Yazarlar |
Nuray Şenyüz Öztürk
Kırşehir Ahi Evran Üniversitesi, Turkey |
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
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 |