Amine and ammonium functionalization of chloromethylsilane-ended dendrimers. Antimicrobial activity studies

Org Biomol Chem. 2008 Sep 21;6(18):3264-9. doi: 10.1039/b809569h. Epub 2008 Jul 29.

Abstract

Novel amine- and ammonium-terminated carbosilane dendrimers of type G(n)-[Si{CH(2)O-(C(6)H(4))-3-NMe(2)}](x) or G(n)-[Si{CH(2)O-(C(6)H(4))-3-NMe(3)(+)I(-)}](x) have been synthesized and characterized up to second generation by phenolysis of (chloromethyl)silyl-terminated dendrimers with 3-dimethylamine phenol and subsequent quaternization with methyl iodide. Quaternized carbosilane dendrimers are stable in protic solvents and can be solubilised in water after the addition of less than 1% of dimethyl sulfoxide. A study of the antimicrobial activity of these cationic dendrimers of first and second generation against both gram-positive and gram-negative bacteria is also described. The results obtained demonstrate that the new ammonium-terminated carbosilane dendrimers can be considered as multivalent biocides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Dendrimers / chemical synthesis*
  • Dendrimers / chemistry
  • Dendrimers / pharmacology*
  • Escherichia coli / drug effects
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Organosilicon Compounds / chemistry*
  • Quaternary Ammonium Compounds / chemistry*
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship

Substances

  • Amines
  • Anti-Bacterial Agents
  • Dendrimers
  • Organosilicon Compounds
  • Quaternary Ammonium Compounds