Hyperbranched polymers versus dendrimers containing a carbosilane framework and terminal ammonium groups as antimicrobial agents

• Published in: Organic & biomolecular chemistry 2011-07, Vol.9 (14), p.5238-5248
• Main Authors: Ortega, Paula, Macarena Cobaleda, Beatriz, Hernández-Ros, Jose Manuel, Fuentes-Paniagua, Elena, Sánchez-Nieves, Javier, Tarazona, Ma Pilar, Copa-Patiño, Jose Luis, Soliveri, Juan, de la Mata, Fco Javier, Gómez, Rafael
• Format: Article
• Language: English
• Subjects: amines; Ammonium; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antimicrobial agents; Biocides; Dendrimers - chemical synthesis; Dendrimers - chemistry; Dendrimers - pharmacology; Escherichia coli - drug effects; Microbial Sensitivity Tests; Molecular Structure; New families; Polymers - chemical synthesis; Polymers - chemistry; Polymers - pharmacology; Quaternary Ammonium Compounds - chemical synthesis; Quaternary Ammonium Compounds - chemistry; Quaternary Ammonium Compounds - pharmacology; Silanes - chemical synthesis; Silanes - chemistry; Silanes - pharmacology; Solvents; Staphylococcus aureus - drug effects; Stereoisomerism
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c1ob05321c

A new family of amine- and ammonium-terminated hyperbranched polycarbosilanes (PCS) and dendrimers has been synthesized. The functionalization of a polycarbosilane matrix was carried out with peripheral allyl groups by two strategies in the case of PCS: 1) hydrosilylation of allyl amines with PCS containing terminal Si-H bonds, or 2) hydrosilylation of PCS-allyl with an aminosilane. Dendrimers with terminal amine groups were synthesized by hydrosilylation of allydimethylamine. Quaternized systems with MeI are soluble and stable in water or other protic solvent. The antibacterial properties of the ammonium-terminated hyperbranched polycarbosilanes and dendrimers have been evaluated showing that they act as potent biocides against Gram-positive and Gram-negative bacterial strains.