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1.
Zhiyong Liu Tianye Cao Yudong Xue Mengting Li Mengsi Wu Jonathan W. Engle Qianjun He Weibo Cai Minbo Lan Weian Zhang 《Angewandte Chemie (International ed. in English)》2020,59(9):3711-3717
Nanocarriers are employed to deliver photosensitizers for photodynamic therapy (PDT) through the enhanced penetration and retention effect, but disadvantages including the premature leakage and non‐selective release of photosensitizers still exist. Herein, we report a 1O2‐responsive block copolymer (POEGMA‐b‐P(MAA‐co‐VSPpaMA) to enhance PDT via the controllable release of photosensitizers. Once nanoparticles formed by the block copolymer have accumulated in a tumor and have been taken up by cancer cells, pyropheophorbide a (Ppa) could be controllably released by singlet oxygen (1O2) generated by light irradiation, enhancing the photosensitization. This was demonstrated by confocal laser scanning microscopy and in vivo fluorescence imaging. The 1O2‐responsiveness of POEGMA‐b‐P(MAA‐co‐VSPpaMA) block copolymer enabled the realization of self‐amplified photodynamic therapy by the regulation of Ppa release using NIR illumination. This may provide a new insight into the design of precise PDT. 相似文献
2.
Metallophthalocyanine‐Based Conjugated Microporous Polymers as Highly Efficient Photosensitizers for Singlet Oxygen Generation 下载免费PDF全文
Dr. Xuesong Ding Prof. Dr. Bao‐Hang Han 《Angewandte Chemie (International ed. in English)》2015,54(22):6536-6539
Singlet oxygen (1O2) is of great interest because of its potential applications in photodynamic therapy, photooxidation of toxic molecules, and photochemical synthesis. Herein, we report novel metallophthalocyanine (MPc) based conjugated microporous polymers (MPc‐CMPs) as photosensitizers for the generation of 1O2. The rigid microporous structure efficiently improves the exposure of the majority of the MPc units to oxygen. The MPc‐CMPs also exhibit an enhanced light‐harvesting capability in the far‐red region through their extended π‐conjugation systems. Their microporous structure and excellent absorption capability for long‐wavelength photons result in the MPc‐CMPs showing high efficiency for 1O2 generation upon irradiation with 700 nm light, as evident by using 1,3‐diphenylisobenzofuran as an 1O2 trap. These results indicate that MPc‐CMPs can be considered as promising photosensitizers for the generation of 1O2. 相似文献
3.
Wenhao Zhai Yongkang Zhang Ming Liu Hao Zhang Junqing Zhang Changhua Li 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(46):16754-16762
Activatable photosensitizers (aPSs) sensitive to specific stimuli hold potential for targeting multiple disease biomarkers and are desirable for photodynamic therapy (PDT). Presented herein is the design of aPSs that can be activated and fully recover from an inhibited state in the presence of specific biomarker. A designed long‐wavelength D‐π‐A photosensitizer, PSSe‐I , with highly efficient photosensitivity for generation of 1O2 was used. Caging of the phenolate donor of PSSe‐I with a biomarker‐sensitive group provided ALP PS , and the drastic activation of its photosensitivity was demonstrated intracellularly. To enhance the flexibility of the design strategy, a clickable azide group was introduced into the scaffold to allow integration of more functionality. Modularly derived mito‐PN PS , equipped with a mitochondria‐targeting group and a specific peroxynitrite‐reactive trigger, was synthesized and demonstrated superior performance in cells. This strategy could lead to customization of aPSs applicable to a specific PDT. 相似文献
4.
