AIMS & OBJECTIVES: In this study, we synthesized thirteen derivatives of gallic acid and evaluated their antibacterial potential against seven multi-drug resistant bacteria, as well as cytotoxic effects against human embryonic kidney cell line in vitro. Methods: 13 compounds were successfully synthesized with moderate to good yield and evaluated. Synthesized derivatives were characterized by using nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transformation infrared spectroscopy. Antibacterial activity was determined using microdilution while cytotoxicyt was assessed using MTT assay.
RESULTS: The results of antibacterial assay showed that seven out of thirteen compounds exhibited antibacterial effects with compound 6 and 13 being most potent against Staphylococcus aureus (MIC 56 μg/mL) and Salmonella enterica (MIC 475 μg/mL) respectively. On the other hand, most of these compounds showed lower cytotoxicity against human embryonic kidney cells (HEK 293), with IC50 values ranging from over 700 μg/mL.
CONCLUSION: Notably, compound 13 was found to be non-toxic at concentrations as high as 5000 μg/mL. These findings suggest that the present synthetic derivatives of gallic acid hold potential for further studies in the development of potent antibacterial agents.
OBJECTIVE: The objective of the present study was to investigate the effects of alkoxy chain length and 1-hydroxy group on anticolorectal cancer activity of a series of 2-bromoalkoxyanthraquinones and corroborate it with their in silico properties.
METHODS: In vitro anticancer activity of 2-bromoalkoxyanthraquinones was evaluated against HCT116, HT29, and CCD841 CoN cell lines, respectively. Molecular docking was performed to understand the interactions of these compounds with putative p53 and KRAS targets (7B4N and 6P0Z).
RESULTS: 2-Bromoalkoxyanthraquinones with the 1-hydroxy group were proven to be more active than the corresponding counterparts in anticancer activity. Among the tested compounds, compound 6b with a C3 alkoxy chain exhibited the most promising antiproliferation activity against HCT116 cells (IC50 = 3.83 ± 0.05 μM) and showed high selectivity for HCT116 over CCD841 CoN cells (SI = 45.47). The molecular docking reveals additional hydrogen bonds between the 1-hydroxy group of 6b and the proteins. Compound 6b has adequate lipophilicity (cLogP = 3.27) and ligand efficiency metrics (LE = 0.34; LLE = 2.15) close to the proposed acceptable range for an initial hit.
CONCLUSION: This work highlights the potential of the 1-hydroxy group and short alkoxy chain on anticolorectal cancer activity of 2-bromoalkoxyanthraquinones. Further optimisation may be warranted for compound 6b as a therapeutic agent against colorectal cancer.