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Novel imidazolium salt-peptide conjugates and their antimicrobial activity

: Reinhardt, Alain; Horn, Markus; Pieper Gen Schmauck, J.; Bröhl, Andreas; Giernoth, Ralf; Oelkrug, Christopher; Schubert, Andreas; Neundorf, Ines


Bioconjugate Chemistry 25 (2014), No.12, pp.2166-2174
ISSN: 1043-1802
Journal Article
Fraunhofer IZI ()

Our study presents innovative research dealing with the synthesis and biological evaluation of conjugates out of antimicrobial peptides (AMPs) and imidazolium cations that are derived from ionic liquids. AMPs are considered as promising alternatives to common antibiotics due to their different activity mechanisms. Antibacterial effects have also been described for ionic liquids bearing imidazolium cations . Besides single coupling of carboxy-functionalized imidazolium cations to the peptide N-terminal we also developed conjugates bearing multiple copies of imidazolium cations. The combination of both compounds resulted in synergistic effects that were most pronounced when more imidazolium cations were attached to the peptides. In addition, antibacterial activity even in drug-resistant bacterial strains could be observed. Moreover, the novel compounds showed good selectivity only against bacterial cells, an observation that was further proven by lipid interaction studies using giant unilamellar vesicles.