Synthesis, crystal structures, molecular docking, in vitro monoamine oxidase-B inhibitory activity of transition metal complexes with 2-{4-[bis (4-fluorophenyl)methyl]piperazin-1-yl} acetic acid

Yang, Dandan; Wang, Riu; Zhu, Jinlong; Cao, Qi-Yue; Qin, Jie; Zhu, Hai‐Liang; Qian, Shao‐Song

doi:10.1016/j.molstruc.2016.08.037

Cited by 16 publications

(4 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Δν values which are less than 200 cm −1 represent the carboxylic bidentate mode, whereas Δν values greater than 200 cm −1 indicate the monodentate mode. [ 32 ] The Δν values were found to be 252 and 180 cm −1 for LH‐Cu(OAc) 2 and LCl‐Cu(OAc) 2, respectively, meaning the monodentate coordination fashion of the carboxyl group in LH‐Cu(OAc) 2 and the bidentate coordination fashion for LCl‐Cu(OAc) 2 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure elucidation, DNA binding and molecular docking studies of novel copper(II) complexes of two 1,3,4‐thiadiazolethiosemicarbazone derivatives

Takroni

Farghaly

Harras

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

Four novel Cu(II) chelates were synthesized by reacting hydrated CuCl2 and Cu(CH3COO)2 with two derivatives of 1,3,4‐thiadiazolethiosemicarbazone. The structures and geometries of the synthesized complexes were deduced applying the alternative analytical and spectral tools confirming the complexes to have the formulae [(LH)Cu(Cl)]•0.5H2O, [(LH)Cu(OAc)(H2O)2]•0.5H2O, [(LCl)Cu(Cl)(H2O)2]•H2O and [(LCl)Cu(OAc)]; where LH and LCl are phenyl and p‐chlorophenyl derivatives of 1,3,4‐thiadiazolethiosemicarbazone ligands, respectively (deprotonated form). IR spectral data confirmed the coordination of the ligands to the copper center as monobasic tridentate in the thiol form. Thermal analysis, UV–Vis spectra and magnetic moment assured the geometry around the copper center to be square planar, trigonal bipyramid and octahedral which have been confirmed by the computational studies. The two ligand derivatives and their copper complexes were applied to evaluate their binding modes with SS‐DNA via UV–Vis spectral titration and viscosity measurements. The DNA‐binding constant (kb) values of the investigated derivatives were calculated and compared with ethidium bromide in order to assess their mode of binding with DNA. Moreover, docking study of these complexes was carried out to recognize the drug–DNA interactions and to calculate their binding energies.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis, structure elucidation, DNA binding and molecular docking studies of novel copper(II) complexes of two 1,3,4‐thiadiazolethiosemicarbazone derivatives

Takroni

Farghaly

Harras

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…In the spectra of all metal complexes, the asymmetric stretching mode ν as (COO) of the coordinated acetate groups appeared within the range 1602–1614 cm −1 while the symmetric stretching mode ν s (COO) for the complexes appeared within the range 1383–1391 cm −1 . The separation value Δ ν ( ν as (COO) − ν s (COO)) for the carboxylic‐based complexes could be used to discriminate the coordination mode of the carboxyl group: Δ ν < 200 cm −1 indicated the bidentate mode, whereas Δ ν > 200 cm −1 indicated the monodentate mode . The Δ ν values for the complexes are found to be within the range 214–237 cm −1 meaning a monodentate mode of coordination of the carboxyl group.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure, antiproliferative activity and molecular docking of divalent and trivalent metal complexes of 4H‐3,5‐diamino‐1,2,4‐triazole and α‐hydroxynaphthaldehyde Schiff base ligand

El‐Ghamry

El-Wakiel

Khamis

2018

Applied Organom Chemis

View full text Add to dashboard Cite

Cu(II), Co(II), Mn(II), Cr(III) and Mn(III) chelates of the ligand obtained by the condensation of 4H-3,5-diamino-1,2,4-triazole and 2-hydroxy-1naphthaldehyde have been isolated and characterized by means of elemental analysis, inductively coupled plasma analysis, mass spectrometry, Fourier transform infrared and UV-visible spectroscopies, magnetic measurements and thermal analysis. The analytical results indicated the formation of the metal complexes in a ligand-to-metal molar ratio of 1:2. The ligand is connected to the metal ion in a tetradentate fashion coordinating to the metal center through the azomethine nitrogens and deprotonated phenolic OH groups.The spectral and magnetic results supported the formation of octahedral geometry around the Cu(II), Mn(III) and Cr(III) centers while Co(II) and Mn(II) centers were confirmed to have tetrahedral geometry. Molecular docking was used to predict the binding between the ligand and the oncogenic protein Hras (121p). The antiproliferative activity of the compounds under study was evaluated in vitro using MTT assay against liver carcinoma (HepG2) and breast cancer (MCF-7) cell lines comparing with cisplatin. The binding mode of selected metal chelates with salmon serum DNA was investigated using the electronic absorption titration method.

show abstract

“…Selective MAO-A inhibitors are preferred as powerful antidepressant agents, whereas selective MAO-B inhibitors are used as effective agents against Parkinson’s disease [ 5 , 6 ]. Rapid consumption of brain monoamines is one of the causes of depression Positron emission tomography studies indicate that there is a substantial increment of MAO-A in the brain of patients with depression in contrast to healthy people [ 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Hydrazone Derivatives for MAO Enzymes Inhibitory Activity

et al. 2017

View full text Add to dashboard Cite

In the present work, 14 new 1-substituted-2-phenylhydrazone derivatives were synthesized to evaluate their inhibitory activity against hMAO enzymes. The structures of the newly synthesized hydrazones 2a–2n were characterized by IR, 1H-NMR, 13C-NMR, HR-MS spectroscopic methods. The inhibitory activity of compounds 2a–2n against hMAO-A and hMAO-B enzymes was elucidated by using an in-vitro Amplex Red® reagent assay based on fluorometric methods. According to the activity studies, 2a and 2b were found to be the most active compounds against hMAO-A enzyme, with IC50 values of 0.342 µM and 0.028 µM, respectively. The most active compounds 2a–2b were evaluated by means of enzyme kinetics and docking studies. Moreover, these compounds were subjected to cytotoxicity and genotoxicity tests to establish their preliminary toxicological profiles and were found to be non-cytotoxic and non-genotoxic. Consequently, the findings of this study display the biological importance of compounds 2a, 2b as selective, irreversible and competitive inhibitors of hMAO-A. Docking studies revealed that there is a strong interaction between hMAO-A and the most active compound 2b.

show abstract

Synthesis, crystal structures, molecular docking, in vitro monoamine oxidase-B inhibitory activity of transition metal complexes with 2-{4-[bis (4-fluorophenyl)methyl]piperazin-1-yl} acetic acid

Cited by 16 publications

References 30 publications

Synthesis, structure elucidation, DNA binding and molecular docking studies of novel copper(II) complexes of two 1,3,4‐thiadiazolethiosemicarbazone derivatives

Synthesis, structure elucidation, DNA binding and molecular docking studies of novel copper(II) complexes of two 1,3,4‐thiadiazolethiosemicarbazone derivatives

Synthesis, structure, antiproliferative activity and molecular docking of divalent and trivalent metal complexes of 4H‐3,5‐diamino‐1,2,4‐triazole and α‐hydroxynaphthaldehyde Schiff base ligand

Synthesis of New Hydrazone Derivatives for MAO Enzymes Inhibitory Activity

Contact Info

Product

Resources

About