Synthesis, characterization and antimicrobial activity of 4-amino-1-alkyl pyridinium salts

Abstract

A series of 4-amino-1-alkyl pyridinium bromide salts (1-10) were synthesized and antimicrobial activity was evaluated by disc diffusion as well as broth macro-dilution method. 4-Amino-1-hexadecylpyridinium bromide (10) which showed good inhibition against Candida albicans and C. glabrata also displayed good germ tube inhibition against C. albicans. Compound 8 shows very low haemolytic activity against human red blood cells. Compound 10 exhibits excellent antibacterial activity against Escherichia coli and Staphylococcus aureus. Inhibition of phospholipase enzyme secretion was also observed against compound 8 to find the possible mode of action.

1-Alkyl-(N,N-dimethylamino)pyridinium bromides: inhibitory effect on virulence factors of Candida albicans and on the growth of bacterial pathogens

“…This result demonstrated that the compound 8 showed good antimicrobial activity and low toxicity to human red blood cells. Hence, it is suggested that the absence of or low level of haemolytic activity can be assumed to be the result of the absence of cytotoxic action, and this finding correlates with a previous report on 4-amino-1-alkyl pyridinium salts (Ilangovan et al, 2012).…”

“…A homologous series of 1-alkyl-(N,N-dimethylamino)pyridinium bromides was prepared by adopting a procedure that has been used previously by us for the synthesis of 1-alkyl-4-aminopyridinium bromides (Ilangovan et al, 2012). Accordingly, a mixture of 4-N,N-dimethylaminopyridine (1 equiv.)…”

“…Polymethylene bis(4-dimethylaminopyridinium bromide) has also been found to be antimicrobially active (Sarkunam & Nallu, 2004). Recently, we reported good antibacterial and antifungal activity of a series of 4-amino-1-alkylpyridinium bromides (Ilangovan et al, 2012). In continuation of this work, here we have evaluated the antimicrobial properties, candidal virulence factor inhibition and haemolytic activity of a series of 1-alkyl-4-(N,N-dimethylamino)pyridinium bromides.…”

“…N-Alkyl quaternary pyridinium salts can be prepared by simple, economical and short synthetic methods. Pyridinium salts, largely of synthetic origin, and some natural products (Timm et al, 2010) have been found to show good antimicrobial activity (Obando et al, 2009;Ilangovan et al, 2012). Pyridinium succinate and acesulfamate showed good antimicrobial and insect deterrent activity (Hough-Troutman et al, 2009).…”

Crystal structure of 3-amino-1-propylpyridinium bromide

“…Aminopyridinium and 1-alkyl-aminopyridinium salts display a wide range of antimicrobial activity (Sundararaman et al, 2013;Ilangovan et al, 2012). They have found many applications such as surfactants (Gama et al, 1981), ionic liquids (Muldoon et al, 2010;Petkovic et al, 2011), liquid-crystal display mediums (Ezaki & Kokeguchi, 2006), ionic crystals for second-order non-linear optics (Anwar et al, 2001), phasetransfer catalysts in organic transformations (Kupetis et al, 2002) and additives for protein refolding processes (Yamamoto et al, 2011).…”