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Ru(II)-base d aggregation-induce d emission (AIE) agents with efficient 1 O2 generation, photo-catalytic NADH oxidation and anticancer activity

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CHINESE CHEMICAL LETTERS 2025年第5期36卷

作者： Xu, Yunli da, xuwen Wang, Lei Peng, Yatong Zhou, Wanpeng Liu, Xiulian Wu, Yao 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

Photodynamic therapy (PDT) has received much attention in recent years. However, traditional photosensitizers (PSs) applied in PDT usually suffer from aggregation-caused quenching (ACQ) effect in H2 O, single and inefficient photochemical mechanism of action (MoA), poor cancer targeting ability, etc . In this work, two novel Ru(II)-based aggregation-induced emission (AIE) agents (Ru1 and Ru2) were developed. Both complexes exhibited long triplet excited lifetimes and nearly 100 % singlet oxygen quantum yields in H2 O. In addition, Ru1 and Ru2 displayed potent photo-catalytic reduced nicotinamide adenine dinucleotide (NADH) oxidation activity with turnover frequency (TOF) values of about 1779 and 20 0 0 h-1 , respectively. Therefore, both Ru1 and Ru2 showed efficient PDT activity towards a series of cancer cells. Moreover, Ru2 was further loaded in bovine serum albumin (BSA) to enhance the tumor targeting ability in vivo , and the obtained Ru2@BSA could selectively accumulate in tumor tissues and effectively inhibit tumor growth on a 4T1 tumor-bearing mouse model. So far as we know, this work represents the first report about Ru(II) AIE agents that possess high singlet oxygen quantum yields and also potent photocatalytic NADH oxidation activity, and may provide new ideas for rational design of novel PSs with efficient PDT activity. (c) 2025 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

关键词： Ru(II) complexes Aggregation-induced emission Photo-catalytic NADH oxidation Photodynamic therapy Turnover frequency

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A highly positively charged Ru(II) complex with photo-labile ligands for selective and efficient photo-inactivation of intracellular aureus

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JOURNAL OF INORGANIC BIOCHEMISTRY 2025年 268卷 112908页

作者： Xu, Yunli da, xuwen Jian, Yao Zhou, Wanpeng Wu, Aifeng Wu, Yao Peng, Yatong Liu, Xiulian Shi, Yu 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

Due to the protection afforded by host cells, intracellular Staphylococcus aureus (S. aureus), particularly methicillin-resistant S. aureus (MRSA), poses a significantly greater challenge to eliminate compared to the extracellular counterparts. It is highly desirable to develop novel antibacterial agents which are capable of selectively and efficiently eradicating intracellular bacteria, including drug-resistant strains, while being less prone to induce bacterial resistance. In this work, two Ru(II) complexes (Ru1 and Ru2) with photo-labile ligands were designed and synthesized. Both Ru1 and Ru2 could covalently bind to DNA after photo-induced ligand dissociation. Compared to Ru1, the incorporation of a triphenylamine group adorned with two positively charged cationic pyridine units significantly boosts the DNA binding constant, bacterial binding/uptake level, and subsequently, the antibacterial activity of Ru2. Ru2 could selectively photo-inactivate intracellular S. aureus and MRSA, being more efficient than vancomycin both in vitro and in vivo. Interestingly, after 20 days' treatment at sublethal concentrations, S. aureus cells exhibited no obvious drug resistance towards Ru2 upon irradiation. Such appealing results may provide new sights for developing novel antibacterial agents against intractable intracellular pathogens and also prevalent drug resistance.

