Experimental and theoretical evaluation of biological properties of a phosphoramide functionalized graphene oxide

In the present study, a novel phosphoramide (L) and corresponding phosphoramide-functionalized graphene oxide (GO-L) were synthesized. L was characterized by FT-IR, 1H NMR, 13C NMR, 31P NMR, and Mass spectroscopy. Functionalization of L on graphene oxide (GO) was investigated by XRD, FT-IR, SEM, EDX, and Map analyses. The cytotoxic effect of L and GO-L against the MCF-7 cell line was assessed by MTT, and flow cytometry (FCM) assay. The cell viability of L and GO-L at different concentrations (0.5-200 mu g. mL-1) was investigated at 24 h experiment. The antitumor effect of L was improved after attachment on GO, and minimum in-hibition concentration (IC50) of GO-L was obtained 23.11 mu g. mL-1. The antimicrobial activity of the synthesized compounds was evaluated against two strains of gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli) bacteria using the disk diffusion method, MIC, and MBC experiments. Quantum calculations were carried out by the DMol3 module based on DFT-D correction to get information on the electronic properties in the Material studio 2017. The key enzymes of E. coli (beta-lactamase (PDB: 4HBT) and S. aureus (beta-Lactamase (PDB: 1MWU)) were chosen for molecular docking assay. Moreover, the molecular docking into TRANSCRIPTION FACTOR STAT3B/DNA COMPLEX (PDB: 1bg1) was done, and GO-L and L were docked stronger compared with GO-COCl and Cpm.

Automated summary

A novel phosphoramide (L) and corresponding phosphoramide-functionalized graphene oxide (GO-L) were synthesized and characterized. The cytotoxic effect of L and GO-L against the MCF-7 cell line was assessed, and it was found that GO-L exhibited improved antitumor effect with a minimum inhibitory concentration of 23.11 μg/mL. The synthesized compounds also showed antimicrobial activity against gram-positive and gram-negative bacteria. Quantum calculations and molecular docking assays provided additional information on the electronic properties and binding affinities of the compounds.