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通过将二氨基马来腈连接到 BODIPY 支架上来构建超快速 Cu 响应型化学传感器,用于活细胞的高对比度荧光成像。

Configuration of super-fast Cu-responsive chemosensor by attaching diaminomaleonitrile to BODIPY scaffold for high-contrast fluorescence imaging of living cells.

机构信息

NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, PR China.

NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, PR China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2024 Jan 5;304:123377. doi: 10.1016/j.saa.2023.123377. Epub 2023 Sep 9.

DOI:10.1016/j.saa.2023.123377
PMID:37776706
Abstract

A highly fluorescent Cu-responsive sensor, 2-amino-3-(BODIPYmethyleneamino)maleonitrile (BD) was constructed by attaching diaminomaleonitrile to a BODIPY scaffold. Cu can be selectively recognized on a 2-s time-scale by way of fluorescence emission. When Cu and BD coexist in solution, typical BODIPY emission was observed and the emission intensity could be increased to 334 times that of the blank dye solution. The mechanism of fluorescence increase is based on the generation of highly fluorescent species by Cu-triggered oxidative cyclization of the attached diaminomaleonitrile. The absolute fluorescence quantum yield (AFQY) of the cyclization product is 98% determined by integrating sphere. The highly emissive character can be attributed to the imidazole ring and dicarbonitrile on the BODIPY scaffold. It surpasses the meso-phenyl substituted analogue in AFQY and detection limits (DL). The specific Cu recognition behavior was also validated in Hela cells with high-contrast fluorescence images.

摘要

一种高荧光的 Cu 响应传感器,2-氨基-3-(BODIPYmethyleneamino)马来腈(BD)是通过将二氨基马来腈连接到 BODIPY 支架上构建的。Cu 可以在 2-s 的时间尺度上通过荧光发射选择性识别。当 Cu 和 BD 共存于溶液中时,观察到典型的 BODIPY 发射,并且发射强度可以增加到空白染料溶液的 334 倍。荧光增强的机制基于附着的二氨基马来腈在 Cu 触发的氧化环化作用下生成高荧光物种。通过积分球测定,环化产物的绝对荧光量子产率(AFQY)为 98%。高发光特性可归因于 BODIPY 支架上的咪唑环和二氰基。它在 AFQY 和检测限(DL)方面超过了中取代苯基类似物。在 HeLa 细胞中也验证了特定的 Cu 识别行为,具有高对比度的荧光图像。

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