Bisquinoline-based fluorescent zinc sensors

Several bisquinoline derivatives, N,N'-bis(2-quinolylmethyl)-N,N'-dialkylethylnediamines (alkyl=methyl, ethyl, isopropyl and t-butyl), have been synthesized and their fluorescent responses toward zinc ion were investigated. These compounds exhibit zinc ion-induced fluorescence and their in...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2009-01 (19), p.3800-3806
Main Authors: Mikata, Yuji, Yamashita, Azusa, Kawamura, Ayano, Konno, Hideo, Miyamoto, Yuka, Tamotsu, Satoshi
Format: Article
Language:English
Subjects:
Animals
Cell Survival
Crystallography, X-Ray
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Hydrogen-Ion Concentration
Intracellular Space - metabolism
Ligands
PC12 Cells
Quinolines - chemical synthesis
Quinolines - chemistry
Rats
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Zinc - analysis
Zinc - metabolism
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Summary:Several bisquinoline derivatives, N,N'-bis(2-quinolylmethyl)-N,N'-dialkylethylnediamines (alkyl=methyl, ethyl, isopropyl and t-butyl), have been synthesized and their fluorescent responses toward zinc ion were investigated. These compounds exhibit zinc ion-induced fluorescence and their intensities decrease as the alkyl groups become larger. The t-butyl derivative (BQDtBEN) exhibited negligible fluorescence even in the presence of zinc ion. The fluorescence intensity of the zinc complex of the bisquinoline derivative (BQDMEN) is higher than that of TQEN (N,N,N',N'-tetrakis(2-quinolylmethyl)ethylenediamine), indicating that the TQEN-Zn complex has an intramolecular quenching mechanism due to the energy transfer among four quinoline rings and the remaining photoinduced electron transfer (PET) mechanism. Introduction of methoxy substituents into the quinoline ring shifted the excitation and emission wavelengths towards a lower-energy direction and increased the fluorescence intensity, which allows N,N'-bis(6-methoxy-2-quinolylmethyl)-N,N'-dimethylethylenediamine (6-MeOBQDMEN) to be used for cellular fluorescent microscopic analysis (lambdaex=331 nm, lambdaem=406 nm and phi=0.28 for 6-MeOBQDMEN-Zn complex).
ISSN:1477-9226
1477-9234
DOI:10.1039/b820763a