Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials – A novel approach to enhance biocompatibility

The peptides of elastin sequences chosen for the present study included tetrapeptides, pentapeptides and tricosapeptides (30 amino acids), synthesized by classical solution phase method and conjugated to [3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole]. The structures of the compounds were confirmed by physical and spectroscopic techniques followed by the antimicrobial evaluation by both agar well diffusion and microdilution methods. Here we wish to report the effect of conjugation of these moieties which enabled us to identify a novel set of peptides conjugated to heterocycle which have exhibited more potent antimicrobial activity than the conventional drugs used. Further, conjugates of tricosamers 34 and 35 were able to inhibit the growth of fungal species at 3–5 μg/mL which is nearly 5 fold more potent than the reference drug.

A novel series of conjugates involving elastin peptide sequences and benzisoxazole derivative were synthesized and characterized. Most of the candidates of the series have exerted the highly potent activity against the human pathogens tested in the present study.Figure optionsDownload as PowerPoint slideResearch highlights
► Novel elastin peptides conjugated to benzisoxazoles and their antimicrobial activity.
► Highly biocompatible, low toxic and more hydrophobic amino acid/peptide conjugates.
► Tricosamers conjugates with 5 fold more potent activity than the conventional drug used.