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荧光苯并硒二唑:细胞内脂滴的合成、表征和定量以及多细胞模型染色。

Fluorescent Benzoselenadiazoles: Synthesis, Characterization, and Quantification of Intracellular Lipid Droplets and Multicellular Model Staining.

机构信息

Laboratory of Medicinal and Technological Chemistry, University of Brası́lia (IQ-UnB), Campus Universita'rio Darcy Ribeiro, CEP, Brasília-DF 70904970, Brazil.

LASOL-CCQFA, Federal University of Pelotas (UFPel), Pelotas, RS 96010-610, Brazil.

出版信息

J Org Chem. 2020 Aug 21;85(16):10561-10573. doi: 10.1021/acs.joc.0c01031. Epub 2020 Aug 10.

Abstract

In this work, we described the synthesis of 10 new fluorescent 2,1,3-benzoselenadiazole small-molecule derivatives and their chemical- and photocharacterizations. The new derivatives could, for the first time, be successfully applied as selective live cell imaging probes (at nanomolar concentrations) and stained lipid-based structures preferentially. Density functional theory (DFT) calculations were used to help in understanding the photophysical data and the intramolecular charge-transfer (ICT) processes of the synthesized dyes. Some derivatives showed impressive cellular responses, allowing them to be tested as probes in a complex multicellular model (i.e., ). When compared with the commercially available dye, the new fluorescent compounds showed far better results both at the cellular level and inside the live worm. Inside the multicellular complex model, the tested probes also showed selectivity, a feature not observed when the commercial dye was used to carry out the bioimaging experiments.

摘要

在这项工作中,我们描述了 10 种新型荧光 2,1,3-苯并硒二唑小分子衍生物的合成及其化学和光化学性质。这些新的衍生物首次成功地被用作选择性活细胞成像探针(纳摩尔浓度),并优先染色基于脂质的结构。密度泛函理论(DFT)计算被用于帮助理解所合成染料的光物理数据和分子内电荷转移(ICT)过程。一些衍生物表现出令人印象深刻的细胞反应,使它们能够在复杂的多细胞模型(即)中作为探针进行测试。与市售染料相比,新的荧光化合物在细胞水平和活体蠕虫内部都显示出更好的结果。在多细胞复杂模型中,测试的探针也表现出选择性,而当使用商业染料进行生物成像实验时,没有观察到这种选择性。

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