engleski

Synthesis of novel analogues of vitamin B6 and evaluation of their antibacterial activity

Pyridinium oximes, such as 2-PAM and toxogonin, are a key component of the nerve-agent antidotes fielded by numerous militaries. In order to assess the potential antimicrobial properties of pyridinium oximes and their structural analogues they were tested against a variety of model organisms for a variety of pathogens. A series of novel pyridinium oximes were prepared by reactions of quaternization of pyridoxal oxime with phenacyl bromide and substituted phenacyl bromides. Four prepared oximes were studied for their antibacterial activity against four gram-negative and four-gram positive microorganisms. In order to examine the influence of anion, bromo derivatives 1-(4’-fluorophenacyl)-3-hydroxy-4-hydroxyiminomethyl-5-hydroxymethyl-2-methylpyridinium bromide (3) and 3-hydroxy-4-hydroxyiminomethyl-5-hydroxymethyl-2-methyl-1-(4’-methoxyphenacyl) pyridinium bromide (5) were converted to chlorides (6) and (7) by halogene exchange reaction. Minimal bactericidal and minimal inhibitory concentration were determined. Minimal bactericidal concentration ranged from 250 ppm to > 1000 ppm while inhibitory concentration was lower, 125 ppm to 1000 ppm. Tested gram-negative bacteria were more sensitive to all synthesized compounds, compared to gram-positive. Compounds with bromide substitution by chloride atom exhibited more potent bactericidal and inhibitory activity. Bacillus subtilis was the most sensitive gram-positive bacteria while, of four tested, Yersinia enterocolitica was the most sensitive gram-negative bacteria to all analyzed pyridinium oximes.

Vitamin B6; pyridinium oximes; antibacterial activity; antimicrobial properties

nije evidentirano