Spectroscopic and biological studies of new mononuclear metal complexes of a bidentate NN and NO hydrazone–oxime ligand derived from egonol

Babahan, İlknur; Emirdağ-Öztürk, Safiye; Poyrazoğlu-Çoban, Esin

doi:10.1016/j.saa.2014.12.074

Cited by 33 publications

(17 citation statements)

References 32 publications

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“…This small shift in peak position of the aldehydic group can support the fact that the aldehydic oxygen plays no part in coordination . These data are in accordance with those of the IR spectral analysis …”

Section: Resultssupporting

confidence: 90%

Synthesis, characterization and in vitro antimicrobial and anti‐breast cancer activity studies of metal complexes of novel pentadentate azo dye ligand

Mahmoud

Sayed

Mohamed

2016

Applied Organom Chemis

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A new azo dye with N3O2 donor set of atoms has been synthesized via coupling reaction of 2,6-diaminopyridine with p-methoxybenzaldehyde. The molecular and electronic structure of the azo dye ligand (L) was optimized theoretically and the quantum chemical parameters were calculated. Molecular docking was used to predict the binding between L and the receptors of breast cancer mutant 3hb5-oxidoreductase, crystal structure of Escherichia coli (3 T88) and crystal structure of Staphylococcus aureus (3q8u). The newly synthesized L was used for complex formation with Cr(III), Mn(II), Fe(III), Co.(II), Ni(II), Cu(II), Zn(II) and Cd (II) ions. The nature of bonding and the stoichiometry of L and its mononuclear complexes were deduced from elemental analyses, spectroscopic, magnetic susceptibility, molar conductance, electron spin resonance and conductivity measurements, thermogravimetric analyses and powder X-ray diffraction. Elemental analysis data show that the complexes have composition of ML type with an octahedral geometry for all the complexes. The activation thermodynamic parameters were calculated. The prepared azo dye and its metal complexes were tested against various Gram-positive and Gram-negative bacteria and a fungus. Most complexes exhibit antibacterial and antifungal activities against these organisms. Anticancer evaluation studies against standard breast cancer cell line were performed using various concentrations. The activity index was calculated.

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Section: Resultssupporting

confidence: 90%

Synthesis, characterization and in vitro antimicrobial and anti‐breast cancer activity studies of metal complexes of novel pentadentate azo dye ligand

Mahmoud

Sayed

Mohamed

2016

Applied Organom Chemis

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“…These atoms have more electronegative charge assuring active sites for chelation. (iii) The estimated dipole moment value of the ligand (H 2 L) is 0.9668 while the calculated dipole moment values for complexes (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) are in the 6.03-21.97 Debye range: the comparison of the estimated values of the dipole moments for the ligand and complexes (2-12) indicating that dipole moment for these complexes are higher than the dipole moment for the free ligand. This may be due the chelation of metal ions with the ligand took place via nitrogen atoms of azomethine and oximato groups.…”

Section: Molecular Parametersmentioning

confidence: 89%

“…If the symmetry is still lowered, the 2 E level will also split into 2 B 1 and 2 B 2 leading to four peaks (Figure 8). [62,63] In case of our VO 2+ complex (2), the EAS displayed three peaks at 475, 550, and 800 nm ascribing to the transitions 2…”

Section: Ft-ir Spectramentioning

confidence: 94%

“…[68] In six coordinated octahedral crystal fields E g , which may manifest around 1,000, 650, and 500 nm consecutively. [62,63,70] For Cu 2+ complex (7) the EAS demonstrated three bands at 1,089, 615, and 538 nm, which assignable to 2 (Figure 2). Occasionally, the appearing of these theoretical elucidations in practice is difficult because of the interference and the difficulty to solve in discrete peaks due to the small difference between the levels of d orbitals in energy.…”

Section: Ft-ir Spectramentioning

confidence: 99%

“…Recently, compounds containing hydrazone and/or oxime linkage attracted the attention of many scholars because of their ability to form stable complexes with various transition metals, in addition to the presence of N-OH moiety, which could be enhance their chelation ability and make it more flexible in the reduction, oxidation, and conjugation with organic and inorganic compounds. These categories of compounds and their transition metal complexes showed biochemical [1] and bioactivity against pathogens resistant as antimicrobial, [2][3][4][5][6][7] antitumor, [3,4,8] anticancer, [9] anticandidal, [10] antitubercular, [11] antioxidant, and [4,12] anti-inflammatory analgesic [4,13] activities. Abdel-Aziz et al showed that the isoindoline-1,3-dione-based oximes and benzene-sulphonamide hydrazones have a selective inhibition of the tumor-associated carbonic anhydrase IX.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, and density functional theory studies of hydrazone–oxime ligand derived from 2,4,6‐trichlorophenyl hydrazine and its metal complexes searching for new antimicrobial drugs

