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Facile synthesis of ultrabright luminogens with specific lipid droplets targeting feature for in vivo two-photon fluorescence retina imaging
Institution:1. Department of Orthopaedic Surgery, The First Affiliated Hospital of Zhengzhou University, Zhengzhou 450052, China;2. Medical Research Center, Guangdong Provincial People''s Hospital, Guangdong Academy of Medical Sciences, Guangzhou 510080, China;3. School of Science and Engineering, Shenzhen Institute of Aggregate Science and Technology, The Chinese University of Hong Kong, Shenzhen 518172, China;4. Laboratory for Neuroscience in Health and Disease, Guangzhou First People''s Hospital, School of Medicine, South China University of Technology, Guangzhou 510180, China;5. School of Materials Science and Engineering, Sun Yat-sen University, Guangzhou 510275, China;1. Key Laboratory of Thermo-Fluid Science and Engineering of Ministry of Education, School of Energy and Power Engineering, Frontier Institute of Science and Technology, Xi''an Jiaotong University, Xi''an 710054, China;2. School of Chemistry, Xi''an Key Laboratory of Sustainable Energy Materials Chemistry, Xi''an Jiaotong University, Xi''an 710049, China;3. School of Materials Science and Engineering, Xi''an Jiaotong University, Xi''an 710049, China;1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China;2. Joint Institute of Tobacco and Health, Yunnan Academy of Tobacco Science, Kunming 650024, China;3. Wuhu Hospital Affiliated to East China Normal University (The Second People''s Hospital of Wuhu), Wuhu 241001, China;1. College of Chemistry and Environmental Science, Chemical Biology Key Laboratory of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Hebei University, Baoding 071002, China;2. CAS Key Laboratory for Biomedical Effects of Nanomaterials and Nanosafety, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology of China, Beijing 100190, China;3. Department of Chemistry, The University of Manchester, Manchester M13 9PL, United Kingdom;1. Xiangya School of Pharmaceutical Sciences, Central South University, Changsha 410013, China;2. Department of Pharmacy, Xiangya Hospital, Central South University, Changsha 410008, China;3. National Clinical Research Center for Geriatric Disorders, Xiangya Hospital, Central South University, Changsha 410008, China
Abstract:The application of fluorescent probes for in vivo retinal imaging is of great importance, which could provide direct and crucial imaging evidence for a better understanding of common eye diseases. Herein, a group of bright organic luminogens with typical electron-donating (D) and electron-accepting (A) structures (abbreviated as LDs-BDM, LDs-BTM, and LDs-BHM) was synthesized through a simple single-step reaction. They were found to be efficient solid-state emitters with high fluorescence quantum yields of above 70% (e.g., 83.7% for LDs-BTM). Their light-emission properties could be tuned by the modulation of π-conjugation effect with methoxy groups at different substituent positions. Their resulting fluorescent nanoparticles (NPs) were demonstrated as specific lipid droplets (LDs) targeting probes with high brightness, good biocompatibility, and satisfactory photostability. LDs-BTM NPs with a large two-photon absorption cross section (σ2 = 249 GM) were further utilized as ultrabright two-photon fluorescence (2PF) nanoprobes for in vivo retina imaging of live zebrafish by NIR excitation at an ultralow concentration (0.5 µmol/L). Integrated histological structures at the tissue level and corresponding fine details at the cellular level of the embryonic retina of live zebrafish were clearly demonstrated. This is the first report of using ultrabright LDs-targeting nanoprobes to accurately measure fine details in the retina with 2PF microscopic technique. These good results are anticipated to open up a new avenue in the development of efficient 2PF emitters for non-invasive bioimaging of living animals.
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