Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions

Detalhes bibliográficos
Autor(a) principal: Kuhn, Bruna Luiza
Data de Publicação: 2021
Outros Autores: Kaminski, Taís Fernanda Andrzejewski, Carvalho, Anderson Ramos, Fuentefria, Alexandre Meneghello, Johann, Bianca de Medeiros Barlett da Costa, Silva, Edilma Elayne da, Silveira, Gustavo Pozza, Silveira, Tássia Limana da, Soares, Felix Alexandre Antunes, Frizzo, Clarissa Piccinin
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFRGS
Texto Completo: http://hdl.handle.net/10183/231528
Resumo: Imidazolium-based dicationic ILs (DILs) presenting antimicrobial activity and relatively low toxicity are highly desirable and are envisioned for use in live tissue to prevent bacterial or fungal infections. In this context,we present here DILswith dicarboxylate anions [Cn(MIM)2[Cn(MIM)2][CO2- (CH2)mCO2], in which n = 4, 6, 8, and 10, and m = 0, 1, 2, 3, 4, and 5. The results showed that DILs with an alkyl chain spacer of ten carbons were active against yeasts and the bacterial strains tested. However, most of the DILs were cytotoxic and toxic at 1 mM. By contrast, DILs with alkyl chains possessing less than ten carbons were active against some specific Candidas and bacteria (mainly S. aureus), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C4(MIM)2][Pim] toward MRSA. For the DILs described herein, their level of toxicity against C. elegans was lower than that of most of the mono- and dicationic IL analogs with other anions. Our results showed that the presence of carboxylate anions reduces the toxicity of DILs compared to DILs containing halide anions, which is particularly significant to the means of designing biologically active compounds in antimicrobial formulations.
id UFRGS-2_5bde7d0726834a094e62b10818f5605d
oai_identifier_str oai:www.lume.ufrgs.br:10183/231528
network_acronym_str UFRGS-2
network_name_str Repositório Institucional da UFRGS
repository_id_str
spelling Kuhn, Bruna LuizaKaminski, Taís Fernanda AndrzejewskiCarvalho, Anderson RamosFuentefria, Alexandre MeneghelloJohann, Bianca de Medeiros Barlett da CostaSilva, Edilma Elayne daSilveira, Gustavo PozzaSilveira, Tássia Limana daSoares, Felix Alexandre AntunesFrizzo, Clarissa Piccinin2021-11-04T04:24:13Z20211999-4923http://hdl.handle.net/10183/231528001127150Imidazolium-based dicationic ILs (DILs) presenting antimicrobial activity and relatively low toxicity are highly desirable and are envisioned for use in live tissue to prevent bacterial or fungal infections. In this context,we present here DILswith dicarboxylate anions [Cn(MIM)2[Cn(MIM)2][CO2- (CH2)mCO2], in which n = 4, 6, 8, and 10, and m = 0, 1, 2, 3, 4, and 5. The results showed that DILs with an alkyl chain spacer of ten carbons were active against yeasts and the bacterial strains tested. However, most of the DILs were cytotoxic and toxic at 1 mM. By contrast, DILs with alkyl chains possessing less than ten carbons were active against some specific Candidas and bacteria (mainly S. aureus), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C4(MIM)2][Pim] toward MRSA. For the DILs described herein, their level of toxicity against C. elegans was lower than that of most of the mono- and dicationic IL analogs with other anions. Our results showed that the presence of carboxylate anions reduces the toxicity of DILs compared to DILs containing halide anions, which is particularly significant to the means of designing biologically active compounds in antimicrobial formulations.application/pdfengPharmaceutics. Basel. Vol. 13, n. 5 (2021), 639, 14 p.Atividade antimicrobianaCitotoxicidadeInfecções bacterianas e micosesFarmáciaDicationic ionic liquidDicarboxylate anionAntimicrobial activityC. elegansCytotoxicityESKAPE panelAntimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anionsEstrangeiroinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFRGSinstname:Universidade Federal do Rio Grande do Sul (UFRGS)instacron:UFRGSTEXT001127150.pdf.txt001127150.pdf.txtExtracted Texttext/plain57076http://www.lume.ufrgs.br/bitstream/10183/231528/2/001127150.pdf.txt5ec2af3486787eccc9c30630061283b0MD52ORIGINAL001127150.pdfTexto completo (inglês)application/pdf1874840http://www.lume.ufrgs.br/bitstream/10183/231528/1/001127150.pdf251b416bb1595a2b0a0b9ae3583d1dadMD5110183/2315282021-11-20 06:00:58.802273oai:www.lume.ufrgs.br:10183/231528Repositório de PublicaçõesPUBhttps://lume.ufrgs.br/oai/requestopendoar:2021-11-20T08:00:58Repositório Institucional da UFRGS - Universidade Federal do Rio Grande do Sul (UFRGS)false
dc.title.pt_BR.fl_str_mv Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
title Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
spellingShingle Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
Kuhn, Bruna Luiza
Atividade antimicrobiana
Citotoxicidade
Infecções bacterianas e micoses
Farmácia
Dicationic ionic liquid
Dicarboxylate anion
Antimicrobial activity
C. elegans
Cytotoxicity
ESKAPE panel
title_short Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
title_full Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
title_fullStr Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
title_full_unstemmed Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
title_sort Antimicrobial and toxicity evaluation of imidazolium-based dicationic ionic liquids with dicarboxylate anions
author Kuhn, Bruna Luiza
author_facet Kuhn, Bruna Luiza
Kaminski, Taís Fernanda Andrzejewski
Carvalho, Anderson Ramos
Fuentefria, Alexandre Meneghello
Johann, Bianca de Medeiros Barlett da Costa
Silva, Edilma Elayne da
Silveira, Gustavo Pozza
Silveira, Tássia Limana da
Soares, Felix Alexandre Antunes
Frizzo, Clarissa Piccinin
author_role author
author2 Kaminski, Taís Fernanda Andrzejewski
Carvalho, Anderson Ramos
Fuentefria, Alexandre Meneghello
Johann, Bianca de Medeiros Barlett da Costa
Silva, Edilma Elayne da
Silveira, Gustavo Pozza
Silveira, Tássia Limana da
Soares, Felix Alexandre Antunes
Frizzo, Clarissa Piccinin
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Kuhn, Bruna Luiza
Kaminski, Taís Fernanda Andrzejewski
Carvalho, Anderson Ramos
Fuentefria, Alexandre Meneghello
Johann, Bianca de Medeiros Barlett da Costa
Silva, Edilma Elayne da
Silveira, Gustavo Pozza
Silveira, Tássia Limana da
Soares, Felix Alexandre Antunes
Frizzo, Clarissa Piccinin
dc.subject.por.fl_str_mv Atividade antimicrobiana
Citotoxicidade
Infecções bacterianas e micoses
Farmácia
topic Atividade antimicrobiana
Citotoxicidade
Infecções bacterianas e micoses
Farmácia
Dicationic ionic liquid
Dicarboxylate anion
Antimicrobial activity
C. elegans
Cytotoxicity
ESKAPE panel
dc.subject.eng.fl_str_mv Dicationic ionic liquid
Dicarboxylate anion
Antimicrobial activity
C. elegans
Cytotoxicity
ESKAPE panel
description Imidazolium-based dicationic ILs (DILs) presenting antimicrobial activity and relatively low toxicity are highly desirable and are envisioned for use in live tissue to prevent bacterial or fungal infections. In this context,we present here DILswith dicarboxylate anions [Cn(MIM)2[Cn(MIM)2][CO2- (CH2)mCO2], in which n = 4, 6, 8, and 10, and m = 0, 1, 2, 3, 4, and 5. The results showed that DILs with an alkyl chain spacer of ten carbons were active against yeasts and the bacterial strains tested. However, most of the DILs were cytotoxic and toxic at 1 mM. By contrast, DILs with alkyl chains possessing less than ten carbons were active against some specific Candidas and bacteria (mainly S. aureus), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C4(MIM)2][Pim] toward MRSA. For the DILs described herein, their level of toxicity against C. elegans was lower than that of most of the mono- and dicationic IL analogs with other anions. Our results showed that the presence of carboxylate anions reduces the toxicity of DILs compared to DILs containing halide anions, which is particularly significant to the means of designing biologically active compounds in antimicrobial formulations.
publishDate 2021
dc.date.accessioned.fl_str_mv 2021-11-04T04:24:13Z
dc.date.issued.fl_str_mv 2021
dc.type.driver.fl_str_mv Estrangeiro
info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10183/231528
dc.identifier.issn.pt_BR.fl_str_mv 1999-4923
dc.identifier.nrb.pt_BR.fl_str_mv 001127150
identifier_str_mv 1999-4923
001127150
url http://hdl.handle.net/10183/231528
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartof.pt_BR.fl_str_mv Pharmaceutics. Basel. Vol. 13, n. 5 (2021), 639, 14 p.
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFRGS
instname:Universidade Federal do Rio Grande do Sul (UFRGS)
instacron:UFRGS
instname_str Universidade Federal do Rio Grande do Sul (UFRGS)
instacron_str UFRGS
institution UFRGS
reponame_str Repositório Institucional da UFRGS
collection Repositório Institucional da UFRGS
bitstream.url.fl_str_mv http://www.lume.ufrgs.br/bitstream/10183/231528/2/001127150.pdf.txt
http://www.lume.ufrgs.br/bitstream/10183/231528/1/001127150.pdf
bitstream.checksum.fl_str_mv 5ec2af3486787eccc9c30630061283b0
251b416bb1595a2b0a0b9ae3583d1dad
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
repository.name.fl_str_mv Repositório Institucional da UFRGS - Universidade Federal do Rio Grande do Sul (UFRGS)
repository.mail.fl_str_mv
_version_ 1815447773053452288