Covalently Assembled Dipeptide Nanospheres as Intrinsic Photosensitizers for Efficient Photodynamic Therapy in Vitro 下载免费PDF全文
Xiaoke Yang Jinbo Fei Qi Li Prof. Dr. Junbai Li 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(19):6477-6481
Monodispersed diphenylalanine‐based nanospheres with excellent biocompatibility are fabricated through a facile covalent reaction‐induced assembly. Interestingly, the nanospheres exhibit red autofluorescence. Most importantly, such assembled dipeptide nanospheres can serve as intrinsic photosensitizer to convert O2 to singlet oxygen (1O2). Thus, photodynamic therapy in vitro can be achieved effectively. The versatile strategy could be extended to other biomolecules containing a primary amine group for the fabrication of potential intrinsic photosensitizers. 相似文献
5.
Shi Kuang Dr. Lingli Sun Xianrui Zhang Xinxing Liao Dr. Thomas W. Rees Dr. Leli Zeng Dr. Yu Chen Dr. Xiting Zhang Prof. Dr. Liangnian Ji Prof. Dr. Hui Chao 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(46):20878-20884
The efficacy of photodynamic therapy is typically reliant on the local concentration and diffusion of oxygen. Due to the hypoxic microenvironment found in solid tumors, oxygen-independent photosensitizers are in great demand for cancer therapy. We herein report an iridium(III) anthraquinone complex as a mitochondrion-localized carbon-radical initiator. Its emission is turned on under hypoxic conditions after reduction by reductase. Furthermore, its two-photon excitation properties (λex=730 nm) are highly desirable for imaging. Upon irradiation, the reduced form of the complex generates carbon radicals, leading to a loss of mitochondrial membrane potential and cell death (IC50light=2.1 μm , IC50dark=58.2 μm , PI=27.7). The efficacy of the complex as a PDT agent was also demonstrated under hypoxic conditions in vivo. To the best of our knowledge, it is the first metal-complex-based theranostic agent which can generate carbon radicals for oxygen-independent two-photon photodynamic therapy. 相似文献
6.
Zhiyong Liu Tianye Cao Yudong Xue Mengting Li Mengsi Wu Prof. Jonathan W. Engle Prof. Qianjun He Prof. Weibo Cai Prof. Minbo Lan Prof. Weian Zhang 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(9):3740-3746
Nanocarriers are employed to deliver photosensitizers for photodynamic therapy (PDT) through the enhanced penetration and retention effect, but disadvantages including the premature leakage and non-selective release of photosensitizers still exist. Herein, we report a 1O2-responsive block copolymer (POEGMA-b-P(MAA-co-VSPpaMA) to enhance PDT via the controllable release of photosensitizers. Once nanoparticles formed by the block copolymer have accumulated in a tumor and have been taken up by cancer cells, pyropheophorbide a (Ppa) could be controllably released by singlet oxygen (1O2) generated by light irradiation, enhancing the photosensitization. This was demonstrated by confocal laser scanning microscopy and in vivo fluorescence imaging. The 1O2-responsiveness of POEGMA-b-P(MAA-co-VSPpaMA) block copolymer enabled the realization of self-amplified photodynamic therapy by the regulation of Ppa release using NIR illumination. This may provide a new insight into the design of precise PDT. 相似文献
7.
PauloF. Santos LucindaV. Reis Isabel Duarte JooP. Serrano Paulo Almeida AnabelaS. Oliveira LuísF.Vieira Ferreira 《Helvetica chimica acta》2005,88(5):1135-1143
Several (multiply) iodinated squarylium cyanine dyes of type 1 and 8 (see Scheme and Table), derived from 1,3‐benzothiazole and 6‐iodo‐1,3‐benzothiazole, were synthesized as potential new photosensitizers, with absorptions in the 700‐nm region. Their ability to generate singlet oxygen (1O2) was assessed by luminescence‐decay measurement in the near‐IR. Some of these new dyes show interesting photophysical properties, and may be potentially used in photodynamic therapy (PDT). 相似文献
8.
