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Nitroreductase-responsive photosensitizers for selective imaging and photo-inactivation of intracellular bacteria

CHEMISTRY-A EUROPEAN JOURNAL 2024年第16期30卷 e202303766-e202303766页

作者： Zhou, Wanpeng da, xuwen Jian, Yao Peng, Yatong Liu, Xiulian Xu, Yunli Wu, Yao Wang, Xuesong Zhou, Qianxiong Chinese Acad Sci Tech Inst Phys & Chem Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 1000490 Peoples R China

Intracellular Staphylococcus aureus (S. aureus), especially the methicillin resistant staphylococcus aureus (MRSA), are difficult to detect and eradicate due to the protection by the host cells. Antibacterial photodynamic therapy (aPDT) offers promise in treating intracellular bacteria, provided that selective damage to the bacteria ranther than host cells can be realized. According to the different nitroreductase (NTR) levels in mammalian cells and S. aureus, herein NTR-responsive photosensitizers (PSs) (T)CyI-NO2 were designed and synthesized. The emission and 1O2 generation of (T)CyI-NO2 are quenched by the 4-nitrobenzyl group, but can be specifically switched on by bacterial NTR. Therefore, selective imaging and photo-inactivation of intracellular S. aureus and MRSA were achieved. Our findings may pave the way for the development of more efficient and selective aPDT agents to combat intractable intracellular infections. Two nitroreductase (NTR)-responsive photosensitizers ((T)CyI-NO2) were designed and synthesized. The quenched fluorescence and singlet oxygen production of (T)CyI-NO2 can be switched on by NTR in S. aureus. Detailed studies displayed TCyI-NO2 was able to selectively image and efficiently photo-inactivate intracellular bacteria with little cytotoxicity. image

关键词： Antibacterial photodynamic therapy Intracellular bacteria treatment Nitroreductase responsive Photosensitizer Staphylococcus aureus

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A bioorthogonal assembly based on metallophilic interactions for selective imaging and PDT treatment of cancer cells

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INORGANIC CHEMISTRY FRONTIERS 2022年第10期9卷 2290-2297页

作者： da, xuwen Yu, Fei-Hu Zhang, Chao Wang, Zhanhua Jian, Yao Hou, Yuanjun Chen, Yong Wang, Xuesong Zhou, Qianxiong Chinese Acad Sci Tech Inst Phys & Chem Key Lab Photochem Convers & Optoelect Mat Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China

Precise control of luminescence and singlet oxygen generation is important for selective photo-theranostic applications. In this work, bioorthogonal assembly based on d(10)MIDLINE HORIZONTAL ELLIPSISd(10) metallophilic interactions was first proposed for selective cancer cell imaging and photodynamic therapy (PDT) treatment as a proof of concept. [Au(NHC)(2)](+) (NHC = N-heterocyclic carbene) cations loaded on hyaluronic acid were selectively taken up by cancer cells. The subsequent incubation with [MX2](-) (M = Au or Cu and X = halide or arylacetylide) anions led to the bioorthogonal assembly of C3 + A5/A10 in cancer cells with luminescence turn-on and singlet oxygen generation upon irradiation. This work not only demonstrates that d(10)MIDLINE HORIZONTAL ELLIPSISd(10) metallophilic interactions can be readily harnessed for developing bioorthogonal assembly to realize precise cancer cell imaging and PDT, but also can stimulate the development of supramolecular interaction based bioorthogonal chemistry.

关键词： Cancer cells

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Thermally-activated upconversion based on triplet fusion for deep red photoactivation of Ru(ii) complexes

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NEW JOURNAL OF CHEMISTRY 2024年第15期48卷 6886-6892页

作者： Niu, Pengfei da, xuwen Hu, Rui Yu, Tianjun Chen, Jinping Zhou, Qianxiong Luo, Guiwen Zeng, Yi Li, Yi Tech Inst Phys & Chem Chinese Acad Sci Key Lab Photochem Convers & Optoelect Mat Beijing 100190 Peoples R China Inst Chem Chinese Acad Sci Key Lab Photochem Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China

Expanding the anti-Stokes shift in triplet-triplet annihilation upconversion (TTA-UC) systems and harvesting light within the biological transparency window (700-900 nm) are of great importance for their biomedical applications. In this study, we have developed a TTA-UC system that converts deep red-light into blue photons using a highly endothermic sensitization pair, wherein the triplet energy level of the sensitizer is 0.19 eV below that of the acceptor. The thermally activated triplet energy transfer compensates the energy loss during intersystem crossing (ISC) of the sensitizer, achieving a 0.82 eV anti-Stokes shift upconversion with over 6% quantum yield. This TTA-UC system activates a Ru(ii)-based photoactivated chemotherapeutic agent, causing DNA to bleach under 700 nm LED irradiation. These results demonstrate a feasible way to develop upconversion systems that operate within the biological transparency window, with potential applications in biological phototherapy.

