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, C. Somlai, B. Penke, Ricardo D. Enriz

Research output: Contribution to journalArticle

42 Citations (Scopus)

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

Fingerprint

Peptides
Cryptococcus neoformans
Molecular mechanics
Candida
Antifungal Agents
Mechanics
Fungi
Static Electricity
Candida albicans
Human Activities
Electrostatics
Therapeutics
In Vitro Techniques

Keywords

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

ASJC Scopus subject areas

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

Cite this

Garibotto, F. M., Garro, A. D., Masman, M. F., Rodríguez, A. M., Luiten, P. G. M., Raimondi, M., ... 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

New small-size peptides possessing antifungal activity. / Garibotto, Francisco M.; Garro, Adriana D.; Masman, Marcelo F.; Rodríguez, Ana M.; Luiten, Paul G M; Raimondi, Marcela; Zacchino, Susana A.; Somlai, C.; Penke, B.; Enriz, Ricardo D.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 1, 01.01.2010, p. 158-167.

Research output: Contribution to journalArticle

Garibotto, FM, Garro, AD, Masman, MF, Rodríguez, AM, Luiten, PGM, Raimondi, M, Zacchino, SA, Somlai, C, Penke, B & Enriz, RD 2010, 'New small-size peptides possessing antifungal activity', Bioorganic and Medicinal Chemistry, vol. 18, no. 1, pp. 158-167. https://doi.org/10.1016/j.bmc.2009.11.009
Garibotto FM, Garro AD, Masman MF, Rodríguez AM, Luiten PGM, Raimondi M et al. New small-size peptides possessing antifungal activity. Bioorganic and Medicinal Chemistry. 2010 Jan 1;18(1):158-167. https://doi.org/10.1016/j.bmc.2009.11.009
Garibotto, Francisco M. ; Garro, Adriana D. ; Masman, Marcelo F. ; Rodríguez, Ana M. ; Luiten, Paul G M ; Raimondi, Marcela ; Zacchino, Susana A. ; Somlai, C. ; Penke, B. ; Enriz, Ricardo D. / New small-size peptides possessing antifungal activity. In: Bioorganic and Medicinal Chemistry. 2010 ; Vol. 18, No. 1. pp. 158-167.
@article{a4eb3bd41f2d4892bfae889337cd2320,
title = "New small-size peptides possessing antifungal activity",
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.",
keywords = "Antifungal activity, Conformational study, Molecular electrostatic potentials, Small-size peptides",
author = "Garibotto, {Francisco M.} and Garro, {Adriana D.} and Masman, {Marcelo F.} and Rodr{\'i}guez, {Ana M.} and Luiten, {Paul G M} and Marcela Raimondi and Zacchino, {Susana A.} and C. Somlai and B. Penke and Enriz, {Ricardo D.}",
year = "2010",
month = "1",
day = "1",
doi = "10.1016/j.bmc.2009.11.009",
language = "English",
volume = "18",
pages = "158--167",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "1",

}

TY - JOUR

T1 - New small-size peptides possessing antifungal activity

AU - Garibotto, Francisco M.

AU - Garro, Adriana D.

AU - Masman, Marcelo F.

AU - Rodríguez, Ana M.

AU - Luiten, Paul G M

AU - Raimondi, Marcela

AU - Zacchino, Susana A.

AU - Somlai, C.

AU - Penke, B.

AU - Enriz, Ricardo D.

PY - 2010/1/1

Y1 - 2010/1/1

N2 - 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.

AB - 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.

KW - Antifungal activity

KW - Conformational study

KW - Molecular electrostatic potentials

KW - Small-size peptides

UR - http://www.scopus.com/inward/record.url?scp=72049105042&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=72049105042&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2009.11.009

DO - 10.1016/j.bmc.2009.11.009

M3 - Article

VL - 18

SP - 158

EP - 167

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 1

ER -