Antimicrobial activity of 1,4-naphthoquinones by metal complexation

Abstract

The effect of metal complexation on the antimicrobial activity of 1,4-naphthoquinones was investigated. Nickel-, chromium-, iron-, copper-, and cobalt-containing metal chelates of 5-amino-8hydroxy-1,4-naphtoquinone (2) and its acyl-derivatives (3-8) were synthesized and characterized, and their antimicrobial activity was evaluated. Data from infrared spectroscopy indicate that naphthoquinones coordinate through oxygen and nitrogen atoms for 2, and through oxygen atoms when ligands were acyl derivatives 3-8. Susceptibility tests for antimicrobial activity showed that 2 and its acyl derivatives were effective on inhibiting the growth of pathogenic bacteria such as Staphylococcus aureus, Streptococcus uberis and Bacillus cereus, but not Gram-negative bacteria. The metal complexation often caused decrease of biological activity. Nickel complex of 2 was the most effective against Gram-positive bacteria, showing MIC values ranging from 375 to 1400 mg/ml. Metal chelates may be useful tools for the understanding of the antimicrobial mechanism of 1,4-naphthoquinones on these bacteria.

Synthesis, characterization, molecular docking, biological activity and density functional theory studies of novel 1,4‐naphthoquinone derivatives and Pd(II), Ni(II) and Co(II) complexes

“…They can also be prepared artificially by laboratory synthesis. Empirical investigations have shown that they display very significant pharmacological properties including anti‐tumour, antimicrobial, antifungal, antivirus, anti‐inflammatory and antipyretic activity . They reportedly have pharmacological effects on cardiovascular and reproductive systems.…”

Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity

“…The effect of metal complexation on naphthoquinone antimicrobial agents has been discussed in the literature. 56 Although metal chelation of the anion of 5-hydroxy-1,4-naphthoquinone (juglone) has resulted in complexes with similar antibacterial effect 57 or higher antibacterial activity, e.g. against Bacillus ssp and S. aureus, than juglone, complexation of the anions of a series of 5-amino-8-hydroxy-1,4-naphthoquinones with M 2+ (M = Ni, Co, Fe, Cu and Cr) resulted in reduced bacterial activity or lack of inhibition effect.…”

Biological and In silico Evaluation of Quinolinedione and Naphthoquinone Derivatives as Potent Antibacterial Agents

“…Mulchin and coworkers recently reported the anticancer, anti‐inflammatory and anti‐tuberculostatic activities of 6,7‐sustituted‐5,8‐quinolinequinone . Also natural and synthetic naphthoquinones have shown important antibacterial and antifungal properties ,. The ability of microorganisms to resist effective treatment of infectious diseases has necessitated the unabated search for new chemotherapeutic agents.…”