New small-size peptides possessing antifungal activity

Francisco M. Garibotto, Adriana D. Garro, Marcelo F. Masman, Ana M. Rodríguez, Paul G.M. Luiten, Marcela Raimondi, Susana A. Zacchino, Csaba Somlai, Botond Penke, Ricardo D. Enriz

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Abstract

The synthesis, in vitro evaluation, and conformational study of a new series of small-size peptides acting as antifungal agents are reported. In a first step of our study we performed a conformational analysis using Molecular Mechanics calculations. The electronic study was carried out using Molecular electrostatic potentials (MEPs) obtained from RHF/6-31G calculations. On the basis of the theoretical predictions three small-size peptides, RQWKKWWQWRR-NH2, RQIRRWWQWRR-NH2, and RQIRRWWQW-NH2 were synthesized and tested. These peptides displayed a significant antifungal activity against human pathogenic strains including Candida albicans and Cryptococcus neoformans. Our experimental and theoretical results allow the identification of a topographical template which can serve as a guide for the design of new compounds with antifungal properties for potential therapeutic applications against these pathogenic fungi.

Original languageEnglish
Pages (from-to)158-167
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number1
DOIs
Publication statusPublished - Jan 1 2010

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Keywords

  • Antifungal activity
  • Conformational study
  • Molecular electrostatic potentials
  • Small-size peptides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Garibotto, F. M., Garro, A. D., Masman, M. F., Rodríguez, A. M., Luiten, P. G. M., Raimondi, M., Zacchino, S. A., Somlai, C., Penke, B., & Enriz, R. D. (2010). New small-size peptides possessing antifungal activity. Bioorganic and Medicinal Chemistry, 18(1), 158-167. https://doi.org/10.1016/j.bmc.2009.11.009