Naphthylhydrazone based selective and sensitive chemosensors for Cu2+ and their application in bioimaging

Abstract

Two new hydroxynaphthyl-hydrazone based fluorogenic chemosensors R1 and R2 have been synthesized by Schiff base condensation of Tris(4-formylphenyl)amine with 1-hydroxynaphthalene-2-hydrazide and 1-hydroxynaphthalene-2-carbohydrazone, respectively. They are examined as highly selective and sensitive receptors for Cu2+ ions in aqueous medium. Electronic absorption as well as fluorescence titration studies of receptors R1 and R2 with different metal cations in H2O/CH3CN medium showed highly selective and very rapid (<2 min) binding affinity towards Cu2+ ions even in the presence of other commonly coexisting metal ions such as Na+, K+, Mg2+, Ca2+, Mn2+, Fe2+, Co2+, Ni2+, Zn2+, Cd2+ and Hg2+. Quantification of the fluorescence titration analysis indicated that these newly synthesized receptors (R1 and R2) can indicate the presence of Cu2+ ions even at very low concentrations of 598 and 676 ppt, respectively. In addition, the propensity of these receptors as bio-imaging fluorescent probes to detect Cu2+ ions in human cervical HeLa cancer cell lines and their cytotoxicity against HeLa cells have been investigated.

Luminescent sensor for copper(II) ion based on imine functionalized monometallic rhenium(I) complexes

“…By forming a biphasic (absorption method) and monobasic (emission method) complexation with Cu 2+ , iminocoumarin derivative in aqueous buffer was able to detect Cu 2+ with an LOD of 2 M and 200 nm by naked eye and emission experiment, respectively [78]. Two hydroxynaphthylhydrazone based fluorogenic chemosensors in H2O/CH3CN mixture became highly selective for Cu 2+ ions over other metal ions, leading to a LOD of 9.40 × 10 −9 M (598 ppt)-10.64 × 10 −9 M (676 ppt) [79].…”

A Phenanthroimidazole‐based Fluorescent Turn‐Off Chemosensor for the Selective Detection of Cu2+ in Aqueous Media

“…[26][27][28][29][30] It is well known that chemical probes with large Stokes shifts are advisable because when incident light and emission signal are separated enough, the self-absorption can be avoided and the detection sensitivity could be improved. [26][27][28][29][30] It is well known that chemical probes with large Stokes shifts are advisable because when incident light and emission signal are separated enough, the self-absorption can be avoided and the detection sensitivity could be improved.…”

Tuning FRET efficiency as a novel approach for improved detection of naphthalene: application to environmental samples

“…Methods for naphthalene determination are mainly based on high-performance liquid chromatography (Diaz et al, 1999;Kishikawa et al, 2003;Gautam et al, 2011) or other chromatography techniques (Hossain et al, 2014;Andreoli et al, 1999). Fluorescence method has several advantages over chromatographic detection such as easy sample preparation protocols, convenient operation, fast response, low cost and high sensitivity (Zhu et al, 2010;Han et al, 2012;Anbu et al, 2012).To the best of our knowledge, fluorescence probe for selective trace level determination of naphthalene is not reported yet. Presently, our research focuses to develop fluorescence probes selective for cations Sahana et al, 2011;Das et al, 2013) anions (Banerjee et al, 2013a;Sahana et al, 2012;Lohar et al, 2013), amino acids Banerjee et al, 2013b) and small molecules.…”