Jian Sun Ke Du Jiajie Diao Xuetong Cai Fude Feng Shu Wang 《Angewandte Chemie (International ed. in English)》2020,59(29):12122-12128
Currently, photosensitizers (PSs) that are microenvironment responsive and hypoxia active are scarcely available and urgently desired for antitumor photodynamic therapy (PDT). Presented herein is the design of a redox stimuli activatable metal‐free photosensitizer (aPS), also functioning as a pre‐photosensitizer as it is converted to a PS by the mutual presence of glutathione (GSH) and hydrogen peroxide (H2O2) with high specificity on a basis of domino reactions on the benzothiadiazole ring. Superior to traditional PSs, the activated aPS contributed to efficient generation of reactive oxygen species including singlet oxygen and superoxide ion through both type 1 and type 2 pathways, alleviating the aerobic requirement for PDT. Equipped with a triphenylphosphine ligand for mitochondria targeting, mito aPS showed excellent phototoxicity to tumor cells with low light fluence under both normoxic and hypoxic conditions, after activation by intracellular GSH and H2O2. The mito aPS was also compatible to near infrared PDT with two photon excitation (800 nm) for extensive bioapplications. 相似文献
9.
Dr. Xian‐Sheng Ke Yingying Ning Juan Tang Ji‐Yun Hu Hao‐Yan Yin Gao‐Xiang Wang Zi‐Shu Yang Jialong Jie Dr. Kunhui Liu Dr. Zhao‐Sha Meng Zongyao Zhang Prof. Dr. Hongmei Su Prof. Dr. Chunying Shu Prof. Dr. Jun‐Long Zhang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(28):9676-9686
Construction of GdIII photosensitizers is important for designing theranostic agents owing to the unique properties arising from seven unpaired f electrons of the Gd3+ ion. Combining these with the advantages of porpholactones with tunable NIR absorption, we herein report the synthesis of GdIII complexes Gd‐1 – 4 ( 1 , porphyrin; 2 , porpholactone; 3 and 4 , cis‐ and trans‐porphodilactone, respectively) and investigated their function as singlet oxygen (1O2) photosensitizers. These Gd complexes displayed 1O2 quantum yields (ΦΔs) from 0.64–0.99 with the order Gd‐1 < Gd‐2 < Gd‐3 < Gd‐4 . The gradually enhanced 1O2 sensitization after β‐oxazolone moiety replacement was ascribed to the narrowing of the energy gap (ΔE) between the lowest triplet states (T1) of the ligand and the energy level of the 1Δg→3Σg transition of 1O2. In particular, Gd‐4 is capable of excitation in the visible to NIR region (400–700 nm) with a quantum yield near unity. These Gd complexes were first demonstrated as efficient photosensitizers in photocatalysis such as oxidative C?H bond functionalization of secondary or tertiary amines, and the oxygenation of the natural product cholesterol. Finally, after glycosylation, these water‐soluble Gd complexes showed potential applications in photodynamic therapy (PDT) in HeLa cells. This work revealed that GdIII complexes of “bioinspired” β‐modified porpholactones are efficient NIR photosensitizers and form a chemical basis to construct appealing photocatalysts and theranostic agents based on lanthanides. 相似文献
10.
Poornenth Pushpanandan Dong‐Hoon Won Shigeki Mori Yuhsuke Yasutake Susumu Fukatsu Masatoshi Ishida Hiroyuki Furuta 《化学:亚洲杂志》2019,14(10):1729-1736
Triplet photosensitizers that generate singlet oxygen efficiently are attractive for applications such as photodynamic therapy (PDT). Extending the absorption band to a near‐infrared (NIR) region (700 nm≈) with reasonable photostability is one of the major demands in the rational design of such sensitizers. We herein prepared a series of mono‐ and bis‐palladium complexes ( 1‐Pd‐H2 , 2‐Pd‐H2 , 1‐Pd‐Pd , and 2‐Pd‐Pd ) based on modified calix[6]phyrins as photosensitizers for singlet oxygen generation. These palladium complexes showed intense absorption profiles in the visible‐to‐NIR region (500–750 nm) depending on the number of central metals. Upon photoirradiation in the presence of 1,5‐dihydroxynaphthalene (DHN) as a substrate for reactive oxygen species, the bis‐palladium complexes generated singlet oxygen with high efficiency and excellent photostability. Singlet oxygen generation was confirmed from the characteristic spectral feature of the spin trapped complex in the EPR spectrum and the intact 1O2 emission at 1270 nm. 相似文献
11.