Shakdofa

Morsy

Rasras

et al. 2020

Applied Organom Chemis

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Novel 13 mononuclear complexes derived from 3-(2-(2,4,6-trichlorophenyl) hydrazono) butan-2-one oxime with various molar ratio, geometry and different mode of interaction were prepared using transition metal Cd 2+ , Zn 2+ , Cu 2+ , Ni 2+ , Co 2+ , Fe 3+ , Mn 2+ , and VO 2+. The structure of these compounds was investigated physically, analytically, and spectrophotometrically. The ligation sites of the free 3-(2-(2,4,6-trichlorophenyl) hydrazono) butan-2-one oxime were designated via molecular modeling calculations. Furthermore, quantum chemical parameters for the ligand and its complexes were calculated. The analytical and spectral data revealed that the complexes (2-13) were formed with molar ratio of (1 M:1 L) or (1 M:2 L) in which hydrazone oxime adhered with the metal ion as a univalent or neutral bidentate chelator, via the imino nitrogen atom of hydrazone moiety and oximato nitrogen atom of deprotonated/protonated oxime moiety adopting different geometrical structures. The electron spin resonance (ESR) spectra of Cu 2+ complexes (7-8) and (10-11) were referred to axial symmetry with g jj > g ┴ > g e , which indicated that unpaired electron is localized in a d (x2 − y2) orbital with notable bonding covalency nature. The thermo analysis (thermogravimetry [TG]) confirmed that the complexes were decayed in one, two, three, or four steps starting with dehydration process, elimination of coordination water molecules, or removal of anions and completed with the whole decomposition of the complexes with the formation of metal oxide. The ligand did not exhibit antimicrobial activities, but its complexes showed variable activities.

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Bio‐Based Anti‐Biofoulant with Copper(II) as Intramolecular Catalyst for Radicals Formation

Chen

Hao

et al. 2023

Adv Materials Inter

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but was completely banned by the International Maritime Organization in 2002 due to its ability to form enrichment effect in organisms through the food chain, affecting food safety. [9,10] At present, copper oxide, organic copper or a combination of several copper-based antifoulants are the mainstream anti-biofoulants used in antifouling coatings. [11,12] Copper oxide is the most widely used antifouling agent due to its low cost and broadspectrum bactericidal effect. [13] However, it has become evident that copper is highly toxic to marine invertebrates in the marine environment, especially to their larvae. Some research have shown that CuCl 2 at a concentration of 0.38 µmol L −1 in the environment can cause complete arrest of oyster (Crassostrea gigas) larvae, while the semi-lethal concentration (LC 50 ) and absolute lethal concentration (LC 100 ) for Virginia oyster (Crassostrea virginica) embryos are 0.78 and 0.98 µmol L −1 , respectively. [14] For crustaceans, copper was able to kill 50% of different crustacean species after 48 h of exposure to the environment, and juveniles were more sensitive than adults. According to statistics, more than 3000 metric tons of copper are currently imported from the coating into seawater each year. [15] Especially in some bays or closed water bodies where water exchange is poor, copper-containing antifouling coating has a significant effect on the copper content of the water body. [13] In addition to copper-containing antifoulants, chlorothalonil, Irgarol 1051, Sea-Nine 211, diuron, zinc dioxane, etc., are commonly used as eco-friendly antifoulants, but these antifoulants are still required to be combined with cuprous oxide or other copper-containing antifoulants because of their weak inhibitory effect on large fouling organisms. [16][17][18] Therefore, the development of efficient and eco-friendly antifoulants that can replace and significantly reduce of copper-containing antifoulants is crucial for antifouling coatings.Oxime compounds are one of the most important precursors for the preparation of biologically active antibacterial, [19] and copper ions can initiate oxime to produce iminoxyl radicals via the homolytic cleavage of OH bonds, [20] which have highly reactive free radicals in exerting effective antibacterial activity in vitro against most Gram-negative organisms. [21] In the early experiment, some of the antifouling coatings were accidentally contaminated by 2,5-diformylfuran dioxime (DFFD) and its metal chelates. These contaminated antifouling coatings were free from any microorganisms, while some control coatings containing antimicrobial agents showed different degree of microbial growth. Additionally, the solubility of DFFD is Highly efficient and eco-friendly antimicrobial agents are crucial to the development of future marine antifouling coatings. A high efficient and low bio-toxicity bio-based anti-biofoulant, 2,5-diformylfuran dioxime chelating with copper ions (E-DFFD-Cu), is evaluated. Its minimal bactericidal concentration and the concentration for 50%...

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Spectroscopic and biological studies of new mononuclear metal complexes of a bidentate NN and NO hydrazone–oxime ligand derived from egonol

Cited by 33 publications

References 32 publications

Synthesis, characterization and in vitro antimicrobial and anti‐breast cancer activity studies of metal complexes of novel pentadentate azo dye ligand

Synthesis, characterization and in vitro antimicrobial and anti‐breast cancer activity studies of metal complexes of novel pentadentate azo dye ligand

Synthesis, characterization, and density functional theory studies of hydrazone–oxime ligand derived from 2,4,6‐trichlorophenyl hydrazine and its metal complexes searching for new antimicrobial drugs

Bio‐Based Anti‐Biofoulant with Copper(II) as Intramolecular Catalyst for Radicals Formation

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