2-(pyridin-4yl)benzothiazole and its benzimidazole-analogue: biophysical and in silico studies on their interaction with urease and in vitro anti-Helicobacter pylori activities

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dc.creatorCamila P. Pereira
dc.creatorLuzia Valentina Modolo
dc.creatorJosué Carinhanha Caldas Santos
dc.creatorÂngelo de Fátima
dc.creatorAna Carolina Fradique de Lyra
dc.creatorBreno Germano de Freitas Oliveira
dc.creatorIgor José dos Santos Nascimento
dc.creatorEdeildo Ferreira da Silva-Júnior
dc.creatorThiago Mendonça de Aquino
dc.creatorFrancesca Sisto
dc.creatorIsis Martins Figueiredo
dc.creatorFelipe Terra Martins
dc.date.accessioned2024-11-13T21:03:52Z
dc.date.accessioned2025-09-08T23:04:16Z
dc.date.available2024-11-13T21:03:52Z
dc.date.issued2022
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.format.mimetypepdf
dc.identifier.doihttps://dx.doi.org/10.21577/0103-5053.20220020
dc.identifier.issn0103-5053
dc.identifier.urihttps://hdl.handle.net/1843/78030
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.rightsAcesso Aberto
dc.subjectUrease - Inibidores
dc.subjectBenzimidazois
dc.subjectHelicobacter pylori
dc.subjectEnzimas
dc.subject.otherUrease
dc.subject.otherUrease inhibitor
dc.subject.otherBenzothiazole
dc.subject.otherBenzimidazole
dc.subject.otherDrug-protein interaction
dc.subject.otherSpectroscopic techniques
dc.title2-(pyridin-4yl)benzothiazole and its benzimidazole-analogue: biophysical and in silico studies on their interaction with urease and in vitro anti-Helicobacter pylori activities
dc.typeArtigo de periódico
local.citation.epage1057
local.citation.issue9
local.citation.spage1041
local.citation.volume33
local.description.resumoIn this study, the interaction between benzothiazole (BTA, concentration of a drug required for 50% inhibition in vitro (IC 50) = 0.77 mM) and benzimidazole (BIA, IC 50 = 2.14 mM) with urease was quantitatively assessed, using UV-Vis, molecular fluorescence, and circular dichroism. The results showed that both compounds interact with urease by a static fluorescence quenching mechanism with a non-fluorescent complex formation. The main forces responsible for stabilizing the supramolecular complex between BTA and urease were hydrophobic while, for BIA, van der Waals interactions and hydrogen bonds were the main ones. Urease conformation changes due to the interaction process were analyzed by circular dichroism and synchronous fluorescence. Besides, a competitive assay with substrate and inhibitors was used to evaluate the preferential urease site of interaction with BTA and BIA. Our experimental and theoretical studies supported that both, BTA and BIA, are mixed-inhibitors of ureases with a slight preference to the active site of such enzymes. Finally, both BTA and BIA showed to possess anti-Helicobacter pylori (one reference strain and six clinical isolates) activity, presenting minimal inhibitory concentration (MIC) values ranging from 38-150 and 20-164 μM, respectively. The urease inhibitors omeprazole and hydroxyurea showed MIC values in the range of 46-185 μM and 1683-> 3366 μM, respectively.
local.identifier.orcidhttps://orcid.org/0000-0002-8033-0434
local.identifier.orcidhttps://orcid.org/0000-0002-9525-5123
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0001-5497-6912
local.identifier.orcidhttps://orcid.org/0000-0002-2664-4336
local.identifier.orcidhttps://orcid.org/0000-0002-1527-4501
local.identifier.orcidhttps://orcid.org/0000-0001-9138-8466
local.identifier.orcidhttps://orcid.org/0000-0003-0166-2164
local.identifier.orcidhttps://orcid.org/0000-0002-1873-5342
local.identifier.orcidhttps://orcid.org/0000-0001-9004-0927
local.publisher.countryBrasil
local.publisher.departmentICB - DEPARTAMENTO DE BOTÂNICA
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://jbcs.sbq.org.br/default.asp?ed=330

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