Synthesis, crystal structure and characterization of three novel copper complexes of Levofloxacin. Study of their DNA binding properties and biological activities

Galani, Angeliki; Efthimiadou, Eleni K.; Mitrikas, George; Sanakis, Yiannis; Psycharis, Vassilis; Raptopoulou, Catherine P.; Κορδάς, Γ.; Karaliota, Alexandra

doi:10.1016/j.ica.2014.08.005

Cited by 25 publications

(18 citation statements)

References 56 publications

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“…reported for the much simpler case of Cu dimers. [62][63][64] Indeed, in the parallel-mode spectrum one characteristic derivativelike signal is observed at a position corresponding to the assumed forbidden transition. Fig.…”

Section: B Solid Powdermentioning

confidence: 96%

Interactions between H-bonded [CuII3(μ₃-OH)] triangles; a combined magnetic susceptibility and EPR study

Boudalis

Turek

Pissas

et al. 2018

Phys. Chem. Chem. Phys.

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The X-ray crystal structure of the CuII complex [Cu3(μ3-OH)(μ-pz)3(PhCOO)3]- (pz- = pyrazolato anion) shows an isosceles triangular core, further forming a hexanuclear H-bonded aggregate. Cleavage of the H-bonds in solution results in isolated trinuclear species. Analysis of variable temperature magnetic susceptibility data of a powder sample shows an antiferromagnetically-coupled Cu3-core with a doublet ground state and isotropic exchange parameters (Jave = -355 cm-1, Hiso = -JijSiSj). The fitting of magnetic data requires the inclusion of antisymmetric exchange, AE (HAE = Gij·Si × Sj) with Gz = 31.2 cm-1 and no detectable inter-Cu3 isotropic exchange. X-band EPR spectroscopy in a frozen tetrahydrofuran solution of the compound indicates isolated Cu3-species with g‖,eff = 2.25, g⊥,eff = 1.67. The small value of g⊥,eff (≪2.0) is consistent with the presence of AE in agreement with the analysis of the magnetic measurements. The parallel component exhibits a hyperfine pattern corresponding to one I = 3/2 nucleus with A‖ = 425 MHz. This implies a specific exchange coupling scheme obeying the order |J12| = |J13| < |J23| consistent with the crystallographically determined two long and one short CuCu distances. The role of AE in modulating the hyperfine parameters in antiferromagnetic Cu3 clusters is studied. EPR spectra at X- and Q-band were performed with powder samples of the cluster at liquid helium temperatures. The spectra in both bands are consistent with two interacting Sa,b = 1/2 species in the point dipolar approximation. Fitting of the spectra reveals that each spin is characterized by g‖ = 2.24, g⊥ = 1.65 which is in agreement with an isolated Cu3 cluster in the ground state. The determined inter-spin distance of 4.4-4.5 Å is very close to the distance between the Cu(1) and Cu(1)' sites of the two trimeric units as imposed crystallographically (4.3 Å). This constitutes further verification of the specific exchange coupling scheme within each trimer. Magnetostructural correlations previously adopted for antiferromagnetically coupled Cu3 clusters are discussed in the light of the combined magnetic measurements and EPR spectroscopy.

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Section: B Solid Powdermentioning

confidence: 96%

Interactions between H-bonded [CuII3(μ₃-OH)] triangles; a combined magnetic susceptibility and EPR study

Boudalis

Turek

Pissas

et al. 2018

Phys. Chem. Chem. Phys.

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“…Generally, the ν (M–N) and ν (M–O) for metal complexes appear as weak bands in the range of 430–576 cm −1 . [ 88–90 ]…”

Section: Resultsmentioning

confidence: 99%

“…[35] Several enrofloxacin complexes have been reported with different transition metal cations. [25,[36][37][38][39][40][41][42][43][44][45][46] Levofloxacin, (Figure 1) is the most potent (À)-(S) enantiomer of the racemic drug substance ofloxacin. [44] The chemical name of levofloxacin (levo) is (À)-(S)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, and the common name is Levaquin with a light yellowish crystalline powder.…”

mentioning

confidence: 99%

“…[49] Several published protocols revealed the existence of the crystal structures of a series of metal levofloxacin complexes. [25,30,45,46,50,51] The proposed mechanism of action might be by inhibiting the deoxyribonucleic acid (DNA) gyrase (topoisomerase II) enzymes, that is necessary for bacteria DNA replication, in the treatment of many bacterial infections. [47,[52][53][54][55] Levofloxacin is a zwitterion by nature, with two functional groups carboxylic acid and piperazinyl ring.…”

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confidence: 99%

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Two novel Cu (II) levofloxacin complexes with different bioactive nitrogen‐based ligands; single‐crystal X‐ray and various biological activities determinations

