Synthesis, characterization, molecular modelling and biological activity of 2‐(pyridin‐1‐ium‐1‐yl) acetate and its Cu2+, Pt4+, Pd2+, Au3+ and Nd3+ complexes

Mlahi, Mosaad R.; Negm, Amr; Azhari, Shaker J.; Mostafa, Mohsen M.

doi:10.1002/aoc.3187

Cited by 7 publications

(7 citation statements)

References 43 publications

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“…The MTT data (Figure ) correlate with the microphotography of the cells. We also observed variation in the cell morphology, as observed under a microscope, such as rounding of cells, membrane blebbing and cell shrinkage, which suggests the induction of apoptosis after the treatment of 3.5, 7.5 and 15 μg ml −1 of each of 1 – 4 for 24 h against the control (untreated cells) showing elongated, adherent with proliferation activity . Therefore coinciding with the results of cell viability assay, the morphology of the cells varied in a dose‐dependent manner.…”

Section: Resultssupporting

confidence: 77%

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

Gurudevaru

Gopalakrishnan

Senthilkumar

et al. 2017

Applied Organom Chemis

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Mononuclear and dinuclear copper(II) complexes with thiophenecarboxylic acid, [Cu(3‐TCA)2(2,2′‐bpy)] (1), [Cu(3‐Me‐2‐TCA)2(H2O)(2,2′‐bpy)] (2), [Cu(5‐Me‐2‐TCA)2(H2O)(2,2′‐bpy)] (3) and [Cu2(2,5‐TDCA)(DMF)2(H2O)2(2,2′‐bpy)2](ClO4)2 (4) (where 3‐TCA = 3‐thiophenecarboxylic acid; 3‐Me‐2‐TCA = 3‐methyl‐2‐thiophenecarboxylic acid; 5‐Me‐2‐TCA = 5‐methyl‐2‐thiophenecarboxylic acid; 2,5‐TDCA = thiophene‐2,5‐dicarboxylic acid; 2,2′‐bpy = 2,2′‐bipyridyl; DMF = N,N‐dimethylformamide), were synthesized. Compounds 1–4 were extensively characterized using both analytical and spectroscopic methods. Additionally, the solid‐state structures of 1 and 4 were unambiguously established from single‐crystal X‐ray diffraction studies. The hexacoordinated Cu(II) centre in 1 (CuO4N2) is a distorted octahedral geometry whereas the pentacoodinated 4 (CuO3N2) has distorted square pyramidal geometry. Compounds 1 and 4 exhibit intermolecular hydrogen bonding which leads to the formation of two‐ and three‐dimensional supramolecular architectures, respectively. Spectrophotometric and computational investigations suggest that these compounds bind with DNA in minor groove binding such that Kb = 4.9 × 105 M−1 and Ksv = 3.4 × 105 M−1, and binding score of −5.26 kcal mol−1. The binding affinity of these complexes to calf thymus DNA is in the order 2 > 3 > 4 > 1. Methyl‐substituted thiophene ring increases the DNA binding affinity whereas unsubstituted thiophene ring DNA binding rate is reduced. The methyl group on the thiophene ring would sterically hinder π–π stacking of the ring with DNA base pairs, and subsequently they are involved in hydrophobic interaction with the DNA surface rather than partial intercalative interaction. Compounds 1–4 show pronounced activity against B16 mouse melanoma skin cancer cell lines as measured by MTT assay yielding IC50 values in the micromolar concentration range. The compounds could prove to be efficient anti‐cancer agents, since at a concentration as low as 2.1 μg ml−1 they exerted a significant cytotoxic effect in cancer cells whereas cell viability was not affected in normal cells.

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Section: Resultssupporting

confidence: 77%

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

Gurudevaru

Gopalakrishnan

Senthilkumar

et al. 2017

Applied Organom Chemis

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“…Through the energies of frontier molecular orbitals ( E HOMO , E LUMO and band gap energy) result from DFT calculations obtained suggests about reactivity, molecular stability and site selectivity in addition to the donating ability. By using Koopman's theorem for closed shell components as electronegativity ( χ ), chemical potential ( μ ), global hardness ( η ), global softness ( S ) and global electrophilicity index (ω) are calculated using equations – listed in Table , HOMO and LUMO orbital of ligand and complexes are shown in Figures and S23–27 . The donating ability of molecule can predicted over the HOMO energy value where high energy values meaning tendency of donating electrons.…”

Section: Resultsmentioning

confidence: 99%

X‐ray crystal of diprotonated tetra‐(2‐pyridyl)pyrazine (H₂TPPZ), aqua Fe³⁺‐phen crystal and new lanthanide complexes of TPPZ and their biochemical studies