关键词： Transparency

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Ru/Pt@BSA nanoparticles for efficient photo-catalytic oxidation of NAD(P)H and targeted cancer treatment under hypoxic conditions

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Chinese Chemical Letters 2023年第12期34卷 440-445页

作者： xuwen da Xiulian Liu Chao Li Yatong Peng Yao Jian Wanpeng Zhou Yunli Xu Yao Wu Xuesong Wang Qianxiong Zhou Key Laboratory of Photochemical Conversion and Optoelectronic Materials Technical Institute of Physics and ChemistryChinese Academy of SciencesBeijing 100190China

Photo-catalytic oxidation of intracellular nicotinamide adenine dinucleotide(2'-phosphate)(NAD(P)H)has attracted much attention for cancer ***,the general oxygen-dependent mechanism heavily depresses the efficacy in hypoxic *** solve this problem,herein platinum nanoparticles(Pt NPs)with catalase-like(CAT-like)and catalytic H_(2)evolution activities were introduced as a powerful assistant to enhance the photo-catalytic NAD(P)H oxidation of Ru1([Ru(phen)2(PIP-OCH_(3))]^(2+),phen=1,10-phenanthroline,PIP-OCH_(3)=2-(4-methoxy phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline)under hypoxic and even oxygen-free ***,Pt NPs can transform the original and in situ formed H_(2)O_(2)once again into O_(2)by the CAT-like activity,thus relieving tumor hypoxia and realizing cyclic utilization(at least in part)of the precious oxygen in ***,Pt NPs can also be served as H_(2)evolution catalysts while using Ru1 as the photosensitizer and NAD(P)H as the electron and proton *** this process,NAD(P)H is oxidized without the participation of oxygen,which can provide an effective way even under oxygen-free *** co-encapsulation of Rul and Pt NPs in bovine serum albumin(BSA)with tumor targeting ability,the resultant Ru/Pt@BSA could photo-catalyze intracellular NAD(P)H oxidation under hypoxic conditions(3%O_(2)),and exhibited an efficient and selective anticancer activity both in vitro and in *** results may provide new sights for efficient and targeted cancer treatment underhypoxic conditions.

关键词： Hypoxic Cancer treatment Photo-catalytic oxidation NAD(P)H Cyclic utilization of oxygen Pt nanoparticle

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A self-enhanced chemiexcited PDT system for targeted and efficient treatment of deeply seated tumors

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INORGANIC CHEMISTRY FRONTIERS 2024年第17期11卷 5598-5611页

作者： da, xuwen Xu, Yunli Wang, Lei Liu, Xiulian Peng, Yatong Wu, Yao Zhou, Wanpeng Wang, Wentao Wang, Xuesong Zhou, Qianxiong Chinese Acad Sci Tech Inst Phys & Chem Key Lab Photochem Convers & Optoelect Mat Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China Univ Chinese Acad Sci Wenzhou Inst Wenzhou 325000 Peoples R China

Traditional photodynamic therapy (PDT) is almost ineffective against deeply seated tumors due to the limited penetration depth of external light. The development of chemiexcited PDT is promising to address this issue, but it is still challenging to construct simple, efficient and targeted chemiexcited PDT systems. In this work, CPPO (bio(3,5,6-trichloro-2-n-pentyloxycarbonylphenyl) oxalate) and [Ru(phen)2(PIP-OCH3)](PF6)2 (Ru3, where phen = 1,10-phenanthroline, PIP-OCH3 = 2-(4-methoxy phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline) with efficient photocatalytic NADH (reduced nicotinamide adenine dinucleotide) oxidation were co-encapsulated with DSPE-PEG 2000 to form Ru3/CPPO@PEG nanoparticles (NP3). Once internalized by cancer cells, Ru3 can be excited with the chemical energy produced by the reaction between CPPO and endogenous H2O2. The subsequent oxidation of intracellular NADH and generation of H2O2in situ by excited Ru3 will further promote the sustained occurrence of the chemical reaction, realizing self-enhanced chemiexcited PDT. NP3 could effectively deplete intracellular NADH, inhibit ATP synthesis, increase the H2O2 content, and produce reactive oxygen species (ROS) within cancer cells, thus exhibiting efficient chemiexcited PDT activity against various cancer cells. Notably, minimal cytotoxicity was observed towards normal cells. Good therapeutic effects against subcutaneously implanted and lung metastatic tumors were also observed for NP3. The current findings may provide new insights for development of novel chemiexcited PDT. NP3 with H2O2 supplementation and self-enhanced chemiexcited PDT system are developed, exhibiting efficient chemiexcited PDT activity towards subcutaneously implanted and lung metastatic tumors, providing new insights for development of novel chemiexcited PDT.

