Structural variety in copper(II) complexes of 3-formylchromone: Synthesis, spectral, thermal, molecular modeling and biological studies

Adly, Omima M.I.; Taha, A.; Elabd, Nouran

doi:10.1016/j.molstruc.2017.06.085

Cited by 38 publications

(21 citation statements)

References 57 publications

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“…All complexes display strong broad bands in the range 3377–3449 cm −1 , which may be attributed to ν(OH) of the non‐coordinated and/or coordinated water molecules. The bands assigned to ν(C&dbond;O) isatinic , ν(C&dbond;O) chromone and ν(C&dbond;N) in the hydrazone ligand show a marked shift to lower wavenumber for all complexes, indicating the contribution of these groups in chelation . In the pure complex, new bands appeared at 1455 and 1315 cm −1 , which may be ascribed to ν as (COO − ) and ν s (COO − ), respectively, of the acetate group.…”

Section: Resultsmentioning

confidence: 90%

New less toxic zeolite‐encapsulated Cu(II) complex nanomaterial for dual applications in biomedical field and wastewater remediation

Khalil

Kishk

EL-Mekkawi

et al. 2019

Applied Organom Chemis

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A new dual‐functional Cu(II) complex and its nanohybrid form encapsulated into NaY zeolite cavities were synthesized. The synthesized compounds were characterized using elemental analyses, X‐ray fluorescence, infrared, 1H NMR, electronic, electron spin resonance and mass spectra, powder X‐ray diffraction, surface area and transmission electron microscopy in addition to conductivity and magnetic susceptibility measurements. The encapsulated Cu(II) complex was catalytically tested for degradation of industrial wastewater. The decolorization and mineralization results indicate that the Cu(II) complex encapsulated into zeolite host is an effective heterogeneous catalyst for real industrial wastewater remediation. In addition, both free and encapsulated Cu(II) complexes were tested as anti‐microbial and anti‐tumour agents. The results show that the Cu(II) complex encapsulated into zeolite has a high activity (IC50 = 14.4 μg ml−1). The results of in vivo toxicity experiments indicate that the Cu(II) complex encapsulated into zeolite is a less toxic biocompatible material (LD50 = 1245 mg kg−1). The catalytic properties, cytotoxicity and toxicity of the new nanohybrid Cu(II) complex encapsulated into zeolite make it a promising eco‐friendly and biocompatible material for water remediation and biomedical applications.

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Section: Resultsmentioning

confidence: 90%

New less toxic zeolite‐encapsulated Cu(II) complex nanomaterial for dual applications in biomedical field and wastewater remediation

Khalil

Kishk

EL-Mekkawi

et al. 2019

Applied Organom Chemis

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“…The shape of the ESR signals is consistent with the octahedral geometry of the Fe (III) complex . On the other hand, the spectrum of complex 2 displays one broad band with g = 2.05 and the profile of the spectrum reveals the square planar geometry of the Cu (II) complex …”

Section: Resultsmentioning

confidence: 99%

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Samy

2020

Applied Organom Chemis

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New mononuclear Fe (III), Cu (II), Ag (I), ZrO ( IV) and UO2(VI) complexes were synthesized by the reaction of metal ions with (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime. The structures of the metal complexes were characterized using analytical, spectral (infrared, electronic, 1H NMR, electron spin resonance (ESR), and mass), magnetic moment, molar conductance, thermal gravimetric analysis, and powder X‐ray diffraction (XRD) measurements. All complexes have octahedral geometries except the Cu (II) complex, which has square planar geometry, and the UO2(VI) complex, in which the coordination number is seven. The ligand acts as a (neutral, monoanionic or dianionic) tridentate with N2O coordinating sites: N‐azomethine, N‐triazine, and O‐oxime. Fluorescence spectral studies were carried out in solid state and in dimethylformamide (DMF). The kinetic parameters of the thermal decomposition stages were calculated using Coats–Redfern equations. The morphological structures of the ligand and some complexes were determined using XRD. The molecular orbital calculations were carried out for the ligand and metal complexes using the Hyperchem 7.52 program on the basis of the PM3 level. The antimicrobial activities of the ligand and its complexes were investigated towards the microorganisms S. aureus and B. subtilis as Gram‐positive bacteria, S. typhimurium and E. coli as Gram‐negative bacteria, C. albicans, and A. fumigatus. The ligand and its complexes showed antitumor activity against Hep G‐2 cell lines, where Cu (II) and Ag (I) complexes seem to be promising as they showed IC50 values that are lower than and comparable to that of the antitumor drug doxorubicin.

