Hydrophobic effect of amphiphilic derivatives of chitosan on the antifungal activity against aspergillus flavus and aspergillus parasiticus

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dc.contributor.authorDe Souza, Ricchard Hallan Felix Viegas [UNESP]
dc.contributor.authorTakaki, Mirelli [UNESP]
dc.contributor.authorDe Oliveira Pedro, Rafael [UNESP]
dc.contributor.authorGabriel, Juliana Dos Santos [UNESP]
dc.contributor.authorTiera, Marcio José [UNESP]
dc.contributor.authorDe Oliveira Tiera, Vera Ap. [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2014-05-27T11:28:49Z
dc.date.available2014-05-27T11:28:49Z
dc.date.issued2013-04-01
dc.description.abstractLow molecular weight amphiphilic derivatives of chitosan were synthesized, characterized and their antifungal activities against Aspergillus flavus and Aspergillus parasiticus were tested. The derivatives were synthesized using as starting material a deacetylated chitosan sample in a two step process: the reaction with propyltrimethylammonium bromide (Pr), followed by reductive amination with dodecyl aldehyde. Aiming to evaluate the effect of the hydrophobic modification of the derivatives on the antifungal activity against the pathogens, the degree of substitution (DS1) by Pr groups was kept constant and the proportion of dodecyl (Dod) groups was varied from 7 to 29% (DS2). The derivatives were characterized by 1H-NMR and FTIR and their antifungal activities against the pathogens were tested by the radial growth of the colony and minimum inhibitory concentration (MIC) methods. The derivatives substituted with only Pr groups exhibited modest inhibition against A. flavus and A. parasiticus, like that obtained with deacetylated chitosan. Results revealed that the amphiphilic derivatives grafted with Dod groups exhibited increasing inhibition indexes, depending on polymer concentration and hydrophobic content. At 0.6 g/L, all amphiphilic derivatives having from 7.0 to 29% of Dod groups completely inhibited fungal growth and the MIC values were found to decrease from 4.0 g/L for deacetylated chitosan to 0.25-0.50 g/L for the derivatives. These new derivatives open up the possibility of new applications and avenues to develop effective biofungicides based on chitosan. © 2013 by the authors.en
dc.description.affiliationDepartment of Chemistry and Environmental Sciences Institute of Biosciences, Humanities and Exact Sciences-IBILCE São Paulo State University-UNESP, Sao Jose do Rio Preto, Sao Paulo, 15054-000
dc.description.affiliationUnespDepartment of Chemistry and Environmental Sciences Institute of Biosciences, Humanities and Exact Sciences-IBILCE São Paulo State University-UNESP, Sao Jose do Rio Preto, Sao Paulo, 15054-000
dc.format.extent4437-4450
dc.identifierhttp://dx.doi.org/10.3390/molecules18044437
dc.identifier.citationMolecules, v. 18, n. 4, p. 4437-4450, 2013.
dc.identifier.doi10.3390/molecules18044437
dc.identifier.file2-s2.0-84876755587.pdf
dc.identifier.issn1420-3049
dc.identifier.lattes8796747160088337
dc.identifier.scopus2-s2.0-84876755587
dc.identifier.urihttp://hdl.handle.net/11449/75030
dc.identifier.wosWOS:000318020100053
dc.language.isoeng
dc.relation.ispartofMolecules
dc.relation.ispartofjcr3.098
dc.relation.ispartofsjr0,855
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.subjectAmphiphilic
dc.subjectAntifungal activity
dc.subjectAspergillus flavus
dc.subjectAspergillus parasiticus
dc.subjectChitosan
dc.subjectDerivatives
dc.titleHydrophobic effect of amphiphilic derivatives of chitosan on the antifungal activity against aspergillus flavus and aspergillus parasiticusen
dc.typeArtigo
dcterms.licensehttp://www.mdpi.com/about/openaccess
unesp.author.lattes8796747160088337
unesp.author.orcid0000-0002-5472-1482[5]
unesp.author.orcid0000-0003-4431-6720[3]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Biociências Letras e Ciências Exatas, São José do Rio Pretopt

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