4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures

The imidazole derivative 4-(4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (probe 1) formed a highly coloured and non-emissive 1:1 stoichiometry complex with Cu(II) in water-acetonitrile 1:1 (v/v) solutions. Among all the amino acids (Lys, Val, Gln, Leu, His, Thr, Trp, Gly, Phe, Arg, Ile, Met, S...

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Bibliographic Details
Main Author: Hazem, E. O. (author)
Other Authors: Sayed, S. E. (author), Ferreira, R. C. M. (author), Costa, Susana P. G. (author), Raposo, M. Manuela M. (author), Martínez-Máñez, R. (author), Sancenón, F. (author)
Format: article
Language:eng
Published: 2018
Subjects:
Glutathione
Chromo-fluorogenic detection
Cu(II) complex
Displacement assay
synthesis
heterocycles
imidazole
optical chemosensor
fluoresecence
Ciências Naturais::Ciências Químicas
Science & Technology
Online Access:http://hdl.handle.net/1822/57133
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/57133
Description
Summary:The imidazole derivative 4-(4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (probe 1) formed a highly coloured and non-emissive 1:1 stoichiometry complex with Cu(II) in water-acetonitrile 1:1 (v/v) solutions. Among all the amino acids (Lys, Val, Gln, Leu, His, Thr, Trp, Gly, Phe, Arg, Ile, Met, Ser, Ala, Pro, Tyr, Gly, Asn, Asp, Glu, Cys and Hcy) and tripeptides (GSH) tested, only GSH induced the bleaching of the 1·Cu(II) solution together with a marked emission enhancement at 411 nm (excitation at 320 nm). These chromo-fluorogenic changes were ascribed to a selective GSH-induced demetallation of the 1·Cu(II) complex that resulted in a recovery of the spectroscopic features of probe 1. In addition to the remarkable selectivity of 1·Cu(II) complex toward GSH a competitive limit of detection as low as 2 μM was determined using fluorescence measurements.

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