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Chen ZJ, Guo JL, Li Z, Zeng Y, Guo YT, Shen Q, Wang ZY. Rational design of dual-state emission fluorophores for sensing nitro explosives by using sulfone unit as an electron acceptor in D-A system. SPECTROCHIMICA ACTA. PART A, MOLECULAR AND BIOMOLECULAR SPECTROSCOPY 2025; 337:126105. [PMID: 40147394 DOI: 10.1016/j.saa.2025.126105] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Received: 01/13/2025] [Revised: 03/12/2025] [Accepted: 03/21/2025] [Indexed: 03/29/2025]
Abstract
Dual-state emission (DSE) fluorescent molecules have become the preferred type in designing sensing fluorescent molecules due to the virtue of their bright emission in both solid and liquid states. In this study, five D-A molecules were successfully designed and synthesized according to the design concept that structural modification of D-A molecules can lead to DSE molecules. Among them, the balance between the electron donor with a strong electron donation capacity and the twisted conformation in the whole molecule makes the compounds 3c-3e DSE molecules with excellent optical performances, showing significant solvatochromic effects and large Stoke shifts. In addition, the feasibility of the sulfone unit as an electron acceptor in the D-A structure is also verified, extending the application of sulfone group in the field of fluorescence. Interestingly, the fluorescence of 3c can exhibit sensitive and selective quenching of nitro aromatic compounds (NACs) under the synergistic mechanism of fluorescence resonance energy transfer (FRET) and photoinduced electron transfer (PET), with LOD as low as 10-8 M and KSV as high as 104 M-1. Furthermore, the selective, efficient, and sensitive detection of NACs by DSE fluorescent molecule 3c in real aqueous samples and loaded on test strips has demonstrated the potential of its practical applications.
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Affiliation(s)
- Zu-Jia Chen
- School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, Guangdong 510006, PR China
| | - Ji-Lin Guo
- School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, Guangdong 510006, PR China
| | - Zong Li
- School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, Guangdong 510006, PR China
| | - Yong Zeng
- School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, Guangdong 510006, PR China
| | - Yu-Ting Guo
- School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, Guangdong 510006, PR China
| | - Qing Shen
- School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, Guangdong 510006, PR China
| | - Zhao-Yang Wang
- School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, Guangdong 510006, PR China.
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2
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Zhou R, Liu G, Fu S, Zheng H, Li D, Dai J, Wei J, Li B, Wang C, Lu G. Labeling selectivity of lipid droplets fluorescent probes: Twisted intramolecular charge transfer (TICT) vs intramolecular charge transfer (ICT). Biosens Bioelectron 2024; 264:116624. [PMID: 39121616 DOI: 10.1016/j.bios.2024.116624] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/28/2024] [Revised: 07/16/2024] [Accepted: 07/31/2024] [Indexed: 08/12/2024]
Abstract
Fluorescence imaging technology is a versatile and essential tool in the field of biomedical research. To obtain excellent imaging results, the precise labeling of fluorescent probes is an important prerequisite. Nevertheless, the labeling selectivity of most fluorescent probes is not satisfactory, new design concepts are desperately needed. In this context, two isomeric lipid droplets (LDs) fluorescent probes Lipi-Cz-1 and Lipi-Cz-2 have been sophisticatedly developed with TICT and ICT-emitting characteristic, respectively. The more environmentally sensitive TICT-emitting Lipi-Cz-1 exhibits a significantly enhanced labeling selectivity in LDs imaging compared to the ICT-emitting Lipi-Cz-2, sufficiently illustrating the effectiveness of TICT-emitting characteristic in improving labeling selectivity. Additionally, Lipi-Cz-1 displays high photostability and biocompatibility. These advantages enable Lipi-Cz-1 to be finely applied in multimode fluorescence imaging, e.g. time-lapse 3D confocal imaging to monitor changes of the number and size of LDs during starvation, two-photon 3D imaging to compare the variations of LDs in various liver tissues, and STED super-resolution imaging to visualize the nanoscale LDs with the resolution of 65 nm. Overall, these imaging findings validate the effectiveness of the new strategy for improving the labeling selectivity.
