A binuclear Zn(II)-Zn(II) complex from a 2-hydroxybenzohydrazide-derived Schiff base for selective detection of pyrophosphate.
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ABSTRACT:
SUBMITTER: Wang J
PROVIDER: S-EPMC4161210 | biostudies-literature | 2014 Oct
REPOSITORIES: biostudies-literature
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Project description:The synthesis of the new cofacial binuclear zinc complex [Zn(2)(L)] of a Schiff-base pyrrole macrocycle is reported. It was discovered that the binuclear microenvironment between the two metals of [Zn(2)(L)] is suited for the encapsulation of anions, leading to the formation of [K(THF)(6)][Zn(2)(μ-Cl)(L)]·2THF and [Bu(n)(4)N][Zn(2)(μ-OH)(L)] which were characterized by X-ray crystallography. Unusually obtuse Zn-X-Zn angles (X = Cl: 150.54(9)° and OH: 157.4(3)°) illustrate the weak character of these interactions and the importance of the cleft preorganization to stabilize the host. In the absence of added anion, aggregation of [Zn(2)(L)] was inferred and investigated by successive dilutions and by the addition of coordinating solvents to [Zn(2)(L)] solutions using NMR spectroscopy as well as isothermal microcalorimetry (ITC). On anion addition, evidence for deaggregation of [Zn(2)(L)], combined with the formation of the 1:1 host-guest complex, was observed by NMR spectroscopy and ITC titrations. Furthermore, [Zn(2)(L)] binds to Cl(-) selectively in THF as deduced from the ITC analyses, while other halides induce only deaggregation. These conclusions were reinforced by density functional theory (DFT) calculations, which indicated that the binding energies of OH(-) and Cl(-) were significantly greater than for the other halides.
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Project description:A new binuclear copper(ii) Schiff base complex [Cu2 L2 - (NO3)2]·2CH3OH (1) [L = 2,6-bis((E)-(p-tolylimino)methyl)-4-methoxyphenol] was synthesized using a template method in which the tridentate N2O Schiff base ligand was derived from [1 + 2] condensation of 2,6-diformyl-4-methoxyphenol and p-methyl aniline in the presence of copper(ii) ions as the template agent. The X-ray diffraction analyses revealed that this complex crystallizes in the monoclinic system with space group P21/n. The most remarkable structural feature of 1 is that it contains two types of 1D right-handed helical chains. The molecules are linked by intermolecular hydrogen bonds and π⋯π interactions, then a 3D supramolecular network was constructed. Moreover, the intermolecular interactions on the crystal packing of 1 have been further studied using Hirshfeld surface analysis and corresponding 2D fingerprint plots. Binding interaction of this complex with calf thymus DNA (CT-DNA) has been investigated using absorption and emission studies, viscosity experiments and circular dichroism studies. Complex 1 shows significant binding to the DNA. The results of fluorescence spectroscopy and UV absorption spectroscopy, CD spectroscopy and viscosity indicated that this complex interacted with CT-DNA in a groove binding mode where the binding constant was 1.3 ± 0.2 × 104 L mol-1. Our fluorimeteric study showed that the reaction between 1 and CT-DNA was exothermic (ΔH = 59.6 kJ mol-1; ΔS = 268.79 J mol-1 K-1). Antibacterial activities of the complex were screened by the disc diffusion method against three Gram-positive bacteria (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 23212 and S. epidermidis ATCC 34384), and three Gram-negative bacteria (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 and Klebsiella pneumonia ATCC 70063). The results indicated that this complex demonstrated acceptable antibacterial activities.
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Project description:Platinum electrodes were modified with polymers of the (±)-trans-N,N'-bis(salicylidene)-1,2-cyclohexanediaminenickel(II) ([Ni(salcn)]) and (±)-trans-N,N'-bis(3,3'-tert-Bu-salicylidene)-1,2-cyclohexanediaminenickel(II) ([Ni(salcn(Bu))]) complexes to study their electrocatalytic and electroanalytical properties. Poly[Ni(salcn)] and poly[Ni(salcn(Bu))]) modified electrodes catalyze the oxidation of catechol, aspartic acid and NO2-. In the case of poly[Ni(salcn)] modified electrodes, the electrocatalysis process depends on the electroactive surface coverage. The films with low electroactive surface coverage are only a barrier in the path of the reducer to the electrode surface. The films with more electroactive surface coverage ensure both electrocatalysis inside the film and oxidation of the reducer directly on the electrode surface. In the films with the most electroactive surface coverage, electrocatalysis occurs only at the polymer-solution interface. The analysis was based on cyclic voltammetry, EQCM (electrochemical quartz crystal microbalance) and rotating disc electrode method.
