A dansyl-appended N-heterocycle for Cu2+ and S2- recognition via a displacement mode

Xu Wang; Peng Xia; Xiaohuan Huang

doi:10.1016/j.saa.2018.11.017

A dansyl-appended N-heterocycle for Cu²⁺ and S^2- recognition via a displacement mode

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Mar 5:210:98-104. doi: 10.1016/j.saa.2018.11.017. Epub 2018 Nov 13.

Authors

Xu Wang¹, Peng Xia¹, Xiaohuan Huang²

Affiliations

¹ Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, PR China.
² Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, PR China. Electronic address: xhuang@hbnu.edu.cn.

PMID: 30448634
DOI: 10.1016/j.saa.2018.11.017

Abstract

A novel l-proline based heterocycle 3 of C₂ symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu²⁺ ion, and their interaction induces a remarkable fluorescence quenching in DMSO:H₂O=9:1 (HEPES buffer, 0.01M, pH7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu²⁺ complex exhibit specific fluorescence recovery upon addition of S^2-, even in the presence of S₂O₃^2-, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of ¹H NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential "on-off-on" fluorescence bio-imaging of the heterocycle 3 to Cu²⁺ and S^2- was carried out in HeLa cells.

Keywords: Amide-containing heterocycle; Cell imaging; Displacement mode; S(2−) recognition.

MeSH terms

Amino Acids / chemistry
Copper / analysis*
Copper / chemistry
Copper / metabolism
HeLa Cells
Heterocyclic Compounds / chemical synthesis
Heterocyclic Compounds / chemistry*
Heterocyclic Compounds / metabolism
Histidine / chemistry
Humans
Limit of Detection
Magnetic Resonance Spectroscopy
Molecular Imaging / methods
Molecular Structure
Phosphatidylcholines / chemistry
Proline / chemistry
Solutions / chemistry
Spectrometry, Fluorescence / methods*
Spectrometry, Mass, Electrospray Ionization
Spectroscopy, Fourier Transform Infrared
Sulfhydryl Compounds / chemistry
Sulfides / analysis*
Sulfides / chemistry
Sulfides / metabolism

Substances

1-myristoyl-2-(12-((5-dimethylamino-1-naphthalenesulfonyl)amino)dodecanoyl)-sn-glycero-3-phosphocholine
Amino Acids
Heterocyclic Compounds
Phosphatidylcholines
Solutions
Sulfhydryl Compounds
Sulfides
Histidine
Copper
Proline