Synthesis and Antibacterial Properties of Novel Hydrolyzable Cationic Amphiphiles. Incorporation of Multiple Head Groups Leads to Impressive Antibacterial Activity

Abstract

Two sets of novel multiheaded cationic amphiphiles bearing one, two, and three trimethylammonium headgroups (T1, T2, and T3) and pyridinium headgroups (P1, P2, and P3), have been synthesized and tested for antimicrobial activities against both Gram-positive and Gram-negative bacteria. The multicationic headgroups in these amphiphiles were attached covalently via scissile ester-type linkages. The results were compared with those for known surface-active, nonhydrolyzable compounds cetyltrimethylammonium bromide (CTAB) and cetylpyridinium bromide (CPB). The killing effects of the new single-headed amphiphiles (T1 and P1) were lower than those of CTAB and CPB, but with an increase in the number of headgroups in the amphiphiles, the killing effects increased for both sets of compounds. It was found that amphiphiles with triple headgroups (T3 and P3) were most active among all the amphiphiles, whereas amphiphile P1 had a very poor killing effect on both types of bacteria. The multiheaded pyridinium amphiphiles were more active compared to their trimethylammonium counterparts. The time needed to kill bacteria with multiheaded amphiphiles was significantly less than that of single-headed amphiphiles. Owing to the presence of a cleavable ester moiety, these new amphiphiles are hydrolyzed spontaneously at physiological conditions. This property enables them to be readily metabolized and therefore have the potential to be superior disinfectants and antiseptics for food and body surfaces.

Quaternary Pyridinium Salts: A Review

“…It was noted that the amphiphiles having triple headgroups were most effective to kill both gram-negative and gram-positive bacteria and required much less time to kill them than that required by single headed salt. However, the multiheaded pyridinium amphiphiles were more active as compared to their trimethylammonium counterparts 51) . Kanji Fugimoto et al evaluated the in vitro antimalarial activity of N,N-hexamethylene bis(4-carbamoyl-1-decylpyridinium bromides) and their derivatives against the plasmodium falciparum FCR-3 strain.…”

Gemini ester quat surfactants and their biological activity

“…The crude reaction products were purified by repeated crystallization from organic solvents (selected individually). The structures of the purified ester quats were confirmed by nuclear magnetic resonance 1 …”

“…Various surfactant architectures have been described in recent literature [1][2][3], including a composition featuring two monomeric surfactant molecules chemically bonded together by a spacer group. These so-called cationic gemini or dimeric cationic surfactants constitute an important class of surface-active compounds [4][5][6][7].…”

Antimicrobial Biomimetics

“…Quaternary ammonium salts are commonly employed as disinfectants, and effective against a wide variety of Gram-positive and Gram-negative bacteria (Tapias et al, 1994;Campanhã et al, 1999;Gilbert & Moore, 2005;Carmona-Ribeiro et al, 2006). Various cationic and www.intechopen.com antimicrobial architectures have been tested such as polyelectrolyte layers (Tiller et al, 2001;Thome et al, 2003;Codling et al, 2003;Cen et al, 2003;Li et al, 2006;Vieira & CarmonaRibeiro, 2008), hyperbranched dendrimers Chen & Cooper, 2002;Abid et al, 2010) and long-chained amphiphiles (Abel et al, 2002;Haldar et al, 2005). The deposition of organic monolayers onto solid surfaces containing quaternary ammonium groups has been shown to prevent deposition and growth of bacterial biofilms (Kugler et al, 2005).…”