Synthesis, structural studies and biological activity of new Cu(II) complexes with acetyl derivatives of 7-hydroxy-4-methylcoumarin

Klepka, Marcin T.; Drzewiecka-Antonik, Aleksandra; Wolska, A.; Rejmak, Paweł; Ostrowska, Kinga; Hejchman, Elżbieta; Kruszewska, Hanna; Czajkowska, Agnieszka; Młynarczuk-Biały, Izabela; Ferenc, W.

doi:10.1016/j.jinorgbio.2015.01.006

Cited by 21 publications

(5 citation statements)

References 36 publications

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“…Initially, the safety properties of precursor, ligands, and Cu(II) complexes were assessed by toxicity assay, as previously described. [21] In brief, age-synchronized young adult worms (n = 100 worms per condition) were transferred to 1 mL of M9 buffer (5 g NaCl, 3 g KH 2 PO 4 , 6 g Na 2 HPO 4 , 1 mL of 1 M MgSO 4, and 1 L distilled H 2 O) containing 5 mg/mL heat-killed E. coli OP50 and different pharmacological doses of precursor, ligands, and metal complexes (5,10,15,20,25, and 30 μM) at 20°C in 24-well microtiter plates. After 24 h, the worms were observed for inactivity/death under an inverted microscope using the touch-provoked method.…”

Section: Dna Viscosity Measurementsmentioning

confidence: 99%

“…Several articles evidence the antimicrobial, DNA cleavage, and anticancer activity of copper complexes containing Schiff bases [9–12] . Coumarins are widely studied naturally occurring compounds, which are well known for their pharmacological and biological responses like antimicrobial, anticoagulant, antitumor, anti‐HIV, chemotherapeutics, and bio‐analytical reagents [13–16] . Certain coumarin derivatives viz .…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12] Coumarins are widely studied naturally occurring compounds, which are well known for their pharmacological and biological responses like antimicrobial, anticoagulant, antitumor, anti-HIV, chemotherapeutics, and bio-analytical reagents. [13][14][15][16] Certain coumarin derivatives viz. clorobiocin and novobiocin are commercialized as prescription drugs.…”

Section: Introductionmentioning

confidence: 99%

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ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

et al. 2021

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Four copper(II) complexes 1-4 of 3-acetylchromene-2-one and substituted 3-acetylchromene-2-one derived Schiff bases were synthesized and structurally characterized using analytical and spectral techniques. The molecular structure of complex 1 has been confirmed by single crystal X-ray diffraction studies, which revealed that ligand 3-acetylchromene-2-one-4 N-semicarbazone is coordinated to the metal as ONO pincer type ligand. Two nitrate molecules are coordinated to the copper ion through oxygen atoms, of which one nitrate molecule was found to coordinate via two oxygen atoms, thereby achieving six-coordination. Preliminary biological studies like DNA and protein binding analyses indicated the binding of the ligands and complexes to CT-DNA (Calf Thymus DNA) and BSA (Bovine Serum Albumin). We investigated the effects of complexes 1-4 against amyloid-β (Aβ) toxicity using transgenic Caenorhabditis elegans strains expressing muscle-and neuronal-specific human Aβ 1-42 . The results showed that the complexes 2-4 remarkably reduced the Aβ-induced paralysis phenotype, Aβ plaque deposition, and other Alzheimer's disease-associated functional deficits in C. elegans by their potent antioxidant and antiaggregative properties. Complexes 2-4 delayed Alzheimer's disease pathologies, providing a basis for further investigating these effects on higher models.

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Section: Dna Viscosity Measurementsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

et al. 2021

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“…[27] So the biological activities and optical properties of coumarin derivatives have been a focus of research. [28,29] In the work reported here, 3-(pyridin-2-yl)-8-tertbutylcoumarin (1; ligand L) and its copper(II) complex [CuL 2 (NO 3 ) 2 ] (2) were synthesized and characterized using infrared (IR), elemental and single-crystal X-ray diffraction analyses. In order to further understand the electronic structure and bonding properties of the studied compounds, density functional theory (DFT) was used to conduct theoretical calculations at the molecular level to explore molecular electrostatic potential (MEP), electron density and natural bond orbital (NBO) charge distribution based on the optimized structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin and its copper(II) complex

Shi

Nie

et al. 2020

Applied Organom Chemis

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A Cu(II)–coumarin complex, [CuL2(NO3)2] (2), where L = 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin (1), was synthesized with Cu(NO3)2⋅3H2O and characterized using elemental, infrared and single‐crystal X‐ray diffraction analyses. The crystal structure of 1 shows that all the pyrone, benzene and pyridine rings are completely coplanar. The crystal structure of 2 is stabilized by intermolecular C–H···O and C–H···N hydrogen bonds and C···C short contacts, which lead to the formation of a two‐dimensional network structure. Density functional theory results give support to the experimentally determined monomeric structure. The in vitro cytotoxic activities of 1 and 2 were investigated against HeLa (cervical carcinoma), A549 (lung), HepG2 (liver) and HUVEC (umbilical vein) cells by MTT assay. The IC50 values show that both 1 and 2 have lower toxicity than doxorubicin and cisplatin in every case. Ligand 1 exhibits higher anti‐HeLa activity than doxorubicin. Complex 2 displays higher anti‐HeLa activity than coumarin but lower than that of cisplatin. Various spectroscopic approaches indicate that 1 and 2 could effectively bind with DNA through intercalation mode.

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“…Current interest in copper(II) complexes is stemming from their potential use as antimicrobial, antiviral, anti-inflammatory, antipyretic, enzyme inhibitors, or chemical nucleases [6][7][8][9][10][11]. For example, Ma et al have synthesized Cu(II) complexes which could inhibit different enzymatic activities and induce cell apoptosis [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure, protein binding of Cu(II) complexes with a tridentate NNO Schiff-base ligand

Huang

Cheng

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Synthesis, structural studies and biological activity of new Cu(II) complexes with acetyl derivatives of 7-hydroxy-4-methylcoumarin

Cited by 21 publications

References 36 publications

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin and its copper(II) complex

Synthesis, structure, protein binding of Cu(II) complexes with a tridentate NNO Schiff-base ligand

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