关键词： Photodynamic therapy

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Cocrystals of axially N-embedded quasi-carbon nanohoops via modulating the electron affinity of guest acceptors

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SCIENCE CHINA-CHEMISTRY 2025年 1-8页

作者： Zhang, Li Qiu, Shuhai Hu, Shunlong Xu, Hanren Sun, xuwen Jiang, Wei Qu, da-Hui Wang, Zhaohui East China Univ Sci & Technol Feringa Nobel Prize Scientist Joint Res Ctr Key Lab Adv Mat & Joint Int Res Lab Precis Chem & Sch Chem & Mol EngnInst Fine ChemFrontiers Sci C Shanghai 200237 Peoples R China Tsinghua Univ Dept Chem Key Lab Organ Optoelect & Mol Engn Beijing 100084 Peoples R China

Organic donor-acceptor cocrystals of pi-conjugated molecues have shown diverse applications in materials science. However, most cocrystals exist in neutral forms dominated by pi-pi interactions, while the ionic congeners and corresponding properties are rarely studied due to difficulties in harnessing the degree of charge transfer. Herein, we report cocrystals of axially N-embedded quasi-carbon nanohoops (DPP-D and DPP-T) with electron deficient guests. By modulating the electron affinity of the acceptor guests, the electronic structures of the complexes can be tuned from neutral to ionic states. Specifically, DPP-D interacts with TCNB molecules to form neutral superstructures via intermolecular pi-pi interactions, giving rise to a deep-red emission in the solid state. In contrast, an ionic complex showing near-infrared region absorptions and paramagnetic character on account of strong charge-transfer interactions is generated when DDQ molecules are involved. Their unique properties can be explained by different degrees of charge transfer and assembly modes, which have clearly been manifested by crystal structures and theoretical calculations. Our studies provide rare examples of pi-conjugated macrocycle-based donor-acceptor cocrystals in both neutral and ionic forms, and give insight to the design of multicomponent carbon nanomaterials.

关键词： n-doped carbon nanohoop donor-acceptor cocrystal charge transfer interaction ionic state

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Boosting catalytic performance of N doped porous carbon derived from coal tar pitch: The role of N species and the contribution of 1O2

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JOURNAL OF WATER PROCESS ENGINEERING 2025年 72卷

作者： Huang, Linlin Zhang, xuwen Wang, Lin Liu, Tingting Li, da Sheng, Tao Sun, Caiyu Li, Lixin Heilongjiang Univ Sci & Technol Coll Environm & Chem Engn Harbin 150022 Peoples R China Harbin Inst Technol State Key Lab Urban Water Resource & Environm Harbin 150090 Peoples R China

In this study, nitrogen-doped carbon material (N-PC-d) derived from coal tar pitch using dicyandiamide as N source was successfully synthesized, exhibiting outstanding catalytic performance in the activation of peroxymonosulfate (PMS) for the degradation of Orange G (OG). By optimizing key parameters such as PMS dosage, NPC dosage, nitrogen source, pH, anions, and PS source, the optimal N-PC-d/PMS system achieved a degradation rate 1.45 times higher than that of the PC/PMS system within a broad pH range (2.0-10.0). Through electron paramagnetic resonance (EPR) and quenching experiments, it was found that singlet oxygen (1O2) was the predominant species accountable for OG degradation, while reactive oxygen species (ROS), including superoxide (O2 & sdot;-), hydroxyl radicals (& sdot;OH), and sulfate radicals (SO4 & sdot;-), played auxiliary roles. Moreover, the structure-activity relationship analysis revealed that functional groups such as C--C, C--O, and pyridine N were mainly involved in PMS activation. The degradation mechanism of OG was further elucidated by high-performance liquid chromatography-mass spectrometry (HPLC-MS). This research presented a cost-efficient N-doped porous carbon material for environmental remediation and provides more profound insights into the mechanisms of PMS activation by N doped carbon-based materials.

