Synthesis and structural studies of novel Cu(II) complexes with hydroxy derivatives of benzo[b]furan and coumarin

Drzewiecka, Aleksandra; Kozioł, Anna E.; Klepka, Marcin T.; Wolska, A.; Przybylińska, H.; Jiménez‐Pulido, Sonia B.; Ostrowska, Kinga; Struga, Marta; Kossakowski, Jerzy; Lis, Tadeusz

doi:10.1016/j.poly.2012.05.042

Cited by 19 publications

(11 citation statements)

References 42 publications

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“…The results of FTIR, XAFS spectroscopy, elemental analysis of compounds 1 and 2 as well as previously reported structures of Cu(II) complexes with ligands containing 2-acetylphenol ring [27] pointed out towards the structural models with Cu(II) being coordinated by two coumarin ligands in planar, bidentate mode. The proposed molecules of complexes 1-2 consist of two HL anions chelating to the metal through the O atom from deprotonated hydroxyl group and O atom from the acetyl substituent.…”

Section: Dft Calculationssupporting

confidence: 70%

“…These data are analogous to the spectra of similar series of Cu(II) complexes in which two bidentate ligands are coordinated to the metal centre via O atoms from the acetyl and hydroxyl groups substituted on the rigid benzo[b]furan system [27]. The main difference between these two series of complexes is the lack of a broad band at 3300-3600 cm 1 region in the IR spectra of coumarin derivatives (1-2).…”

Section: Ftir Spectroscopysupporting

confidence: 63%

“…Cytotoxic activity was reported for many Cu(II) κ 2 -O, O complexes with planar environment of central ion [37]. However, up to the our best knowledge, no such activity was reported for complexes with Cu(II) being chelated by 2-acetylphenol type ligand prior to our previous work [27]. Proposed mechanisms for antitumour activities of Cu complexes include DNA binding or topoisomerase inhibition.…”

Section: Antitumour Activitymentioning

confidence: 78%

“…The DFT studies showed that both isomers have the same energetic stability. Taking into account that X-ray crystal structure analysis on similar Cu(II) complexes reported centrosymmetric type of coordination [27][28][29][30], such type of coordination was considered as the most probable and used as an initial model for XANES data analysis (see Fig. 5).…”

Section: Dft Calculationsmentioning

confidence: 99%

See 3 more Smart Citations

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

Klepka

Drzewiecka-Antonik

Wolska

et al. 2015

Journal of Inorganic Biochemistry

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Section: Dft Calculationssupporting

confidence: 70%

Section: Ftir Spectroscopysupporting

confidence: 63%

Section: Antitumour Activitymentioning

confidence: 78%

Section: Dft Calculationsmentioning

confidence: 99%

See 2 more Smart Citations

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

Klepka

Drzewiecka-Antonik

Wolska

et al. 2015

Journal of Inorganic Biochemistry

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“…For example, electron paramagnetic resonance (EPR) is able to give the geometrical information about paramagnetic metallic cations (e.g., Cu), and qualitative and quantitative information about unpaired electrons of heavy metals after complexation. X-ray absorption fine structure (XAFS) analysis is another important means to describe the local structure including bond distance, coordination number, and type of nearneighbors surrounding a specific element 11,12 , which is very sensitive to molecular complexation. The density functional theory (DFT) calculation provides useful information about the interpretation of experimental spectroscopic data to identify possible coordination environments of adsorbed Cu [13][14][15] .…”

mentioning

confidence: 99%

Experimental and Theoretical Approaches for the Surface Interaction between Copper and Activated Sludge Microorganisms at Molecular Scale

Luo¹,

Chen²,

Sheng³

et al. 2016

Environmental Engineering and Activated Sludge Processes

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Interactions between metals and activated sludge microorganisms substantially affect the speciation, immobilization, transport, and bioavailability of trace heavy metals in biological wastewater treatment plants. In this study, the interaction of Cu(II), a typical heavy metal, onto activated sludge microorganisms was studied in-depth using a multi-technique approach. The complexing structure of Cu(II) on microbial surface was revealed by X-ray absorption fine structure (XAFS) and electron paramagnetic resonance (EPR) analysis. EPR spectra indicated that Cu(II) was held in inner-sphere surface complexes of octahedral coordination with tetragonal distortion of axial elongation. XAFS analysis further suggested that the surface complexation between Cu(II) and microbial cells was the distorted inner-sphere coordinated octahedra containing four short equatorial bonds and two elongated axial bonds. To further validate the results obtained from the XAFS and EPR analysis, density functional theory calculations were carried out to explore the structural geometry of the Cu complexes. These results are useful to better understand the speciation, immobilization, transport, and bioavailability of metals in biological wastewater treatment plants. Interactions between metals and microorganisms play an important role in the geochemical cycling of trace heavy metals. In biological wastewater treatment processes, microorganisms in activated sludge have a high metal complexation capacity and then substantially affect the speciation, immobilization, transport, and bioavailability of metals in biological wastewater treatment plants. Previous study showed that there are many heavy metals (e.g., copper) in municipal and industrial wastewaters 1 . It is of great significance to study the surface complexation of metals on microorganisms and to understand their fates in biological wastewater treatment plants. In addition, extracellular polymeric substances (EPS), high-molecular weight compounds secreted by microorganisms, also have a significant impact on the fates of heavy metals 2,3 . The relevant functional groups involved in the interaction between metals and microorganisms are reported to be -COOH, -OH, -NH 2 , and -PO 4 , etc 4 . However, there are contradictory reports about the interaction between heavy metals and microbial cells in the presence and absence of EPS. In some studies it was found that the presence of EPS did not significantly affect the interaction 5 ; while others reported that the presence of EPS had a substantial effect on the interaction 6 . Such a contradiction may be attributed to the different experimental techniques employed in these works. Furthermore, the complicated structures of activated sludge and high water content make it difficult to explore the interaction mechanisms between heavy metals and microbial cells at a microscale. Previous studies showed that activated sludge microorganisms had high complexing capability to Cu [7][8][9] , which was particle-diffusion-controlled, and followed the pseudo-sec...

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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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Synthesis and structural studies of novel Cu(II) complexes with hydroxy derivatives of benzo[b]furan and coumarin

Cited by 19 publications

References 42 publications

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

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

Experimental and Theoretical Approaches for the Surface Interaction between Copper and Activated Sludge Microorganisms at Molecular Scale

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

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