具有生物活性的芳基咪唑并邻菲啰啉衍生物的合成及用作pH荧光传感探针

doi:10.7503/cjcu20130759

高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (4): 750.doi: 10.7503/cjcu20130759

具有生物活性的芳基咪唑并邻菲啰啉衍生物的合成及用作pH荧光传感探针

柴金华, 王越, 徐德青, 王雪, 朱长安, 国阳, 张成路()

辽宁省生物与制药重点实验室, 辽宁师范大学化学化工学院, 大连 116029

收稿日期:2013-08-05 出版日期:2014-04-10 发布日期:2013-11-25
作者简介:联系人简介: 张成路, 男, 博士, 教授, 主要从事有机合成的研究. E-mail: zhangchenglu@lnnu.edu.cn
基金资助:
辽宁省教育厅高校创新团队基金(批准号: 2008T107)和辽宁省教育厅科学技术资助项目(批准号: 2009A426)资助

Synthesis of Bioactive Aryl Imidazole Derivatives and Their Applications for the pH-Induced Luminescence Sensing Probe^†

CHAI Jinhua, WANG Yue, XU Deqing, WANG Xue, ZHU Changan, GUO Yang, ZHANG Chenglu^*()

Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China

Received:2013-08-05 Online:2014-04-10 Published:2013-11-25
Contact: ZHANG Chenglu E-mail:zhangchenglu@lnnu.edu.cn
Supported by:
† Supported by the University Innovation Team Program of Liaoning Provincial Department of Education, China(No.2008T107) and Science and Technology Research Program of Liaoning ProvinciaL Department of Education, China(No.2009A426).

摘要/Abstract

摘要：

以1,10-邻菲啰啉为基本骨架设计合成了6种咪唑[4,5-f][1,10]邻菲啰啉的衍生物(3a~3f); 研究了目标化合物对蛋白酪氨酸磷酸酶1B(PTP1B)的抑制作用, 其最高抑制率可达(84.56±1.78)%, 是潜在的PTP1B的抑制剂药物; 基于1,10-邻菲啰啉优良的光学性能, 通过荧光测试研究了不同pH对化合物3a~3f的影响, 探讨了化合物在Britton-Robison(B-R)缓冲溶液中的质子化和去质子化现象; 以硫酸奎宁为参比, 计算了相应的荧光量子产率. 结果表明, 目标化合物均有较高的荧光量子产率, 最高可达0.53.

关键词: 咪唑[4,5-f][1,10]邻菲啰啉, 蛋白酪氨酸磷酸酶1B(PTP1B)抑制剂, pH荧光传感探针, 荧光量子产率

Abstract:

Six kinds of imidazo[4,5-f][1,10]phenanthroline derivatives(3a—3f) were designed and synthesized based on [1,10]phenanthroline skeleton. The inhibition of the target compounds on PTP1B was studied and the highest inhibition rate could be up to (84.56±1.78)%. The results indicated that the target compounds could be used as the potential PTP1B inhibitors and provide important therapy reference for the modern Ⅱ diabetes and obesity. Owing to the excellent optical performance of 1,10-phenanthroline, the effects of pH on the luminescence properties of the target products(3a—3f) were also studied and the phenomenon of the protonation and deprotonation in the B-R buffer solution were explored. Taking quinine bisulphate as a refe-rence, the highest luminescence quantum yield of compounds 3 was 0.53. With the increase in pH value, the luminescence intensity of compounds 3 increased. In the range of pH=6—8, compounds 3 gave a strong and steady luminescence. However, the luminescence intensity of compounds 3 reduced when pH value was higher than 8. As a result, compounds 3 could be used as pH luminescence sensing probe.

Key words: Imidazo[4,5-f][1,10]phenanthroline, PTP1B inhibitor, pH-Induced luminescence sensing probe, Luminescence quantum yield

中图分类号:

O626.23

TrendMD:

柴金华, 王越, 徐德青, 王雪, 朱长安, 国阳, 张成路. 具有生物活性的芳基咪唑并邻菲啰啉衍生物的合成及用作pH荧光传感探针. 高等学校化学学报, 2014, 35(4): 750.

CHAI Jinhua, WANG Yue, XU Deqing, WANG Xue, ZHU Changan, GUO Yang, ZHANG Chenglu. Synthesis of Bioactive Aryl Imidazole Derivatives and Their Applications for the pH-Induced Luminescence Sensing Probe^†. Chem. J. Chinese Universities, 2014, 35(4): 750.

图/表 4

参考文献 22

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Number	Activity	Sample name	Protocolid	Concentration/ (μg·mL^-1)	Type	Result(%)
1		3a	25	20	Inhibition(%)	1.75±	0.36
2	*	3b	25	20	Inhibition(%)	59.21±	3.81
3		3c	25	20	Inhibition(%)	26.41±	4.82
4	*	3d	25	20	Inhibition(%)	84.22±	0.32
5	*	3e	25	20	Inhibition(%)	84.56±	1.78
6	*	3f	25	20	Inhibition(%)	65.07±	1.07
REF00055		Oleanolic acid	25	20	IC₅₀(μg/mL)	84.00±	0.04

Number	Activity	Sample name	Protocolid	Concentration/ (μg·mL^-1)	Type	Result(%)
1		3a	25	20	Inhibition(%)	1.75±	0.36
2	*	3b	25	20	Inhibition(%)	59.21±	3.81
3		3c	25	20	Inhibition(%)	26.41±	4.82
4	*	3d	25	20	Inhibition(%)	84.22±	0.32
5	*	3e	25	20	Inhibition(%)	84.56±	1.78
6	*	3f	25	20	Inhibition(%)	65.07±	1.07
REF00055		Oleanolic acid	25	20	IC₅₀(μg/mL)	84.00±	0.04

具有生物活性的芳基咪唑并邻菲啰啉衍生物的合成及用作pH荧光传感探针

Synthesis of Bioactive Aryl Imidazole Derivatives and Their Applications for the pH-Induced Luminescence Sensing Probe^†

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具有生物活性的芳基咪唑并邻菲啰啉衍生物的合成及用作pH荧光传感探针

Synthesis of Bioactive Aryl Imidazole Derivatives and Their Applications for the pH-Induced Luminescence Sensing Probe†

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Synthesis of Bioactive Aryl Imidazole Derivatives and Their Applications for the pH-Induced Luminescence Sensing Probe^†