DFT, TD-DFT and Biological Activity Studies of Some Maleanilic Acid Derivatives Ligands and Their Organometallic Complexes

Oraby, Kholoud R.; Hassan, Fatma S M; Zayed, Mohamed A.; Mohamed, Adila E.; Abdellah, Islam M.


This study is a complementary study to our previous study that included the synthesis and characterization of some maleanilic acid derivatives ligands (L1-4) and their metal carbonyl complexes (2-4)a-d as effective compounds for cancer cell inhibition against three cancer cell lines: HCT-116 (colon cancer), HepG-2 cells (Hepatocellular cancer) and MCF-7 (breast cancer). The activity data manifested that p-nitrophenyl maleanilic acid ligand (L2) and its chromium complex (2b) showed higher inhibitory than the other complexes against the tested cancer cells. Additionally, DFT and TD-DFT studies were performed to investigate their frontier molecular orbital (FMO), optical properties, and the correlation between the structure and biological activity. The calculated optical energy gap (Eg) was in the range of 1.78- 2.13 eV, and electron cloud delocalization of HOMO/LUMO levels revealed that all complexes show effective charge separation. DFT results show a great relation between Eg values of the carbonyl complexes and their experimental biological activity. Where it was obvious that complex (2b) with the lowest (Eg) value exhibits the highest inhibition potency against cancer cells. In contrast, complex (2d) with the highest (Eg) value exhibits the lowest inhibition potency. These results translate the reverse relationship between Eg values of the complexes and the inhibition potency against cancer cells.


Maleanilic acid derivatives, Organometallic complexes, Anticancer activity, DFT, HOMO/LUMO, TD-DFT

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