Choline-Based Ionic Liquids: Improvement of Antimicrobial Activity

Filipa Siopa, Teresa Figueiredo, Raquel F. M. Frade, Iris Neto, Ana Meirinhos, Catarina P. Reis, Rita G. Sobral, Carlos A. M. Afonso, Patrícia Rijo

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Antibiotic resistance is a global public health concern. The choline-based ionic liquids (ILs) have raised particular attention in the design of “greener” ILs and can exert a broad-spectrum of antimicrobial activity. To improve antimicrobial chemotherapy, we herein tested the antimicrobial activity and toxicity of a wide range of choline-based ILs. Two series of compounds were synthesized -dimethylethanolamine monoquaternary ammonium salts (Series A) and -methyl diethanolamine, diethanolamine and triethanolamine monoquaternary ammonium salts (Series B). The antimicrobial screening revealed that compounds N-(2-hydroxyethyl)-N,N-dimethyl-1-tetradecanaminium bromide ([N1,1,14,2(OH)]Br), N-(2-hydroxyethyl)-N,N-dimethyl-1-hexadecanaminium bromide ([N1,1,16,2(OH)]Br) and N-(2-hydroxyethyl)-N,N-dimethyl-1-octadecanaminium bromide ([N1,1,18,2(OH)]Br) are potent antimicrobial agents. The presence of a hydroxyethyl group and as mention previously in the literature, the C14 to C16 linker in a choline compound improves the antimicrobial activity and lowers the cytotoxic properties of this class of compounds.

Original languageEnglish
Pages (from-to)5909-5916
Number of pages8
JournalChemistrySelect
Volume1
Issue number18
DOIs
Publication statusPublished - 1 Jan 2016

Keywords

  • Antimicrobia
  • Cholines
  • Cytotoxicity
  • Ionic liquids
  • Monocationic

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