333303-11-0Relevant articles and documents
Deep-Red and Near-Infrared Xanthene Dyes for Rapid Live Cell Imaging
Niu, Guangle,Liu, Weimin,Zhou, Bingjiang,Xiao, Hongyan,Zhang, Hongyan,Wu, Jiasheng,Ge, Jiechao,Wang, Pengfei
, p. 7393 - 7399 (2016/09/09)
In this work, two xanthene dyes (H-hNR and TF-hNR) have been synthesized by a convenient and efficient method. These two dyes exhibited deep-red and near-infrared emissions, high fluorescence quantum yields, and good photostability. Their structure-optical properties were investigated by X-ray crystal structure analysis and density functional theory calculations. Live cell imaging data revealed that H-hNR and TF-hNR could rapidly stain both A549 and HeLa cells with low concentrations. The excellent photophysical and imaging properties render them as promising candidates for use in live cell imaging.
Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications
Niu, Guangle,Liu, Weimin,Wu, Jiasheng,Zhou, Bingjiang,Chen, Jianhong,Zhang, Hongyan,Ge, Jiechao,Wang, Ying,Xu, Haitao,Wang, Pengfei
, p. 3170 - 3175 (2015/03/30)
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.
Synthesis and fluorescence properties of substituted 7-aminocoumarin-3-carboxylate derivatives
Corrie,Munasinghe,Rettig
, p. 1447 - 1455 (2007/10/03)
4-Trifluoromethyl- or 6-bromo-substituted 7-diethylaminocoumarin-3-carboxamide derivatives 2 and 3, each containing a maleimide have been synthesized as potential fluorescent labeling reagents for thiol groups in proteins and their fluorescence properties have been determined. The 4-trifluoromethyl substituted compound 2 has a significantly greater Stokes shift than the comparable compound lacking this group, but both the new coumarins have low fluorescence quantum yields (φf). When a 4-trifluoromethyl substituent is present, the 3-carboxamide is unusually labile to hydrolysis. Bromination of ethyl 7-diethylaminocoumarin-3-carboxylate 17 gave the 6- and 8-bromo derivatives 18 and 19 respectively, and also the 8-bromo-7-monoethylamino compound 20. φf for the latter compound is 100-fold greater than for its diethylamino analogue 19. Fluorescence lifetime measurements support an interpretation based on the twisted intramolecular charge transfer (TICT) model to explain these large differences in φf.
