Fast-Acting Antibacterial, Self-Deactivating Polyionene Esters

Abstract

Biocidal compounds that quickly kill bacterial cells and are then deactivated in the surrounding without causing environmental problems are of great current interest. Here, we present new biodegradable antibacterial polymers based on polyionenes with inserted ester functions (PBI esters). The polymers are prepared by polycondensation reaction of 1,4-dibromobutene and different tertiary diaminodiesters. The resulting PBI esters are antibacterially active against a wide range of bacterial strains and were found to quickly kill these cells within 1 to 10 min. Because of hydrolysis of the ester groups, the PBI esters are degraded and deactivated in aqueous media. The degradation rate depends on the backbone structure and the pH. The structure of the polymers also controls the deactivation mechanism. While the more hydrophilic polymers require hydrolyses of only 19 to 30% of the ester groups to become practically inactive, the more hydrophobic PBI esters require up to 85% hydrolysis to achieve the same result. Thus, depending on the environmental conditions and the chemical nature, the PBI esters can be active for only 20 min or for at least one week.

Robust Grafting of Polyionenes: New Potent and Versatile Antimicrobial Surfaces

“…The MIC values measured here were close to the values reported recently in literature for similar polymers. [ 27,28,33 ] We can therefore conclude on the effective bacteriostatic properties of PI regarding MIC results. However, it should be noted that similar PI also displayed biocidal properties, [ 27,29 ] leading in some case to bacteria lysis within two minutes (over S. aureus ).…”

“…In this context, hydrophilic polyionenes (PI) or ionenes that contain quaternary ammonium charges separated by aliphatic spacers along the chain backbone, are particularly good candidates. [ 27–33 ] Agarwal group [ 29 ] have introduced both ethoxyethyl and aliphatic spacers within the PI structure to improve their biocompatibility, before evaluating the influence of these spacers on the antibacterial activity. Tiller and co‐workers [ 30 ] also demonstrate that polyionenes exhibit efficient antimicrobial properties while being not hemocytotoxic.…”

eDNA Inactivation and Biofilm Inhibition by the PolymericBiocide Polyhexamethylene Guanidine Hydrochloride (PHMG-Cl)

“…Cationic polymers are now being considered as a new generation of biocides due to their enhanced antimicrobial activity, as well as their low toxicity to human cells, compared to common low-molecular cationic surfactants [ 60 , 61 ]. A wide variety of biocidal cationic polymers comprising quaternary ammonium, pyridinium, phosphonium, and guanidinium cations in main chains or as pendant groups has been reported [ 60 , 61 , 62 , 63 ]. The high activity of cationic polymers against microorganisms is caused by the presence of multiple positive charges within a single molecule that are able to compensate the negative charges present on the outer cell membranes of microbes.…”

Designing Imidazolium Poly(amide-amide) and Poly(amide-imide) Ionenes and Their Interactions with Mono- and Tris(imidazolium) Ionic Liquids

“…There have been abundant research efforts in recent decades dedicated to the design and applications surrounding polyelectrolytes and ionomers which contain charged features pendant to the main chain, highlighted in several reviews [1][2][3][4][5][6]. The design of ionic liquids (ILs) undoubtably serves as an influential synthetic inspiration for polyelectrolytes, which possess essentially The utility of ionenes has been demonstrated in separations and CO2 capture [8][9][10][11][12][13], ionexchange or conducting membranes [14], antimicrobial coatings [15][16][17][18], batteries [19][20][21], electrochromic devices [22], hydrogels and gelators [23][24][25], water treatment [26], and fiber applications [12,27,28]. Nearly all known ionenes bear cationic moieties such as ammonium, phosphonium, pyrrolidinium, pyridinium, triazolium, and imidazolium groups [8,14,20,22,23,[29][30][31][32][33][34].…”

“…The utility of ionenes has been demonstrated in separations and CO 2 capture [ 8 , 9 , 10 , 11 , 12 , 13 ], ion-exchange or conducting membranes [ 14 ], antimicrobial coatings [ 15 , 16 , 17 , 18 ], batteries [ 19 , 20 , 21 ], electrochromic devices [ 22 ], hydrogels and gelators [ 23 , 24 , 25 ], water treatment [ 26 ], and fiber applications [ 12 , 27 , 28 ]. Nearly all known ionenes bear cationic moieties such as ammonium, phosphonium, pyrrolidinium, pyridinium, triazolium, and imidazolium groups [ 8 , 14 , 20 , 22 , 23 , 29 , 30 , 31 , 32 , 33 , 34 ].…”