Cationic antimicrobial polymers and their assemblies

Ana Maria Carmona-Ribeiro, Letícia Dias de Melo Carrasco, Ana Maria Carmona-Ribeiro, Letícia Dias de Melo Carrasco

Abstract

Cationic compounds are promising candidates for development of antimicrobial agents. Positive charges attached to surfaces, particles, polymers, peptides or bilayers have been used as antimicrobial agents by themselves or in sophisticated formulations. The main positively charged moieties in these natural or synthetic structures are quaternary ammonium groups, resulting in quaternary ammonium compounds (QACs). The advantage of amphiphilic cationic polymers when compared to small amphiphilic molecules is their enhanced microbicidal activity. Besides, many of these polymeric structures also show low toxicity to human cells; a major requirement for biomedical applications. Determination of the specific elements in polymers, which affect their antimicrobial activity, has been previously difficult due to broad molecular weight distributions and random sequences characteristic of radical polymerization. With the advances in polymerization control, selection of well defined polymers and structures are allowing greater insight into their structure-antimicrobial activity relationship. On the other hand, antimicrobial polymers grafted or self-assembled to inert or non inert vehicles can yield hybrid antimicrobial nanostructures or films, which can act as antimicrobials by themselves or deliver bioactive molecules for a variety of applications, such as wound dressing, photodynamic antimicrobial therapy, food packing and preservation and antifouling applications.

Figures

Figure 1
Figure 1
Polyquaternium-1 (PQ-1) (adapted from [15]), 3,3-ionene (I3,3) and x,y-ionene (Ix,y) (adapted with permission from [87]).
Figure 2
Figure 2
Amphiphilic polynorbornene derivatives with variable hydrophobic moieties in the repeating unities. Adapted with permission from [92].
Figure 3
Figure 3
Polyhexamethylene biguanide (PHMB) and its derivatives. Adapted with permission from [106].
Figure 4
Figure 4
Self-assembled antimicrobial films and dispersions driven by the electrostatic or by the ion-dipole interaction. (A) The layer-by-layer (LbL) approach to optimize delivery of antimicrobial cationic peptide from films (adapted with permission from [212]); (B) Microbicidal PDDA polymer from microbicidal dispersions of cationic lipid/carboxymethylcellulose/polydiallyldimethylammonium bromide unloaded (adapted with permission from [45]) or loaded with yellow amphotericin B (adapted from [223]); (C) QACs impregnating PMMA films obtained by spin-coating also displayed bactericidal activity (adapted with permission from [216]).
Figure 5
Figure 5
Chemical structure of rosin substituted polyesters with quaternary ammonium sandwiched between the polymer backbone and hydrophobic hydrophenanthrene [247].
Figure 6
Figure 6
Antimicrobial peptide (AMP)-mimetic polypeptide QC8 bearing an alkyl quaternary ammonium moiety in its chemical structure. Adapted with permission from [256].
Figure 7
Figure 7
Cryo-transmission electron micrograph of bovine serum albumin (BSA)/PDDA coacervates at pH 8.5 and 100 mM of ionic strength. Adapted with permission from [287].

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