A nanostructured lipid system as a strategy to improve the in Vitro antibacterial activity of copper(II) complexes
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Outros Autores: | , , , , , , , , , |
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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Repositório Institucional da UNESP |
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2946 |
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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) |
repository.mail.fl_str_mv |
|
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1808128580558782464 |