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

Fingerprint

Antifungal Agents
Melanocyte-Stimulating Hormones
Cryptococcus neoformans
Bioactivity
Conformations
Derivatives
histidyl-phenylalanyl-arginyl-tryptophanamide
tyrosyl-argininamide
In Vitro Techniques

Keywords

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

ASJC Scopus subject areas

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

Cite this

Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties. / Masman, Marcelo F.; Rodríguez, Ana M.; Svetaz, Laura; Zacchino, Susana A.; Somlai, Csaba; Csizmadia, Imre G.; Penke, Botond; Enriz, Ricardo D.

In: Bioorganic and Medicinal Chemistry, Vol. 14, No. 22, 15.11.2006, p. 7604-7614.

Research output: Contribution to journalArticle

Masman, Marcelo F. ; Rodríguez, Ana M. ; Svetaz, Laura ; Zacchino, Susana A. ; Somlai, Csaba ; Csizmadia, Imre G. ; Penke, Botond ; Enriz, Ricardo D. / Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties. In: Bioorganic and Medicinal Chemistry. 2006 ; Vol. 14, No. 22. pp. 7604-7614.
@article{c2f21e009c4f4e10a14861d6903d1974,
title = "Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties",
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.",
keywords = "Antifungal activities, Conformational and electronic study, His-Phe-Arg-Trp-NH, Small peptides",
author = "Masman, {Marcelo F.} and Rodr{\'i}guez, {Ana M.} and Laura Svetaz and Zacchino, {Susana A.} and Csaba Somlai and Csizmadia, {Imre G.} and Botond Penke and Enriz, {Ricardo D.}",
year = "2006",
month = "11",
day = "15",
doi = "10.1016/j.bmc.2006.07.007",
language = "English",
volume = "14",
pages = "7604--7614",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "22",

}

TY - JOUR

T1 - Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties

AU - Masman, Marcelo F.

AU - Rodríguez, Ana M.

AU - Svetaz, Laura

AU - Zacchino, Susana A.

AU - Somlai, Csaba

AU - Csizmadia, Imre G.

AU - Penke, Botond

AU - Enriz, Ricardo D.

PY - 2006/11/15

Y1 - 2006/11/15

N2 - 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.

AB - 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.

KW - Antifungal activities

KW - Conformational and electronic study

KW - His-Phe-Arg-Trp-NH

KW - Small peptides

UR - http://www.scopus.com/inward/record.url?scp=33749257681&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33749257681&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2006.07.007

DO - 10.1016/j.bmc.2006.07.007

M3 - Article

VL - 14

SP - 7604

EP - 7614

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 22

ER -