Structure-antifungal activity relationship of His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 and analogues

Marcelo F. Masman, Csaba Somlai, Francisco M. Garibotto, Ana M. Rodríguez, Agustina de la Iglesia, Susana A. Zacchino, Botond Penke, Ricardo D. Enriz

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Abstract

The synthesis, in vitro evaluation and conformational study of His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 and analogues acting as antifungal agents are reported. Among them, His-Phe-Lys-Trp-Gly-Arg-Phe-Val-NH2 exhibited a moderate but significant antifungal activity against Cryptococcus neoformans, Candida albicans and Candida tropicalis. A theoretical study allows us to propose a biologically relevant conformation for these octapeptides acting as antifungal agents. In addition, these theoretical calculations allow us to determine the minimal structural requirements to produce the antifungal response and can provide a guide for the design of compounds with this biological activity.

Original languageEnglish
Pages (from-to)4347-4358
Number of pages12
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number8
DOIs
Publication statusPublished - Apr 15 2008

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Keywords

  • Antifungal peptides
  • Conformation
  • Electronic properties
  • Octapeptides
  • α-MSH analogues

ASJC Scopus subject areas

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

Cite this

Masman, M. F., Somlai, C., Garibotto, F. M., Rodríguez, A. M., de la Iglesia, A., Zacchino, S. A., Penke, B., & Enriz, R. D. (2008). Structure-antifungal activity relationship of His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 and analogues. Bioorganic and Medicinal Chemistry, 16(8), 4347-4358. https://doi.org/10.1016/j.bmc.2008.02.072