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Affiliation(s)
- Ri Zhou
- College of Materials Science and Engineering, Jilin University, Changchun, 130012, China; State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Guannan Liu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Shengjie Fu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Huanlong Zheng
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Di Li
- College of Materials Science and Engineering, Jilin University, Changchun, 130012, China.
| | - Jianan Dai
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China.
| | - Jinbei Wei
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Bai Li
- Department of Colorectal & Anal Surgery, General Surgery Center, The First Hospital of Jilin University, Jilin University, Changchun, 130021, China.
| | - Chenguang Wang
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Geyu Lu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
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3
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Zuo Y, Gou Z, Lin W. Polymeric microenvironment enhancing polarity response sensitivity for discriminating lipid droplets in cancer cells. Anal Chim Acta 2024; 1297:342330. [PMID: 38438225 DOI: 10.1016/j.aca.2024.342330] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/30/2023] [Revised: 01/17/2024] [Accepted: 02/02/2024] [Indexed: 03/06/2024]
Abstract
Cellular micro-environment analysis via fluorescence probe has become a powerful method to explore the early-stage cancer diagnosis and pathophysiological process of relevant diseases. The polarity change of intracellular lipid droplets (LDs) is closely linked with disorders or diseases, which result in various physiological and pathological processes. However, the efficient design strategy for lipid droplet polarity probes with high sensitivity is lacking. To overcome this difficulty, two kinds of LDs-targeting and polarity-sensitive fluorescent probes containing carbazole and siloxane groups were rationally designed and synthesized. With the carbazole-based rotor and bridge-like siloxanes, two probes (P1 and P2) behave high sensitivity to polarity changes and show different fluorescent intensity in normal and cancer cells. Notably, polysiloxanes groups promoted the response sensitivity of the probes dramatically for the polymeric microenvironment. In addition, due to the polarity changes of LDs in cancer cells, the distinct fluorescent intensities in different channels of laser scanning confocal microscope were observed between NHA cell and U87 cells. This work could offer an opportunity to monitor the dynamic behaviors of LDs and further provide a powerful tool to be potentially applied in the early-stage diagnosis of cancer.
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Affiliation(s)
- Yujing Zuo
- Institute of Fluorescent Probes for Biological Imaging, School of Materials Science and Engineering, School of Chemistry and Chemical Engineering, University of Jinan, Shandong, 250022, PR China
| | - Zhiming Gou
- Institute of Fluorescent Probes for Biological Imaging, School of Materials Science and Engineering, School of Chemistry and Chemical Engineering, University of Jinan, Shandong, 250022, PR China
| | - Weiying Lin
- Institute of Fluorescent Probes for Biological Imaging, School of Materials Science and Engineering, School of Chemistry and Chemical Engineering, University of Jinan, Shandong, 250022, PR China; Institute of Optical Materials and Chemical Biology, Guangxi Key Laboratory of Electrochemical Energy Materials, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi, 530004, PR China.
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4
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Wang K, Wen XL, Chen XY, Yue Y, Yang YS, Zhu HL, Wang MY, Jiang HX. Promoting In Vivo NIR-II Fluorescent Imaging for Lipid in Lipid Metabolism Diseases Diagnosis. Anal Chem 2024; 96:2264-2272. [PMID: 38266388 DOI: 10.1021/acs.analchem.3c05676] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/26/2024]
Abstract
Lipid metabolism diseases have become a tremendous risk worldwide, along with the development of productivity and particular attention to public health. It has been an urgent necessity to exploit reliable imaging strategies for lipids and thus to monitor fatty liver diseases. Herein, by converting the NIR-I signal to the NIR-II signal with IR1061 for the monitoring of lipid, the in vivo imaging of fatty liver disease was promoted on the contrast and visual effect. The main advantages of the imaging promotion in this work included a long emission wavelength, rapid response, and high signal-background-ratio (SBR) value. After promoting the NIR-I signal to NIR-II signal, IR1061 achieved higher SBR value and exhibited a dose-dependent fluorescence intensity at 1100 nm along with the increase of the EtOH proportion as well as steady and selective optical responses toward liposomes. IR1061 was further applied in the in vivo imaging of lipid in fatty liver diseases. In spite of the differences in body weight gain and TC level between healthy mice and fatty liver diseases two models, IR1061 achieved high-resolution imaging in the liver region to monitor the fatty liver disease status. This work might be informatic for the clinical diagnosis and therapeutical treatments of fatty liver diseases.
