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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

邮发代号 80-969

2019 Impact Factor: 3.552

Frontiers of Chemical Science and Engineering  2020, Vol. 14 Issue (1): 97-104   https://doi.org/10.1007/s11705-019-1828-x
  本期目录
Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores
Dan Wu, Gonzalo Durán-Sampedro, Donal F. O’Shea()
Department of Chemistry, Royal College of Surgeons in Ireland (RCSI), Dublin 2, Ireland
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Abstract

Bis-alkylsulfonic acid and polyethylene glycol (PEG)-substituted BF2 azadipyrromethenes have been synthesized by an adaptable and versatile route. Only four synthetic stages were required to produce the penultimate fluorophore compounds, containing either two alcohol or two terminal alkyne substituents. The final synthetic step introduced either sulfonic acid or polyethylene glycol groups to impart aqueous solubility. Sulfonic acid groups were introduced by reaction of the bis-alcohol-substituted fluorophore with sulfur trioxide, and a double Cu(I)-catalyzed cycloaddition reaction between the bis-alkyne fluorophore and methoxypolyethylene glycol azide yielded a neutral bis-pegylated derivative. Both fluorophores exhibited excellent near-infrared (NIR) photophysical properties in methanol and aqueous solutions. Live cell microscopy imaging revealed efficient uptake and intracellular labelling of cells for both fluorophores. Their simple synthesis, with potential for last-step structural modifications, makes the present NIR-active azadipyrromethene derivatives potentially useful as NIR fluorescence imaging probes for live cells.

Key wordsNIR-fluorophores    live cell imaging    NIR-AZA
收稿日期: 2018-12-19      出版日期: 2020-01-20
Corresponding Author(s): Donal F. O’Shea   
 引用本文:   
. [J]. Frontiers of Chemical Science and Engineering, 2020, 14(1): 97-104.
Dan Wu, Gonzalo Durán-Sampedro, Donal F. O’Shea. Synthesis and properties of water-soluble 1,9-dialkyl-substituted BF2 azadipyrromethene fluorophores. Front. Chem. Sci. Eng., 2020, 14(1): 97-104.
 链接本文:  
https://academic.hep.com.cn/fcse/CN/10.1007/s11705-019-1828-x
https://academic.hep.com.cn/fcse/CN/Y2020/V14/I1/97
Fig.1  
Fig.2  
Fig.3  
Fig.4  
NIR-AZA labs,max /nm
CHCl3 (MeOH)
lflu,max /nm
CHCl3 (MeOH)
Ffa)
CHCl3 (MeOH)
1a 660 (650) 695 (678) 0.27 (0.14)
1b 653 (651) 680 (677) 0.21 (0.16)
Tab.1  
Fig.5  
Fig.6  
Fluorophore Solvent labs, max /nm lflu, max /nm Ff
MB PBS 670 690 0.01
6a MeOH 650 675 0.12
6a PBS 651 690 0.03
6a DMEM 651 691 0.03
6b MeOH 651 679 0.12
6b PBS 657 694 0.06
6b DMEM 658 694 0.05
Tab.2  
Fig.7  
Fig.8  
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[1] FCE-18105-OF-WD_suppl_1 Download
[2] FCE-18105-WD-Cell_vesicles_stained_with_6a Download
[3] FCE-18105-WD-Cell_vesicles_stained_with_6b Download
[4] FCE-18105-WD-Z-stack_of_cell_with_6a Download
[5] FCE-18105-WD-Z-stack_of_cell_with_6b Download
[6] FCE-18105-WD-Z-stack_of_cell_with_6a Download
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