Antibacterial Activity and Molecular Docking Studies of a Selected Series of Hydroxy-3-arylcoumarins

Abstract

Antibiotic resistance is one of the main public health concerns of this century. This resistance is also associated with oxidative stress, which could contribute to the selection of resistant bacterial strains. Bearing this in mind, and considering that flavonoid compounds are well known for displaying both activities, we investigated a series of hydroxy-3-arylcoumarins with structural features of flavonoids for their antibacterial activity against different bacterial strains. Active compounds showed selectivity against the studied Gram-positive bacteria compared to Gram-negative bacteria. 5,7-Dihydroxy-3-phenylcoumarin (compound 8) displayed the best antibacterial activity against Staphylococcus aureus and Bacillus cereus with minimum inhibitory concentrations (MICs) of 11 g/mL, followed by Staphylococcus aureus (MRSA strain) and Listeria monocytogenes with MICs of 22 and 44 g/mL, respectively. Moreover, molecular docking studies performed on the most active compounds against Staphylococcus aureus tyrosyl-tRNA synthetase and topoisomerase II DNA gyrase revealed the potential binding mode of the ligands to the site of the appropriate targets. Preliminary structure–activity relationship studies showed that the antibacterial activity can be modulated by the presence of the 3-phenyl ring and by the position of the hydroxyl groups at the coumarin scaffold.

In Silico, Molecular Docking and In Vitro Antimicrobial Activity of the Major Rapeseed Seed Storage Proteins

“…In in-silico molecular docking studies of bio-active peptides or chemical drug molecules that exert their action by binding with specific receptors provides evidence on binding conformation, pattern and affinity. In this study, to determine the potential antimicrobial activity of napin and cruciferin proteins, their interaction with known bacterial receptors, including topoisomerase II (PDB ID: 1JIJ), DNA gyrase subunit b (PDB ID:1KZN) (Gullapelli et al, 2017), Staphylococcus aureus tyrosyl-tRNA synthetase (PDB id: 1JIJ), topoisomerase II DNA gyrase (PDB id: 2XCT) (Pisano et al, 2019), dihydrofolate reductase (PDB ID 3FYV), Staphylococcus aureus gyrase B (PDB ID 4URM), and S. aureus sortase A (PDB ID 2MLM) (Barakat et al, 2016), S aureus dihydrofolate reductase (PDB ID 3FRA) and the 50S ribosomal subunit from Deinococcus radiodurans (PDB ID: 1XBP) (Deng et al, 2019) were tested.…”

Substitution Effects on the Optoelectronic Properties of Coumarin Derivatives

“…On the other hand, replacement of phenyl ring in position 3 with thiophene (a heterocyclic compound) resulted in a 3-heteroarylcoumarin moiety [14], with promising applications in coumarin based dyes [15], florescence microscopy and nanoscopy [16]. A significant number of research studies have investigated the potential of 3-phenylcoumarins [17][18][19][20] and 3-heteroarylcoumarins [21][22][23] derivatives as inhibitors against many target enzymes that are associated to different biological diseases [18,24].…”

IN SILICO STUDY OF CEPHALOSPORIN DERIVATIVES TO INHIBIT THE ACTIONS OF Pseudomonas aeruginosa

“…However, over 70% pathogenic bacteria have become more resistant to multiple types of antibiotics. Multidrug-resistant (MDR) bacteria formally referred to as "superbugs" are the major causes of infections because of failure to respond to conventional treatment (Pisano et al, 2019). Besides, the inappropriate use of antibiotics in medicine have made some serious infections become more difficult to treat (Abrigach et al 2018).…”