A simple oxazoline as fluorescent sensor for Zn 2+ in aqueous media

Che, Weilong; Yu, Tiecheng; Jin, Dan; Ren, Xin-Yao; Zhu, Dongxia; Su, Zhong‐Min

doi:10.1016/j.inoche.2016.03.025

Cited by 19 publications

(4 citation statements)

References 35 publications

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“…Although many zinc(II) coordination compounds are stable in a tetrahedral geometry, some five-coordinated complexes have been reported in recent years [ 60 , 61 , 62 ]. One notable example is provided by DMSO coordination [ 63 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

et al. 2021

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The novel zinc(II) µ-oxo-bridged-dimeric complex [Zn2(µ-O)2(BMIP)2] (BMIP = 1,3-bis(5-methoxy-1-methyl-1H-indol-3-yl)propane-1,3-dione), 1, was synthetized and fully characterized. The spectral data indicate a zincoxane molecular structure, with the BMIP ligand coordinating in its neutral form via its oxygen atoms. Structural changes in 1 in dimethylsulfoxide (DMSO) were evidenced by means of spectroscopic techniques including infrared absorption and nuclear magnetic resonance, showing DMSO entrance in the coordination sphere of the metal ion. The resulting complex [Zn2(µ-O)2(BMIP)2(DMSO)], 2, readily reacts in the presence of N-methyl-imidazole (NMI), a liquid-phase nucleoside mimic, to form [Zn2(µ-O)2(BMIP)2(NMI)], 3, through DMSO displacement. The three complexes show high thermal stability, demonstrating that 1 has high affinity for hard nucleophiles. Finally, with the aim of probing the suitability of this system as model scaffold for new potential anticancer metallodrugs, the interactions of 1 with calf thymus DNA were investigated in vitro in pseudo-physiological environment through UV-Vis absorption and fluorescence emission spectroscopy, as well as time-resolved fluorescence studies. The latter analyses revealed that [Zn2(µ-O)2(BMIP)2(DMSO)] binds to DNA with high affinity upon DMSO displacement, opening new perspectives for the development of optimized drug substances.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

et al. 2021

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“…Due to this reason, 5-coordinate Zn complex is considered unusual and expected to be unstable. Nevertheless, 5-coordinate Zn complexes were previously reported [10][11][12][13][14]. Similar to 4-coordinate Zn complexes, the common oxidation state for Zn ion in 5-coordinate Zn complexes is +2; however, the one reported by Song et al is in 0 oxidation state [13].…”

Section: Introductionmentioning

confidence: 86%

Five-Coordinate Zinc(II) Complex: Synthesis, Characterization, Molecular Structure, and Antibacterial Activities of Bis-[(E)-2-hydroxy-N′-{1-(4-methoxyphenyl)ethylidene}benzohydrazido]dimethylsulfoxidezinc(II) Complex

Liu

Tiong

et al. 2017

International Journal of Inorganic Chemistry

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The titled Zn(II) complex was synthesized by reacting the compound (E)-2-hydroxy-N -{1-(4-methoxyphenyl)ethylidene}benzohydrazide with zinc(II) acetate dihydrate in alkaline DMSO and ethanol solution under reflux condition for 28 hours. The resulting solid was filtered and recrystallized from the mixture of ethanol and DMSO. The hydrazone Schiff base and its Zn(II) complex were characterized using 1 H, 13 C NMR, FTIR, UV-Vis spectroscopy, and single crystal X-ray diffraction analysis. Meanwhile, their antibacterial activities were examined using disc diffusion method. The spectral studies showed that the hydrazone Schiff base underwent keto-enol tautomerization, forming a bidentate ligand (N,O) towards Zn(II) ion. Surprisingly, on top of the two hydrazone Schiff base molecules which coordinated to the Zn metal center, an additional DMSO molecule was found attached to the Zn metal center in the crystal data, resulting in a 5-coordinate distorted trigonal bipyramidal Zn(II) complex. Both hydrazone Schiff base and its Zn(II) complexes were found to exhibit low antibacterial activity even when the concentrations were increased to 800 ppm.

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“…Fluorescent chemosensors for Zn 2+ include various classes of compounds, viz., di-2-picolylamine-based, quinoline-based, bipyridine-based, acyclic and cyclic polyamine-based, iminodiacetic acid-based, triazole-based, and Schiff base-based sensors . In addition, anthracene-based, fluorescein-based, , oxazoline-based, 1,10-phenanthroline-based, coumarin-based, , benzimidazole-based, , rhodamine-based, BINOL-based, pyrazoline-based, pyrene-based, , and porphyrin and corrole analogue-based , compounds have also been reported as fluorescent chemosensors for Zn 2+ . Generally, photoinduced electron transfer (PET)- and intermolecular charge transfer (ICT)-based mechanisms for the fluorescence signaling for Zn 2+ sensors have been observed .…”

Section: Introductionmentioning

confidence: 99%

Design of a Highly Selective Benzimidazole-Based Derivative for Optical and Solid-State Detection of Zinc Ion

et al. 2022

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A novel series of benzimidazole-based molecules mimicking biological receptors, which exhibit selective coordination with zinc ions, were designed and synthesized. The photochromic behavior of these derivatives with various metal ions suggests a selective interaction of one of the receptors 2-(pyridin-2-yl)-4,7-di(thiophen-2-yl)-3H-benzo[d]imidazole (2c) with zinc ion. The lower limit of detection by photoluminescence quenching was determined to be 16 nM. The mechanism of selective complexation was elucidated by 1 H nuclear magnetic resonance titrations and dynamic light scattering analysis. The stoichiometry of the formation of the Zn(2c) 2 complex was evaluated by single-crystal X-ray diffraction and mass spectral techniques and calculated to be 2:1 (L:M). A change in the electronic energy levels on the sensor analyte interaction was observed by both ultraviolet photoelectron spectroscopy analysis and by density functional theory calculations, suggesting an electroactive semiconductor behavior. A symmetric Schottky structured sensor device was fabricated using the receptor 2c as the active sensing layer. A distinct change in current−voltage characteristics between the receptor and the complex suggests that the fabricated device could be used as a solid-state sensor for detecting zinc ion.

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A simple oxazoline as fluorescent sensor for Zn 2+ in aqueous media

Cited by 19 publications

References 35 publications

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

Five-Coordinate Zinc(II) Complex: Synthesis, Characterization, Molecular Structure, and Antibacterial Activities of Bis-[(E)-2-hydroxy-N′-{1-(4-methoxyphenyl)ethylidene}benzohydrazido]dimethylsulfoxidezinc(II) Complex

Design of a Highly Selective Benzimidazole-Based Derivative for Optical and Solid-State Detection of Zinc Ion

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