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Affiliation(s)
- Kai Wang
- Affiliated Children's Hospital of Jiangnan University, Wuxi 214023, China
- State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210023, China
| | - Xiao-Lin Wen
- Affiliated Children's Hospital of Jiangnan University, Wuxi 214023, China
| | - Xu-Yang Chen
- Affiliated Children's Hospital of Jiangnan University, Wuxi 214023, China
- State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210023, China
| | - Ying Yue
- Affiliated Children's Hospital of Jiangnan University, Wuxi 214023, China
| | - Yu-Shun Yang
- State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210023, China
| | - Hai-Liang Zhu
- State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210023, China
| | - Miao-Yan Wang
- Affiliated Children's Hospital of Jiangnan University, Wuxi 214023, China
| | - Hao-Xiang Jiang
- Affiliated Children's Hospital of Jiangnan University, Wuxi 214023, China
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5
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Liu G, Zheng H, Zhou R, Li H, Dai J, Wei J, Li D, Meng X, Wang C, Lu G. Ultrabright organic fluorescent probe for quantifying the dynamics of cytosolic/nuclear lipid droplets. Biosens Bioelectron 2023; 241:115707. [PMID: 37783066 DOI: 10.1016/j.bios.2023.115707] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/18/2023] [Revised: 09/15/2023] [Accepted: 09/21/2023] [Indexed: 10/04/2023]
Abstract
Lipid droplets (LDs) are extremely active organelles that play a crucial role in energy metabolism, membrane formation, and the production of lipid-derived signaling molecules by regulating lipid storage and release. Nevertheless, directly limited by the lack of superior fluorescent probes, studies of LDs dynamic motion velocity have been rarely reported, especially for nuclear LDs. Herein, a novel organic fluorescent probe Lipi-Bright has been rationally developed based on bridged cyclization of distyrylbenzene. The fully ring-fused molecule structure endows the probe with high photostability. Moreover, this new fluorescent probe displays the features of excellent LDs staining specificity as well as ultrahigh fluorescence brightness. Lipi-Bright labeled LDs was dozens of times brighter than representative probes BODIPY 493/503 or Nile Red. Consequently, by in-situ time-lapse fluorescence imaging, the dynamics of LDs have been quantitatively studied. For instance, the velocities of cytosolic LDs (37 ± 15 nm/s) are found to be obviously faster than those of nuclear LDs (24 ± 4 nm/s), and both the cytosolic LDs and the nuclear LDs would be moved faster or slower depend on the various stimulations. Overall, this work providing plentiful information on LDs dynamics will greatly facilitate the in-depth investigation of lipid metabolism.
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Affiliation(s)
- Guannan Liu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Huanlong Zheng
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Ri Zhou
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China.
| | - Huaiyu Li
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Jianan Dai
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Jinbei Wei
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
| | - Di Li
- College of Materials Science and Engineering, Jilin University, Changchun, 130012, China
| | - Xing Meng
- School of Medical Engineering and Technology, Xinjiang Medical University, Urumqi, 830017, China
| | - Chenguang Wang
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China.
| | - Geyu Lu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science and Engineering, Jilin University, Changchun, 130012, China
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Samanta S, Lai K, Wu F, Liu Y, Cai S, Yang X, Qu J, Yang Z. Xanthene, cyanine, oxazine and BODIPY: the four pillars of the fluorophore empire for super-resolution bioimaging. Chem Soc Rev 2023; 52:7197-7261. [PMID: 37743716 DOI: 10.1039/d2cs00905f] [Citation(s) in RCA: 31] [Impact Index Per Article: 15.5] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 09/26/2023]
Abstract
In the realm of biological research, the invention of super-resolution microscopy (SRM) has enabled the visualization of ultrafine sub-cellular structures and their functions in live cells at the nano-scale level, beyond the diffraction limit, which has opened up a new window for advanced biomedical studies to unravel the complex unknown details of physiological disorders at the sub-cellular level with unprecedented resolution and clarity. However, most of the SRM techniques are highly reliant on the personalized special photophysical features of the fluorophores. In recent times, there has been an unprecedented surge in the development of robust new fluorophore systems with personalized features for various super-resolution imaging techniques. To date, xanthene, cyanine, oxazine and BODIPY cores have been authoritatively utilized as the basic fluorophore units in most of the small-molecule-based organic fluorescent probe designing strategies for SRM owing to their excellent photophysical characteristics and easy synthetic acquiescence. Since the future of next-generation SRM studies will be decided by the availability of advanced fluorescent probes and these four fluorescent building blocks will play an important role in progressive new fluorophore design, there is an urgent need to review the recent advancements in designing fluorophores for different SRM methods based on these fluorescent dye cores. This review article not only includes a comprehensive discussion about the recent developments in designing fluorescent probes for various SRM techniques based on these four important fluorophore building blocks with special emphasis on their effective integration into live cell super-resolution bio-imaging applications but also critically evaluates the background of each of the fluorescent dye cores to highlight their merits and demerits towards developing newer fluorescent probes for SRM.
