Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties

Marcelo F. Masman, Ana M. Rodríguez, Laura Svetaz, Susana A. Zacchino, Csaba Somlai, Imre G. Csizmadia, Botond Penke, Ricardo D. Enriz

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The synthesis, in vitro evaluation, and conformational study of His-Phe-Arg-Trp-NH2 and related derivatives acting as antifungal agents are reported. Among them, His-Phe-Arg-Trp-NH2 and His-Tyr-Arg-Trp-NH2 exhibited antifungal activity against Cryptococcus neoformans. Antifungal activity of these compounds appears to be closely related to the α-MSH effect. A conformational and electronic study allows us to propose a biologically relevant conformation for these tetrapeptides acting as antifungal agents. In addition, these theoretical calculations permit us to determine the minimal structural requirements to produce the antifungal response and may provide a guide for the design of compounds with this biological activity.

Original languageEnglish
Pages (from-to)7604-7614
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number22
DOIs
Publication statusPublished - Nov 15 2006

Keywords

  • Antifungal activities
  • Conformational and electronic study
  • His-Phe-Arg-Trp-NH
  • Small peptides

ASJC Scopus subject areas

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

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