Penetratin and derivatives acting as antibacterial agents

Adriana D. Garro, Mónica S. Olivella, José A. Bombasaro, Beatriz Lima, Alejandro Tapia, Gabriela Feresin, Andras Perczel, Csaba Somlai, Botond Penke, Javier López Cascales, Ana M. Rodríguez, Ricardo D. Enriz

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The synthesis, in vitro evaluation and conformational study of penetratin and structurally related derivatives acting as antibacterial agents are reported. Among the compounds evaluated here, two methionine sulphoxide derivatives (RQIKIWFQNRRM[O]KWKK-NH2 and RQIKIFFQNRRM[O]KFKK-NH2) exhibited the strongest antibacterial effect in this series. In order to better understand the antimicrobial activity obtained for these peptides, we performed an exhaustive conformational analysis using different approaches. Molecular dynamics simulations were performed using two different media (water and trifluoroethanol/water). The results of these theoretical calculations were corroborated using experimental CD measurements. The electronic study for these peptides was carried out using molecular electrostatic potentials obtained from RHF/6-31G(d) calculations. In addition, the non-apeptide RQIRRWWQR-NH2 showed strong inhibitory action against the Gram-negative and Gram-positive bacteria tested in this study. In this study we report the synthesis, in vitro evaluation, and conformational study of penetratin and structurally related derivatives acting as antibacterial agents. Among the compounds evaluated two methionine sulfoxide derivatives (RQIKIWFQNRRM[O] KWKK-NH2 and RQIKIFFQNRRM[O]KFKK-NH2) and a nonapeptide (RQIRRWWQR-NH2) exhibited the strongest antibacterial effect against the Gram-negative and Gram-positive bacteria tested in this study.

Original languageEnglish
Pages (from-to)167-177
Number of pages11
JournalChemical Biology and Drug Design
Volume82
Issue number2
DOIs
Publication statusPublished - Aug 1 2013

Keywords

  • Antibacterial activity
  • Conformational study
  • Methionine sulphoxide derivatives
  • Penetratin
  • Small-size peptides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Garro, A. D., Olivella, M. S., Bombasaro, J. A., Lima, B., Tapia, A., Feresin, G., Perczel, A., Somlai, C., Penke, B., López Cascales, J., Rodríguez, A. M., & Enriz, R. D. (2013). Penetratin and derivatives acting as antibacterial agents. Chemical Biology and Drug Design, 82(2), 167-177. https://doi.org/10.1111/cbdd.12143