Dr. Jacky C. H. Chu Dr. Clarence T. T. Wong Prof. Dennis K. P. Ng 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2023,135(2):e202214473
Targeted delivery and specific activation of photosensitizers can greatly improve the treatment outcome of photodynamic therapy. To this end, we report herein a novel dual receptor-mediated bioorthogonal activation approach to enhance the tumor specificity of the photodynamic action. It involves the targeted delivery of a biotinylated boron dipyrromethene (BODIPY)-based photosensitizer, which is quenched in the native form by the attached 1,2,4,5-tetrazine unit, and an epidermal growth factor receptor (EGFR)-targeting cyclic peptide conjugated with a bicycle[6.1.0]non-4-yne moiety. Only for cancer cells that overexpress both the biotin receptor and EGFR, the two components can be internalized preferentially where they undergo an inverse electron-demand Diels–Alder reaction, leading to restoration of the photodynamic activity of the BODIPY core. By using a range of cell lines with different expression levels of these two receptors, we have demonstrated that this stepwise “deliver-and-click” approach can confine the photodynamic action on a specific type of cancer cells. 相似文献
12.
Dr. Luca Conti Prof. Andrea Bencini Prof. Camilla Ferrante Dr. Cristina Gellini Prof. Paolo Paoli Dr. Matteo Parri Prof. Giangaetano Pietraperzia Prof. Barbara Valtancoli Prof. Claudia Giorgi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(45):10606-10615
A comparative study between two novel, highly water soluble, ruthenium(II) polypyridyl complexes, [Ru(phen)2 L ′] and [Ru(phen)2Cu(II) L ′] ( L and L -CuII), containing the polyaazamacrocyclic unit 4,4′-(2,5,8,11,14-pentaaza[15])-2,2′-bipyridilophane ( L ′), is herein reported. L and L -CuII interact with calf-thymus DNA and efficiently cleave DNA plasmid when light-activated. They also possess great penetration abilities and photo-induced biological activities, evaluated on an A375 human melanoma cell line, with L -CuII being the most effective. Our study highlights the key role of the Fenton active CuII center within the macrocycle framework, that would play a synergistic role with light activation in the formation of cytotoxic ROS species. Based on these results, an optimal design of RuII polypyridyl systems featuring specific CuII-chelating polyamine units could represent a suitable strategy for the development of novel and effective photosensitizers in photodynamic therapy. 相似文献
13.
Huan Chen Shengliang Li Min Wu Kenry Zhongming Huang Chun‐Sing Lee Bin Liu 《Angewandte Chemie (International ed. in English)》2020,59(2):632-636
Traditional photosensitizers (PSs) show reduced singlet oxygen (1O2) production and quenched fluorescence upon aggregation in aqueous media, which greatly affect their efficiency in photodynamic therapy (PDT). Meanwhile, non‐targeting PSs generally yield low efficiency in antibacterial performance due to their short lifetimes and small effective working radii. Herein, a water‐dispersible membrane anchor (TBD‐anchor) PS with aggregation‐induced emission is designed and synthesized to generate 1O2 on the bacterial membrane. TBD‐anchor showed efficient antibacterial performance towards both Gram‐negative (Escherichia coli) and Gram‐positive bacteria (Staphylococcus aureus). Over 99.8 % killing efficiency was obtained for methicillin‐resistant S. aureus (MRSA) when they were exposed to 0.8 μm of TBD‐anchor at a low white light dose (25 mW cm?2) for 10 minutes. TBD‐anchor thus shows great promise as an effective antimicrobial agent to combat the menace of multidrug‐resistant bacteria. 相似文献
14.
