Synthesis, characterization, crystal structures, DFT, TD-DFT, molecular docking and DNA binding studies of novel copper(II) and zinc(II) complexes bearing halogenated bidentate N,O-donor Schiff base ligands

• Published in: Polyhedron Vol. 195; pp. 114988 - 115000
• Main Authors: Kargar, Hadi, Behjatmanesh-Ardakani, Reza, Torabi, Vajiheh, Kashani, Maryam, Chavoshpour-Natanzi, Zahra, Kazemi, Zahra, Mirkhani, Valiollah, Sahraei, Atefeh, Tahir, Muhammad Nawaz, Ashfaq, Muhammad, Munawar, Khurram Shahzad
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.02.2021; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Crystallography; DNA-binding; Molecular docking; Physical Sciences; Schiff base complex; Science & Technology; Theoretical calculation; X-ray structure; Theoretical calculation; Schiff base complex; X-ray structure; Molecular docking; DNA-binding; INHIBITION; ANTIMICROBIAL ACTIVITIES; CU(II); SPECTROSCOPIC CHARACTERIZATION; CATALYTIC-ACTIVITY; NI(II)
• ISSN: 0277-5387; 1873-3719
• DOI: 10.1016/j.poly.2020.114988

Preparation, characterization and some applications of novel Cu(II) and Zn(II) compounds with halogenated bis-N,O-bidentate Schiff base ligands is reported. The structural elucidations of the synthesized compounds were confirmed by various spectroscopic and physicochemical methods. DNA binding experiments and molecular docking simulations illustrated that the ligands bound in minor grooves of DNA. The oxygen of the ethoxy group has played an important role in DNA binding investigations. [Display omitted] •New metal complexes bearing halogenated bidentate N,O-donor Schiff base were synthesized and characterized.•Single crystal X-ray analysis was used to structure determination.•Computational calculations were carried out by DFT and TD-DFT.•The interactions of ligands and complexes with DNA were studied by spectroscopic and computational methods.•The results obtained from theoretical calculations support our experimental studies. A novel series of transition metal complexes of Cu(II) and Zn(II), including: [Cu(L1)2]: C1, [Cu(L2)2]: C2, [Cu(L3)2]: C3, [Cu(L4)2]: C4, [Zn(L1)2]: Z1, [Zn (L2)2]: Z2, [Zn (L3)2]: Z3, and [Zn (L4)2]: Z4, with four halogenated bis-N,O-bidentate Schiff base ligands (HL1: 2-ethoxy-6-[(4-fluorophenyl)iminomethyl]phenol; HL2: 2-ethoxy-6-[(4-chlorophenylimino)methyl]phenol; HL3: 2-ethoxy-6-[(4-bromophenyl)iminomethyl]phenol; HL4: 2-ethoxy-6-[(4-iodophenylimino)methyl]phenol have been synthesized and characterized by elemental analyses, FT-IR, UV–Vis and 1H NMR spectroscopic techniques. Furthermore, the crystal structures of HL2, HL4, Z1 and Z2 were determined by single crystal X-ray analysis. These bidentate ligands coordinated to the metal(II) ions through the deprotonated phenolic oxygens and the azomethine nitrogens. The X-ray diffraction analysis revealed that Z1 and Z2 adapted distorted tetrahedral geometries. Theoretical calculation of the synthesized compounds, carried out by DFT as well as TD-DFT using B3LYP method with employing the Def2-TZVP basis set, indicated that the calculated results are in accordance with the experimental findings. NBO analysis has been used to elucidate charge transfer information of the HL2, HL4, Z1 and Z2. Moreover, binding ability of the Schiff base ligands and their metal complexes with FS-DNA was studied by spectroscopic and computational methods. The results of both methods showed that the ligands bound in minor grooves of DNA. The oxygen of the ethoxy group has played an important role in DNA binding investigations.