benzophenone as a heavy atom-free spin converter dopant in carbon nitride via the facile copolymerization . With proper energy level matching between the heavy atom-free spin converter and various ligands based on carbon nitride precursors, the proper combination can decrease the singlet-triplet energy gap (ΔE ST ) and hence generate 1 O 2 effectively. Due to its significant and selectivity for 1 O 2 generation, the as-prepared carbon nitride-based photosensitizer shows a high selective photooxidation activity for 1,5-dihydroxy-naphthalene (1,5-DHN). The product yield reached 71.8% after irradiation for 60 min, which was higher than that of cyclometalated Pt II complexes (53.6%) in homogeneous photooxidation. This study can broaden the application of carbon nitride in the field of selective heterogeneous photooxidation due to simple operation, low cost, and high efficiency, making it a strong candidate for future industrialization.

研究领域: 材料科学 · 光化学 · 环境科学
✓ 已验证 产品关联 DOI 高影响因子
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DYES AND PIGMENTS · 2023 · IF 4.5

Design the synthesis of AIEgen photosensitizers for regulating the level of PTX in drug-resistant tumor cells

Huifang Yao,Xiaobo Xiong,Feng Wu,Xiangyang Hu

The general mechanism of chemotherapeutic resistance is related to changes in the uptake and efflux rate of chemotherapeutic drugs or intracellular transport. In the progress of photodynamic and PTX combination therapy, the excessive use of photosensitizers (PSs) may cause side effects. Since PSs are exposed to light, they can still cause ongoing damage to normal cells. To effectively reduce this side effect, we propose a strategy to regulate the concentration of PTX in resistant cells using low concentrations of AIEgen PSs. In this work, the molecular structure of four AIEgen PSs ( TPEPy , TPECPy , TPAPy , and TPESPy ) were designed and synthesized featuring different “D−π−A” type structures. They displayed excellent optical properties , good biocompatibility , good PDT effect, mitochondrial targeting and cell imaging . Among these AIEgen PSs, TPESPy exhibited the strongest PDT effect in tumor cells and PTX resistant tumor cells. The reversal coefficient of PTX resistant tumor cells can be achieved as 2214. In addition, to demonstrate the transport mechanism of PTX within tumor cells, we further study the effect of uptake and expel PTX in the PTX resistant SKOV-3 cells. The results show the rate of uptake and expel PTX for PTX resistant SKOV-3 cells can be effectively changed by controlling the concentration of AIEgen PSs and light irradiation time, providing precise treatment options for drug-resistant tumor cells.

CAS / MDL: 307554-62-7
研究领域: 生物化学 · 肿瘤学 · 药理学
✓ 已验证 产品关联 DOI 高影响因子
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Biomaterials Science · 2016 ·Vol. 5 ·期 2 ·274-284 · IF 3.614

Intracellular GSH-activated galactoside photosensitizers for targeted photodynamic therapy and chemotherapy

Chaochao Wang,Lichao Liu,Hongliang Cao,Weian Zhang

Ligand-targeted cancer therapeutics has been developed to minimize non-specific cytotoxicity via ligand–drug conjugates during the past few decades. We present here the design and synthesis of a GSH-activated amphiphilic photosensitizer conjugated with galactose (TPP-S-S-Gal) for targeted photodynamic therapy. Furthermore, the galactoside photosensitizer as supramolecular amphiphiles can self-assemble into micelles, which can be applied in integrative cancer treatment with chemotherapy drugs such as camptothecin (CPT) encapsulated in the hydrophobic core of micelles. Upon reaction with free thiol GSH that is relatively abundant in tumor cells, disulfide bond cleavage occurs as well as the active photosensitizer TPP and chemotherapy drug CPT release, which can cause cell apoptosis. The in vitro biological assessment of TPP-S-S-Gal micelles against the A549 cell line was evaluated by MTT assay, flow cytometry and confocal scanning laser microscopy, respectively. According to the MTT assay, TPP-S-S-Gal micelles exhibited low dark toxicity and efficient integrative efficacy of PDT and chemotherapy towards A549 cells after light irradiation.

研究领域: 药理学 · 肿瘤学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ORGANIC & BIOMOLECULAR CHEMISTRY · 2018 ·Vol. 16 ·期 31 ·5598-5608 · IF 3.423

Application of a bodipy–C70 dyad in triplet–triplet annihilation upconversion of perylene as a metal-free photosensitizer

Yaxiong Wei,Min Zheng,Qiaohui Zhou,Xiaoguo Zhou,Shilin Liu

A bodipy–C70 dyad was synthesized and applied in triplet–triplet annihilation (TTA) upconversion of perylene as a novel metal-free organic photosensitizer. The photophysical processes were investigated by the methods of steady-state UV-Vis absorption and fluorescence spectroscopy, nanosecond time-resolved transient absorption spectroscopy, cyclic voltammetry, and density functional theory calculations. The bodipy–C70 dyad showed an increased molar extinction coefficient up to 82 300 mol−1 cm−1 at 518 nm compared with the C70 monomer. With photo-excitation of the bodipy moiety at 532 nm, the intramolecular singlet–singlet energy transfer between bodipy and C70 units was efficient with a quantum yield of nearly 100%, and the lowest triplet state of the dyad was subsequently populated via ISC of the C70 moiety, with a lifetime of ca. 80 μs in toluene. Electrochemical investigation suggested that the intramolecular electron transfer of the excited dyad was thermodynamically prohibited in toluene due to the positive ΔGCS for charge-separation. With the presence of perylene in solution as the triplet energy acceptor and emitter, the TTA upconverted fluorescence was observed with a maximum quantum yield of 10.3%. The overall upconversion capability of 4417 M−1 cm−1 exceeded that of C70 approximately two-fold. Moreover, the bodipy–C70 dyad also exhibited an enhanced optical stability under intense irradiation. All data indicated that the dyad was another ideal photosensitizer for TTA upconversion of perylene in the fullerene derivative family.

