Synthesis and antimicrobial activity of triazine dendrimers with DABCO groups

Abstract

Triazine dendrimers and smaller dendritic scaffolds that present 1,4-diazabicyclo[2.2.2]octane (DABCO) on the periphery were prepared and assessed for antimicrobial activity and human cell toxicity. Hydrophilic linkers on the periphery of these multivalent scaffolds were derivatized with 2 to 6 DABCO groups that presented either methyl, benzyl, or dodecyl substituents. All of these derivatives were highly soluble in water. Antimicrobial assays against Staphylococcus aureus (Newman), methicillin-resistant S. aureus (MRSA; Sanger 252) and Escherichia coli (K-12) revealed that antimicrobial activity is influenced by two factors; the alkyl substituent on the DABCO group and the valency of the construct. Antimicrobial activity decreased from dodecyl > benzyl > methyl. Divalent and trivalent compounds showed greater activity than tetravalent and hexavalent compounds.