CN108395889A - 苯并咪唑[1,2-a]并吡啶类衍生物的汞离子荧光探针及其应用 - Google Patents

苯并咪唑[1,2-a]并吡啶类衍生物的汞离子荧光探针及其应用 Download PDF

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CN108395889A
CN108395889A CN201810518845.8A CN201810518845A CN108395889A CN 108395889 A CN108395889 A CN 108395889A CN 201810518845 A CN201810518845 A CN 201810518845A CN 108395889 A CN108395889 A CN 108395889A
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benzimidazole
pyridine
fluorescence probe
formula
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葛燕青
吉瑞雪
刘爱坤
徐志扬
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Taishan Medical University
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract

本发明公开了一种苯并咪唑[1,2‑a]并吡啶肼衍生物Hg2+荧光探针，所述探针是异硫氰酸苯甲酰取代的2‑苯基苯并咪唑[1,2‑a]并吡啶‑3‑甲酰肼，其化学结构式如式（1）所示。本发明的荧光探针在PBS/EtOH(8/2 v/v)缓冲溶液（pH=7.40）中对Hg2+有较好的荧光选择性、较高的灵敏度及较强的抗其它离子干扰能力，应用前景广泛。

Description

苯并咪唑[1,2-a]并吡啶类衍生物的汞离子荧光探针及其 应用
技术领域
本发明涉及有机小分子荧光探针领域，尤其涉及一种Hg2+的荧光探针苯并咪唑[1,2-a]并吡啶衍生物的合成及其应用。
背景技术
汞是一种应用非常广泛的重金属， 日常使用的荧光灯、电脑、手机、电池等电子产品都不同程度的使用了含汞材料。这些电子产品在用完废弃后， 部分汞最终以离子形式进入环境， 对环境造成了严重的污染。汞离子对动植物和人体健康都有很大的影响，例如，汞离子对人的大脑、肾脏、肠胃和神经系统有很强的毒性。因此， 汞离子的识别和检测在环境科学、生命科学和医学等领域都有着重要的应用。目前已报道的检测汞离子的方法很多，如原子发射光谱法、原子吸收光谱法、电化学方法和电感耦合等离子体质谱( ICP-MS) 等。然而这些方法通常需要较为复杂的操作和昂贵的仪器， 严重制约了这些检测方法的使用。因此， 开发操作简便、选择性好、灵敏度高且成本低廉的汞离子检测方法有非常重要的意义。
荧光探针因选择性好,灵敏度高,操作简单,成本低并且可以实现实时监测等优点,现广泛应用于细胞内Hg2+含量的测定。尽管已有多种检测Hg2+荧光探针被报道,但是目前荧光探针的荧光团比较单一，因此开发新的荧光团来合成检测Hg2+的荧光探针具有重要的意义。
发明内容
本发明解决的问题是提供一种Hg2+的荧光探针苯并咪唑[1,2-a]并吡啶衍生物的合成及其应用。
本发明的技术方案是：一种苯并咪唑[1,2-a]并吡啶衍生物Hg2+荧光探针，其化学结构式如式（1）所示：
(1)
本发明还包括苯并咪唑[1,2-a]并吡啶衍生物Hg2+荧光探针的应用，式（1）化合物在PBS/EtOH (8/2 v/v)缓冲溶液（pH=7.40）对Hg2+有较好的荧光选择性。
本发明还包括苯并咪唑[1,2-a]并吡啶衍生物Hg2+荧光探针的合成方法，在乙腈溶液中，将2-苯基苯并咪唑[1,2-a]并吡啶-3-甲酰肼与异硫氰酸苯甲酰按照摩尔比1:8投料，常温下反应12小时，得到苯并咪唑[1,2-a]并吡啶衍生物。
配制苯并咪唑[1,2-a]并吡啶衍生物的二甲亚砜溶液，分别加入定量的MgCl2,CaCl2, AlCl3, SnCl2 .2H2O, PbSO4，CrCl3·6H2O, MnCl2·4H2O, FeCl3·6H2O, CoCl2·6H2O, NiCl2·6H2O, PdCl2，ZnCl2, HgCl2·2H2O, CdCl2·2½H2O, AgNO3的水溶液，通过荧光光谱测试来研究对不同金属离子的选择性，测其荧光发射波谱强度变化发现：本发明所述苯并咪唑[1,2-a]并吡啶肼衍生物即式（1）化合物对Hg2+有较好的荧光选择性，如图1所示。逐渐加入Hg2+至2当量后，化合物1在475nm处荧光强度明显增强，如图2所示。因此，苯并咪唑[1,2-a]并吡啶肼衍生物作为Hg2+荧光探针具有巨大的应用。
附图说明
图1：式（1）化合物（5×10-7M）的PBS/EtOH (8/2 v/v) 缓冲溶液（pH=7.40）中加入2当量的不同金属离子后的荧光强度变化柱状图，图1中纵坐标为475nm处的光强度。
图2：式（1）化合物（5×10-7M）的PBS/EtOH (8/2 v/v) 缓冲溶液（pH=7.40）中进行Hg2+荧光滴定图。图中FL Intensity为光强，Wavelength为波长，equiv为倍数。
图3：式（1）化合物（5×10-7M）和2当量的其它金属离子共存的PBS/EtOH (8/2 v/v)缓冲溶液（pH=7.40）中加入2当量Hg2+的后荧光强度变化的柱状图。
图4是式（1）化合物合成方法反应式图。
具体实施方式
实施例1：式（1）化合物的合成方案如下式所示：
具体合成步骤如下：
在50 mL圆底烧瓶中依次加入0.22g（0.30 mmol）2-苯基苯并咪唑[1,2-a]并吡啶-3-甲酰肼，0.21g（2.4 mmol）异硫氰酸苯甲酰，20 mL乙腈，常温下反应12小时。反应中有沉淀产生，抽滤，固体柱层析得0.18g黄色固体，产率75%。
实施例2：
向式（1）化合物（5×10-7M）的PBS/EtOH (8/2 v/v) 缓冲溶液（pH=7.40）中分别加入2当量的Mg2+, Ca2+, Al3+, Sn2+, Pb2+, Cr3+, Mn2+, Fe3+, Co2+, Ni2+, Zn2+, Cd2+, Pd2+,Hg2+ 和Ag+后，测其在475nm荧光发射强度变化发现：式（1）化合物对Hg2+有较好的荧光选择性，加入2当量的Hg2+后，化合物1在475nm处荧光强度明显升高，如图1，图2所示。
实施例3：
分别于式（1）化合物（5×10-7M）和2当量的Mg2+, Ca2+, Al3+, Sn2+, Pb2+, Cr3+, Mn2+,Fe3+, Co2+, Ni2+, Zn2+, Cd2+, Pd2+, Hg2+ 和Ag+不同金属离子溶液中，加入2当量的Hg2+后，测其在475nm荧光发射强度变化发现：式（1）化合物对其它离子有较强的抗干扰能力，如图3所示。

