A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.molstruc.2021.130316 http://hdl.handle.net/11449/207536 |
Resumo: | Platinum complexes have received special attention due to their biological properties with emphasis on the antitumor and antibacterial activities. In this manuscript, we report the synthesis of a novel water-soluble Pt(II) complex with the amino acid deoxyalliin (S-allyl-L-cysteine, sac), [Pt(sac)2], and its characterization by a set of chemical and spectroscopic techniques besides its preliminary antibacterial activity assays. Elemental and high-resolution mass spectrometric data (ESI-MS) indicated its 1:2 metal/ligand molar composition, with the molecular formula [Pt(C6H10NO2S)2]⋅H2O. The crystal structure of the complex was solved by single-crystal X-ray diffraction studies, where the two molecules of deoxyalliin were shown to be coordinated to the metal in a bidentate N,S-mode and in a trans-configuration. The 1H, 13C and 195Pt nuclear magnetic resonance (NMR) results and the infrared spectroscopic data reinforced the N,S-coordination of deoxyalliin to the metal. The coordination mode of the ligand was supported by density functional theory (DFT) calculations. The antibacterial activity of the complex was preliminarily evaluated by the minimum inhibitory concentration (MIC) assay. The experiments were performed for the complex and the free ligand over Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacterial strains. The [Pt(sac)2] complex did not show inhibitory effect in bacterial growth even at the highest concentration of 3.75 mmol L−1 considered in the present study. |
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A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activityAntibacterial activityCrystal structureDeoxyalliinDFT studiesMass spectrometryPlatinum(II)Platinum complexes have received special attention due to their biological properties with emphasis on the antitumor and antibacterial activities. In this manuscript, we report the synthesis of a novel water-soluble Pt(II) complex with the amino acid deoxyalliin (S-allyl-L-cysteine, sac), [Pt(sac)2], and its characterization by a set of chemical and spectroscopic techniques besides its preliminary antibacterial activity assays. Elemental and high-resolution mass spectrometric data (ESI-MS) indicated its 1:2 metal/ligand molar composition, with the molecular formula [Pt(C6H10NO2S)2]⋅H2O. The crystal structure of the complex was solved by single-crystal X-ray diffraction studies, where the two molecules of deoxyalliin were shown to be coordinated to the metal in a bidentate N,S-mode and in a trans-configuration. The 1H, 13C and 195Pt nuclear magnetic resonance (NMR) results and the infrared spectroscopic data reinforced the N,S-coordination of deoxyalliin to the metal. The coordination mode of the ligand was supported by density functional theory (DFT) calculations. The antibacterial activity of the complex was preliminarily evaluated by the minimum inhibitory concentration (MIC) assay. The experiments were performed for the complex and the free ligand over Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacterial strains. The [Pt(sac)2] complex did not show inhibitory effect in bacterial growth even at the highest concentration of 3.75 mmol L−1 considered in the present study.Institute of Chemistry University of Campinas – UNICAMP, P.O. Box 6154Faculty of Pharmaceutical Sciences University of Campinas – UNICAMPChemistry Collegiate Federal University of Tocantins-UFT, Campus Gurupi, PO Box 66Institute of Chemistry Federal University of Goiás – UFG, Campus SamambaiaGraduate Program in Biotechnology Regenerative Medicine and Medicinal Chemistry University of Araraquara - UNIARADepartment of Analytical Physicochemical and Inorganic Chemistry Institute of Chemistry – São Paulo State University - UNESPDepartment of Analytical Physicochemical and Inorganic Chemistry Institute of Chemistry – São Paulo State University - UNESPUniversidade Estadual de Campinas (UNICAMP)Federal University of Tocantins-UFTUniversidade Federal de Goiás (UFG)University of Araraquara - UNIARAUniversidade Estadual Paulista (Unesp)Quintanilha, Mariana MazzoSchimitd, Bianca AlvesCosta, Adão Marcos FerreiraNakahata, Douglas HidekiSimoni, Déborah de AlencarClavijo, Juan Carlos TenorioPereira, Douglas HenriqueMassabni, Antonio Carlos [UNESP]Lustri, Wilton RogérioCorbi, Pedro Paulo2021-06-25T10:56:54Z2021-06-25T10:56:54Z2021-07-15info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.molstruc.2021.130316Journal of Molecular Structure, v. 1236.0022-2860http://hdl.handle.net/11449/20753610.1016/j.molstruc.2021.1303162-s2.0-85103382178Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Molecular Structureinfo:eu-repo/semantics/openAccess2021-10-23T17:30:41Zoai:repositorio.unesp.br:11449/207536Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T16:25:11.225086Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity |
