Organelle-selective di-(2-picolyl)amine-appended water-soluble fluorescent sensors for Cu(II): synthesis, photophysical and in vitro studies

  • Yun Hak Lee
  • Peter Verwilst
  • Nayoung Park
  • Joung Hae Lee
  • Jong Seung Kim
Original Article


A novel water-soluble fluorescent naphthalimide derivative as a sensor for Cu(II) has been synthesized. The sensor, conjugated with DPA (as the Cu(II)-binding moiety) and TPP (as the mitochondrial-targeting moiety) was further decorated with a galactose unit at the fluorophore’s terminal using the click reaction. Although confocal fluorescence imaging revealed that probe 1 was not localized in mitochondria, and was neither quenched under Cu-overloading conditions, probe 1 did exhibit a high selectivity for Cu(II) ions over various metal ions in HEPES-buffered solutions. Furthermore the fluorescence was dramatically quenched upon the addition 1 equivalent of Cu(II), and the response was stable in the range of pH 6–10.

Graphical abstract

A fluorophore conjugated with DPA (as the Cu(II)-binding moiety) and TPP (as the mitochondrial-targeting moiety) was further decorated with a galactose unit at the fluorophore’s terminal. The sensor exhibited selectivity over other biologically relevant ions.


Fluorescence Copper ions Cell-imaging Subcellular environment 



This work was supported by CRI project (No. 2009-0081566) from the National Research Foundation of The Ministry of Science, ICT & Future Planning in Korea (JSK) and the Korea University Researcher Support Program (PV).

Supplementary material

10847_2015_482_MOESM1_ESM.docx (326 kb)
Supplementary material 1 (DOCX 325 kb)


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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  1. 1.Department of ChemistryKorea UniversitySeoulKorea
  2. 2.Korea Research Institute of Standards and ScienceDaejeonKorea

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