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

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

Research output: Contribution to journalArticle

9 Citations (Scopus)

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

Fingerprint

Candida
Antifungal Agents
Structure-Activity Relationship
Candida tropicalis
Cryptococcus neoformans
Bioactivity
Candida albicans
Conformations
Theoretical Models
ACTH (6-9)
In Vitro Techniques
cyanea-RFamide III

Keywords

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

ASJC Scopus subject areas

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

Cite this

Masman, M. F., Somlai, C., Garibotto, F. M., Rodríguez, A. M., de la Iglesia, A., Zacchino, S. A., ... 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

Structure-antifungal activity relationship of His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 and analogues. / Masman, Marcelo F.; Somlai, C.; Garibotto, Francisco M.; Rodríguez, Ana M.; de la Iglesia, Agustina; Zacchino, Susana A.; Penke, B.; Enriz, Ricardo D.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 8, 15.04.2008, p. 4347-4358.

Research output: Contribution to journalArticle

Masman, MF, Somlai, C, Garibotto, FM, Rodríguez, AM, de la Iglesia, A, Zacchino, SA, Penke, B & Enriz, RD 2008, 'Structure-antifungal activity relationship of His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 and analogues', Bioorganic and Medicinal Chemistry, vol. 16, no. 8, pp. 4347-4358. https://doi.org/10.1016/j.bmc.2008.02.072
Masman, Marcelo F. ; Somlai, C. ; Garibotto, Francisco M. ; Rodríguez, Ana M. ; de la Iglesia, Agustina ; Zacchino, Susana A. ; Penke, B. ; Enriz, Ricardo D. / Structure-antifungal activity relationship of His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 and analogues. In: Bioorganic and Medicinal Chemistry. 2008 ; Vol. 16, No. 8. pp. 4347-4358.
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