α-メチルトリプタミンの特異的検出を向上させる分子プローブ戦略を開発(Researchers Develop Molecular Probe Strategy to Enhance Specific Detection of α-Methyltryptamine)

2025-03-07 中国科学院(CAS)

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• https://english.cas.cn/newsroom/research_news/chem/202503/t20250310_903606.shtml
• https://pubs.acs.org/doi/10.1021/acs.analchem.4c05950

α-メチルトリプタミンに対するπ共役ブリッジブースト特異的検出の精密な電子吸引強度制御 Precise Electron-Withdrawing Strength Regulation of π-Conjugate Bridge-Boosted Specific Detection toward α-Methyltryptamine

Zhenzhen Cai,Zhiheng Huo,Gaosheng Li,Xu Cheng,Fang Xiao,Yuwan Du,Baiyi Zu,Xincun Dou

Analytical Chemistry  Published: January 23, 2025

DOI:https://doi.org/10.1021/acs.analchem.4c05950

Abstract

The specific fluorescent detection of α-methyltryptamine (AMT) presents a great challenge because similar amine groups and benzene rings exist in a variety of amines. Here, we show the precise modulation of the electron-withdrawing strength of the π-conjugate bridge in aldehyde-containing Schiff base-based fluorescent probes for ultratrace AMT discrimination. It is found that different electron-withdrawing groups -C₆H₄, -C₆H₂N₂, and -C₆H₂Br₂ as the π-conjugate bridge of the 2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF)-based probes can classify and identify organic amines with different amine nucleophilicities. Notably, the probe with -C₆H₂Br₂ as the π-conjugate bridge, denoted as BrFS–TCF, which has the highest electrophilicity of the recognition site, shows a superior nM-level limit of detection (LOD) and an instant response time (<0.1 s) toward AMT. Especially, it shows an excellent selectivity facing the secondary amines, tertiary amines, aromatic amines, and even primary amines. The present strategy would provide a new pathway for chemical substances with similar structures and properties and especially for fighting against illegal drugs.