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Affiliation(s)
- Soham Samanta
- Center for Biomedical Optics and Photonics & Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
| | - Kaitao Lai
- Center for Biomedical Optics and Photonics & Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
| | - Feihu Wu
- Center for Biomedical Optics and Photonics & Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
| | - Yingchao Liu
- Center for Biomedical Optics and Photonics & Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
| | - Songtao Cai
- Center for Biomedical Optics and Photonics & Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
| | - Xusan Yang
- Institute of Physics, Chinese Academy of Sciences, Beijing, 100190, China
| | - Junle Qu
- Center for Biomedical Optics and Photonics & Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
| | - Zhigang Yang
- Center for Biomedical Optics and Photonics & Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China.
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7
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Si-Jia W, Peng-Yuan L, Hang Z, Lei S, Dong L, Guang-Yue L. TDDFT study on the simultaneous sensing mechanism for peroxynitrite and glutathione by a bifunctional fluorescent probe. SPECTROCHIMICA ACTA. PART A, MOLECULAR AND BIOMOLECULAR SPECTROSCOPY 2023; 291:122314. [PMID: 36621031 DOI: 10.1016/j.saa.2022.122314] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Received: 08/23/2022] [Revised: 12/03/2022] [Accepted: 12/31/2022] [Indexed: 06/17/2023]
Abstract
Using time-dependent density functional theory (TDDFT) method, the response mechanism of a reported bifunctional fluorescent probe for simultaneous recognition of peroxynitrite and glutathione (Chem. Commun. 2018, 54, 11336) was theoretically studied. Calculated vertical excitation energies based on the ground-state and excited-state geometries were consistent with the corresponding experimental ultraviolet-visible and fluorescence spectra. In the ground state, electron delocalization in the probe was limited because its geometry was restrained by steric hindrance. Frontier molecular orbital analysis has shown that the probe should undergo photoinduced electron transfer (PET) from the benzothiazole moiety to the maleimide moiety after excitation. The nonplanar structure together with PET led to fluorescence quenching of the probe. The probe could be dealkylated by peroxynitrite anion. The resulting intramolecular hydrogen bond increasesd the planarity of the molecule, while also gave rise to an excited-state proton-transfer process. Moreover, the addition reaction between the probe and glutathione inhibited the PET process. These two analytes together contributed to the fluorescence enhancement of the final product. This theoretical sensing mechanism for peroxynitrite and glutathione may potentially be important for the design and enhancement of novel probes.
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Affiliation(s)
- Wang Si-Jia
- College of Chemical Engineering, North China University of Science and Technology, Tangshan 063210, PR China
| | - Li Peng-Yuan
- College of Chemical Engineering, North China University of Science and Technology, Tangshan 063210, PR China
| | - Zhang Hang
- Modern Technology and Education Centre, North China University of Science and Technology, Tangshan 063210, PR China
| | - Shi Lei
- College of Chemical Engineering, North China University of Science and Technology, Tangshan 063210, PR China
| | - Liu Dong
- College of Chemical Engineering, North China University of Science and Technology, Tangshan 063210, PR China.
| | - Li Guang-Yue
- College of Chemical Engineering, North China University of Science and Technology, Tangshan 063210, PR China.