关键词： Ru(II) complexes Photo-induced ligand dissociation Intracellular bacteria DNA binding Drug resistance

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HClO-responsive dinuclear Ru(II) complexes for selective imaging and efficient photo-inactivation of intracellular bacteria

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CHINESE CHEMICAL LETTERS 2025年第6期36卷

作者： Zhou, Wanpeng da, xuwen Xu, Yunli Peng, Yatong Liu, Xiulian Wu, Yao Shi, Yu Wu, Aifeng Yao, Yishan Wang, Xuesong Zhou, Qianxiong Chinese Acad Sci Key Lab Photochem Convers & Optoelect Mat Tech Inst Phys & Chem Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China Beijing Inst Pharmacol & Toxicol Beijing 100850 Peoples R China

Intracellular bacteria (ICB), cloaked by the protective barriers of host cells, pose a formidable challenge to selective and efficient eradication. The employment of activatable photosensitizers based antibacterial photodynamic therapy (aPDT) holds significant potential for selective imaging and photo-inactivation of ICB while minimizing side effects on normal cells. Drawing inspiration from the elevated hypochlorous acid (HClO) levels in ICB infected phagocytes, herein we firstly designed and synthesized a series of HClOresponsive dinuclear Ru(II) complexes (Ru1-Ru3) to achieve such a goal. Initially, the luminescence, 1 O2 generation and aPDT activity of these Ru(II) complexes were suppressed due to the quenching effect of the azo group, but were recovered after reaction with HClO in solutions or within ICB infected phagocytes. The detailed results revealed that Ru1 and Ru3 could not only selectively visualize ICB, but also demonstrated remarkable aPDT activity against ICB, surpassing vancomycin both in vitro and in vivo . (c) 2025 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

关键词： Intracellular bacteria HClO-responsive Ru(II) complexes Antibacterial photodynamic therapy Selective imaging and photo-inactivation

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Glutathione promoted Fenton degradation: a cocatalyst based on the -HS/-S-S- cycle with hydroxyl radicals

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ENVIRONMENTAL SCIENCE-WATER RESEARCH & TECHNOLOGY 2020年第3期6卷 515-522页

作者： da, xuwen Tang, daojian Wang, Ling Ma, Jiahai Univ Chinese Acad Sci Sch Chem Sci Beijing 100049 Peoples R China Chinese Acad Sci Inst Proc Engn Key Lab Green Proc & Engn Beijing Key Lab Ionic Liquids Clean Proc Beijing 100190 Peoples R China

Glutathione, a kind of tripeptide with a thiol group, was introduced into the traditional Fenton system. It was found that target pollutant degradation is greatly improved when adding glutathione into the Fenton system, due to it accelerating the Fe(II)/Fe(III) cycle, thus generating more hydroxyl radicals. The variation of the concentrations of Fe(II) and H2O2 and the generation of HO center dot were monitored to verify the catalytic action of glutathione. Operating variables such as pH, molar ratios and different atmospheres were examined, and cyclic degradation experiments were performed to explore the stability of catalysts. Electrospray ionization mass spectrometry (ESI-MS) was used to determine the transformation of different forms of glutathione to explore the catalytic mechanism. More importantly, it was found that other thiol compounds can also promote the Fenton degradation through a cycle of thiol compounds and their oxidized forms. In conclusion, it is a cocatalyst based on the -HS/-S-S- cycle with hydroxyl radicals, which has not been reported previously.

关键词： Molar ratio

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A Ru-anthraquinone dyad with triple functions of PACT, photoredox catalysis and PDT upon red light irradiation

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daLTON TRANSACTIONS 2021年第31期50卷 10845-10852页

作者： Zhang, Chao Guo, Xusheng da, xuwen Wang, Zhanhua Wang, Xuesong Zhou, Qianxiong Chinese Acad Sci Tech Inst Phys & Chem Lab Photochem Convers & Optoelect Mat Beijing 100190 Peoples R China Univ Chinese Acad Sci Beijing 100049 Peoples R China

Phototherapy for cancer treatment has received much attention in recent years, and compounds with multiple anticancer mechanisms upon irradiation are particularly appealing. In this work, a nitro-anthra-quinone group was attached to a biq (2,2'-biquinoline) ligand based Ru(II) complex, endowing the resultant Ru1 compound with multiple anticancer mechanisms upon 600 nm light irradiation. Ru1 can undergo biq ligand photodissociation, showing its potential as a photoactivated chemotherapy (PACT) agent. Moreover, a Ru(III) centre and an anthraquinone anion centre may be generated upon irradiation, which can further oxidize NADH/NADPH and generate O-2(center dot-), successfully eliciting photoredox catalysis and photodynamic therapy (PDT). Compared to the control complex Ru2 without the nitroanthraquinone group, Ru1 exhibited much enhanced photocytotoxicity towards a series of cancer cell lines and 3D multicellular spheroids upon red light irradiation.