Claims (2)

1.一种苯并咪唑[1,2-a]并吡啶衍生物Hg2+荧光探针，其特征在于：它是异硫氰酸苯甲酰取代的2-苯基苯并咪唑[1,2-a]并吡啶-3-甲酰肼，其化学结构式如式（1）所示：
（1）
式（1）化合物在PBS/EtOH (8/2 v/v) 缓冲溶液（pH=7.40）中对Hg2+有较好的荧光选择性。
2.权利要求1所述苯并咪唑[1,2-a]并吡啶衍生物Hg2+荧光探针的合成方法，其特征在于：在乙腈溶液中，将2-苯基苯并咪唑[1,2-a]并吡啶-3-甲酰肼与异硫氰酸苯甲酰按照摩尔比1:8投料，常温下反应12小时，得到苯并咪唑[1,2-a]并吡啶衍生物。
CN201810518845.8A 2018-05-25 2018-05-25 苯并咪唑[1,2-a]并吡啶类衍生物的汞离子荧光探针及其应用 Pending CN108395889A (zh)

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CN112480110A (zh) * 2020-12-02 2021-03-12 广东省测试分析研究所（中国广州分析测试中心） 一种多响应氮杂环甲醛荧光探针分子及其制备方法和应用
CN112538051A (zh) * 2020-12-17 2021-03-23 桂林理工大学 一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108892681A (zh) * 2018-09-12 2018-11-27 泰山医学院 一种咪唑并[1,2-a]吡啶类汞离子比率型荧光探针及其应用
CN112480110A (zh) * 2020-12-02 2021-03-12 广东省测试分析研究所（中国广州分析测试中心） 一种多响应氮杂环甲醛荧光探针分子及其制备方法和应用
CN112538051A (zh) * 2020-12-17 2021-03-23 桂林理工大学 一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法
CN112538051B (zh) * 2020-12-17 2022-03-22 桂林理工大学 一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法

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