Synthesis, characterization and molecular docking studies of phenoxyimine based ligands: Cytotoxicity, hemolytic activity and antioxidant assessment

• Published in: Journal of molecular structure 2022-10, Vol.1265, p.133457, Article 133457
• Main Authors: Sajjan, Vinodkumar P., Anigol, Lakkappa B., Gurubasavaraj, Prabhuodeyara M., Kotresha, D., Pradhan, S.S., Venkatesh, S., Patil, Dhanashree
• Format: Article
• Language: English
• Subjects: Cytocompatibility assay; Cytotoxicity activity; Hemolytic assay; Molecular docking; Phenoxyimine compound; Schiff base
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.133457

•Series of phenoxyimine compounds are synthesized.•Compounds were characterized by spectroscopic and analytical methods.•Cytotoxicity of synthesized compounds were performed and compounds exhibit good activity.•Docking studies were carried out to understand structure-activity relationship.•Antioxidant, cytocompatibility and haemolytic acitvities showed that compounds are nontoxic to healthy cells. A series of phenoxyimine compounds were designed and synthesized by the condensation of different substituted salicylaldehyde and aniline at the molar ratio of 1:1 in one step reaction. All synthesized compounds were characterized by analytical and spectroscopic techniques. All compounds were screened for cytotoxicity activities against different cancer cell lines. Compound 3 exhibits significant cytotoxic activity with an IC50 value of 1.099 µM, 1.132 µM against COLO-205 (Colorectal adenocarcinoma) and A-549 (Lung carcinoma) cell line respectively, while compound 4 exhibits noteworthy cytotoxic activity with an IC50 value of 0.52 µM against MDA-MB-231(Breast adenocarcinoma). Similarly, other compounds also exhibited good cytotoxicity properties. Furthermore, the phenoxyimine compounds showed the greatest antioxidant activity against DPPH radicals. The nontoxic activity was confirmed by cytocompatibility assay on L929 normal cell line and hemolysis assay on human red blood cells. Additionally, in silico molecular docking of all compounds were carried out against EGFR, HER-2 and VEGF. Compound 3 having minimum binding energy ΔGb = -8.81 kcal/mol, ΔGb = -10.49 kcal /mol, ΔGb = -9.99 kcal /mol, was bound into the active pocket of EGFR, HER-2 and VEGF respectively.