A novel water-soluble platinum(II) complex with the amino acid deoxyalliin: synthesis, crystal structure, theoretical studies and investigations about its antibacterial activity

Detalhes bibliográficos
Autor(a) principal: Quintanilha, Mariana Mazzo
Data de Publicação: 2021
Outros Autores: 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
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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spelling 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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