title |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity |
spellingShingle |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity Quintanilha, Mariana Mazzo Antibacterial activity Crystal structure Deoxyalliin DFT studies Mass spectrometry Platinum(II) |
title_short |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity |
title_full |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity |
title_fullStr |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity |
title_full_unstemmed |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity |
title_sort |
A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity |
author |
Quintanilha, Mariana Mazzo |
author_facet |
Quintanilha, Mariana Mazzo Schimitd, Bianca Alves Costa, Adão Marcos Ferreira Nakahata, Douglas Hideki Simoni, Déborah de Alencar Clavijo, Juan Carlos Tenorio Pereira, Douglas Henrique Massabni, Antonio Carlos [UNESP] Lustri, Wilton Rogério Corbi, Pedro Paulo |
author_role |
author |
author2 |
Schimitd, Bianca Alves Costa, Adão Marcos Ferreira Nakahata, Douglas Hideki Simoni, Déborah de Alencar Clavijo, Juan Carlos Tenorio Pereira, Douglas Henrique Massabni, Antonio Carlos [UNESP] Lustri, Wilton Rogério Corbi, Pedro Paulo |
author2_role |
author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual de Campinas (UNICAMP) Federal University of Tocantins-UFT Universidade Federal de Goiás (UFG) University of Araraquara - UNIARA Universidade Estadual Paulista (Unesp) |
dc.contributor.author.fl_str_mv |
Quintanilha, Mariana Mazzo Schimitd, Bianca Alves Costa, Adão Marcos Ferreira Nakahata, Douglas Hideki Simoni, Déborah de Alencar Clavijo, Juan Carlos Tenorio Pereira, Douglas Henrique Massabni, Antonio Carlos [UNESP] Lustri, Wilton Rogério Corbi, Pedro Paulo |
dc.subject.por.fl_str_mv |
Antibacterial activity Crystal structure Deoxyalliin DFT studies Mass spectrometry Platinum(II) |
topic |
Antibacterial activity Crystal structure Deoxyalliin DFT studies Mass spectrometry Platinum(II) |
description |
Platinum complexes have received special attention due to their biological properties with emphasis on the antitumor and antibacterial activities. In this manuscript, we report the synthesis of a novel water-soluble Pt(II) complex with the amino acid deoxyalliin (S-allyl-L-cysteine, sac), [Pt(sac)2], and its characterization by a set of chemical and spectroscopic techniques besides its preliminary antibacterial activity assays. Elemental and high-resolution mass spectrometric data (ESI-MS) indicated its 1:2 metal/ligand molar composition, with the molecular formula [Pt(C6H10NO2S)2]⋅H2O. The crystal structure of the complex was solved by single-crystal X-ray diffraction studies, where the two molecules of deoxyalliin were shown to be coordinated to the metal in a bidentate N,S-mode and in a trans-configuration. The 1H, 13C and 195Pt nuclear magnetic resonance (NMR) results and the infrared spectroscopic data reinforced the N,S-coordination of deoxyalliin to the metal. The coordination mode of the ligand was supported by density functional theory (DFT) calculations. The antibacterial activity of the complex was preliminarily evaluated by the minimum inhibitory concentration (MIC) assay. The experiments were performed for the complex and the free ligand over Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacterial strains. The [Pt(sac)2] complex did not show inhibitory effect in bacterial growth even at the highest concentration of 3.75 mmol L−1 considered in the present study. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-06-25T10:56:54Z 2021-06-25T10:56:54Z 2021-07-15 |
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/10.1016/j.molstruc.2021.130316 Journal of Molecular Structure, v. 1236. 0022-2860 http://hdl.handle.net/11449/207536 10.1016/j.molstruc.2021.130316 2-s2.0-85103382178 |
url |
http://dx.doi.org/10.1016/j.molstruc.2021.130316 http://hdl.handle.net/11449/207536 |
identifier_str_mv |
Journal of Molecular Structure, v. 1236. 0022-2860 10.1016/j.molstruc.2021.130316 2-s2.0-85103382178 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Molecular Structure |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
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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1808128647403405312 |