New mixed ligand zinc(II) complexes based on the antiepileptic drug sodium valproate and bioactive nitrogen-donor ligands. Synthesis, structure and biological properties

Darawsheh, Mohanad; Ali, H. Abu; Abuhijleh, A. Latif; Rappocciolo, Emilia; Akkawi, Mutaz; Jaber, Suhair; Maloul, Salam; Hussein, Yasmeen Ali

doi:10.1016/j.ejmech.2014.01.067

Cited by 45 publications

(30 citation statements)

References 85 publications

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“…N‐Zn bond distances (2.128(2) Å and 2.115(2) Å) are also similar to previously reported values i.e. (2.097 Å) )…”

Section: Resultssupporting

confidence: 90%

“…In addition, both intramolecular and intermolecular hydrogen bonding play a crucial role in the enhancement of complex stability, for example, H‐bonds give conformational stability of protein and other complex structures such as . The bond distances of O‐Zn (2.0269(19) Å, 2.155(2) Å, 2.0253(19) Å and 2.201(2) Å) are similar to previously reported values (1.84–2.33 Å) in Zn(II) diclofenac, valproate, indomethacine, ibuprofen, naproxen and sulindac complexes with various nitrogen base ligands . N‐Zn bond distances (2.128(2) Å and 2.115(2) Å) are also similar to previously reported values i.e.…”

Section: Resultssupporting

confidence: 84%

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Novel structures of Zn(II) biometal cation with the biologically active substituted acetic acid and nitrogen donor ligands: Synthesis, spectral, phosphate diester catalytic hydrolysis and anti‐microbial studies

Ali

Kamel

Shamma

2017

Applied Organom Chemis

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The complexes [Zn(methoxyacetate) 2 1,10-phenanthroline] 1 and [Zn 2 (phenylacetate) 4 (quinoline) 2 ] 2, were prepared and characterized by IR-spectroscopy, UV-Visible spectroscopy, 1 H and 13 C NMR spectroscopy, single crystal X-ray diffraction. BNPP hydrolysis of the complexes and their parent nitrogen ligands were scanned, the results indicated that the hydrolysis rates of BNPP were 4.5 × 10 4 and 6.2 × 10 5 for (1) and (2), respectively. In addition, anti-bacterial activities were scanned to investigate the effect of complexation on their activity against Gram-positive (S. epidermidis, S. aureus, E. faecalis, M. luteus and B. Subtilis) and Gram-negative (K. pneumonia, E. coli, P. Mirabilis and P. Aeruginosa) bacteria using agar well-diffusion method. Complex 1 showed high activity against G − and G + bacteria except against E. faecalis and P. Aeruginosa. Complex 2 did not show any activity against G − or G + bacteria.

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“…N‐Zn bond distances (2.128(2) Å and 2.115(2) Å) are also similar to previously reported values i.e. (2.097 Å) )…”

Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 84%

Novel structures of Zn(II) biometal cation with the biologically active substituted acetic acid and nitrogen donor ligands: Synthesis, spectral, phosphate diester catalytic hydrolysis and anti‐microbial studies

Ali

Kamel

Shamma

2017

Applied Organom Chemis

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“…A similar coordination was recently reported for Zn-Valp-N-donor ligands complexes. 51 The Cu−O and Cu−N bond distances and angles are equivalent for the three metal atoms. Six Valp moieties, grouped exactly in the middle of the unit cell, were the aliphatic chains that form the center of cell (Figure 3).…”

Section: Crystallographic Studiesmentioning

confidence: 99%

Mixed Ternary Mononuclear Copper(II) Complexes Based on Valproic Acid with 1,10-Phenanthroline and 2,2’-Bipyridine Ligands: DNA Interaction and Cytotoxicity in V79 Cells

Pich¹,

Santos²,

Fortunato³

et al. 2018

J. Braz. Chem. Soc.

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This paper reports the DNA interaction and cytotoxicity of binary and ternary copper(II) complexes of valproic acid with phenanthroline or bipyridine and the complementary characterization of Cu(Valp) 2 Bipy by crystallography. Circular dichroism, plasmid and oligonucleotide assays have shown that the complexes interact with DNA in different manners and are able to cleave plasmid DNA and oligonucleotides at concentrations from 10 to 1000 mol L-1. The plasmid DNA cleavage is enhanced 650, 375 and 285 times by photo activation with UVB light for the complexes Cu(Valp) 2 Phen, Cu(Valp) 2 Bipy and Cu 2 (Valp) 4 , respectively. Cytotoxicity assays demonstrated that V79 cells were more sensitive to Cu II derivatives than sodium valproate as evaluated by 3-(4,5-dimethylthiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) and clonogenic assays, where the cytotoxic profile of the compounds was: Cu(Valp) 2 Phen higher than Cu(Valp) 2 Bipy, higher than Cu 2 (Valp) 4. Therefore, we report two copper complexes, which interact with DNA and promote its cleavage, leading to an enhanced cytotoxicity when compared to valproic acid.

