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Polydiacetylene Liposome with Phenylboronic Acid Tags: A Fluorescence Turn-On Sensor for Sialic Acid Detection and Cell Surface Glycan Imaging

Abstract

Sialic acid (SA) located at the terminal end of glycans on cell membrane has been shown to play important yet distinctive role in various biological and pathological processes. Effective methods for facile, sensitive and in situ analysis of SA on living cell surface are of great significance in terms of clinical diagnostics and therapeutics. Here, a new polydiacetylene (PDA) liposome based sensor system bearing phenylboronic acid (PBA) and 1,8-naphthalimide derived fluorophore moieties was developed as a fluorescence turn-on sensor for the detection of free SA in aqueous solution and in situ imaging of SA-terminated glycans on living cell surface. In the sensor system, three diacetylene monomers, PCDA-pBA, PCDA-Nap and PCDA-EA, were designed and synthesized to construct the composite PDA liposome sensor. The monomer PCDA-pBA modified with PBA molecule was employed as a receptor for SA recognition, while the monomer PCDA-Nap containing a 1,8-naphthalimide derivative fluorophore was used for fluorescence signaling. When the composite PDA liposomes were formed, the energy transfer between the fluorophore and conjugated backbone could directly quenched the fluorescence of the fluorophore. In the presence of additional SA or SA abundant cells, the strong binding of SA with PBA moieties disturbed the pendent side chain conformation, resulting the fluorescence restoration of the fluorophore. The proposed methods realized the fluorescence turn on detection of free SA in aqueous solution and in situ imaging of SA on living MCF-7 cell surfaces. This work provided a new potential tool for simple and selective analysis of SA on living cell membrane.

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Publication details

The article was received on 16 Nov 2017, accepted on 31 Jan 2018 and first published on 31 Jan 2018


Article type: Paper
DOI: 10.1039/C7NR08557E
Citation: Nanoscale, 2018, Accepted Manuscript
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    Polydiacetylene Liposome with Phenylboronic Acid Tags: A Fluorescence Turn-On Sensor for Sialic Acid Detection and Cell Surface Glycan Imaging

    D. wang, J. Yan, J. Jiang, X. Liu, C. Tian, J. Xu, M. Yuan, X. Han and J. Wang, Nanoscale, 2018, Accepted Manuscript , DOI: 10.1039/C7NR08557E

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