关键词： Irradiation

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Strongly prolonged hydroxyl radical production for Fenton-like reactions: The golden touch of Cu

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SEPARATION AND PURIFICATION TECHNOLOGY 2019年 213卷 500-506页

作者： da, xuwen Ji, Hongwei Zhao, Zhenwen Lan, Rongshan Li, Tuo Ma, Jiahai Univ Chinese Acad Sci Sch Chem Sci Beijing 100049 Peoples R China Chinese Acad Sci Inst Chem Key Lab Photochem Beijing 100190 Peoples R China Chinese Acad Sci Beijing Mass Spectrum Ctr Inst Chem Beijing 100190 Peoples R China

Hydroxyl radicals are believed as the most reactive species in the Fenton-like reactions and perform well at the beginning stage of the reaction due to very short lifetime. A reaction system with strongly prolonged hydroxyl radical lifetime is rarely reported. Adding Cu ions, an unreactive catalyst for hydrogen peroxide activation, the Fe/Cu/CDBQ/H2O2 system efficiently prolonged hydroxyl radical lifetime with two orders. This study found a strong, prolonged hydroxyl radical generation in a Fenton-like system using iron, copper ions and 2,5-dihydroxy-1,4-benzoquinone restricted in cyclodextrin (CDBQ). Meanwhile, rapid degradation and substantial mineralization of organics was achieved in this system. Further, the Cu ions could promote the efficiency of other Fenton-like system.

关键词： Hydroxyl radical Fenton reaction Copper ion

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UCNP@BSA@Ru nanoparticles with tumor-specific and NIR-triggered efficient PACT activity in vivo

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daLTON TRANSACTIONS 2021年第22期50卷 7715-7724页

作者： Zhang, Chao Guo, Xusheng da, xuwen Yao, Yishan Xiao, Haihua 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 Beijing Inst Pharmacol & Toxicol Beijing 100850 Peoples R China Chinese Acad Sci Beijing Natl Lab Mol Sci Inst Chem State Key Lab Polymer Phys & Chem Beijing 100190 Peoples R China

Ru(ii)-based photoactivated chemotherapy (PACT) agents are promising;however, their short wavelength absorption (generally <550 nm) and poor tumor accumulation ability limit their in vivo applications. Herein, bovine serum albumin (BSA) coated lanthanide-doped upconversion nanoparticles (NaYF4:Yb:Tm@NaYF4 (UCNPs)) were loaded with a Ru(ii) PACT agent, i.e. [Ru(dip)(2)(spc)](+) (dip = 4,7-diphenyl-1,10-phenanthroline;spc = 2-sulfonic acid pyridine-3-carboxylic acid). The resultant UCNP@BSA@Ru can transfer [Ru(dip)(2)(spc)](+) to tumor cells in vitro as well as tumor tissues in vivo highly efficiently and selectively owing to the targeting ability of BSA and the enhanced permeability and retention effect of the nanoparticles. The subsequent near infrared (NIR) light irradiation at 980 nm or visible light irradiation at 470 nm can initiate dissociation of the spc ligand, and the released Ru(ii) aqua compounds ([Ru(dip)(2)(H2O)(2)](2+)) may exert a potent cytotoxicity towards a series of cancer cells but a much weaker effect on the normal IOSE80 cells. The in vivo (mouse) results showed that UCNP@BSA@Ru could inhibit tumor growth upon 980 nm irradiation more efficiently than in the dark and more efficiently than cisplatin (in the dark).

