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合成 2-甲基-6-甲氧基-4-喹啉羧酸 N-羟基琥珀酰亚胺酯(MMQC-OSu),用于基于 HPLC 的环境样品中脂肪胺的流畅、高效荧光检测。

Synthesis of 2-methyl-6-methoxy-4-quinolinecarboxylic acid N-hydroxysuccinimide ester (MMQC-OSu) for streamlined and effective HPLC-based fluorescence detection of aliphatic amines in environmental samples.

机构信息

The Key Laboratory for Biomedical Photonics of MOE at Wuhan National Laboratory for Optoelectronics - Hubei Bioinformatics & Molecular Imaging Key Laboratory, Systems Biology Theme, Department of Biomedical Engineering, College of Life Science and Technology, Huazhong University of Science and Technology, Wuhan 430074, China.

The Key Laboratory for Biomedical Photonics of MOE at Wuhan National Laboratory for Optoelectronics - Hubei Bioinformatics & Molecular Imaging Key Laboratory, Systems Biology Theme, Department of Biomedical Engineering, College of Life Science and Technology, Huazhong University of Science and Technology, Wuhan 430074, China; Department of Epidemiology and Health Statistics, School of Public Health, Fujian Medical University, Fuzhou 350122, China.

出版信息

J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Nov 1;1248:124348. doi: 10.1016/j.jchromb.2024.124348. Epub 2024 Nov 4.

DOI:10.1016/j.jchromb.2024.124348
PMID:39509966
Abstract

Aliphatic amines are widely distributed in the environment and food sources, posing potential health risks through skin and mucosal irritation. Consequently, their quantitative detection is crucial for assessing environmental health. Despite high reactivity and fluorescence properties of succinimidyl ester-based derivatization reagents, their application in the aliphatic amines detection is hampered by challenges such as limited detection sensitivity and fluorescence interference. We established an innovative synthetic approach to produce a series of succinimidyl esters with the desirable substituents. This advancement enabled the creation of efficient and highly sensitive reagents for the detection of aliphatic amines. Among them, 2-methyl-6-methoxy-4-quinolinecarboxylic acid N-hydroxysuccinimide ester (MMQC-OSu) exhibited the best detection performance. MMQC-OSu reacted with aliphatic amines at 40 °C in pH 8.0 buffer for 20 min, which was subsequently separated in a C18 chromatographic column with the fluorescence detection wavelength of 336/432 nm. This detection approach featured a rapid and mild reaction process, minimal interference from corresponding hydrolysis products, and impressive sensitivity (0.05 nM). These characteristics indicate that MMQC-OSu significantly surpassing commercial aliphatic amines detection reagents. Finally, the detection strategy of MMQC-OSu was successfully applied in environmental sample analysis, with recovery rate of 93 %-108 % and RSDs between 1.4 % and 6.5 %.

摘要

脂肪胺广泛存在于环境和食物源中,通过皮肤和黏膜刺激对健康构成潜在风险。因此,定量检测脂肪胺对于评估环境健康至关重要。尽管琥珀酰亚胺酯类衍生化试剂具有高反应性和荧光特性,但由于检测灵敏度有限和荧光干扰等挑战,其在脂肪胺检测中的应用受到限制。我们建立了一种创新的合成方法来生产具有理想取代基的一系列琥珀酰亚胺酯。这一进展为检测脂肪胺创造了高效和高灵敏度的试剂。其中,2-甲基-6-甲氧基-4-喹啉羧酸 N-羟基琥珀酰亚胺酯(MMQC-OSu)表现出最佳的检测性能。MMQC-OSu 在 40°C 和 pH 8.0 缓冲液中与脂肪胺反应 20 分钟,然后在 C18 色谱柱中分离,荧光检测波长为 336/432nm。这种检测方法具有快速温和的反应过程、最小的对应水解产物干扰和令人印象深刻的灵敏度(0.05 nM)。这些特性表明 MMQC-OSu 显著优于商业脂肪胺检测试剂。最后,MMQC-OSu 的检测策略成功应用于环境样品分析,回收率为 93%-108%,RSD 在 1.4%-6.5%之间。

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