A BINOL-based ratiometric fluorescent sensor for Zn2+ and in situ generated ensemble for selective recognition of histidine in aqueous solution

Abstract

A novel BINOL-based ratiometric fluorescent sensor (R2) is presented, which can selectively respond to Zn(2+) over Cd(2+) and other metal ions with fluorescence enhancement in aqueous solution. The R2 was successfully applied in the imaging of Zn(2+) in living cells. Additionally, the in situ generated R2-Zn(II) ensemble could further serve as a probe to distinguish histidine from other amino acids via a displacement mode.

Fluorescent/luminescent detection of natural amino acids by organometallic systems

“…1,1′-binaphthyl derivatives have been widely used as optical fluorophores due to their special C 2 axial chirality, rigid structure, relatively high emission efficience and readily selective functionalization Figure 13) via a displacement mode [62]. Upon titration of the 31-Zn 2+ ensemble with His, the fluorescence intensity decreased, which could be attributed to dechelation of 31-Zn 2+ and formation of the His-Zn 2+ complex.…”

A Phenyl Thioether‐Based Probe: Zn2+ Ion Sensor, Structure Determination and Live Cell Imaging†

“…Herein we report, a diformyl thioether based fluorescent chemosensor, H 2 ‐SAP , prepared by simple Schiff base condensation procedure ( Scheme S1 ) which displays selective fluorescence sensitivity towards Zn 2+ by chelation enhancement fluorescence effect (CHEF) process in presence of large number of ions and could identify Zn 2+ in nM level, much lower than so far reported results . The composition of the complex formed between Zn 2+ and H 2 ‐SAP has been supported by spectroscopic data (Mass, Job's plot) and single crystal X‐ray crystallography.…”

“…Chemical sensing via fluorescence signal recognition has been first established during 1980s . Since then researchers are engaged to design various types of fluorogenic sensors to detect Zn 2+ in different environment including intracellular measurements, Fluorogenic motifs like naphthyl, Diformyl derivative, terpyridyl, quinoline,, imidazoylpyridyl,, bipyridyl,, pyrenyl derivatives, terphenyl‐based motif, pyrimidinyl attached Schiff‐base, pyrazolyl,, BINOL, rhodamine,, catechol appended Schiff base, coumarinyl Schiff base, thiazolyl derivative etc. have successfully been used.…”

Chiral Zinc Complexes Used as Fluorescent Sensor for Natural Amino Acids

“…It is well known that sensing natural amino acids in aqueous solution has vital necessity, because all living processes occur in aqueous media. Moreover, the zinc complex exhibited strong blue fluorescence under UV excitation in water and Zn 2+ has strong ability to form complex with amino acids . Therefore, we chose S ‐ Zn as the representative to discuss the fluorescent response of zinc complexes to various amino acids.…”

“…The effective sense of amino acids can be achieved by constructing a metal complex with special structure through reasonable design. The metal ions of these complexes can serve as active sites for amino acids, and the unique spatial structure of the complexes can limit it interact with special amino acids through supramolecular interaction These unique characteristics make it possible to sense amino acids.…”