Tuning Organelle Specificity and Photodynamic Therapy Efficiency by Molecular Function Design
Efficient organic photosensitizers (PSs) have attracted much attention because of their promising applications in photodynamic therapy (PDT). However, guidelines on their molecular design are rarely reported. In this work, a series of PSs are designed and synthesized based on a triphenylamine-azaflu...
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| Published in | ACS nano Vol. 13; no. 10; pp. 11283 - 11293 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
22.10.2019
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Efficient organic photosensitizers (PSs) have attracted much attention because of their promising applications in photodynamic therapy (PDT). However, guidelines on their molecular design are rarely reported. In this work, a series of PSs are designed and synthesized based on a triphenylamine-azafluorenone core. Their structure–property-application relationships are systematically studied. Cationization is an effective strategy to enhance the PDT efficiency of PSs by targeting mitochondria. From the molecularly dispersed state to the aggregate state, the fluorescence and the reactive oxygen species generation efficiency of PSs with aggregation-induced emission (AIE) increase due to the restriction of the intramolecular motions and enhancement of intersystem crossing. Cationized mitochondrion-targeting PSs show higher PDT efficiency than that of nonionized ones targeting lipid droplets. The ability of AIE PSs to kill cancer cells can be further enhanced by combination of PDT with radiotherapy. Such results should trigger research enthusiasm for designing and synthesizing AIE PSs with better PDT efficiency and properties. |
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| AbstractList | Efficient organic photosensitizers (PSs) have attracted much attention because of their promising applications in photodynamic therapy (PDT). However, guidelines on their molecular design are rarely reported. In this work, a series of PSs are designed and synthesized based on a triphenylamine-azafluorenone core. Their structure–property-application relationships are systematically studied. Cationization is an effective strategy to enhance the PDT efficiency of PSs by targeting mitochondria. From the molecularly dispersed state to the aggregate state, the fluorescence and the reactive oxygen species generation efficiency of PSs with aggregation-induced emission (AIE) increase due to the restriction of the intramolecular motions and enhancement of intersystem crossing. Cationized mitochondrion-targeting PSs show higher PDT efficiency than that of nonionized ones targeting lipid droplets. The ability of AIE PSs to kill cancer cells can be further enhanced by combination of PDT with radiotherapy. Such results should trigger research enthusiasm for designing and synthesizing AIE PSs with better PDT efficiency and properties. Efficient organic photosensitizers (PSs) have attracted much attention because of their promising applications in photodynamic therapy (PDT). However, guidelines on their molecular design are rarely reported. In this work, a series of PSs are designed and synthesized based on a triphenylamine-azafluorenone core. Their structure-property-application relationships are systematically studied. Cationization is an effective strategy to enhance the PDT efficiency of PSs by targeting mitochondria. From the molecularly dispersed state to the aggregate state, the fluorescence and the reactive oxygen species generation efficiency of PSs with aggregation-induced emission (AIE) increase due to the restriction of the intramolecular motions and enhancement of intersystem crossing. Cationized mitochondrion-targeting PSs show higher PDT efficiency than that of nonionized ones targeting lipid droplets. The ability of AIE PSs to kill cancer cells can be further enhanced by combination of PDT with radiotherapy. Such results should trigger research enthusiasm for designing and synthesizing AIE PSs with better PDT efficiency and properties.Efficient organic photosensitizers (PSs) have attracted much attention because of their promising applications in photodynamic therapy (PDT). However, guidelines on their molecular design are rarely reported. In this work, a series of PSs are designed and synthesized based on a triphenylamine-azafluorenone core. Their structure-property-application relationships are systematically studied. Cationization is an effective strategy to enhance the PDT efficiency of PSs by targeting mitochondria. From the molecularly dispersed state to the aggregate state, the fluorescence and the reactive oxygen species generation efficiency of PSs with aggregation-induced emission (AIE) increase due to the restriction of the intramolecular motions and enhancement of intersystem crossing. Cationized mitochondrion-targeting PSs show higher PDT efficiency than that of nonionized ones targeting lipid droplets. The ability of AIE PSs to kill cancer cells can be further enhanced by combination of PDT with radiotherapy. Such results should trigger research enthusiasm for designing and synthesizing AIE PSs with better PDT efficiency and properties. |