关键词： N-doped porous carbon Coal tar pitch PMS Singlet oxygen Orange G

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An Alkynyl-dangling Ru(II) Polypyridine Complex for Targeted Antimicrobial Photodynamic Therapy

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CHEMISTRY-A EUROPEAN JOURNAL 2022年第6期28卷 e202103359-e202103359页

作者： Jian, Yao Jin, Zhihui Qi, Shuang da, xuwen Wang, Zhanhua Wang, Xuesong Zhou, Qianxiong Chinese Acad Sci Tech Inst Phys & Chem Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China

To realize clinical application of antibacterial photodynamic therapy (aPDT), one of the most arduous challenges is how to render aPDT agents high selectivity against bacterial pathogens. In light of the fact that amino group-containing lipids are rich on the outer surfaces of Gram-positive bacteria, we herein constructed an alkynyl-dangling ruthenium(II) polypyridine complex (Ru2) to preferentially label Staphylococcus aureus (S. aureus) and methicillin-resistant Staphylococcus aureus (MRSA) over mammalian cells via the amino-yne bio-orthogonal click reaction. Thanks to the strong singlet oxygen generation ability, Ru2 could photo-inactivate S. aureus and MRSA effectively and specifically. Phosphatidylethanolamine (PE) molecules also exist in mammalian cells but are not accessible for Ru2, leading to its poor binding/uptake and negligible cytotoxicity in the dark and upon irradiation towards mammalian cells as well as low hemolysis, all favorable for aPDT application.

关键词： amino-yne click reaction antibacterial photodynamic therapy methicillin-resistant Staphylococcus aureus ruthenium(II) polypyridyl complexes Staphylococcus aureus

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A tumor-targeted multifunctional nanosystem with light-triggered NO generation for synergistic photodynamic/gas therapy

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INORGANICA CHIMICA ACTA 2024年 567卷

作者： Peng, Yatong da, xuwen Zhou, Wanpeng Xu, Yunli Wu, Yao Liu, Xiulian Wang, Xuesong Zhou, Qianxiong Chinese Acad Sci Tech Inst Phys & Chem Key Lab Photochem Convers & Optoelect Mat Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China

Photodynamic therapy (PDT) has emerged as a promising strategy for cancer treatment. Nevertheless, PDT alone still faces a considerable challenge in efficiently eliminating cancer cells, and combination with other therapeutic strategies can significantly improve anticancer efficacy. Herein, a multifunctional nanosystem (Ru-PArg-HA) composed of biocompatible and tumor-targeted hyaluronic acid (HA), a photosensitizer [Ru(phen)(2)(PIP-OCH3)](2+) (termed Ru, phen = 1,10-phenanthroline, PIP-OCH3 = 2-(4-methoxy phenyl)-1H-imidazo[4,5-f] [1,10] phenanthroline) and a NO donor poly-L-arginine (PArg), was fabricated via electrostatic interactions. Under 470 nm light irradiation, Ru-PArg-HA could not only catalyze 1,4-dihydronicotinamide adenine dinucleotide (NADH) oxidation to produce H2O2, but also could generate a large amount of reactive oxygen species (ROS, including O-1(2) and O-2(center dot-)) for PDT therapy. The light-driven production of O-1(2) and H2O2 could further convert PArg into nitric oxide (NO), enabling synergistic gas therapy. The experimental outcomes demonstrated that Ru-PArg-HA exhibited much enhanced anticancer activity compared to traditional mono-modal PDT. This finding provides new inspiration for the development of multifunctional nanosystems with efficient and targeted anti-cancer activity.

关键词： Photodynamic therapy Gas therapy Ru(II) photosensitizer Nitric oxide Tumor-targeted

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Cocrystals of axially N-embedded quasi-carbon nanohoops via modulating the electron affinity of guest acceptors

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Science China Chemistry 2025年

作者： Li Zhang Shuhai Qiu Shunlong Hu Hanren Xu xuwen Sun Wei Jiang da-Hui Qu Zhaohui Wang Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research Center Frontiers Science Center for Materi-obiology and Dynamic Chemistry Institute of Fine Chemicals School of Chemistry and Molecular Engineering East China University of Science and Technology Key Laboratory of Organic Optoelectronics and Molecular Engineering Department of Chemistry Tsinghua University

Organic donor-acceptor cocrystals of π-conjugated molecues have shown diverse applications in materials science. However,most cocrystals exist in neutral forms dominated by π-π interactions, while the ionic congeners and corresponding properties are rarely studied due to difficulties in harnessing the degree of charge transfer. Herein, we report cocrystals of axially N-embedded quasi-carbon nanohoops(DPP-D and DPP-T) with electron deficient guests. By modulating the electron affinity of the acceptor guests, the electronic structures of the complexes can be tuned from neutral to ionic states. Specifically, DPP-D interacts with TCNB molecules to form neutral superstructures via intermolecular π-π interactions, giving rise to a deep-red emission in the solid state. In contrast, an ionic complex showing near-infrared region absorptions and paramagnetic character on account of strong charge-transfer interactions is generated when DDQ molecules are involved. Their unique properties can be explained by different degrees of charge transfer and assembly modes, which have clearly been manifested by crystal structures and theoretical calculations. Our studies provide rare examples of π-conjugated macrocycle-based donor-acceptor cocrystals in both neutral and ionic forms, and give insight to the design of multicomponent carbon nanomaterials.

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