Anticancer 4: Anticancer and DNA cleavage studies of some new Schiff base titanium (IV) complexes

El‐Shekeil, Ali; Abu‐Bakr, Abeer O.; Al-Aghbari, Sama; Nassar, Mogahid Yahya

doi:10.5155/eurjchem.5.3.410-414.996

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…Many Schiff base compounds have been reported to show high response when tested for in vitro and in vivo biological activities [5][6][7]. The wide range of pharmacological profiles exhibited by Schiff bases includes anticancer activity [6,[8][9][10][11][12], anticonvulsant [13], analgesic, and anti-inflammatory activities [14]. Cancer is caused by an abnormal and uncoordinated growth of a mass of tissue, which continues to multiply after cessation of the stimuli which initiated it [15].…”

Section: Introductionmentioning

confidence: 99%

N'-(Pyridin-3-ylmethylene)benzenesulfonohydrazide: Crystal structure, DFT, Hirshfeld surface and in silico anticancer studies

et al. 2021

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A new Schiff base, N'-(pyridin-3-ylmethylene)benzenesulfonohydrazide, was synthesized and characterized by elemental analysis, IR, Mass, 1H NMR and 13C NMR spectroscopy, and single-crystal X-ray determination. The asymmetric molecule crystallized in the monoclinic crystal system and P2(1)/c space group. Crystal data for C12H11N3O2S: a = 9.7547(4) Å, b = 9.8108(4) Å, c = 13.1130(5) Å, β = 109.038(2)°, V = 1186.29(8) Å3, Z = 4, μ(MoKα) = 0.270 mm-1, Dcalc = 1.463 g/cm3, 13338 reflections measured (5.296° ≤ 2Θ ≤ 55.484°), 2790 unique (Rint = 0.0494, Rsigma = 0.0400) which were used in all calculations. The final R1 was 0.0345 (I > 2σ(I)) and wR2 was 0.0914 (all data). In the crystal structure of the compound C12H11N3O2S, molecules are linked in a continuous chain by intermolecular of N∙∙∙HN=N hydrogen bonds. The pyridine moiety is planar, while the benzenesulfonohydrazide group adopts a gauche conformation about C-S-N angle (105.54°). The Hirshfeld surface analysis and fingerprint plots were used to establish the presence, nature, and percentage contribution of the different intermolecular interactions, including N-H∙∙∙N, C-H∙∙∙O, C-H∙∙∙C, and π∙∙∙π interactions, with the C-H contacts having the most significant contribution. The pairwise interaction energies were calculated at the B3LYP/6-31G(d,p) level of theory, and interaction energy profiles showed that the electrostatic forces had the most significant contribution to the total interaction energies of the different molecular pairs in the crystal. In-silico technique was used to examine the compound as a possible anticancer agent. The molecule demonstrated zero violation of the criteria of Lipinski’s rule of five with a polar surface area of 116.03 Å2. The molecule displayed favorable binding interactions with ten selected validated anticancer protein targets ranging from -9.58 to -11.95 kcal/mol and -2.73 to -5.73 kcal/mol on scoring and rescoring, respectively, with London dG and Affinity dG scoring functions. Two proteins; farnesyl transferase and signaling protein, preferred interactions with the Schiff-base over their co-crystallized inhibitors according to London dG scoring. Analysis of binding poses indicated that the Schiff-base made contact with amino acid residues of the two proteins through the N-H, sulphonyl oxygen, and phenyl groups, and this could be exploited in chemical and structural modification towards activity optimization.

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Section: Introductionmentioning

confidence: 99%

N'-(Pyridin-3-ylmethylene)benzenesulfonohydrazide: Crystal structure, DFT, Hirshfeld surface and in silico anticancer studies

et al. 2021

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“…Many coordination compounds of biologically active ligands have been synthesized and received much attention [1][2][3] . Chelation causes drastic change in the biological properties same applies to ligands and metal moieties 4 . Azomethines exhibit a wide range of pharmacological activities like antimicrobial 5 , anti-parasitic 6 , anti-inflammatory 7 and anticancer 8 .…”

Section: Introductionmentioning

confidence: 99%

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2021

IJPSR

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A series of metal complexes, namely, Ni (II), Zn (II), Cu (II) and Pt (II), have been synthesized with newly prepared biologically active ligands. These ligands and their functional groups were carefully designed and selected to display DNA cleavage effect. Schiff base compoundof 2methyl -3 -aminobenzopyrimidine -4 -one (L 1 ) was prepared by condensation of an equimolar mixture of 2-methyl-3-aminobenzopyrimidine-4-one (0.01 mole) and 2-hydroxybenzaldehyde (0.01 mole) in ethanol (25 ml). Schiff base (L 2 ) compound was prepared by condensation of a mixture of Schiff base (1) (0.02 mole) and o-phenylenediamine (0.01 mole) in ethanol (25 ml) and a catalytic amount of KOH. The mixture was refluxed for 36 hrs. Ligand L 2 (1 mmole) was dissolved in hot methanol. The metal chloride (1 mmole) was then added and the mixture was stirred under reflux for 24 h. The structures of ligands and their complexes have been confirmed by spectroscopic data i.e. IR, 1HNMR, MS, electronic and elemental (CHN) analysis. All Compounds were screened for DNA cleavage and showed complete cleavage of CT-DNA. EXPERIMENTAL:Chemicals: Anthranilic acid, hydrazine hydrate, 2hydroxybenzaldehyde and 1, 2-phenylenediamine were obtained commercially from BDH chemicals. The anhydrous metal chlorides of (Cu (II), Zn (II)), K 2 PtCl 4 , FeCl 3 .6H 2 O and Ni (II).6H 2 O (BDH) were used as received. The solvents were reagent grade and were used as received: acetic anhydride, dry absolute ethanol, butanol and diethyl ether.

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“…Chelation causes drastic change in the biological properties or the ligands and also the metal moieties [4]. Azomethines exhibit a wide range of pharmacological activities like antimicrobial [5], anti-parasitic [6], anti-inflammatory [7] and anticancer [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Anticancer Activity Studies of New Schiff Base Pt (II) Complex

Al-Aghbari¹,

Al‐Shuja'a²,

Al-Badani³

et al. 2019

MSCE

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A New Schiff base ligand and its Pt (II) complex were synthesized. The ligand was prepared by condensation of 2-(4-isobutylphenyl)propanehydrazide with 2,3,4-trihydroxy benzaldehyde this novel ligand and its functional group was carefully designed and selected from well-known biological drugs. The structure of the ligand and its Pt-complex have been confirmed by spectroscopic data, i.e. elemental (CHN) analysis, FT-IR, electronic spectra, NMR spectra. The ligand and its Pt-complex were investigated for their in vitro anticancer potential using HeLa and PC3 cells. The Pt-complex showed a higher cytotoxic activity than the ligand towards Hela cells and PC3 cells.

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Anticancer 4: Anticancer and DNA cleavage studies of some new Schiff base titanium (IV) complexes

Cited by 5 publications

References 28 publications

N'-(Pyridin-3-ylmethylene)benzenesulfonohydrazide: Crystal structure, DFT, Hirshfeld surface and in silico anticancer studies

N'-(Pyridin-3-ylmethylene)benzenesulfonohydrazide: Crystal structure, DFT, Hirshfeld surface and in silico anticancer studies

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Synthesis, Characterization and Anticancer Activity Studies of New Schiff Base Pt (II) Complex

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