| Author | Lam, Jacky W. Y Zou, Hang Shan, Guo-Gang Kwok, Ryan T. K Zhang, Pengfei Liu, Zhiyang Zheng, Lei Zhao, Zheng Tang, Ben Zhong |
| AuthorAffiliation | Guangdong Key Laboratory of Nanomedicine, Shenzhen, Engineering Laboratory of Nanomedicine and Nanoformulations, CAS Key Lab for Health Informatics HKUST Shenzhen Research Institute Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Division of Life Science and State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, Department of Chemical and Biological Engineering and Institute for Advanced Study Department of Laboratory Medicine, Nanfang Hospital Center for Aggregation-Induced Emission, SCUT-HKUST Joint Research Institute, State Key Laboratory of Luminescent Materials and Devices Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences |
| AuthorAffiliation_xml | – name: HKUST Shenzhen Research Institute – name: Department of Laboratory Medicine, Nanfang Hospital – name: Center for Aggregation-Induced Emission, SCUT-HKUST Joint Research Institute, State Key Laboratory of Luminescent Materials and Devices – name: Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Division of Life Science and State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, Department of Chemical and Biological Engineering and Institute for Advanced Study – name: Guangdong Key Laboratory of Nanomedicine, Shenzhen, Engineering Laboratory of Nanomedicine and Nanoformulations, CAS Key Lab for Health Informatics – name: Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences |
| Author_xml | – sequence: 1 givenname: Zhiyang orcidid: 0000-0002-5522-2853 surname: Liu fullname: Liu, Zhiyang organization: HKUST Shenzhen Research Institute – sequence: 2 givenname: Hang surname: Zou fullname: Zou, Hang organization: Department of Laboratory Medicine, Nanfang Hospital – sequence: 3 givenname: Zheng surname: Zhao fullname: Zhao, Zheng organization: Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Division of Life Science and State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, Department of Chemical and Biological Engineering and Institute for Advanced Study – sequence: 4 givenname: Pengfei surname: Zhang fullname: Zhang, Pengfei organization: Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences – sequence: 5 givenname: Guo-Gang surname: Shan fullname: Shan, Guo-Gang organization: Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Division of Life Science and State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, Department of Chemical and Biological Engineering and Institute for Advanced Study – sequence: 6 givenname: Ryan T. K orcidid: 0000-0002-6866-3877 surname: Kwok fullname: Kwok, Ryan T. K organization: Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Division of Life Science and State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, Department of Chemical and Biological Engineering and Institute for Advanced Study – sequence: 7 givenname: Jacky W. Y surname: Lam fullname: Lam, Jacky W. Y organization: Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Division of Life Science and State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, Department of Chemical and Biological Engineering and Institute for Advanced Study – sequence: 8 givenname: Lei surname: Zheng fullname: Zheng, Lei email: nfyyzhenglei@smu.edu.cn organization: Department of Laboratory Medicine, Nanfang Hospital – sequence: 9 givenname: Ben Zhong orcidid: 0000-0002-0293-964X surname: Tang fullname: Tang, Ben Zhong email: tangbenz@ust.hk organization: Center for Aggregation-Induced Emission, SCUT-HKUST Joint Research Institute, State Key Laboratory of Luminescent Materials and Devices |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31525947$$D View this record in MEDLINE/PubMed |
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| Snippet | Efficient organic photosensitizers (PSs) have attracted much attention because of their promising applications in photodynamic therapy (PDT). However,... |
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| Title | Tuning Organelle Specificity and Photodynamic Therapy Efficiency by Molecular Function Design |
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