Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging
Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system d...
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| Format: | Article |
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MDPI AG
2018-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/9/2290 |
| _version_ | 1818384529276010496 |
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| author | Liyan Liu Yaohui Lei Jianhui Zhang Na Li Fan Zhang Huaqiao Wang Feng He |
| author_facet | Liyan Liu Yaohui Lei Jianhui Zhang Na Li Fan Zhang Huaqiao Wang Feng He |
| author_sort | Liyan Liu |
| collection | DOAJ |
| description | Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (ФF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging. |
| first_indexed | 2024-12-14T03:23:42Z |
| format | Article |
| id | doaj.art-ea57275865a34b5189b95e79dd8c4924 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-14T03:23:42Z |
| publishDate | 2018-09-01 |
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| series | Molecules |
| spelling | doaj.art-ea57275865a34b5189b95e79dd8c49242022-12-21T23:18:58ZengMDPI AGMolecules1420-30492018-09-01239229010.3390/molecules23092290molecules23092290Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-ImagingLiyan Liu0Yaohui Lei1Jianhui Zhang2Na Li3Fan Zhang4Huaqiao Wang5Feng He6School of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, ChinaSchool of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, ChinaSchool of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, ChinaSchool of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, ChinaDepartment of Anatomy and Neurobiology, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou 510080, ChinaSchool of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, ChinaFluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (ФF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.http://www.mdpi.com/1420-3049/23/9/2290AIEEmulticolorflavonefluorophoresmitochondria |
| spellingShingle | Liyan Liu Yaohui Lei Jianhui Zhang Na Li Fan Zhang Huaqiao Wang Feng He Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging Molecules AIEE multicolor flavone fluorophores mitochondria |
| title | Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging |
| title_full | Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging |
| title_fullStr | Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging |
| title_full_unstemmed | Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging |
| title_short | Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging |
| title_sort | rational design for multicolor flavone based fluorophores with aggregation induced emission enhancement characteristics and applications in mitochondria imaging |
| topic | AIEE multicolor flavone fluorophores mitochondria |
| url | http://www.mdpi.com/1420-3049/23/9/2290 |
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