用于生物应用的具有深红色至近红外发射的氨基苯并呋喃稠合罗丹明染料。
Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications.
作者信息
Niu Guangle, Liu Weimin, Wu Jiasheng, Zhou Bingjiang, Chen Jianhong, Zhang Hongyan, Ge Jiechao, Wang Ying, Xu Haitao, Wang Pengfei
机构信息
†Key Laboratory of Photochemical Conversion and Optoelectronic Materials and CityU-CAS Joint Laboratory of Functional Materials and Devices, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
‡University of Chinese Academy of Sciences, Beijing 100049, China.
出版信息
J Org Chem. 2015 Mar 20;80(6):3170-5. doi: 10.1021/acs.joc.5b00077. Epub 2015 Feb 26.
Aminobenzofuran-fused rhodamine dyes (AFR dyes) containing an amino group were constructed by an efficient condensation based on 3-coumaranone derivatives. AFR dyes exhibited significantly improved properties, including deep-red and near-infrared emissions, a large Stokes shift, good photostability, and wide pH stability. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium assay experiments show that these AFR dyes are biocompatible for their low cytotoxicity to both A549 and HeLa cells. Cell imaging data reveal that AFR1, AFR1E, and AFR2 are mainly located in the mitochondria, while AFR3 is a lysosome tracker. As far as we know, NIR AFR3 is the longest fluorescent rhodamine derivative containing the amino group. These amino group-containing AFR dyes hold great potential in fluorogenic detection, biomolecule labeling, and cell imaging.
基于3-香豆满酮衍生物，通过高效缩合反应构建了含氨基的氨基苯并呋喃稠合罗丹明染料（AFR染料）。AFR染料表现出显著改善的性能，包括深红色和近红外发射、大斯托克斯位移、良好的光稳定性和宽pH稳定性。3-(4,5-二甲基噻唑-2-基)-2,5-二苯基-2H-四唑溴盐检测实验表明，这些AFR染料对A549和HeLa细胞的细胞毒性较低，具有生物相容性。细胞成像数据显示，AFR1、AFR1E和AFR2主要位于线粒体中，而AFR3是一种溶酶体追踪剂。据我们所知，近红外AFR3是含氨基的最长荧光罗丹明衍生物。这些含氨基的AFR染料在荧光检测、生物分子标记和细胞成像方面具有巨大潜力。
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