Construction of long-wavelength fluorescein analogues and their application as fluorescent probes

Xiaoqing Xiong; Fengling Song; Gengwen Chen; Wen Sun; Jingyun Wang; Pan Gao; Yukang Zhang; Bo Qiao; Wenfang Li; Shiguo Sun; Jiangli Fan; Xiaojun Peng

doi:10.1002/chem.201300418

Construction of long-wavelength fluorescein analogues and their application as fluorescent probes

Chemistry. 2013 May 17;19(21):6538-45. doi: 10.1002/chem.201300418. Epub 2013 Apr 15.

Authors

Xiaoqing Xiong¹, Fengling Song, Gengwen Chen, Wen Sun, Jingyun Wang, Pan Gao, Yukang Zhang, Bo Qiao, Wenfang Li, Shiguo Sun, Jiangli Fan, Xiaojun Peng

Affiliation

¹ State Key Laboratory of Fine Chemicals, Dalian University of Technology, 2 Linggong Road, Dalian 116025, PR China.

PMID: 23589345
DOI: 10.1002/chem.201300418

Abstract

Born to dye: Five fluorescein analogues were synthesised (see scheme). One analogue was found to emit in the NIR region with a high quantum yield, excellent photostability and good permeability. Three derivatives were found to specifically stain mitochondria and one dye responds to thiols with a strong turn-on NIR fluorescence signal and colorimetric change, in vitro and in vivo.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cysteine / analysis*
Cysteine / chemistry
Female
Fluoresceins / chemical synthesis*
Fluoresceins / chemistry
Fluorescence
Fluorescent Dyes / chemical synthesis*
Fluorescent Dyes / chemistry
HeLa Cells
Humans
Male
Mice
Mice, Inbred ICR
Molecular Structure
Spectroscopy, Near-Infrared
Sulfhydryl Compounds
Tumor Cells, Cultured

Substances

Fluoresceins
Fluorescent Dyes
Sulfhydryl Compounds
2',7'-dichlorofluorescein
Cysteine