Al-Assy

Mohamed

Husein

et al. 2019

Applied Organom Chemis

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New complexes derived from M3+ salts with polyazine as monometallic such as [Fe (TPPZ)Cl3].½H2O (1), [Cr (TPPZ)2Cl2]Cl.2EtOH (2), [La (TPPZ)(NO3)2(H2O)2]NO3.H2O (3) in addition to [Fe (Phen)3]3Cl.7H2O (4) were isolated. Three bimetallic, [H2TPPZ][(AuCl4)2]. H2O (5), [Ce2(TPPZ)EtOH (NO3)3]3NO3 (6) and [Nd2TPPZCl2(H2O)4]4Cl.CHCl3. 4H2O (7) and mixed ligand complexes, [Fe (TPPZ)(Phen)2]Cl3 (8), [Fe (TPPZ) (Phen)2][TPPZCl3] (9), [La2(TPPZ)(Phen)2(EtOH)2]6Cl.CHCl3.EtOH.H2O (10) and [Nd2(TPPZ)(Phen)Cl4]2Cl.3H2O (11) were synthesized and characterized. Crystal data of (4) is tetragonal, I41/a, a = b 35.951 (3) Å, c = 11.9055 (8) Å, α = 80.201 (2)° β = 78.846 (2)°, γ = 89.687 (2)° V = 741.06 (5)Å3, Z = 1 while triclinic, P1, a = 7.3913 (3) Å, b = 9.7344 (4) Å, c = 10.6577 (4) Å, α = β = γ = 90°, V = 741.06 (5)Å3 and Z = 170 for (5). Analyses, spectral and cyclic voltammetry studies indicate the bonding and the redox properties. Anticancer studies promised to be effective in lanthanides and some complexes were screened against antibacterial or antifungal.

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“…(i) The E HOMO and E LUMO and their neighboring orbitals are all negative, which indicate that the prepared complexes are stable [44]. (ii) The FMO's theory predicts sites of coordination (electrophilic attack) on aromatic compounds.…”

Section: Geometry Optimization With Dft Methodsmentioning

confidence: 99%

Comparative studies between 4-allyl-, 4-phenyl- and 4-ethyl-1-(2-hydroxybenzoyl) thiosemicarbazides and the synthesis, characterization and DFT calculations of binary and ternary complexes derived from 4-ethyl (L1) and 2,2′-dipyridyl

Azhari

Mlahi

Mostafa

2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Synthesis, characterization, molecular modelling and biological activity of 2‐(pyridin‐1‐ium‐1‐yl) acetate and its Cu²⁺, Pt⁴⁺, Pd²⁺, Au³⁺ and Nd³⁺ complexes

Cited by 7 publications

References 43 publications

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

X‐ray crystal of diprotonated tetra‐(2‐pyridyl)pyrazine (H₂TPPZ), aqua Fe³⁺‐phen crystal and new lanthanide complexes of TPPZ and their biochemical studies

Comparative studies between 4-allyl-, 4-phenyl- and 4-ethyl-1-(2-hydroxybenzoyl) thiosemicarbazides and the synthesis, characterization and DFT calculations of binary and ternary complexes derived from 4-ethyl (L1) and 2,2′-dipyridyl

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Synthesis, characterization, molecular modelling and biological activity of 2‐(pyridin‐1‐ium‐1‐yl) acetate and its Cu2+, Pt4+, Pd2+, Au3+ and Nd3+ complexes

Cited by 7 publications

References 43 publications

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

X‐ray crystal of diprotonated tetra‐(2‐pyridyl)pyrazine (H2TPPZ), aqua Fe3+‐phen crystal and new lanthanide complexes of TPPZ and their biochemical studies

Comparative studies between 4-allyl-, 4-phenyl- and 4-ethyl-1-(2-hydroxybenzoyl) thiosemicarbazides and the synthesis, characterization and DFT calculations of binary and ternary complexes derived from 4-ethyl (L1) and 2,2′-dipyridyl

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Synthesis, characterization, molecular modelling and biological activity of 2‐(pyridin‐1‐ium‐1‐yl) acetate and its Cu²⁺, Pt⁴⁺, Pd²⁺, Au³⁺ and Nd³⁺ complexes

X‐ray crystal of diprotonated tetra‐(2‐pyridyl)pyrazine (H₂TPPZ), aqua Fe³⁺‐phen crystal and new lanthanide complexes of TPPZ and their biochemical studies