Peptide conjugates of lactoferricin analogues and antimicrobials-Design, chemical synthesis, and evaluation of antimicrobial activity and mammalian cytotoxicity

Peptides. 2019 Jul:117:170079. doi: 10.1016/j.peptides.2019.04.006. Epub 2019 Apr 5.

Abstract

Eight new peptide conjugates composed of modified bovine lactoferricin truncated analogues (LFcinB) and one of the three antimicrobials - ciprofloxacin (CIP), levofloxacin (LVX), and fluconazole (FLC) - were synthesized. Four different linkers were applied to connect a peptide and an antimicrobial agent. The FLC-containing peptidic conjugates were synthesized using the "click chemistry" method. This novel approach is reported here for the first time. Unlike their components, CIP- and LVX-based conjugates exerted activity against Candida yeast. Similarly to the constituent peptides, synthesized conjugates showed activity against Gram-positive bacteria, especially S. epidermidis. The most active were the conjugates containing CIP linked to the peptide by the redox-sensitive disulfide bridge. Our results show a significant role of a linker between antimicrobial agent and a peptide. This was also confirmed by the lack of synergistic effects on the antimicrobial activity of the constituent compounds. Moreover, cytotoxicity assays revealed that the proposed conjugates cause a comparatively low cytotoxic effect in reference to antibiotics widely used in therapies. Therefore, they can be deliberated as attractive leading structures for the development of drugs.

Keywords: Antimicrobial peptides; Click chemistry; Disulfide bridge; Lactoferricin; Peptide conjugates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • A549 Cells
  • Anti-Infective Agents* / chemical synthesis
  • Anti-Infective Agents* / chemistry
  • Anti-Infective Agents* / pharmacology
  • Candida / growth & development*
  • Drug Evaluation, Preclinical
  • HEK293 Cells
  • HL-60 Cells
  • Humans
  • Lactoferrin* / chemistry
  • Lactoferrin* / pharmacology
  • Peptides* / chemical synthesis
  • Peptides* / chemistry
  • Peptides* / pharmacology
  • Staphylococcus epidermidis / growth & development*

Substances

  • Anti-Infective Agents
  • Peptides
  • lactoferricin B
  • Lactoferrin