Zhijia Wang Ling Huang Yuxin Yan Ahmed M. El‐Zohry Antonio Toffoletti Jianzhang Zhao Antonio Barbon Bernhard Dick Omar F. Mohammed Gang Han 《Angewandte Chemie (International ed. in English)》2020,59(37):16114-16121
Intersystem crossing (ISC) of triplet photosensitizers is a vital process for fundamental photochemistry and photodynamic therapy (PDT). Herein, we report the co‐existence of efficient ISC and long triplet excited lifetime in a heavy atom‐free bodipy helicene molecule. Via theoretical computation and time‐resolved EPR spectroscopy, we confirmed that the ISC of the bodipy results from its twisted molecular structure and reduced symmetry. The twisted bodipy shows intense long wavelength absorption (?=1.76×105 m ?1 cm?1 at 630 nm), satisfactory triplet quantum yield (ΦT=52 %), and long‐lived triplet state (τT=492 μs), leading to unprecedented performance as a triplet photosensitizer for PDT. Moreover, nanoparticles constructed with such helical bodipy show efficient PDT‐mediated antitumor immunity amplification with an ultra‐low dose (0.25 μg kg?1), which is several hundred times lower than that of the existing PDT reagents. 相似文献
15.
Cationic Chalcogenoviologen Derivatives for Photodynamic Antimicrobial Therapy and Skin Regeneration
Kun Zhou Ran Tian Guoping Li Xinyu Qiu Letian Xu Mengying Guo Dongdong Chigan Prof. Dr. Yanfeng Zhang Prof. Dr. Xin Chen Prof. Dr. Gang He 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(59):13472-13478
A series of water-soluble cationic chalcogenoviologen-based photosensitizers for photodynamic antimicrobial therapy (PDAT) is reported. The Se-containing derivatives (SeMV2+) 5 b and 6 b showed good antimicrobial activities due to the presence of chalcogen atoms and a cationic scaffold. The former efficiently enhanced the generation of reactive oxygen species (ROS), and the latter facilitated the ROS delivery to bacteria, resulting in their death. Interestingly, alkyl-modified photosensitizers showed higher antimicrobial activities than commonly reported photosensitizers with quaternary ammonium (QA) groups. In particular, the SeMV2+ ( 6 b ) with excellent antibacterial activities efficiently promoted the healing of infected wounds in mice. Simple yet novel, nontoxic and biocompatible chalcogenoviologens provided a promising strategy to develop new efficient photosensitizers for photodynamic antimicrobial therapy and skin regeneration. 相似文献
16.
Van‐Nghia Nguyen Yubin Yim Sangin Kim Bokyeong Ryu K. M. K. Swamy Gyoungmi Kim Nahyun Kwon C‐Yoon Kim Sungnam Park Juyoung Yoon 《Angewandte Chemie (International ed. in English)》2020,59(23):8957-8962
Novel BODIPY photosensitizers were developed for imaging‐guided photodynamic therapy. The introduction of a strong electron donor to the BODIPY core through a phenyl linker combined with the twisted arrangement between the donor and the BODIPY acceptor is essential for reducing the energy gap between the lowest singlet excited state and the lowest triplet state (ΔEST), leading to a significant enhancement in the intersystem crossing (ISC) of the BODIPYs. Remarkably, the BDP‐5 with the smallest ΔEST (ca. 0.44 eV) exhibited excellent singlet oxygen generation capabilities in both organic and aqueous solutions. BDP‐5 also displayed bright emission in the far‐red/near‐infrared region in the condensed states. More importantly, both in vitro and in vivo studies demonstrated that BDP‐5 NPs displayed a high potential for photodynamic cancer therapy and bioimaging. 相似文献
17.