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Project description:In a simple, one-step reaction, we have synthesized a pyridoxal-based chemosensor by reacting tris(hydroxymethyl)aminomethane (TRIS) together with pyridoxal hydrochloride to yield a Schiff-base ligand that is highly selective for the detection of Zn(ii) ion. Both the ligand and the Zn(ii) complex have been characterized by 1H & 13C NMR, ESI-MS, CHN analyses, and X-ray crystallography. The optical properties of the synthesized ligand were investigated in an aqueous buffer solution and found to be highly selective and sensitive toward Zn(ii) ion through a fluorescence turn-on response. The competition studies reveal the response for zinc ion is unaffected by all alkali and alkaline earth metals; and suppressed by Cu(ii) ion. The ligand itself shows a weak fluorescence intensity (quantum yield, Φ = 0.04), and the addition of zinc ion enhanced the fluorescence intensity 12-fold (quantum yield, Φ = 0.48). The detection limit for zinc ion was 2.77 × 10-8 M, which is significantly lower than the WHO's guideline (76.5 μM). Addition of EDTA to a solution containing the ligand-Zn(ii) complex quenched the fluorescence, indicating the reversibility of Zn(ii) binding. Stoichiometric studies indicated the formation of a 2 : 1 L2Zn complex with a binding constant of 1.2 × 109 M-2 (±25%). The crystal structure of the zinc complex shows the same hydrated L2Zn complex, with Zn(ii) ion binding with an octahedral coordination geometry. We also synthesized the copper(ii) complex of the ligand, and the crystal structure showed the formation of a 1 : 1 adduct, revealing 1-dimensional polymeric networks with octahedral coordinated Cu(ii). The ligand was employed as a sensor to detect zinc ion in HEK293 cell lines derived from human embryonic kidney cells grown in tissue culture which showed strong luminescence in the presence of Zn(ii). We believe that the outstanding turn-on response, sensitivity, selectivity, lower detection limit, and reversibility toward zinc ion will find further application in chemical and biological science.
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Project description:BackgroundBased on the potential of Schiff base compounds to act as sources for the development of cancer chemotherapeutic agents, this in vivo study was performed to investigate the inhibitory properties of the synthetic Schiff base compound Cu(BrHAP)2 on colonic aberrant crypt foci (ACF).MethodologyThis study involved five groups of male rats. The negative control group was injected with normal saline once a week for 2 weeks and fed 10% Tween 20 for 10 weeks, the cancer control group was subcutaneously injected with 15 mg/kg azoxymethane once per week for two consecutive weeks, the positive control group was injected with 15 mg/kg azoxymethane once per week for two consecutive weeks and 35 mg/kg 5-fluorouracil (injected intra-peritoneally) for 4 weeks, and the experimental groups were first injected with 15 mg/kg azoxymethane once per week for two consecutive weeks and then fed 2.5 or 5 mg/kg of the Schiff base compound once a day for 10 weeks. Application of the Schiff base compound suppressed total colonic ACF formation by up to 72% to 74% (P<0.05) when compared with the cancer control group. Analysis of colorectal specimens revealed that treatments with the Schiff base compound decreased the mean crypt scores in azoxymethane-treated rats. Significant elevations of superoxide dismutase, glutathione peroxidase and catalase activities and a reduction in the level of malondialdehyde were also observed. Histologically, all treatment groups exhibited significant decreases in dysplasia compared to the cancer control group (P<0.05). Immunohistochemical staining demonstrated down-regulation of the PCNA protein. Comparative western blot analysis revealed that COX-2 and Bcl2 were up-regulated and Bax was down-regulated compared with the AOM control group.ConclusionThe current study demonstrated that the Cu(BrHAP)2 compound has promising chemoprotective activities that are evidenced by significant decreases in the numbers of ACFs in azoxymethane-induced colon cancer.
| S-EPMC3949758 | biostudies-literature
Project description:The development of chemosensors able to detect analytes in a variety of sample matrices through a low-cost, fast, and direct approach is of current interest in food, health, industrial, and environmental fields. This contribution presents a simple approach for the selective and sensitive detection of Cu2+ ions in aqueous solution based on a transmetalation process of a fluorescent substituted Zn(salmal) complex. Transmetalation is accompanied by relevant optical absorption changes and quenching of the fluorescence emission, leading to high selectivity and sensitivity of the chemosensor, with the advantage of not requiring any sample pretreatment or pH adjustment. Competitive experiments demonstrate a high selectivity of the chemosensor towards Cu2+ with respect to the most common metal cations as potential interferents. A limit of detection down to 0.20 μM and a dynamic linear range up to 40 μM are achieved from fluorometric data. By exploiting the fluorescence quenching upon formation of the copper(II) complex, simple paper-based sensor strips, visible to naked eyes under UV light, are used for the rapid, qualitative, and quantitative in situ detection of Cu2+ ions in aqueous solution over a wide concentration range, up to 10.0 mM, in specific environments, such as in industrial wastewater, where higher concentrations of Cu2+ ions can occur.
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