Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications

Guangle Niu; Weimin Liu; Jiasheng Wu; Bingjiang Zhou; Jianhong Chen; Hongyan Zhang; Jiechao Ge; Ying Wang; Haitao Xu; Pengfei Wang

doi:10.1021/acs.joc.5b00077

Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications

Guangle Niu, Weimin Liu^*, Jiasheng Wu, Bingjiang Zhou, Jianhong Chen, Hongyan Zhang, Jiechao Ge, Ying Wang, Haitao Xu, Pengfei Wang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3170-3175
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	80
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.5b00077
Publication status	Published - 20 Mar 2015
Externally published	Yes

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title = "Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications",

abstract = "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.",

author = "Guangle Niu and Weimin Liu and Jiasheng Wu and Bingjiang Zhou and Jianhong Chen and Hongyan Zhang and Jiechao Ge and Ying Wang and Haitao Xu and Pengfei Wang",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acs.joc.5b00077",

language = "English",

volume = "80",

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T1 - Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications

AU - Niu, Guangle

AU - Liu, Weimin

AU - Wu, Jiasheng

AU - Zhou, Bingjiang

AU - Chen, Jianhong

AU - Zhang, Hongyan

AU - Ge, Jiechao

AU - Wang, Ying

AU - Xu, Haitao

AU - Wang, Pengfei

PY - 2015/3/20

Y1 - 2015/3/20

N2 - 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.

AB - 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.

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SN - 0022-3263

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EP - 3175

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications

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