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Synthesis, single crystal investigations, DFT studies, biological activities, DNA cytotoxicity and molecular docking studies of copper(II) complex derived from the new o-vanillin Schiff base ligand   
Yazarlar
Nuray Şenyüz Öztürk
Kırşehir Ahi Evran Üniversitesi, Turkey
Dr. Öğr. Üyesi Murat ÇINARLI Dr. Öğr. Üyesi Murat ÇINARLI
Kırşehir Ahi Evran Üniversitesi, Türkiye
Çiğdem Yüksektepe Ataol
Çankiri Karatekin Üniversitesi, Turkey
Celal Tuğrul Zeyrek
Çankiri Karatekin Üniversitesi, Turkey
Dr. Öğr. Üyesi Esin KIRAY Dr. Öğr. Üyesi Esin KIRAY
Kırşehir Ahi Evran Üniversitesi, Türkiye
Ayşe Nur Coşkun Demirkalp
Kırşehir Ahi Evran Üniversitesi, Turkey
Özet
A novel Schiff base derivative, (E)-N’-(2-hydroxy-3-methoxybenzylidene)-2-phenylacetohydrazide (HMPH, H2L), and its Cu(II) complex were synthesized through the direct condensation of o-vanillin with phenylacetichydrazide in ethanol under reflux conditions. The synthesized ligand was identified using elemental analysis, Fourier transform infrared (FTIR) and ultraviolet–visible (UV–Vis.) spectroscopy. The structures of HMPH (C16H16N2O3)2 and its Cu(II) complex [Cu(L)(H2O)]·H2O (C16H16N2CuO4·H2O) were analysed by single crystal X-ray diffraction technique. The X-ray diffraction results showed that HMPH crystallised in an orthorhombic Pca21 space group with a Z value of 8, while [Cu(L)(H2O)]·H2O crystallised in a monoclinic C 2/c space group with the same z value. The Cu(II) ion is coordinated to the acetohydrazide ligands via hydrazone nitrogen, aceto oxygen (N(2) and O(1)) and hydroxyl O(2) atoms. In addition to the single crystal structures of HMPH and [Cu(L)(H2O)]·H2O, the optimised molecular structures, molecular electrostatic potential meps, molecular orbital energy values, and interactions between DNA bases and molecular structures are determined by DFT/B3LYP/6-311G(d, p) for HMPH and DFT/B3LYP/LanL2DZ for [Cu(L)(H2O)]·H2O. The copper complex was found to be more potent than the organic ligand in terms of antimicrobial activity, with a strong anti-biofilm effect even at low MIC values. The cytotoxicity of the synthesized compounds was investigated on MDA-MB-231 cell lines. The [Cu(L)(H2O)]·H2O complex was found to be more lethal than the HMPH ligand. Furthermore, molecular docking studies of HMPH and [Cu(L)(H2O)]·H2O with P. aeruginosa ATCC27853 (PDB ID: 6P8U) were presented to explain the observed antibacterial activity and the mechanism-of-action.
Anahtar Kelimeler
anti-biofilm | Copper complex | Molecular docking | o-vanillin Schiff base | X-ray
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale
Dergi Adı Polyhedron
Dergi ISSN 0277-5387
Dergi Grubu Q2
Makale Dili İngilizce
Basım Tarihi 02-2025
Cilt No 267
Sayı 1
Doi Numarası 10.1016/j.poly.2024.117315
Talent Yazılım
UNIS: Akademik Veri Yönetim Sistemi
Talentsoft Yazılım