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CHEN Yue, HAO Meixi, JU Caoyun, ZHANG Can. Design, synthesis and application of AIE fluorescent probe for lipid raft[J]. Journal of China Pharmaceutical University, 2020, 51(5): 514-521. DOI: 10.11665/j.issn.1000-5048.20200502
Citation: CHEN Yue, HAO Meixi, JU Caoyun, ZHANG Can. Design, synthesis and application of AIE fluorescent probe for lipid raft[J]. Journal of China Pharmaceutical University, 2020, 51(5): 514-521. DOI: 10.11665/j.issn.1000-5048.20200502

Design, synthesis and application of AIE fluorescent probe for lipid raft

Funds: This study was supported by the National Natural Science Foundation of China (No.81930099,No.81773664,No.81473153)
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  • Received Date: May 24, 2020
  • Revised Date: September 09, 2020
  • Lipid rafts composed of saturated phospholipids,sphingomyelin,and cholesterol are usually defined as liquid ordered microdomains located in the cell membrane. Lipid rafts are involved in many physiological and pathological processes of cells. Based on the difference in composition and distribution between lipid raft and non-raft domains,a lipid raft probe with aggregation-induced emission (AIE),cholesterol-triethylene glycol-tetraphenylethylene (TCHS-TPE),was designed and synthesized for convenient and specific imaging of lipid raft domains on cell membranes in this study. In this paper,TCHS-TPE was successfully synthesized,and the photophysical properties of TCHS-TPE were measured to evaluate its AIE characteristics. And finally the specific imaging of TCHS-TPE on the lipid raft region of B16F10 melanoma cell membrane was studied using confocal laser scanning microscopy. Compared with the existing lipid raft probe cholera toxin B (CTxB),the TCHS-TPE lipid raft probe has the advantages of simple operation and high specificity. The successful synthesis of the fluorescent probe will provide a useful tool for studying the physiological and pathological processes related to lipid raft domains,and offer a theoretical basis for the design of imaging probes for other lipid raft domains.
  • [1]
    .Nature,1997,387(6633):569?572.
    [2]
    Sodt AJ,Pastor RW,Lyman E.Hexagonal substructure and hydrogen bonding in liquid-ordered phases containing palmitoyl sphingomyelin[J].Biophys J,2015,109(5):948?955.
    [3]
    Ramstedt B,Slotte JP.Interaction of cholesterol with sphingomyelins and acyl-chain-matched phosphatidylcholines:a comparative study of the effect of the chain length[J].Biophys J,1999,76(2):908?915.
    [4]
    Lingwood D,Binnington B,Róg T,et al.Cholesterol modulates glycolipid conformation and receptor activity[J].Nat Chem Biol,2011,7(5):260?262.
    [5]
    Laganowsky A,Reading E,Allison TM,et al.Membrane proteins bind lipids selectively to modulate their structure and function[J].Nature,2014,510(7503):172?175.
    [6]
    Sezgin E,Levental I,Grzybek M,et al.Partitioning,diffusion,and ligand binding of raft lipid analogs in model and cellular plasma membranes[J].Biochim Biophys Acta,2012,1818(7):1777?1784.
    [7]
    Englund PT.The structure and biosynthesis of glycosyl phosphatidylinositol protein anchors[J].Annu Rev Biochem,1993,62:121?138.
    [8]
    Lingwood D,Simons K.Lipid rafts as a membrane-organizing principle[J].Science,2010,327(5961):46?50.
    [9]
    Sch?fer B,Orbán E,Borics A,et al.Preparation of semisynthetic lipoproteins with fluorescent cholesterol anchor and their introduction to the cell membrane with minimal disruption of the membrane[J].Bioconjug Chem,2013,24(10):1684?1697.
    [10]
    Kim HM,Jeong BH,Hyon JY,et al.Two-photon fluorescent turn-on probe for lipid rafts in live cell and tissue[J].J Am Chem Soc,2008,130(13):4246?4247.
    [11]
    Tian MG,Liu Y,Sun YM,et al.A single fluorescent probe enables clearly discriminating and simultaneously imaging liquid-ordered and liquid-disordered microdomains in plasma membrane of living cells[J].Biomaterials,2017,120:46?56.
    [12]
    Sezgin E,Levental I,Mayor S,et al.The mystery of membrane organization:composition,regulation and roles of lipid rafts[J].Nat Rev Mol Cell Biol,2017,18(6):361?374.
    [13]
    Levental I,Levental KR,Heberle FA.Lipid rafts:controversies resolved,mysteries remain[J].Trends Cell Biol,2020,30(5):341?353.
    [14]
    Luo J,Xie Z,Lam JW,et al.Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J].Chem Commun(Camb),2001(18):1740?1741.
    [15]
    Cai YJ,Gui C,Samedov K,et al.An acidic pH independent piperazine-TPE AIEgen as a unique bioprobe for lysosome tracing[J].Chem Sci,2017,8(11):7593?7603.
    [16]
    Merritt EA,Sarfaty S,van den Akker F,et al.Crystal structure of cholera toxin B-pentamer bound to receptor GM1 pentasaccharide[J].Protein Sci,1994,3(2):166?175.
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