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8
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Feng Z, Zhang D, Guo H, Su W, Tian Y, Tian X. Lighting up RNA-specific multi-photon and super-resolution imaging using a novel zinc complex. NANOSCALE 2023; 15:5486-5493. [PMID: 36852659 DOI: 10.1039/d2nr05392f] [Citation(s) in RCA: 5] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/18/2023]
Abstract
Ribonucleic acid (RNA) probes are critical for understanding the role of RNA dynamics in cellular function but are in short supply due to the lack of optimized imaging systems and excellent fluorescence emission performance. Here, the terpyridine Zn(II) complex (Zn-T) with D-π-A configuration and bright aggregation-induced fluorescence emission (AIE) has been fabricated for the selective detection and real-time monitoring of RNA. Impressively, Zn-T exhibits a large Stokes shift and three-photon absorption (3PA) activity and responds specifically through hydrophobic interactions with an RNA pocket. The combination of AIE-assisted two-photon fluorescence and stimulated emission depletion (STED) microscopy of Zn-T for imaging nuclear RNA has higher spatial resolution and brightness, thus providing an imaging platform for studying RNA-related physiological or pathological processes.
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Affiliation(s)
- Zhihui Feng
- Huaxi MR Research Centre (HMRRC), Functional and Molecular Imaging Key Laboratory of Sichuan Province, Department of Radiology and National Clinical Research Center for Geriatrics, West China Hospital of Sichuan University, Chengdu 610000, Sichuan Province, China.
| | - Dongxue Zhang
- Huaxi MR Research Centre (HMRRC), Functional and Molecular Imaging Key Laboratory of Sichuan Province, Department of Radiology and National Clinical Research Center for Geriatrics, West China Hospital of Sichuan University, Chengdu 610000, Sichuan Province, China.
- Equipment and Material Department, West China Hospital, Sichuan University, Chengdu, China
| | - Hui Guo
- College of Chemistry and Chemical Engineering, Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Institutes of Physical Science and Information Technology, Anhui University, Hefei, 230601, P.R. China
| | - Wenqing Su
- College of Chemistry and Chemical Engineering, Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Institutes of Physical Science and Information Technology, Anhui University, Hefei, 230601, P.R. China
| | - Yupeng Tian
- College of Chemistry and Chemical Engineering, Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Institutes of Physical Science and Information Technology, Anhui University, Hefei, 230601, P.R. China
| | - Xiaohe Tian
- Huaxi MR Research Centre (HMRRC), Functional and Molecular Imaging Key Laboratory of Sichuan Province, Department of Radiology and National Clinical Research Center for Geriatrics, West China Hospital of Sichuan University, Chengdu 610000, Sichuan Province, China.
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9
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Huang H, Bu Y, Yu ZP, Rong M, Li R, Wang Z, Zhang J, Zhu X, Wang L, Zhou H. Solvatochromic Two-Photon Fluorescent Probe Enables In Situ Lipid Droplet Multidynamics Tracking for Nonalcoholic Fatty Liver and Inflammation Diagnoses. Anal Chem 2022; 94:13396-13403. [PMID: 36136967 DOI: 10.1021/acs.analchem.2c01960] [Citation(s) in RCA: 19] [Impact Index Per Article: 6.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/08/2023]
Abstract
Intracellular lipid storage and regulation occur in lipid droplets, which are of great significance to the physiological activities of cells. Herein, a lipid droplet-specific fluorescence probe (lip-YB) with a high quantum yield (QYlip-YB = 73.28%), excellent photostability, and quickly polarity sensitivity was constructed successfully. Interestingly, lip-YB exhibited remarkable two-photon (TP) characteristics, which first realized real-time monitoring of the lipid droplet multidynamics process, diagnosing nonalcoholic fatty liver disease (NAFLD) and inflammation in living mice via TP fluorescence imaging. It is found that the as-prepared lip-YB provides a new avenue to design lipid droplet-specific imaging probes, clarifies its roles and mechanisms in cell metabolism, and can timely intervene in lipid droplet-related diseases during various physiological and pathological processes.
