Synthesis, structure, theoretical calculation and antibacterial property of two novel Zn(II)/Ni(II) compounds based on 3, 5-dichlorosalicylaldehyde thiocarbamide ligand

• Published in: Bioorganic chemistry 2024-03, Vol.144, p.107140-107140, Article 107140
• Main Authors: Wang, Yuan-Peng, Jiang, Ting-Ting, Sun, Jie, Han, Yu, Yan, Wen-Fu, Wang, Yu-Chang, Lu, Jing, Jin, Juan, Liu, Yong-Feng, Li, Qing
• Format: Article
• Language: English
• Subjects: Antibacterial; Coordination polymer; DFT; Molecular docking
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2024.107140

Two new compounds namely [Zn(L1)phen]31 and Ni(L1)phen(MeOH) 2 (L1 = 3, 5-dichlorosalicylaldehyde thiosemicarbazone) were synthesized by the slow evaporation method at room temperature. The structure of ligand L1 was determined using 1H NMR and 13C NMR spectra. X-ray single crystal diffraction analysis revealed that compounds 1–2 can form 3D supramolecular network structures through π···π stacking and hydrogen bonding interactions. The DFT calculation shows that the coordination of ligand and metal is in good agreement with the experimental results. Hirshfeld surface analysis revealed that H…H and Cl…H interactions were the predominant interactions in compounds 1–2. Energy framework analysis indicated that dispersion energy played a dominant role in the energy composition of compounds 1–2. The inhibitory effects of compounds 1–2 against Escherichia coli (E. coli) and Methicillin-resistant Staphylococcus aureus (MRSA) were tested using the paper disk diffusion method (1: E. coli: 18 mm, MRSA: 17 mm, 2: E. coli: 15 mm, MRSA: 16 mm). Ion releasing experiments were conducted to assess the ion release capacity of compounds 1–2 (Zn2+, 4 days, 38.33 µg/mL; Ni2+, 4 days, 29.12 µg/mL). Molecular docking demonstrated the interaction modes of compounds 1–2 with UDP-N-acetylenolpyruvoylglucosamine reductase (MurB) and dihydrofolate reductase (DHFR) in bacteria, involving hydrophobic, stacking, hydrogen bonding and halogen bonding interactions. The generation of reactive oxygen species (ROS) in bacteria under the presence of compounds 1–2 were evaluated using a fluorescent dye known as dichlorodihydrofluorescein diacetate (DCFH-DA). Potential antibacterial mechanisms of compounds 1–2 were proposed. [Display omitted] •Two new compounds [Zn(L1)phen]31 and Ni(L1)phen(MeOH) 2 were synthesized under room temperature.•Compounds 1–2 were both extended into a 3D supermolecule network structure via π···π stacking and hydrogen bonding interactions.•Compounds 1–2 were both potential antibacterial bacterial for E. coli and MRSA (1: E. coli: 18 mm, MRSA: 17 mm, 2: E. coli: 15 mm, MRSA: 16 mm).•Molecular docking of protein and DNA for compounds 1–2 were investigated.•The potential antibacterial mechanism of compounds 1–2 was proposed via combining with theoretical calculation and experimental results. Two new compounds namely [Zn(L1)phen]31 and Ni(L1)phen(MeOH) 2 (L1 = 3, 5-dichlorosalicylaldehyde thiosemicarbazone) were synthesized by the slow evaporation method at room temperature