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

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 co...

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Bibliographic Details
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
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob05321c