Mubarak

Ali

Metani

2021

Applied Organom Chemis

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Two new copper (II) complexes with the third generation quinolone antibacterial agent levofloxacin, 2‐aminopyridine and 2,2′‐bipyridine nitrogen‐based ligands with the following molecular structures [Cu (levo)2(2‐ampy)].6.25H2O (1) and [Cu (levo)(H2O)(2,2‐bipy)](NO3).2.5H2O (2) were synthesized. The complexes were characterized by spectroscopic methods and others. The crystal structure of complex 1 revealed that the Cu (II) cation is coordinated to two bidentate chelating levofloxacinato ligands, and one monodentate 2‐ampy ligand in the axial position forming a slightly distorted square pyramidal geometry. The mononuclear cationic complex 2 was determined in the triclinic crystal system and the chiral space group P1 with four molecules per unit cell in which the Cu (II) cation is coordinated to one bidentate chelating levofloxacinato ligand, one bidentate 2,2‐bipy, and one water molecule in a distorted square pyramidal geometry. In vitro antibacterial activities for the complexes and their parent ligands against four gram‐negative bacteria (Proteus mirabilis, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia) and four gram‐positive bacteria (Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, and Enterococcus faecalis) using the agar diffusion method have been determined with inhibition zone diameter (IZD) values between 29 and 46 mm. In addition, the minimum inhibition concentration (MIC) and the minimum bactericidal concentration (MBC) have been investigated. The MIC results of complexes 1 and 2 showed significant antibacterial activities against the P. mirabilis and B. subtilis than levofloxacin.

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“…[1][2][3][4][5][6][7][8] Among them, the synthesis and study of multinuclear copper(II) complexes has attracted considerable interest due to exploration of their structures, and also because the function of copper(II) centers in many important biological process. [8][9][10][11][12] There are a variety of strategies for synthesizing homo-and hetero-multinuclear complexes. The bridging ligands such as halides, pseudo-halides, oxalate, sulfate, etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Characterization of a Double Helical Dinuclear Copper(II) Complex With Tetradentate Biacetyl Bis(benzoylhydrazone)

Vafazadeh

Abdollahi²,

Willis³

2017

ACSi

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The reaction of tetradentate hydrazone ligand H 2 babh with Cu(CH 3 COO) 2 in methanol solvent leads to the formation of the mono-nuclear complex [Cu(babh)]. However, on being dissolved in dichloromethane solvent and on addition of ethanol solvent, a dinuclear complex of [Cu 2 (μ 1,3 -babh) 2 (C 2 H 5 OH) 2 ] is obtained. The X-ray crystallography indicates that the dinuclear helical complex formation is caused due to the unsymmetrical twisting of the H 2 babh ligand. One oxygen and two nitrogen atoms from the ligand and one oxygen atom from the other ligand coordinate to each copper(II) center. Both the copper(II) centers in a dinuclear unit are penta-coordinate with a slightly distorted square pyramidal geometry. The IR spectra of mono-and dinuclear copper(II) complexes have different bands. The absorption spectra of mono-and di-nuclear complexes are quite similar in methanol solvent. However, the electronic absorption spectra of the two complexes are basically different in the solid state.

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Synthesis, crystal structure and characterization of three novel copper complexes of Levofloxacin. Study of their DNA binding properties and biological activities

Cited by 25 publications

References 56 publications

Interactions between H-bonded [CuII3(μ₃-OH)] triangles; a combined magnetic susceptibility and EPR study

Interactions between H-bonded [CuII3(μ₃-OH)] triangles; a combined magnetic susceptibility and EPR study

Two novel Cu (II) levofloxacin complexes with different bioactive nitrogen‐based ligands; single‐crystal X‐ray and various biological activities determinations

Synthesis and Structural Characterization of a Double Helical Dinuclear Copper(II) Complex With Tetradentate Biacetyl Bis(benzoylhydrazone)

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Synthesis, crystal structure and characterization of three novel copper complexes of Levofloxacin. Study of their DNA binding properties and biological activities

Cited by 25 publications

References 56 publications

Interactions between H-bonded [CuII3(μ3-OH)] triangles; a combined magnetic susceptibility and EPR study

Interactions between H-bonded [CuII3(μ3-OH)] triangles; a combined magnetic susceptibility and EPR study

Two novel Cu (II) levofloxacin complexes with different bioactive nitrogen‐based ligands; single‐crystal X‐ray and various biological activities determinations

Synthesis and Structural Characterization of a Double Helical Dinuclear Copper(II) Complex With Tetradentate Biacetyl Bis(benzoylhydrazone)

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Interactions between H-bonded [CuII3(μ₃-OH)] triangles; a combined magnetic susceptibility and EPR study

Interactions between H-bonded [CuII3(μ₃-OH)] triangles; a combined magnetic susceptibility and EPR study