Novel Cu2+-specific “Turn-ON” fluorescent probe based on [5]helicene with very large Stokes shift and its potential application in living cells†,New Journal of Chemistry

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Novel Cu2+-specific “Turn-ON” fluorescent probe based on [5]helicene with very large Stokes shift and its potential application in living cells†
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2018-03-15 00:00:00 , DOI: 10.1039/c7nj05176j
Nirawit Kaewnok _{1,

2,

3,

4,

5} , Anuwut Petdum _{1,

2,

3,

4,

5} , Jitnapa Sirirak _{1,

2,

3,

4,

5} , Adisri Charoenpanich _{2,

3,

4,

5,

6} , Waraporn Panchan _{5,

7,

8} , Somboon Sahasithiwat _{5,

7,

8} , Thanasat Sooksimuang _{5,

7,

8} , Nantanit Wanichacheva _{1,

2,

3,

4,

5}

Affiliation

A novel fluorescent sensor based on a [5]helicene dye bearing hydrazine (1) was synthesized through a simple reaction. The sensor was fully characterized by NMR, single crystal X-ray analysis, and HRMS spectrometry. Fluorescence technique was also employed to study the ability of 1 for the detection of Cu²⁺ among different ions. It was found that 1 exhibited a highly sensitive fluorescence response toward Cu²⁺ with a “Turn-ON” fluorescence enhancement and a very large Stokes shift of ∼183 nm. The sensor selectively bound to Cu²⁺ in the presence of various metal ions, such as Cd²⁺, Ag⁺, Pb²⁺, Zn²⁺, Ni²⁺, Hg²⁺, K⁺, Li⁺, Ba²⁺, Al³⁺, Fe²⁺, Co²⁺, Mn²⁺, Ca²⁺, Na⁺, and Mg²⁺ in aqueous acetonitrile solution. The Cu²⁺ detection limit was 2.6 ppb (3σ/slope), which was lower than the permissible concentration in drinking water determined by the US EPA and WHO. In addition, the sensor can enhance fluorescence from the intracellular area in the HepG2 cellular system. Hence, it has the potential for the detection of Cu²⁺ in biological samples.

中文翻译：

基于具有非常大斯托克斯位移的[5]螺旋烯的新型Cu ²⁺特异性“ Turn-ON”荧光探针及其在活细胞中的潜在应用†

通过一种简单的反应合成了一种新型的基于[5]带有肼的dye烯染料的荧光传感器（1）。通过NMR，单晶X射线分析和HRMS光谱对传感器进行了全面表征。还采用荧光技术来研究1在不同离子中检测Cu ²⁺的能力。发现1对Cu ²⁺表现出高度敏感的荧光响应，“ Turn-ON”荧光增强，斯托克斯位移非常大，约为183 nm。在各种金属离子（例如Cd 2 ⁺，Ag ⁺，Pb 2 ⁺，Zn）存在下，传感器选择性地结合到Cu ²⁺水溶液中的2⁺，Ni 2⁺，Hg 2⁺，K⁺，Li⁺，Ba 2⁺，Al³⁺，Fe 2⁺，Co 2⁺，Mn 2⁺，Ca 2⁺，Na⁺和Mg²⁺乙腈溶液。Cu^2+的检出限为2.6 ppb（3σ/斜率），低于美国EPA和WHO所确定的饮用水中允许的浓度。另外，该传感器可以增强来自HepG2细胞系统中细胞内区域的荧光。因此，它具有检测生物样品中Cu²⁺的潜力。

更新日期：2018-03-15

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