关键词： Tumors

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A photo-degradable BODIPY-modified Ru(ii) photosensitizer for safe and efficient PDT under both normoxic and hypoxic conditions

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daLTON TRANSACTIONS 2024年第8期53卷 3579-3588页

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

Photodynamic therapy (PDT) is promising for cancer treatment but still suffers from some limitations. For instance, PDT based on O-1(2) generation (in a type-II mechanism) is heavily dependent on high oxygen concentrations and will be significantly depressed in hypoxic tumors. In addition, the residual photosensitizers after PDT treatment may cause severe side-effects under light irradiation. To solve these problems, herein a BODIPY (boron dipyrromethene)-modified Ru(II) complex [Ru(dip)(2)(tpy-BODIPY)](2+) (complex 1, dip = 4,7-diphenyl-1,10-phenanthroline, tpy = 2,2':6',2''-terpyridine) was designed and synthesized. Complex 1 exhibited both high singlet oxygen quantum yield (Phi = 0.7 in CH3CN) and excellent superoxide radical (O-2(center dot)-) generation, and thus demonstrated efficient PDT activity under both normoxic and hypoxic conditions. Moreover, complex 1 is photo-degradable in water, and greatly loses its ROS generation ability after PDT treatment. These novel properties of complex 1 make it promising for efficient PDT under both normoxic and hypoxic conditions with reduced side-effects.

关键词： Photosensitizers

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A targeted and efficient CDT system with photocatalytic supplement of H2O2 and hydroxyl radical production at a neutral pH

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INORGANIC CHEMISTRY FRONTIERS 2022年第11期9卷 2544-2556页

作者： da, xuwen Wang, Zhanhua Jian, Yao Zhang, Chao Hou, Yuanjun Yao, Yishan 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 Beijing Inst Pharmacol & Toxicol Beijing 100850 Peoples R China

The bottleneck problems of chemodynamic therapy (CDT) are the dependence on an acidic pH (2.0-4.0), insufficient H2O2 level in tumor tissues, and potential systematic toxicity of inorganic nanomaterials-based CDT agents. In this study, the new tricks of two old compounds, i.e. [Ru(phen)(2)(PIP-OCH3)](PF6)(2) (Ru3, phen = 1,10-phenanthroline, PIP-OCH3 = 2-(4-methoxy phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline) and Fe(tpy)Cl-3 (tpy = 2,2 ':6 ',2 '-terpyridine), were harnessed to construct an ideal CDT system. Ru3 was able to efficiently photo-catalyze NADH oxidation accompanied by the production of H(2)O(2)in situ with a high yield of 73.2%, which can be converted into cytotoxic hydroxyl radicals by the biocompatible Fe(tpy)Cl-3 at a neutral pH. By loading both Ru3 and Fe(tpy)Cl-3 in tumor-targeting bovine serum albumin (BSA), the obtained BSA@Fe/Ru nanoparticles exhibited a highly efficient, selective, and photo-controlled CDT activity both in vitro and in vivo. This work may provide new sights for overcoming the issues confronted in CDT.

关键词： Ruthenium compounds

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Biocompatible hypocrellin A-Fe(iii) nanoparticles exhibiting efficient photo-activated CDT in vitro and in vivo

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daLTON TRANSACTIONS 2022年第8期51卷 3225-3233页

作者： Wang, Zhanhua Gao, Chuan da, xuwen Jian, Yao Zhang, Chao Yao, Yishan 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 Beijing Inst Pharmacol & Toxicol Beijing 100850 Peoples R China

Chemodynamic therapy (CDT) is novel and promising for cancer treatment, however, the potential systematic toxicity of the used nanoparticles is still a big concern. In this work the biocompatible hypocrellin A-Fe(iii) nanoparticles (HA-Fe(iii) NPs) were synthesized and studied. The CDT effect of HA-Fe(iii) NPs in the dark is negligible but can be photo-activated upon red light irradiation, which is meaningful to realize precise CDT treatment by selective light irradiation. Moreover, HA-Fe(iii) NPs can also generate O-2(-), which may be converted into H2O2 to further enhance the CDT effect. As a result, HA-Fe(iii) NPs had little cytotoxicity in the dark at the concentration up to 200 mu g ml(-1), but exhibited efficient CDT activity upon red light irradiation under both normoxic and hypoxic conditions. The in vivo results also showed that HA-Fe(iii) NPs can efficiently inhibit tumor growth upon 628 nm light irradiation.

关键词： Nanoparticles

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