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Affiliation(s)
- Houshi Huang
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Yingcui Bu
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Zhi-Peng Yu
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Mengtao Rong
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Rui Li
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Zhijie Wang
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Jie Zhang
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Xiaojiao Zhu
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Lianke Wang
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
| | - Hongping Zhou
- School of Chemistry and Chemical Engineering, Institute of Physical Science and Information Technology, College of Life Science, Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education, Hefei 230601, P. R. China
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10
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Peng G, Dai J, Zhou R, Liu G, Liu X, Yan X, Liu F, Sun P, Wang C, Lu G. Highly Efficient Red/NIR-Emissive Fluorescent Probe with Polarity-Sensitive Character for Visualizing Cellular Lipid Droplets and Determining Their Polarity. Anal Chem 2022; 94:12095-12102. [PMID: 36006461 DOI: 10.1021/acs.analchem.2c02077] [Citation(s) in RCA: 25] [Impact Index Per Article: 8.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/19/2022]
Abstract
Lipid droplets (LDs), which are ubiquitous organelles existing in almost all eukaryotic cells, have attracted a lot of attention in the field of cell biology over the last decade. For the biological study of LDs via fluorescence imaging, the superior LD fluorescent probes with environmental polarity-sensitive character are highly desired and powerful but are very scarce. Herein, we have newly developed such a kind of fluorescent probe named LDs-Red which enables us to visualize LDs and to further reveal their polarity information. This fluorescent probe displays the advantages of intense red/near-infrared emission, high LD staining specificity, and good photostability; thus, it would be very useful for LD fluorescence imaging application. As a result, the three-dimensional confocal imaging to visualize spatial distribution of LDs and the multicolor confocal imaging to simultaneously observe LDs and other cellular organelles have been realized using this new LD fluorescent probe. Furthermore, the polarity-sensitive emission character of this probe enables us to quantitatively determine the LD polarity via spectral scan imaging. Consequently, the cancer cells (HepG2, HeLa, and Panc02) displaying lower polarity of LDs than the normal cells (L929, U251, and HT22) have been systematically demonstrated. In addition, this polarity-sensitive probe displaying shorter fluorescence wavelengths in cancer cells than in normal cells has an important and potential ability to distinguish them.
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Affiliation(s)
- Guishan Peng
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Jianan Dai
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Ri Zhou
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Guannan Liu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Xiaomin Liu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Xu Yan
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Fangmeng Liu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Peng Sun
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Chenguang Wang
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China
| | - Geyu Lu
- State Key Laboratory of Integrated Optoelectronics, Key Laboratory of Advanced Gas Sensors of Jilin Province, College of Electronic Science & Engineering, Jilin University, Changchun 130012, China.,International Center of Future Science, Jilin University, Changchun 130012, China
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11
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Wang S, Zhou M, Chen L, Ren M, Bu Y, Wang J, Yu ZP, Zhu X, Zhang J, Wang L, Zhou H. Polarity-Sensitive Probe: Dual-Channel Visualization of the "Chameleon" Migration with the Assistance of Reactive Oxygen Species. ACS APPLIED BIO MATERIALS 2022; 5:3554-3562. [PMID: 35797702 DOI: 10.1021/acsabm.2c00488] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
Abstract
The real-time and differentiated visualization of the organelles is favorable for exploring the distribution and interaction. However, most visual probes emit monochromatic fluorescence and target a single organelle, which impedes the in-depth study of their interplay. To overcome this obstacle, we tactfully conceived a polarity-sensitive fluorescent DPDO-C that could accurately discriminate polarity changes in the cellular environment, exhibiting distinct fluorescence in lipid droplets (LDs) and mitochondria. Remarkably, the probe DPDO-C could migrate from mitochondria to LDs with the assistance of reactive oxygen species, which was conducive to further monitoring of the number and size of LDs as well as the interactions between LDs and other organelles. Moreover, the nuanced difference between normal and fatty liver tissues was also distinguished by two-color fluorescence imaging, which could act as a promising candidate for the early diagnosis of fatty liver.
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Affiliation(s)
- Shengnan Wang
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Minghua Zhou
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Lei Chen
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Mengjuan Ren
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Yingcui Bu
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Junjun Wang
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Zhi-Peng Yu
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Xiaojiao Zhu
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Jie Zhang
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Lianke Wang
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
| | - Hongping Zhou
- College of Chemistry and Chemical Engineering in Anhui University and Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University) Ministry of Education; Faculty of Health Sciences, Institute of Physical Science and Information Technology, Anhui University, 230039 Hefei, China
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