Penetratin analogues acting as antifungal agents

Francisco M. Garibotto, Adriana D. Garro, Ana M. Rodríguez, Marcela Raimondi, Susana A. Zacchino, Andras Perczel, Csaba Somlai, Botond Penke, Ricardo D. Enriz

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12 Citations (Scopus)


The synthesis, in vitro evaluation, and conformational study of penetratin analogues acting as antifungal agents are reported. Different peptides structurally related with penetratin were evaluated. Analogues of penetratin rich in Arg, Lys and Trp amino acids were tested. In addition, HFRWRQIKIWFQNRRM[O]KWKK-NH2, a synthetic 20 amino acid peptide was also evaluated. These penetratin analogues displayed antifungal activity against human pathogenic strains including Candida albicans and Cryptococcus neoformans. In contrast, Tat peptide, a well-known cell penetrating peptide, did not show a significant antifungal activity against fungus tested here. We also performed a conformational study by means experimental and theoretical approaches (CD spectroscopic measurements and MD simulations). The electronic structure analysis was carried out from Molecular Electrostatic Potentials (MEP) obtained by using RHF/6-31G ab initio calculations. Our experimental and theoretical results permitted us to identify a topographical template which may provide a guide for the design of new peptides with antifungal effects.

Original languageEnglish
Pages (from-to)370-377
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Issue number1
Publication statusPublished - Jan 1 2011



  • Antifungals
  • Candida albicans
  • Conformational study
  • Cryptococcus neoformans
  • Molecular electrostatic potentials
  • Peptides

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

Garibotto, F. M., Garro, A. D., Rodríguez, A. M., Raimondi, M., Zacchino, S. A., Perczel, A., Somlai, C., Penke, B., & Enriz, R. D. (2011). Penetratin analogues acting as antifungal agents. European Journal of Medicinal Chemistry, 46(1), 370-377.