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“…In the IR spectra of complexes 1-3, the characteristic bands assigned to υ(HC=O) and υ(-C=O) of 3-formylchromone derivatives observed at 1694 and 1671 cm -1 ,respectively were shifted to lower wave number by 15-25 cm -1 indicating the complexation of these groups with metal ions (Fig. S1) [26]. The bands which appeared at 592 cm -1 and 1263 cm -1 were assigned to υ(C-Br) and υ(C-F) stretching vibrations, respectively.…”

Section: Spectroscopic Characterizationmentioning

confidence: 99%

Copper (II)-based halogen-substituted chromone antitumor drug entities: Studying biomolecular interactions with ct-DNA mediated by sigma hole formation and cytotoxicity activity

Arjmand¹,

Khursheed²,

Roisnel³

et al. 2020

Bioorganic Chemistry

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Copper-based antitumor drug entities 1-3 derived from substituted (F -, Br -, -CH 3 ) 3formylchromone pharmacophore were synthesized and thoroughly characterized by spectroscopic and single X-ray crystallographic studies. These complexes show structural novelty due to presence of the X-bonds in chromone scaffold which could facilitate higher propensity for nucleic acids via sigma σ-hole interactions. Therefore, structure-activity relationship of 1-3 was studied by performing ct-DNA binding, pBR322 cleavage and cytotoxicity activity to validate their potential to act as chemotherapeutic drug entities. The binding studies of 1-3 with ct-DNA were carried out employing many biophysical techniques and the corroborative results of these experiments showed intercalation mode of binding and the order of binding was found to be 2 > 1 >3. The structure of drug entities could facilitated strong halogen bonding interaction(in case of 1 &2) and stability of X bond was rationalized by sigma hole region of positive electrostatic potential on the surface of C-X covalent bond, as determined by gas phase B3LYP computational DFT studies. Interestingly, 2 exhibited most avid binding affinity due to presence of Brelectron withdrawing and polarizable group. Further, cleavage studies of 1-3 with pBR322 plasmid DNA were performed which demonstrated significant cleavage activity , the supercoiled form (Form I) of plasmid DNA was converted to nicked form (Form II) with the appearance of linearized form(Form III) in between two, implicating lethal double strand breaks of DNA. 2 showed predominantly higher cleavage activity following the similar trend as observed for binding studies.The cytotoxicity of the complexes 1-3 was evaluated by MTT assay against the human liver carcinoma (Huh-7) and prostate cancer (DU-145) cell lines; complex 2 exhibited specific and selective cytotoxicity for the DU-145 cancer cell line with LC 50 value of 1.6μM. Highlights Substituted chromone Copper (II) complexes were synthesized and characterized.  DFT computational studies were also performed.  Electrophoretic studies revealed an oxidative cleavage pathway.  Cytotoxicity was evaluated against the human liver carcinoma (Huh-7) and prostate cancer (DU-145) cell lines.  Copper (II) complex 2 exhibited selective cytotoxicity against DU-145 cell line at GI 50 =1.6μM.

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Structural variety in copper(II) complexes of 3-formylchromone: Synthesis, spectral, thermal, molecular modeling and biological studies

Cited by 38 publications

References 57 publications

New less toxic zeolite‐encapsulated Cu(II) complex nanomaterial for dual applications in biomedical field and wastewater remediation

New less toxic zeolite‐encapsulated Cu(II) complex nanomaterial for dual applications in biomedical field and wastewater remediation

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Copper (II)-based halogen-substituted chromone antitumor drug entities: Studying biomolecular interactions with ct-DNA mediated by sigma hole formation and cytotoxicity activity

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