Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies

4-Chlorothiobenzoic acid S-benzyl ester (I), 3-nitrothiobenzoic acid S-benzyl ester (II), 4-nitrothiobenzoic acid S-benzyl ester (III) and 4-methylthiobenzoic acid S-benzyl ester (IV) were prepared and characterized by 1H and 13C NMR, Mass spectrometry and IR spectroscopy. Quantum chemical calculati...

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Autores:: Henao Castañeda I.C.
Pereañez, Jaime Andrés
Jios J.L.

Tipo de recurso:: Article of journal

Fecha de publicación:: 2012

Institución:: Universidad Cooperativa de Colombia

Repositorio:: Repositorio UCC

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repository_id_str
spelling	Henao Castañeda I.C.Pereañez, Jaime AndrésJios J.L.2021-12-16T22:15:36Z2021-12-16T22:15:36Z2012https://doi.org/10.1080/00986445.2015.107489800222860https://hdl.handle.net/20.500.12494/41551Henao IC,Pereañez JA,Jios JL. Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies. J MOL STRUCT. 2012. 1028. p. 7-12. .4-Chlorothiobenzoic acid S-benzyl ester (I), 3-nitrothiobenzoic acid S-benzyl ester (II), 4-nitrothiobenzoic acid S-benzyl ester (III) and 4-methylthiobenzoic acid S-benzyl ester (IV) were prepared and characterized by 1H and 13C NMR, Mass spectrometry and IR spectroscopy. Quantum chemical calculations were performed with Gaussian 09 to calculate the geometric parameters and vibrational spectra. Phospholipase A 2 (PLA 2) was purified from Crotalus durissus cumanensis venom by molecular exclusion chromatography, followed by reverse phase-high performance liquid chromatography. Two studies of the inhibition of phospholipase A 2 activity were performed using phosphatidilcholine and 4-nitro-3-octanoyloxybenzoic acid as substrates, in both cases compound II showed the best inhibitory ability, with 74.89% and 69.91% of inhibition, respectively. Average percentage of inhibition was 52.49%. Molecular docking was carried out with Autodock Vina using as ligands the minimized structures of compounds (I-IV) and as protein PLA 2 (PDB code 2QOG). The results suggest that compounds I-IV could interact with His48 at the active site of PLA 2. In addition, all compounds showed Van der Waals interactions with residues from hydrophobic channel of the enzyme. This interaction would impede normal catalysis cycle of the PLA 2. © 2012 Elsevier B.V. All rights reserved.12-7Elsevier BVActive siteAs-ligandsAutodockComputational studiesConformational analysisDFT calculationGaussiansGeometric parameterMolecular dockingMolecular exclusionPhospholipase APotential inhibitorsQuantum chemical calculationsSnake venomsThiobenzoic acidThioestersVan Der Waals interactionsDockingCrotalusCrotalus durissus cumanensisSubstituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studiesArtículohttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articlehttp://purl.org/redcol/resource_type/ARTinfo:eu-repo/semantics/publishedVersionJ MOL STRUCTinfo:eu-repo/semantics/closedAccesshttp://purl.org/coar/access_right/c_14cbPublication20.500.12494/41551oai:repository.ucc.edu.co:20.500.12494/415512024-08-20 16:17:37.067metadata.onlyhttps://repository.ucc.edu.coRepositorio Institucional Universidad Cooperativa de Colombiabdigital@metabiblioteca.com
dc.title.spa.fl_str_mv	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies
title	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies
spellingShingle	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies Active site As-ligands Autodock Computational studies Conformational analysis DFT calculation Gaussians Geometric parameter Molecular docking Molecular exclusion Phospholipase A Potential inhibitors Quantum chemical calculations Snake venoms Thiobenzoic acid Thioesters Van Der Waals interactions Docking Crotalus Crotalus durissus cumanensis
title_short	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies
title_full	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies
title_fullStr	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies
title_full_unstemmed	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies
title_sort	Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies
dc.creator.fl_str_mv	Henao Castañeda I.C. Pereañez, Jaime Andrés Jios J.L.
