文献类型：期刊文献

英文题名：Stable, Bright, and Long-Fluorescence-Lifetime Dyes for Deep-Near-Infrared Bioimaging

作者：Li, Jin[1,2];Dong, Yan[1,2];Wei, Ruwei[1,2];Jiang, Guanyu[3];Yao, Cheng[1,2];Lv, Meng[3];Wu, Yuyang[4];Gardner, Sarah H.[5,6];Zhang, Feng[7];Lucero, Melissa Y.[5,6];Huang, Jian[8];Chen, Hao[4];Ge, Guangbo[7];Chan, Jefferson[5,6];Chen, Jinquan[3];Sun, Haitao[3];Luo, Xiao[1,2];Qian, Xuhong[1,2,9];Yang, Youjun[1,2]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Me, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Me, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[3]East China Normal Univ, Sch Phys & Elect Sci, State Key Lab Precis Spect, Shanghai 200241, Peoples R China;[4]Chinese Acad Sci, Mol Imaging Ctr, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China;[5]Univ Illinois, Dept Chem, Urbana, IL 61801 USA;[6]Univ Illinois, Beckman Inst Adv Sci & Technol, Urbana, IL 61801 USA;[7]Shanghai Univ Tradit Chinese Med, Shanghai Frontiers Sci Ctr Chinese Med Chem Biol, Inst Interdisciplinary Integrat Med Res, Shanghai 201203, Peoples R China;[8]Shanghai Inst Food & Drug Control, Pharmacol & Toxicol Div, Shanghai 201203, Peoples R China;[9]East China Normal Univ, Sch Chem & Mol Engn, Shanghai 200241, Peoples R China

年份：2022

卷号：144

期号：31

起止页码：14351

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20223412606767);WOS:【SCI-EXPANDED(收录号:WOS:000933409300001)】；

基金：This work was supported by the National Natural Science Foundation of China (Nos. 21822805, 21908065, 12034008, 91850202, 21873030, 11674101, 81922070, and 22078098), the China Postdoctoral Science Foundation (Nos. 2019M651427 and 2020T130197), Shanghai Rising-Star Program (No. 21QA1402600), the Research Fund of Happiness Flower ECNU (2020JK2103), and Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission).

语种：英文

外文关键词：Biocompatibility - Chlorine compounds - Fluorophores - Infrared devices - Medical applications - Photobleaching - Scaffolds - Scaffolds (biology)

摘要：Near-infrared (NIR) fluorophores absorbing maximally in the region beyond 800 nm, i.e., deep-NIR spectral region, are actively sought for biomedical applications. Ideal dyes are bright, nontoxic, photostable, biocompatible, and easily derivatized to introduce functionalities (e.g., for bioconjugation or aqueous solubility). The rational design of such fluorophores remains a major challenge. Silicon-substituted rhodamines have been successful for bioimaging applications in the red spectral region. The longer-wavelength silicon-substituted congeners for the deep-NIR spectral region are unknown to date. We successfully prepared four silicon-substituted bis-benzannulated rhodamine dyes (ESi5a-ESi5d), with an efficient five-step cascade on a gram-scale. Because of the extensive overlapping of their HOMO-LUMO orbitals, ESi5a-ESi5d are highly absorbing (lambda(abs) approximate to 865 nm and epsilon > 10(5) cm(-1) M-1). By restraining both the rotational freedom via annulation and the vibrational freedom via silicon-imparted strain, the fluorochromic scaffold of ESi5 is highly rigid, resulting in an unusually long fluorescence lifetime (tau > 700 ps in CH2Cl2) and a high fluorescence quantum yield (phi = 0.14 in CH2Cl2). Their half-lives toward photobleaching are 2 orders of magnitude longer than the current standard (ICG in serum). They are stable in the presence of biorelevant concentration of nucleophiles or reactive oxygen species. They are minimally toxic and readily metabolized. Upon tail vein injection of ESi5a (as an example), the vasculature of a nude mouse was imaged with a high signal-to-background ratio. ESi5 dyes have broad potentials for bioimaging in the deep-NIR spectral region.