CAS / MDL: 115383-22-7 198-55-0
研究领域: 材料科学 · 光化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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EUROPEAN POLYMER JOURNAL · 2024 · IF 5.8

Developing high-efficiency photoinitiation systems by Leveraging highly Matched Interplays between photosensitizer and photoinitiator for enhanced energy transfer

Azhu Wang,Xianwei Zhao,Zhiwei Shi,Chunyu Lv,Pei Li,Jun Yu,Han Rao,Haining Chen,Huicong Liu,Weiping Li,Xiaoyu Jiang

Synthesizing highly compatible photosensitizer provides new directions for constructing high-efficiency photoinitiation systems (PSs). Here, a 2,4-Bis(4-(diethylamino)benzylidene)cyclobutanone (C4) was synthesized and used to form a three-component PSs (C4/HABI/MBO) with a biimidazole (HABI), 2-mercaptobenzoxazole (MBO). The photosensitizer has a more efficient energy transfer properties attributed to the higher fluorescence emission capacity, narrower energy band gap, lower free energy of electron transfer (Δ G et ) and improved matching with photoinitiator. Meanwhile, a double-cycle reaction mechanism is proposed, in which the improved matching seems to encourage this cycle to occur. As a result, the C4/HABI/MBO photoinitiation system well improved the diffraction efficiency of photopolymers up to 96% and demonstrated promising performance in recording and reproducing reflection holograms, which provide a new research idea for designing photoinitiation system.

研究领域: 材料科学 · 光学
✓ 已验证 产品关联 DOI 高影响因子
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

Activating the photocatalytic activity of insulator barium silicate: A liquid-phase alkalized tetracycline photosensitizer and its self-destruction

Xueli Hu,Peng Lu,Min Fu,Yongheng Zhang,Xinyu Cao,Jiabo Chen,Shutao Lin,Juanjuan Yao,Zhi Zhang

Breaking through the inherent thinking, activating insulators with abundant and economical sources as photocatalysts to promote the practical application of photocatalysis has attracted attention. Herein, an insulator photocatalyst barium silicate (BSO) was successfully prepared by the hydrothermal method, and a solid–liquid photocatalytic reaction system combining solid-phase photocatalyst with liquid-phase antibiotic photosensitizer was constructed. In this reaction system, the insulator BSO achieved excellent photocatalytic activity, and the degradation of 30 mg/L tetracycline reached 93.2 % after 12 W LED illumination for 2 h. The mechanism of tetracycline as a liquid-phase photosensitizer to activate the photocatalytic activity of BSO was explored. Lewis acid-base interaction not only alkalizes tetracycline to expand BSO light absorption, but also constitutes an electron transport channel between the BSO and alkalization tetracycline to facilitate the separation of photogenerated carriers. Alkalized tetracycline as a photosensitizer improves the response of BSO to visible light, and is decomposed by active substances such as 1 O 2 and O 2 − , thereby purifying the water body. This work reveals for the first time the mechanism of action of antibiotic photosensitizers to activate the photocatalytic activity of insulators, and provides a new perspective for the activation and development of insulators in photocatalysis.

研究领域: 环境科学 · 材料科学 · 生物学
✓ 已验证 DOI 高影响因子
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BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS · 2017 · IF 2.466

Overcome the limitation of hypoxia against photodynamic therapy to treat cancer cells by using perfluorocarbon nanodroplet for photosensitizer delivery

Xiaolei Tang,Yuhao Cheng,Shiting Huang,Feng Zhi,Ahu Yuan,Yiqiao Hu,Jinhui Wu

The low oxygen concentration limits the therapeutic efficacy of photodynamic therapy in treating cancer cells in hypoxia, since the cytotoxic 1 O 2 can't be effectively generated in this condition. To overcome this, we load photosensitizer into perfluorocarbon nanodroplet, which has a high oxygen capacity to enrich O 2 for photodynamic consumption. Under the well-controlled hypoxic condition, we test its efficacy both in vitro and in vivo . This method can be successfully used for destroying cancer cells in hypoxic condition.

研究领域: 肿瘤学 · 生物医学工程 · 治疗学
✓ 已验证 DOI PubMed 高影响因子
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LANGMUIR · 2021 · IF 3.882

Photosensitizer Functionalized Nanodiamonds for Raman Imaging and Photodynamic Therapy of Cancer Cells

Kuikui Zhang,Qingyue Guo,Qi Zhao,Futao Wang,Hui Wang,Jinfang Zhi,Chongxin Shan

One novel nanoplatform with multiple functions including Raman imaging and photodynamic therapy (PDT) capacities was constructed through modifying nanodiamonds (NDs) with photosensitizer chlorin e6 (Ce6). The NDs-Ce6 nanoparticles show enhanced singlet oxygen generation efficiency relative to free Ce6. Cytotoxicity tests indicate that NDs-Ce6 have negligible influence toward HeLa cells vitality under dark condition but enhanced photodynamic ablation upon 660 nm laser irradiation in comparison with free Ce6. In addition, the NDs-Ce6 could be used as Raman imaging probes toward HeLa cells. These results demonstrate that the NDs-Ce6 multifunctional nanoplatform have attractive features using for Raman imaging and PDT. Additionally, a new idea could be provided for designing the multifunctional platform from the work.

研究领域: 生物医学工程 · 肿瘤学 · 纳米医学
✓ 已验证 DOI PubMed 高影响因子
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