dc.contributor.author.none.fl_str_mv	Henao Castañeda I.C. Pereañez, Jaime Andrés Jios J.L.
dc.subject.spa.fl_str_mv	Active site As-ligands Autodock Computational studies Conformational analysis DFT calculation Gaussians Geometric parameter Molecular docking Molecular exclusion Phospholipase A Potential inhibitors Quantum chemical calculations Snake venoms Thiobenzoic acid Thioesters Van Der Waals interactions Docking Crotalus Crotalus durissus cumanensis
topic	Active site As-ligands Autodock Computational studies Conformational analysis DFT calculation Gaussians Geometric parameter Molecular docking Molecular exclusion Phospholipase A Potential inhibitors Quantum chemical calculations Snake venoms Thiobenzoic acid Thioesters Van Der Waals interactions Docking Crotalus Crotalus durissus cumanensis
description	4-Chlorothiobenzoic acid S-benzyl ester (I), 3-nitrothiobenzoic acid S-benzyl ester (II), 4-nitrothiobenzoic acid S-benzyl ester (III) and 4-methylthiobenzoic acid S-benzyl ester (IV) were prepared and characterized by 1H and 13C NMR, Mass spectrometry and IR spectroscopy. Quantum chemical calculations were performed with Gaussian 09 to calculate the geometric parameters and vibrational spectra. Phospholipase A 2 (PLA 2) was purified from Crotalus durissus cumanensis venom by molecular exclusion chromatography, followed by reverse phase-high performance liquid chromatography. Two studies of the inhibition of phospholipase A 2 activity were performed using phosphatidilcholine and 4-nitro-3-octanoyloxybenzoic acid as substrates, in both cases compound II showed the best inhibitory ability, with 74.89% and 69.91% of inhibition, respectively. Average percentage of inhibition was 52.49%. Molecular docking was carried out with Autodock Vina using as ligands the minimized structures of compounds (I-IV) and as protein PLA 2 (PDB code 2QOG). The results suggest that compounds I-IV could interact with His48 at the active site of PLA 2. In addition, all compounds showed Van der Waals interactions with residues from hydrophobic channel of the enzyme. This interaction would impede normal catalysis cycle of the PLA 2. © 2012 Elsevier B.V. All rights reserved.
publishDate	2012
dc.date.issued.none.fl_str_mv	2012
dc.date.accessioned.none.fl_str_mv	2021-12-16T22:15:36Z
dc.date.available.none.fl_str_mv	2021-12-16T22:15:36Z
dc.type.none.fl_str_mv	Artículo
dc.type.coar.fl_str_mv	http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.coar.none.fl_str_mv	http://purl.org/coar/resource_type/c_6501
dc.type.coarversion.none.fl_str_mv	http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.driver.none.fl_str_mv	info:eu-repo/semantics/article
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dc.type.version.none.fl_str_mv	info:eu-repo/semantics/publishedVersion
format	http://purl.org/coar/resource_type/c_6501
status_str	publishedVersion
dc.identifier.none.fl_str_mv	https://doi.org/10.1080/00986445.2015.1074898
dc.identifier.issn.spa.fl_str_mv	00222860
dc.identifier.uri.none.fl_str_mv	https://hdl.handle.net/20.500.12494/41551
dc.identifier.bibliographicCitation.spa.fl_str_mv	Henao IC,Pereañez JA,Jios JL. Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies. J MOL STRUCT. 2012. 1028. p. 7-12. .
url	https://doi.org/10.1080/00986445.2015.1074898 https://hdl.handle.net/20.500.12494/41551
identifier_str_mv	00222860 Henao IC,Pereañez JA,Jios JL. Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies. J MOL STRUCT. 2012. 1028. p. 7-12. .
dc.relation.ispartofjournal.spa.fl_str_mv	J MOL STRUCT
dc.rights.accessrights.none.fl_str_mv	info:eu-repo/semantics/closedAccess
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dc.format.extent.spa.fl_str_mv	12-7
dc.publisher.spa.fl_str_mv	Elsevier BV
institution	Universidad Cooperativa de Colombia
repository.name.fl_str_mv	Repositorio Institucional Universidad Cooperativa de Colombia
repository.mail.fl_str_mv	bdigital@metabiblioteca.com
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Substituted thiobenzoic acid S-benzyl esters as potential inhibitors of a snake venom phospholipase A 2: Synthesis, spectroscopic and computational studies

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