Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles

Autores
Martinez, Sol Romina; Miana, Gisele Emilse; Albesa, Inés; Mazzieri, Maria Rosa; Becerra, María Cecilia
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two N-benzenesulfonyl (BS) derivatives of 1,2,3,4-tetrahydroquinoline (THQ) were designed, prepared,and screened for antibacterial activity. This approach was based on combining the two privileged structures,BS and THQ, which are known to be active. The objective of this study was to evaluate the antibacterial activityof BS-THQ and its analogue 4-NH2BS-THQ, and to investigate the roles of reactive oxygen species andreactive nitrogen species in their lethality. Both showed bactericidal activity against Staphylococcus aureus ATCC 29213 and methicillin-resistant S. aureus (MRSA) ATCC 43300, with transmission electron microscopy revealing a disturbed membrane architecture. Furthermore, an increase of reactive oxygen species (ROS) in strains treated with BS-THQ with respect to the control was detected when fluorescent microscopy and spectrophotometric techniques were used. The analogue 4-NH2BS-THQ demonstrated a broader spectrum of activity than BS-THQ, with a minimum inhibitory concentration of 100 μg/mL against reference strains of S. aureus, Escherichia coli and Pseudomonas aeruginosa. The assayed compounds represent promising structures for the development of new synthetic classes of antimicrobials.
Fil: Martinez, Sol Romina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Miana, Gisele Emilse. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Albesa, Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Mazzieri, Maria Rosa. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Becerra, María Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Materia
BACTERIA
BIOLOGICAL ACTIVITY
N-BENZENESULFONYL DERIVATIVE
HETEROCYCLE
RADICAL
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/22607
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocyclesMartinez, Sol RominaMiana, Gisele EmilseAlbesa, InésMazzieri, Maria RosaBecerra, María CeciliaBACTERIABIOLOGICAL ACTIVITYN-BENZENESULFONYL DERIVATIVEHETEROCYCLERADICALhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two N-benzenesulfonyl (BS) derivatives of 1,2,3,4-tetrahydroquinoline (THQ) were designed, prepared,and screened for antibacterial activity. This approach was based on combining the two privileged structures,BS and THQ, which are known to be active. The objective of this study was to evaluate the antibacterial activityof BS-THQ and its analogue 4-NH2BS-THQ, and to investigate the roles of reactive oxygen species andreactive nitrogen species in their lethality. Both showed bactericidal activity against Staphylococcus aureus ATCC 29213 and methicillin-resistant S. aureus (MRSA) ATCC 43300, with transmission electron microscopy revealing a disturbed membrane architecture. Furthermore, an increase of reactive oxygen species (ROS) in strains treated with BS-THQ with respect to the control was detected when fluorescent microscopy and spectrophotometric techniques were used. The analogue 4-NH2BS-THQ demonstrated a broader spectrum of activity than BS-THQ, with a minimum inhibitory concentration of 100 μg/mL against reference strains of S. aureus, Escherichia coli and Pseudomonas aeruginosa. The assayed compounds represent promising structures for the development of new synthetic classes of antimicrobials.Fil: Martinez, Sol Romina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Miana, Gisele Emilse. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Albesa, Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Mazzieri, Maria Rosa. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Becerra, María Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaPharmaceutical Soc Japan2016-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/22607Martinez, Sol Romina; Miana, Gisele Emilse; Albesa, Inés; Mazzieri, Maria Rosa; Becerra, María Cecilia; Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles; Pharmaceutical Soc Japan; Chem. Pharm. Bull.; 64; 2; 1-2016; 135-1410009-23631347-5223CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1248/cpb.c15-00682info:eu-repo/semantics/altIdentifier/url/https://www.jstage.jst.go.jp/article/cpb/64/2/64_c15-00682/_articleinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:54:33Zoai:ri.conicet.gov.ar:11336/22607instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:54:33.65CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
title Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
spellingShingle Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
Martinez, Sol Romina
BACTERIA
BIOLOGICAL ACTIVITY
N-BENZENESULFONYL DERIVATIVE
HETEROCYCLE
RADICAL
title_short Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
title_full Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
title_fullStr Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
title_full_unstemmed Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
title_sort Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles
dc.creator.none.fl_str_mv Martinez, Sol Romina
Miana, Gisele Emilse
Albesa, Inés
Mazzieri, Maria Rosa
Becerra, María Cecilia
author Martinez, Sol Romina
author_facet Martinez, Sol Romina
Miana, Gisele Emilse
Albesa, Inés
Mazzieri, Maria Rosa
Becerra, María Cecilia
author_role author
author2 Miana, Gisele Emilse
Albesa, Inés
Mazzieri, Maria Rosa
Becerra, María Cecilia
author2_role author
author
author
author
dc.subject.none.fl_str_mv BACTERIA
BIOLOGICAL ACTIVITY
N-BENZENESULFONYL DERIVATIVE
HETEROCYCLE
RADICAL
topic BACTERIA
BIOLOGICAL ACTIVITY
N-BENZENESULFONYL DERIVATIVE
HETEROCYCLE
RADICAL
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Two N-benzenesulfonyl (BS) derivatives of 1,2,3,4-tetrahydroquinoline (THQ) were designed, prepared,and screened for antibacterial activity. This approach was based on combining the two privileged structures,BS and THQ, which are known to be active. The objective of this study was to evaluate the antibacterial activityof BS-THQ and its analogue 4-NH2BS-THQ, and to investigate the roles of reactive oxygen species andreactive nitrogen species in their lethality. Both showed bactericidal activity against Staphylococcus aureus ATCC 29213 and methicillin-resistant S. aureus (MRSA) ATCC 43300, with transmission electron microscopy revealing a disturbed membrane architecture. Furthermore, an increase of reactive oxygen species (ROS) in strains treated with BS-THQ with respect to the control was detected when fluorescent microscopy and spectrophotometric techniques were used. The analogue 4-NH2BS-THQ demonstrated a broader spectrum of activity than BS-THQ, with a minimum inhibitory concentration of 100 μg/mL against reference strains of S. aureus, Escherichia coli and Pseudomonas aeruginosa. The assayed compounds represent promising structures for the development of new synthetic classes of antimicrobials.
Fil: Martinez, Sol Romina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Miana, Gisele Emilse. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Albesa, Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Mazzieri, Maria Rosa. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Becerra, María Cecilia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
description Two N-benzenesulfonyl (BS) derivatives of 1,2,3,4-tetrahydroquinoline (THQ) were designed, prepared,and screened for antibacterial activity. This approach was based on combining the two privileged structures,BS and THQ, which are known to be active. The objective of this study was to evaluate the antibacterial activityof BS-THQ and its analogue 4-NH2BS-THQ, and to investigate the roles of reactive oxygen species andreactive nitrogen species in their lethality. Both showed bactericidal activity against Staphylococcus aureus ATCC 29213 and methicillin-resistant S. aureus (MRSA) ATCC 43300, with transmission electron microscopy revealing a disturbed membrane architecture. Furthermore, an increase of reactive oxygen species (ROS) in strains treated with BS-THQ with respect to the control was detected when fluorescent microscopy and spectrophotometric techniques were used. The analogue 4-NH2BS-THQ demonstrated a broader spectrum of activity than BS-THQ, with a minimum inhibitory concentration of 100 μg/mL against reference strains of S. aureus, Escherichia coli and Pseudomonas aeruginosa. The assayed compounds represent promising structures for the development of new synthetic classes of antimicrobials.
publishDate 2016
dc.date.none.fl_str_mv 2016-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/22607
Martinez, Sol Romina; Miana, