A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes

Detalhes bibliográficos
Autor(a) principal: Da Silva, Patricia B. [UNESP]
Data de Publicação: 2015
Outros Autores: Bonifácio, Bruna V. [UNESP], Frem, Regina C. G. [UNESP], Netto, Adelino V. Godoy [UNESP], Mauro, Antonio E. [UNESP], Da Costa Ferreira, Ana M., De Lopes, Erica O. [UNESP], Raddi, Maria S. G. [UNESP], Bauab, Tais M. [UNESP], Pavan, Fernando R. [UNESP], Chorilli, Marlus [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.3390/molecules201219822
http://hdl.handle.net/11449/177719
Resumo: The aim of this study was to construct a nanostructured lipid system as a strategy to improve the in vitro antibacterial activity of copper(II) complexes. New compounds with the general formulae [CuX2(INH)2]·nH2O (X = Cl- and n = 1 (1); X = NCS- and n = 5 (2); X = NCO- and n = 4 (3); INH = isoniazid, a drug widely used to treat tuberculosis) derived from the reaction between the copper(II) chloride and isoniazid in the presence or absence of pseudohalide ions (NCS- or NCO-) were synthesized and characterized by infrared spectrometry, electronic absorption spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, elemental analysis, melting points and complexometry with 2,2′,2″,2″-(Ethane-1,2-diyldinitrilo)tetraacetic acid (EDTA). The characterization techniques allowed us to confirm the formation of the copper(II) complexes. The Cu(II) complexes were loaded into microemulsion (MEs) composed of 10% phase oil (cholesterol), 10% surfactant [soy oleate and Brij® 58 (1:2)] and 80% aqueous phase (phosphate buffer pH = 7.4) prepared by sonication. The Cu(II) complex-loaded MEs displayed sizes ranging from 158.0 ± 1.060 to 212.6 ± 1.539 nm, whereas the polydispersity index (PDI) ranged from 0.218 ± 0.007 to 0.284 ± 0.034. The antibacterial activity of the free compounds and those that were loaded into the MEs against Staphylococcus aureus ATCC® 25923 and Escherichia coli ATCC® 25922, as evaluated by a microdilution technique, and the cytotoxicity index (IC50) against the Vero cell line (ATCC® CCL-81™) were used to calculate the selectivity index (SI). Among the free compounds, only compound 2 (MIC 500 μg/mL) showed activity for S. aureus. After loading the compounds into the MEs, the antibacterial activity of compounds 1, 2 and 3 was significantly increased against E. coli (MIC's 125, 125 and 500 μg/mL, respectively) and S. aureus (MICs 250, 500 and 125 μg/mL, respectively). The loaded compounds were less toxic against the Vero cell line, especially compound 1 (IC50 from 109.5 to 319.3 μg/mL). The compound 2- and 3-loaded MEs displayed the best SI for E. coli and S. aureus, respectively. These results indicated that the Cu(II) complex-loaded MEs were considerably more selective than the free compounds, in some cases, up to 40 times higher.
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spelling A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexesAntibacterial activityCopper(II) complexesEscherichia coliNanostructured lipid systemStaphylococcus aureusThe aim of this study was to construct a nanostructured lipid system as a strategy to improve the in vitro antibacterial activity of copper(II) complexes. New compounds with the general formulae [CuX2(INH)2]·nH2O (X = Cl- and n = 1 (1); X = NCS- and n = 5 (2); X = NCO- and n = 4 (3); INH = isoniazid, a drug widely used to treat tuberculosis) derived from the reaction between the copper(II) chloride and isoniazid in the presence or absence of pseudohalide ions (NCS- or NCO-) were synthesized and characterized by infrared spectrometry, electronic absorption spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, elemental analysis, melting points and complexometry with 2,2′,2″,2″-(Ethane-1,2-diyldinitrilo)tetraacetic acid (EDTA). The characterization techniques allowed us to confirm the formation of the copper(II) complexes. The Cu(II) complexes were loaded into microemulsion (MEs) composed of 10% phase oil (cholesterol), 10% surfactant [soy oleate and Brij® 58 (1:2)] and 80% aqueous phase (phosphate buffer pH = 7.4) prepared by sonication. The Cu(II) complex-loaded MEs displayed sizes ranging from 158.0 ± 1.060 to 212.6 ± 1.539 nm, whereas the polydispersity index (PDI) ranged from 0.218 ± 0.007 to 0.284 ± 0.034. The antibacterial activity of the free compounds and those that were loaded into the MEs against Staphylococcus aureus ATCC® 25923 and Escherichia coli ATCC® 25922, as evaluated by a microdilution technique, and the cytotoxicity index (IC50) against the Vero cell line (ATCC® CCL-81™) were used to calculate the selectivity index (SI). Among the free compounds, only compound 2 (MIC 500 μg/mL) showed activity for S. aureus. After loading the compounds into the MEs, the antibacterial activity of compounds 1, 2 and 3 was significantly increased against E. coli (MIC's 125, 125 and 500 μg/mL, respectively) and S. aureus (MICs 250, 500 and 125 μg/mL, respectively). The loaded compounds were less toxic against the Vero cell line, especially compound 1 (IC50 from 109.5 to 319.3 μg/mL). The compound 2- and 3-loaded MEs displayed the best SI for E. coli and S. aureus, respectively. These results indicated that the Cu(II) complex-loaded MEs were considerably more selective than the free compounds, in some cases, up to 40 times higher.School of Pharmaceutical Sciences UNESP-University Estadual Paulista Campus AraraquaraChemistry Institute UNESP-University Estadual Paulista Campus AraraquaraChemistry Institute USP-University São Paulo Campus São Paulo São PauloSchool of Pharmaceutical Sciences UNESP-University Estadual Paulista Campus AraraquaraChemistry Institute UNESP-University Estadual Paulista Campus AraraquaraUniversidade Estadual Paulista (Unesp)Universidade de São Paulo (USP)Da Silva, Patricia B. [UNESP]Bonifácio, Bruna V. [UNESP]Frem, Regina C. G. [UNESP]Netto, Adelino V. Godoy [UNESP]Mauro, Antonio E. [UNESP]Da Costa Ferreira, Ana M.De Lopes, Erica O. [UNESP]Raddi, Maria S. G. [UNESP]Bauab, Tais M. [UNESP]Pavan, Fernando R. [UNESP]Chorilli, Marlus [UNESP]2018-12-11T17:26:46Z2018-12-11T17:26:46Z2015-12-16info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article22534-22545application/pdfhttp://dx.doi.org/10.3390/molecules201219822Molecules, v. 20, n. 12, p. 22534-22545, 2015.1420-3049http://hdl.handle.net/11449/17771910.3390/molecules2012198222-s2.0-849543489862-s2.0-84954348986.pdf792767705365081985341388134171610000-0002-0057-79640000-0003-1574-681XScopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengMolecules0,855info:eu-repo/semantics/openAccess2024-06-24T13:45:19Zoai:repositorio.unesp.br:11449/177719Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T15:53:56.173191Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
title A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
spellingShingle A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
Da Silva, Patricia B. [UNESP]
Antibacterial activity
Copper(II) complexes
Escherichia coli
Nanostructured lipid system
Staphylococcus aureus
title_short A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
title_full A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
title_fullStr A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
title_full_unstemmed A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
title_sort A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
author Da Silva, Patricia B. [UNESP]
author_facet Da Silva, Patricia B. [UNESP]
Bonifácio, Bruna V. [UNESP]
Frem, Regina C. G. [UNESP]
Netto, Adelino V. Godoy [UNESP]
Mauro, Antonio E. [UNESP]
Da Costa Ferreira, Ana M.
De Lopes, Erica O. [UNESP]
Raddi, Maria S. G. [UNESP]
Bauab, Tais M. [UNESP]
Pavan, Fernando R. [UNESP]
Chorilli, Marlus [UNESP]
author_role author
author2 Bonifácio, Bruna V. [UNESP]
Frem, Regina C. G. [UNESP]
Netto, Adelino V. Godoy [UNESP]
Mauro, Antonio E. [UNESP]
Da Costa Ferreira, Ana M.
De Lopes, Erica O. [UNESP]
Raddi, Maria S. G. [UNESP]
Bauab, Tais M. [UNESP]
Pavan, Fernando R. [UNESP]
Chorilli, Marlus [UNESP]
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (Unesp)
Universidade de São Paulo (USP)
dc.contributor.author.fl_str_mv Da Silva, Patricia B. [UNESP]
Bonifácio, Bruna V. [UNESP]
Frem, Regina C. G. [UNESP]
Netto, Adelino V. Godoy [UNESP]
Mauro, Antonio E. [UNESP]
Da Costa Ferreira, Ana M.
De Lopes, Erica O. [UNESP]
Raddi, Maria S. G. [UNESP]
Bauab, Tais M. [UNESP]
Pavan, Fernando R. [UNESP]
Chorilli, Marlus [UNESP]
dc.subject.por.fl_str_mv Antibacterial activity
Copper(II) complexes
Escherichia coli
Nanostructured lipid system
Staphylococcus aureus
topic Antibacterial activity
Copper(II) complexes
Escherichia coli
Nanostructured lipid system
Staphylococcus aureus
description The aim of this study was to construct a nanostructured lipid system as a strategy to improve the in vitro antibacterial activity of copper(II) complexes. New compounds with the general formulae [CuX2(INH)2]·nH2O (X = Cl- and n = 1 (1); X = NCS- and n = 5 (2); X = NCO- and n = 4 (3); INH = isoniazid, a drug widely used to treat tuberculosis) derived from the reaction between the copper(II) chloride and isoniazid in the presence or absence of pseudohalide ions (NCS- or NCO-) were synthesized and characterized by infrared spectrometry, electronic absorption spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, elemental analysis, melting points and complexometry with 2,2′,2″,2″-(Ethane-1,2-diyldinitrilo)tetraacetic acid (EDTA). The characterization techniques allowed us to confirm the formation of the copper(II) complexes. The Cu(II) complexes were loaded into microemulsion (MEs) composed of 10% phase oil (cholesterol), 10% surfactant [soy oleate and Brij® 58 (1:2)] and 80% aqueous phase (phosphate buffer pH = 7.4) prepared by sonication. The Cu(II) complex-loaded MEs displayed sizes ranging from 158.0 ± 1.060 to 212.6 ± 1.539 nm, whereas the polydispersity index (PDI) ranged from 0.218 ± 0.007 to 0.284 ± 0.034. The antibacterial activity of the free compounds and those that were loaded into the MEs against Staphylococcus aureus ATCC® 25923 and Escherichia coli ATCC® 25922, as evaluated by a microdilution technique, and the cytotoxicity index (IC50) against the Vero cell line (ATCC® CCL-81™) were used to calculate the selectivity index (SI). Among the free compounds, only compound 2 (MIC 500 μg/mL) showed activity for S. aureus. After loading the compounds into the MEs, the antibacterial activity of compounds 1, 2 and 3 was significantly increased against E. coli (MIC's 125, 125 and 500 μg/mL, respectively) and S. aureus (MICs 250, 500 and 125 μg/mL, respectively). The loaded compounds were less toxic against the Vero cell line, especially compound 1 (IC50 from 109.5 to 319.3 μg/mL). The compound 2- and 3-loaded MEs displayed the best SI for E. coli and S. aureus, respectively. These results indicated that the Cu(II) complex-loaded MEs were considerably more selective than the free compounds, in some cases, up to 40 times higher.
publishDate 2015
dc.date.none.fl_str_mv 2015-12-16
2018-12-11T17:26:46Z
2018-12-11T17:26:46Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.3390/molecules201219822
Molecules, v. 20, n. 12, p. 22534-22545, 2015.
1420-3049
http://hdl.handle.net/11449/177719
10.3390/molecules201219822
2-s2.0-84954348986
2-s2.0-84954348986.pdf
7927677053650819
8534138813417161
0000-0002-0057-7964
0000-0003-1574-681X
url http://dx.doi.org/10.3390/molecules201219822
http://hdl.handle.net/11449/177719
identifier_str_mv Molecules, v. 20, n. 12, p. 22534-22545, 2015.
1420-3049
10.3390/molecules201219822
2-s2.0-84954348986
2-s2.0-84954348986.pdf
7927677053650819
8534138813417161
0000-0002-0057-7964
0000-0003-1574-681X
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Molecules
0,855
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 22534-22545
application/pdf
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
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