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《天津医科大学学报》[ISSN:1006-8147/CN:12-1259/R]

卷:

30卷

期数:

2024年05期

页码:

462-467

栏目:

药学

出版日期:

2024-09-25

文章信息/Info

Title:

Synthesis and application of a carbazole-based fluorescent probe for recognizing tyramine

文章编号:

1006-8147（2024）05-0462-06

作者:

刘圆¹; 2; 董林毅¹

（1. 天津医科大学药学院药物分析学系，天津300070；2.诺维信（中国）生物技术有限公司，天津300457）

Author(s):

LIU Yuan¹; 2; DONG Linyi¹

（1. Department of pharmaceutical Analysis，School of Pharmacy，Tianjin Medical University，Tianjin 300070，China；2. Novozymes（China） Biotechnology Company Limited，Tianjin 300457，China）

关键词:

酪胺; 咔唑; 荧光探针; ESIPT机制; 希夫碱

Keywords:

tyramine; carbazole; fluorescent probe; ESIPT mechanism; schiff base

分类号:

R9

DOI:

10.20135/j.issn.1006-8147.2024.05.0462

文献标志码:

A

摘要:

目的：基于激发态分子内质子转移（ESIPT）机制，研发一种用于酪胺检测的新型小分子荧光探针CPIM。方法：通过4-（9H-咔唑-9-基）苯胺和3，5-二碘水杨醛反应缩合得到咔唑类小分子荧光探针CPIM，采用核磁共振氢谱、红外光谱、高分辨质谱表征其结构。通过紫外光谱和荧光光谱等方法研究荧光探针对酪胺的检测性能。通过Job′s曲线、红外光谱和核磁共振氢谱对检测机制进行研究。采用标准加入法验证荧光探针的实际应用性。结果：在365 nm紫外灯下，CPIM可以实现酪胺分子的可视化检测。CPIM对酪胺识别具有良好的选择性、灵敏性、抗干扰性、稳定性和重现性，在0~5.0 × 10-6 mol/L浓度范围内，体系荧光强度与酪胺浓度呈良好的线性关系，其检测限为4.36×10-7 mol/L，与酪胺的结合常数为9.98×104 M-1。CPIM与酪胺以1 ∶ 1结合脱水后形成复合物，进而抑制ESIPT过程，并生成大的p-π共轭体系导致荧光显著增强。此外，CPIM还可对实际样品中的酪胺进行检测。结论：CPIM具有良好的酪胺检测能力，具有选择性高、灵敏性好、检测限低、稳定性好的特点。

Abstract:

Objective：To develop a turn-on small molecule fluorescent probe CPIM for tyramine detection based on the excited state intramolecular transfer（ESIPT） mechanism. Methods：The carbazole small molecule fluorescent probe CPIM was obtained by the reaction and condensation of 4-（9H-carbazol-9-yl）aniline and 3，5-diiodosalicylaldehyde，and the structure of CPIM was characterized by 1H nuclear magnetic resonance spectrometry（1H NMR），infrared spectroscopy（IR），and high resolution mass spectrometry（HR-MS）. The performance of CPIM in detecting tyramine was studied by UV spectrum，fluorescence spectroscopy and other methods. The detection mechanism was investigated by Job′s plot，IR，and 1H NMR. The practical applicability of fluorescent probe was verified by the standard addition method. Results：The visual detection of CPIM for tyramine can be realized under 365 nm UV chamber.CPIM has good selectivity，sensitivity，anti-inference，stability and repeatability for the recognition of tyramine. There was a good linear relationship between the fluorescence intensity of probe CPIM and the concentration of tyramine in a range of 0 to 5.0×10-6 mol/L，with the detection limit of 4.36×10-7 mol/L. The binding constant of tyramine with CPIM was 9.98×104 M-1.CPIM binds to tyramine in a 1 ∶ 1 ratio and dehydrates to form a complex，which in turn inhibits the ESIPT process and generates a large p-π conjugation system leading to a significant enhancement of fluorescence.Besides，CPIM can be used for the detection of real samples. Conclusion：CPIM has good tyramine detection ability with high selectivity，good sensitivity，low detection limit and good stability.

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相似文献/References:

备注/Memo

备注/Memo:

基金项目 天津市教委科研重点项目（2022ZD053）
作者简介 刘圆（1989-），女，工程师，硕士在读，研究方向：药物分析；通信作者：董林毅，E-mail：donglinyi@tmu.edu.cn。

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更新日期/Last Update: 2024-09-20