Amphiphilic block and statistical siloxane copolymers with antimicrobial activity

Abstract

Statistical and block all‐siloxane copolymers containing quaternary ammonium salt (QAS) groups with biocidal activity as lateral substituents were synthesized as models for the study of the effect of the arrangement of the QAS groups in the copolymer chain on their antimicrobial activity. The bioactive siloxane unit was [3‐n‐octyldimethylammoniopropyl]methylsiloxane, and the neutral unit was dimethylsiloxane. The copolymers also contained siloxane units with unreacted precursor 3‐chloropropyl or 3‐bromopropyl groups. A small number of units containing highly hydrophilic 3‐(3‐hydroxypropyl‐dimethylammonio)propyl groups were introduced to increase the solubility of the copolymers in water. The bioactive and bioneutral units were arranged in the polymer chain either in blocks or in statistical order. The block copolymers differed in the number and length of segments. The copolymers were obtained by the quaternization of tertiary amines by chloropropyl or bromopropyl groups attached to polysiloxane chains. The arrangement of the bioactive groups was controlled by the arrangement of the halogenopropyl groups in the bioactive copolymer precursor. All model siloxane copolymers showed high bactericidal activity in a water solution toward the gram‐negative bacteria Escherichia coli and the gram‐positive bacteria Staphylococcus aureus. However, no essential differences in the activities of the copolymers with block and statistical arrangements of units were detected. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 2939–2948, 2003

Antimicrobial Polymers: Mimicking Amino Acid Functionali ty, Sequence Control and Three-dimensional Structure of Host-defen se Peptides

“…Homopolymers of NM maintained low MIC values against drug-resistant strains of C. albicans (3.1 µg/mL for K1 and Gu5 strains). Applying these NM subunit homopolymers to biofilms of C. albicans proved their ability to inhibit fungal biofilm growth down to SMIC 80 (concentration to inhibit 80% of biofilm formation) values of 9.4 µg/mL, whilst displaying very little RBC lysis, even at 2000 µg/mL. 65 When NM subunits were supplemented with hydrophobic groups (CP, CH and CO), antifungal activity was diminished, although the more hydrophobic subunits displayed less dramatic decreases in activity relative to CP, attributed to their antifungal effects.…”

“…79 Amphiphilic block copolymers, in comparison to random copolymers, are more likely to undergo phase segregation in an aqueous environment and are, therefore, the subject of recent studies. An early investigation performed by Sauvet and coworkers 80 compared multiblock poly(siloxane)s bearing quarternized ammonium units with their statistical pendants. No influence of the polymer architecture on the antimicrobial activity was observed.…”

Antimicrobial Agents and Applications on Polymeric Materials

“…Chlorohexidine (CHX) membrane of E. coli 23) . QACs such as benzalkoium chloride, dodecyltrimethyl ammonium bromide (DTAB) and cetylpyridinium chloride (CPC), destroy outer membrane surfaces on many pathogens.…”

Synthesis of antibacterial polymers from 2-dimethylamino ethyl methacrylate quaternized by dimethyl sulfate

“…Polymeric quaternary ammonium compounds (PQACs) are among commonly used inherently antibacterial materials, as they have good antibacterial activity, low volatility, high chemical stability, low toxicity and low skin irritation potential. [11][12][13] They have been successfully used in the antibacterial surface modification of materials. [14][15][16] It should be noted that the properties of quaternization agents have an important role in the antibacterial performance of PQACs.…”