CN108373916A - 咪唑并[1,5-a]吡啶酰肼衍生物类汞离子荧光探针及其应用 - Google Patents

咪唑并[1,5-a]吡啶酰肼衍生物类汞离子荧光探针及其应用 Download PDF

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CN108373916A
CN108373916A CN201810505217.6A CN201810505217A CN108373916A CN 108373916 A CN108373916 A CN 108373916A CN 201810505217 A CN201810505217 A CN 201810505217A CN 108373916 A CN108373916 A CN 108373916A
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imidazo
formula
pyridine
fluorescence probe
hydrazide derivatives
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葛燕青
徐志扬
刘爱坤
吉瑞雪
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Taishan Medical University
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Abstract

本发明公开了一种咪唑并[1,5‑a]吡啶酰肼衍生物类Hg2+荧光探针，其化学结构式如式（1）所示。本发明的荧光探针在PBS/DMSO(体积比6:4)缓冲溶液中（pH=7.40）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

咪唑并[1,5-a]吡啶酰肼衍生物类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+荧光探针咪唑并[1,5-a]吡啶酰肼衍生物及其应用。
背景技术
Hg2+是危险的重金属污染物,它容易通过生物膜如皮肤,呼吸道,胃肠道组织进入人类食物链，进入人体之后,与生物体内的蛋白质和酶中的巯基具备很高的亲和性,生成硫醇盐,从而导致细胞的功能性障碍和随之而来的健康问题。此外,它可以在植物和人体中富集,减少光合作用和蒸腾作用。因此，开发有效的汞离子监测方法具有重要意义。在各种检测方法中，荧光探针因成本低廉、快速、简便，被广泛适用于环保、医疗、生化领域。本发明提供了一种咪唑并[1,5-a]吡啶酰肼衍生物类Hg2+荧光探针及其应用。
发明内容
本发明解决的问题是提供一种Hg2+荧光探针咪唑并[1,5-a]吡啶酰肼衍生物及其应用。
本发明的技术方案是：一种咪唑并[1,5-a]吡啶酰肼衍生物类Hg2+荧光探针，其化学结构式如式（1）所示：
本发明还包括咪唑并[1,5-a]吡啶酰肼衍生物类Hg2+荧光探针的应用，式（1）化合物在PBS/DMSO(体积比6:4)缓冲溶液中（pH=7.40）对Hg2+有较好的荧光选择性。
本发明还包括咪唑并[1,5-a]吡啶酰肼衍生物类Hg2+荧光探针的合成方法，在无水乙腈中，将3-丁基-1-氯咪唑并[1,5-a]吡啶-7-甲酰肼与苯甲酰基异硫氰酸酯按照摩尔比1:1投料比例，常温下反应1小时，得到式（1）化合物。
配制咪唑并[1,5-a]吡啶酰肼衍生物类Hg2+荧光探针的二甲亚砜溶液，分别加入定量的MgCl2，CaCl2，AlCl3，CuCl2· 2H2O，PbSO4，CrCl3· 6H2O，MnCl2· 4H2O，FeCl3·6H2O，CoCl2·6H2O，NiCl2·6H2O，KCl，NaCl，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：本发明所述咪唑并[1,5-a]吡啶酰肼衍生物即式（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4当量后，化合物1在472nm处荧光强度明显增强，如图2所示。因此，咪唑并[1,5-a]吡啶酰肼衍生物作为Hg2+荧光探针具有巨大的应用前景。
附图说明
图1：式（1）化合物（10-6M）的PBS/DMSO(体积比6:4)缓冲溶液中（pH=7.40）加入4当量的不同金属离子后的荧光强度变化图。
图2：式（1）化合物（10-6M）的PBS/DMSO(体积比6:4)缓冲溶液中（pH=7.40）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（10-6M）和4当量的其它金属离子共存的PBS/DMSO(体积比6:4)缓冲溶液中（pH=7.40）加入4当量Hg2+后的荧光强度变化柱状图，纵坐标为472nm处的光强。
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30mL无水乙腈，0.19g（1.0 mmol）3-丁基-1-氯咪唑并[1,5-a]吡啶-7-甲酰肼，0.20g（1.0 mmol）苯甲酰基异硫氰酸酯，常温下反应1小时。TLC检测反应完成后，浓缩，柱层析得0.212g鲜绿色固体，产率69.24%。
实施例2：
向式（1）化合物（10-6M）的PBS/DMSO(体积比6:4)缓冲溶液中（pH=7.40）分别加入4当量的Mg2+，Ca2+，Al3+，Cu2+，Pb2+，Cr3+，Mn2+，Fe3+，Co2+，Ni2+，K+，Na+，Zn2+，Cd2+，Hg2+和Ag+后，测其在472nm处荧光发射强度发现：式（1）化合物对Hg2+有较好的荧光选择性，加入4当量的Hg2+后，化合物1在472nm处荧光强度明显增强，如图1所示。
实施例3：
分别于式（1）化合物（10-6M）和4当量的Mg2+，Ca2+，Al3+，Cu2+,Pb2+，Cr3+，Mn2+，Fe3+，Co2+，Ni2+，K+，Na+，Zn2+，Cd2+，和Ag+不同金属离子溶液中，加入4当量的Hg2+后，测其在472nm处荧光发射强度发现：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)

1.一种咪唑并[1,5-a]吡啶酰肼衍生物类Hg2+荧光探针，其特征在于：它是咪唑并[1,5-a]吡啶酰肼的衍生物，其化学结构式如式（1）所示：
式（1）化合物在PBS/DMSO(体积比6:4)缓冲溶液中（pH=7.40）对Hg2+有较好的荧光选择性。
2.权利要求1所述咪唑并[1,5-a]吡啶酰肼衍生物类Hg2+荧光探针的合成方法，其特征在于：在无水乙腈溶液中，将3-丁基-1-氯咪唑并[1,5-a]吡啶-7-甲酰肼与苯甲酰基异硫氰酸酯按照摩尔比1:1投料比例，常温下反应1小时，得到式（1）化合物。
CN201810505217.6A 2018-05-24 2018-05-24 咪唑并[1,5-a]吡啶酰肼衍生物类汞离子荧光探针及其应用 Pending CN108373916A (zh)

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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
CN115246831A (zh) * 2021-12-20 2022-10-28 陕西学前师范学院 一种Hg2+敏感性腙类衍生物及其制备和应用

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Cited By (3)

* 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
CN115246831A (zh) * 2021-12-20 2022-10-28 陕西学前师范学院 一种Hg2+敏感性腙类衍生物及其制备和应用

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