Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and Mechanochromism
Lipid-related cancers cause a large number of deaths worldwide. Therefore, development of highly efficient Lipid droplets (LDs) fluorescent imaging probes will be beneficial to our understanding of lipid-related cancers by allowing us to track the metabolic process of LDs. In this work, a LDs-specif...
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| Format: | Article |
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MDPI AG
2023-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/4/1814 |
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| author | Yongbo Wei Wei Liu Zexin Wang Nannan Chen Jingming Zhou Tong Wu Yuqiu Ye Yanbing Ke Hong Jiang Xin Zhai Lijun Xie |
| author_facet | Yongbo Wei Wei Liu Zexin Wang Nannan Chen Jingming Zhou Tong Wu Yuqiu Ye Yanbing Ke Hong Jiang Xin Zhai Lijun Xie |
| author_sort | Yongbo Wei |
| collection | DOAJ |
| description | Lipid-related cancers cause a large number of deaths worldwide. Therefore, development of highly efficient Lipid droplets (LDs) fluorescent imaging probes will be beneficial to our understanding of lipid-related cancers by allowing us to track the metabolic process of LDs. In this work, a LDs-specific NIR (<i>λ<sub>max</sub></i> = 698 nm) probe, namely BY1, was rationally designed and synthesized via a one-step reaction by integrating triphenylamine (electron–donor group) unit into the structure of rofecoxib. This integration strategy enabled the target BY1 to form a strong Donor–Acceptor (D-A) system and endowed BY1 with obvious aggregation-induced emission (AIE) effect. Meanwhile, BY1 also showed observable solvent effect and reversible mechanochromatic luminescent property, which could be interpreted clearly via density functional theory (DFT) calculations, differential scanning calorimetry (DSC), powder X-ray diffraction (XPRD), and single crystal X-ray data analysis. More importantly, BY1 exhibited highly specific fluorescent imaging ability (Pearson’s correlation = 0.97) towards lipid droplets in living HeLa cells with low cytotoxicity. These results demonstrated that BY1 is a new promising fluorescent probe for lipid droplets imaging, and it might be beneficial to facilitate biological research of lipid-related cancers. |
| first_indexed | 2024-03-11T08:21:16Z |
| format | Article |
| id | doaj.art-b9736a58483247e582b82c878032a15c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T08:21:16Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b9736a58483247e582b82c878032a15c2023-11-16T22:23:35ZengMDPI AGMolecules1420-30492023-02-01284181410.3390/molecules28041814Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and MechanochromismYongbo Wei0Wei Liu1Zexin Wang2Nannan Chen3Jingming Zhou4Tong Wu5Yuqiu Ye6Yanbing Ke7Hong Jiang8Xin Zhai9Lijun Xie10Fujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaKey Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaFujian Provincial Key Laboratory of Screening for Novel Microbial Proucts, Fujian Institute of Microbiology, Fuzhou 350007, ChinaLipid-related cancers cause a large number of deaths worldwide. Therefore, development of highly efficient Lipid droplets (LDs) fluorescent imaging probes will be beneficial to our understanding of lipid-related cancers by allowing us to track the metabolic process of LDs. In this work, a LDs-specific NIR (<i>λ<sub>max</sub></i> = 698 nm) probe, namely BY1, was rationally designed and synthesized via a one-step reaction by integrating triphenylamine (electron–donor group) unit into the structure of rofecoxib. This integration strategy enabled the target BY1 to form a strong Donor–Acceptor (D-A) system and endowed BY1 with obvious aggregation-induced emission (AIE) effect. Meanwhile, BY1 also showed observable solvent effect and reversible mechanochromatic luminescent property, which could be interpreted clearly via density functional theory (DFT) calculations, differential scanning calorimetry (DSC), powder X-ray diffraction (XPRD), and single crystal X-ray data analysis. More importantly, BY1 exhibited highly specific fluorescent imaging ability (Pearson’s correlation = 0.97) towards lipid droplets in living HeLa cells with low cytotoxicity. These results demonstrated that BY1 is a new promising fluorescent probe for lipid droplets imaging, and it might be beneficial to facilitate biological research of lipid-related cancers.https://www.mdpi.com/1420-3049/28/4/1814lipid droplets (LDs)aggregation-induced emission (AIE)near-infrared (NIR)solvatochromismrofecoxib |
| spellingShingle | Yongbo Wei Wei Liu Zexin Wang Nannan Chen Jingming Zhou Tong Wu Yuqiu Ye Yanbing Ke Hong Jiang Xin Zhai Lijun Xie Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and Mechanochromism Molecules lipid droplets (LDs) aggregation-induced emission (AIE) near-infrared (NIR) solvatochromism rofecoxib |
| title | Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and Mechanochromism |
| title_full | Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and Mechanochromism |
| title_fullStr | Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and Mechanochromism |
| title_full_unstemmed | Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and Mechanochromism |
| title_short | Facile Transformation from Rofecoxib to a New Near-Infrared Lipid Droplet Fluorescent Probe and Its Investigations on AIE Property, Solvatochromism and Mechanochromism |
| title_sort | facile transformation from rofecoxib to a new near infrared lipid droplet fluorescent probe and its investigations on aie property solvatochromism and mechanochromism |
| topic | lipid droplets (LDs) aggregation-induced emission (AIE) near-infrared (NIR) solvatochromism rofecoxib |
| url | https://www.mdpi.com/1420-3049/28/4/1814 |
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