Polydiacetylene liposomes with phenylboronic acid tags: a fluorescence turn-on sensor for sialic acid detection and cell-surface glycan imaging†,Nanoscale

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Polydiacetylene liposomes with phenylboronic acid tags: a fluorescence turn-on sensor for sialic acid detection and cell-surface glycan imaging†
Nanoscale ( IF 5.8 ) Pub Date : 2018-01-31 00:00:00 , DOI: 10.1039/c7nr08557e
Dong-En Wang _{1,

2,

3,

4,

5} , Jiahang Yan _{1,

2,

3,

4} , Jingjing Jiang _{1,

2,

3,

4} , Xiang Liu _{1,

2,

3,

4} , Chang Tian _{2,

3,

4,

6} , Juan Xu _{1,

2,

3,

4} , Mao-Sen Yuan _{1,

2,

3,

4} , Xiang Han _{1,

2,

3,

4} , Jinyi Wang _{1,

2,

3,

4}

Affiliation

Sialic acid (SA) located at the terminal end of glycans on cell membranes has been shown to play an important yet distinctive role in various biological and pathological processes. Effective methods for the facile, sensitive and in situ analysis of SA on living cell surfaces 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 the in situ imaging of SA-terminated glycans on living cell surfaces. 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 molecules 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 the conjugated backbone could directly quench 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 in the fluorescence restoration of the fluorophore. The proposed methods realized the fluorescence turn-on detection of free SA in aqueous solution and the in situ imaging of SA on living MCF-7 cell surfaces. This work provides a new potential tool for simple and selective analysis of SA on living cell membranes.

中文翻译：

具有苯基硼酸标签的聚二乙炔脂质体：荧光开启传感器，用于唾液酸检测和细胞表面聚糖成像†

已经表明，位于细胞膜上聚糖末端的唾液酸（SA）在各种生物学和病理学过程中起着重要而又独特的作用。在活细胞表面上进行SA的简便，灵敏和原位分析的有效方法，在临床诊断和治疗方面具有重要意义。在这里，开发了一种新的基于聚二乙炔（PDA）脂质体的传感器系统，该系统带有苯基硼酸（PBA）和1,8-萘二甲酰亚胺衍生的荧光团部分，作为一种荧光开启传感器，可以检测水溶液中的游离SA，并就地检测SA端聚糖在活细胞表面的成像。在传感器系统中，设计并合成了三种二乙炔单体PCDA-pBA，PCDA-Nap和PCDA-EA，以构建复合PDA脂质体传感器。用PBA分子修饰的单体PCDA-pBA被用作SA识别的受体，而包含1,8-萘二甲酰亚胺衍生物荧光团的单体PCDA-Nap被用于荧光信号。当形成复合PDA脂质体时，荧光团和结合的主链之间的能量转移可以直接猝灭荧光团的荧光。在存在额外的SA或SA丰富的细胞的情况下，SA与PBA部分的牢固结合会干扰侧链的侧构象，从而导致荧光团的荧光恢复。在活MCF-7细胞表面上SA的原位成像。这项工作为简单和选择性分析活细胞膜上的SA提供了一个新的潜在工具。

更新日期：2018-01-31

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