Marta Jakubaszek Jeremie Rossier Johannes Karges Joachim Delasoie Bruno Goud Gilles Gasser Fabio Zobi 《Helvetica chimica acta》2019,102(7)
The current photosensitizers (PSs) for photodynamic therapy (PDT) lack selectivity for cancer cells. To tackle this drawback, in view of selective cancer delivery, we envisioned conjugating two ruthenium polypyridyl complexes to vitamin B12 (Cobalamin, Cbl) to take advantage of the solubility and active uptake of the latter. Ultimately, our results showed that the transcobalamin pathway is unlikely involved for the delivery of these ruthenium‐based PDT PSs, emphasizing the difficulty in successfully delivering metal complexes to cancer cells. 相似文献
18.
Phthalocyanine‐Assembled Nanodots as Photosensitizers for Highly Efficient Type I Photoreactions in Photodynamic Therapy 下载免费PDF全文
Dr. Xingshu Li Dayoung Lee Prof. Jian‐Dong Huang Prof. Juyoung Yoon 《Angewandte Chemie (International ed. in English)》2018,57(31):9885-9890
Owing to their unique, nanoscale related optical properties, nanostructures assembled from molecular photosensitizers (PSs) have interesting applications in phototheranostics. However, most nanostructured PS assemblies are super‐quenched, thus, preventing their use in photodynamic therapy (PDT). Although some of these materials undergo stimuli‐responsive disassembly, which leads to partial recovery of PDT activity, their therapeutic potentials are unsatisfactory owing to a limited ability to promote generation reactive oxygen species (ROS), especially via type I photoreactions (i.e., not by 1O2 generation). Herein we demonstrate that a new, nanostructured phthalocyanine assembly, NanoPcA, has the ability to promote highly efficient ROS generation via the type I mechanism. The results of antibacterial studies demonstrate that NanoPcA has potential PDT applications. 相似文献
19.
Yilin Liu Jie Zhao Xia Xu Yang Xu Wei Cui Yang Yang Prof. Dr. Junbai Li 《Angewandte Chemie (International ed. in English)》2023,62(33):e202308019
Two-photon-excited photodynamic therapy (TPE-PDT) has significant advantages over conventional photodynamic therapy (PDT). However, obtaining easily accessible TPE photosensitizers (PSs) with high efficiency remains a challenge. Herein, we demonstrate that emodin (Emo), a natural anthraquinone (NA) derivative, is a promising TPE PS with a large two-photon absorption cross-section (TPAC: 380.9 GM) and high singlet oxygen (1O2) quantum yield (31.9 %). When co-assembled with human serum albumin (HSA), the formed Emo/HSA nanoparticles (E/H NPs) possess a giant TPAC (4.02×107 GM) and desirable 1O2 generation capability, thus showing outstanding TPE-PDT properties against cancer cells. In vivo experiments reveal that E/H NPs exhibit improved retention time in tumors and can ablate tumors at an ultra-low dosage (0.2 mg/kg) under an 800 nm femtosecond pulsed laser irradiation. This work is beneficial for the use of natural extracts NAs for high-efficiency TPE-PDT. 相似文献
20.
Wen Chen Yuan Zhang Prof. Hai-Bo Yi Prof. Fenglin Wang Prof. Xia Chu Prof. Jian-Hui Jiang 《Angewandte Chemie (International ed. in English)》2023,62(17):e202300162
Type I photodynamic therapy (PDT) represents a promising treatment modality for tumors with intrinsic hypoxia. However, type I photosensitizers (PSs), especially ones with near infrared (NIR) absorption, are limited and their efficacy needs improvement via new targeting tactics. We develop a NIR type I PS by engineering acridinium derived donor-π-acceptor systems. The PS exhibits an exclusive type I PDT mechanism due to effective intersystem crossing and disfavored energy transfer to O2, and shows selective binding to G-quadruplexes (G4s) via hydrogen bonds identified by a molecular docking study. Moreover, it enables fluorogenic detection of G4s and efficient O2⋅− production in hypoxic conditions, leading to immunogenic cell death and substantial variations of gene expression in RNA sequencing. Our strategy demonstrates augmented antitumor immunity for effective ablation of immunogenic cold tumor, highlighting its potential of RNA-targeted type I PDT in precision cancer therapy. 相似文献