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一种基于新型荧光团的新型高选择性荧光氰化物传感器及其在生物成像中的应用。

A new highly selective fluorescent sensor based on a novel fluorophore for cyanide and its applications in bioimaging.

机构信息

College of Chemistry, Jilin University, Changchun, China.

Key Laboratory of Lymphatic Surgery Jilin Province, China-Japan Union Hospital of Jilin University, Changchun, China.

出版信息

Luminescence. 2021 Mar;36(2):336-344. doi: 10.1002/bio.3946. Epub 2020 Oct 13.

DOI:10.1002/bio.3946
PMID:32914537
Abstract

A novel highly active fluorescence chemical sensor (TBI) for CN was synthesized based on triphenylamine-benzothiazole as a new fluorophore, and was used for the first time as a fluorophore for detection of CN . Fluorescence quantum yield of the probe clearly increased when using triphenylamine-benzothiazole as the group. The probe possessed good selectivity towards CN and had anti-interference ability over common ions. After adding CN , the UV-visible spectrum of TBI changed clearly and underwent a dramatic colour change from red to colourless, which could be observed clearly by the naked eye. The limit of detection for CN was calculated to be 2.62 × 10 M, which was well below the WHO cut-off point of 1.9 μM. The novel probe displayed fast sensing of CN . The detection mechanism was a nucleophilic addition reaction between CN and a carbon atom -C = N- in indole salt. The π-conjugation and intramolecular charge transfer (ICT) transition in the TBI molecule were destroyed by this addition, which resulted in a change of fluorescence before and after the addition of CN . The mechanism was verified using theoretical calculation, H NMR titration, and mass spectra. In addition, the probe showed low cytotoxicity and could be used for biological imaging in HeLa cells.

摘要

一种新型的高活性荧光化学传感器(TBI)基于三苯胺-苯并噻唑作为新的荧光团,首次被用作检测 CN 的荧光团。使用三苯胺-苯并噻唑作为基团时,探针的荧光量子产率明显增加。该探针对 CN 具有良好的选择性,并且对常见离子具有抗干扰能力。加入 CN 后,TBI 的紫外-可见光谱明显改变,并发生从红色到无色的剧烈颜色变化,肉眼可清晰观察到。CN 的检测限计算为 2.62×10 M,远低于世界卫生组织规定的 1.9 μM 截止值。该新型探针对 CN 具有快速的感应能力。检测机制是 CN 与吲哚盐中碳原子 -C = N- 之间的亲核加成反应。这种加成破坏了 TBI 分子中的π共轭和分子内电荷转移(ICT)跃迁,导致 CN 加入前后荧光的变化。该机制通过理论计算、 1 H NMR 滴定和质谱得到了验证。此外,该探针显示出低细胞毒性,可用于 HeLa 细胞的生物成像。

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