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“…In previous work, we used valproic acid (used commercially as an anti-epileptic agent and mood stabilizer; Fig. 1) to prepare mono-and dinuclear complexes in combination with pyridine-based ligands (Abu Ali et al, 2013;Darawsheh et al, 2014). Since valproic acid is a branched short-chain fatty acid having neither an aromatic ring nor an N atom, we explore here the self-assembly of a core-shell-like discrete polynuclear cluster and a 2D layered network.…”

Section: Introductionmentioning

confidence: 99%

Combining valproate and bipyridyl ligands to construct a 0D core-shell Zn₅(μ₃-OH)₂ cluster and a 2D layered coordination network with a [Zn₃(μ₃-OH)]₂ SBU

Ali¹,

Darawsheh²

2020

Acta Crystallogr C

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Starting from the proposed zinc carboxylate cluster tetrakis(μ-2-propylpentanoato)dizinc(II), Zn2(μ2-valp)4 (I), of valproic acid, a branched short-chain fatty acid, and bipyridine ligands, two new mixed-ligand coordination compounds, namely, bis(2,2′-bipyridine)di-μ3-hydroxido-hexakis(μ-2-propylpentanoato)bis(2-propylpentanoato)pentazinc(II), [Zn5(C8H15O2)8(OH)2(C10H8N2)2] (II), and poly[[bis(μ-4,4′-bipyridine)di-μ3-hydroxido-octakis(μ-2-propylpentanoato)bis(2-propylpentanoato)hexazinc(II)] dimethylformamide disolvate], {[Zn6(C8H15O2)10(OH)2(C10H8N2)2]·2C3H7NO} n (III), were synthesized. Compound II is a core-shell-type zero-dimensional discrete Zn5(μ3-OH)2 metal–organic cluster with Zn ions in double-triangle arrangements that share one Zn ion coincident with an inversion centre. The cluster contains three crystallographically non-equivalent Zn ions exhibiting three different coordination geometries (tetrahedral, square pyramidal and octahedral). The cluster cores are well separated and embedded in a protective shell of the aliphatic branched short chains of valproate. As a result, there is no specific interaction between the discrete clusters. Conversely, compound III, a 2D layered coordination network with a secondary building unit (SBU), is formed by Zn6(μ3-OH)2 clusters exhibiting a chair-like hexagonal arrangement. This SBU is formed from two Zn3(μ3-OH) trimers related by inversion symmetry and connected by two syn–anti bridging carboxylate groups. Each SBU is connected by four 4,4′-bipyridine ligands producing a 63-hcb net topology. 2D coordination layers are sandwiched within layers of dimethylformamide molecules that do not interact strongly with the network due to the hydrophobic protection provided by the valproate ligands.

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New mixed ligand zinc(II) complexes based on the antiepileptic drug sodium valproate and bioactive nitrogen-donor ligands. Synthesis, structure and biological properties

Cited by 45 publications

References 85 publications

Novel structures of Zn(II) biometal cation with the biologically active substituted acetic acid and nitrogen donor ligands: Synthesis, spectral, phosphate diester catalytic hydrolysis and anti‐microbial studies

Novel structures of Zn(II) biometal cation with the biologically active substituted acetic acid and nitrogen donor ligands: Synthesis, spectral, phosphate diester catalytic hydrolysis and anti‐microbial studies

Mixed Ternary Mononuclear Copper(II) Complexes Based on Valproic Acid with 1,10-Phenanthroline and 2,2’-Bipyridine Ligands: DNA Interaction and Cytotoxicity in V79 Cells

Combining valproate and bipyridyl ligands to construct a 0D core-shell Zn₅(μ₃-OH)₂ cluster and a 2D layered coordination network with a [Zn₃(μ₃-OH)]₂ SBU

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New mixed ligand zinc(II) complexes based on the antiepileptic drug sodium valproate and bioactive nitrogen-donor ligands. Synthesis, structure and biological properties

Cited by 45 publications

References 85 publications

Novel structures of Zn(II) biometal cation with the biologically active substituted acetic acid and nitrogen donor ligands: Synthesis, spectral, phosphate diester catalytic hydrolysis and anti‐microbial studies

Novel structures of Zn(II) biometal cation with the biologically active substituted acetic acid and nitrogen donor ligands: Synthesis, spectral, phosphate diester catalytic hydrolysis and anti‐microbial studies

Mixed Ternary Mononuclear Copper(II) Complexes Based on Valproic Acid with 1,10-Phenanthroline and 2,2’-Bipyridine Ligands: DNA Interaction and Cytotoxicity in V79 Cells

Combining valproate and bipyridyl ligands to construct a 0D core-shell Zn5(μ3-OH)2 cluster and a 2D layered coordination network with a [Zn3(μ3-OH)]2 SBU

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Combining valproate and bipyridyl ligands to construct a 0D core-shell Zn₅(μ₃-OH)₂ cluster and a 2D layered coordination network with a [Zn₃(μ₃-OH)]₂ SBU