A series of 10-aryl substituted azo dyes were synthesized by coupling of β-naphthol, catechol, and quinol with different aromatic amines. The synthetic compounds were screened for their in vitro antimicrobial, antioxidant, and anti-inflammatory activities. The characterization of the synthesized compounds was carried out by UV, IR, 1H NMR and Mass spectroscopy. 13C NMR was employed to confirm the structural identity of some of the compounds. After screening for the presence of antimicrobial constituents in the azo compounds using HTSPOTi culture method, quinol compounds 7 [(E)-2(2nitrophenyl) diazenyl) benzene-1,4-diol] and 10 [(E)-2-(3-nitrophenyl) diazinyl) benzene-1,4-diol] were the most active in terms of broad spectrum activity against Gram-positives [Staphylococcus aureus (ATCC 25923), Streptococcus pyrogenes (clinical strain), Enterococcus faecalis (ATCC 29212)],, Gram-negatives [Salmonella typhi (clinical strain), Escherichia coli (ATCC 251922)] and Pseudomonas aeruginosa (ATCC 27853) and the Candida albicans at minimum inhibitory concentrations of 15.63-31.25 µg/mL. A quinol derivative, [(E)-2-(2nitrophenyl) diazinyl) benzene-1, 4-diol], exhibited the best anti-inflammatory activity in the heat-denatured egg albumin assay. Compounds [ethyl (Z)-4-(3-hydroxynapthalen-1-yl (diazinyl) benzoate] and (E)-2-((3-nitrophenyl) diazenyl) benzene-1,4-diol showed high DPPH free radical scavenging activity during the antioxidant assay.
Introduction: Antimicrobial resistance has increasingly been a global health concern over the past decades and that has necessitated the quest to increase the pool of antibiotics. Methods: Five (5) azo compounds were synthesised by diazotization and coupling procedures with yields of 60 – 92%. They were characterized by melting point determination, Ultra-Violet Visible, and Infra-red spectroscopy. High-throughput spot culture growth inhibition (HT-SPOTi) antimicrobial assay was used to evaluate the compounds. Computational studies was also employed to predict some pharmacokinetic properties of the azo compounds Results: From the in silico studies, none of the compounds violated Lipinski’s rule and therefore, have the potential to be developed into an oral drug. They also showed Total Polar Surface Area (TPSA) values < 140 A2 (74.91 – 100.98 A2) and percentage absorption of 74 – 83 %. They were placed in category III of acute oral drugs. From the high-throughput spot culture growth inhibition antimicrobial assay, all the compounds possessed inhibitory activity against the ESKAPE human pathogens and Mycobacterium smegmatis, with MICs range of 3.9 \(\geq\) 500 \(\mu g/mL\). Except for 4e which showed liver toxicity, all the compounds demonstrated mutagenic and hepatotoxic tendencies. The modulatory assay of the azo compounds revealed that 4c and 4e modulated the antimicrobial activity of ciprofloxacin against Pseudomonas aeruginosa and Staphylococcus aureus. 4c and 4e also modulated the antimicrobial activity of rifampicin against Mycobacterium smegmatis. Exploiting the ability of 4c and 4e to act by a mode of action revealed that they have biofilm formation inhibitory potential. Conclusion: Compounds 4c and 4e exhibited the best antimicrobial activity in terms of resistant modulation and biofilm inhibition against Pseudomonas aeruginosa, Staphylococcus aureus and Mycobacterium smegmatis.
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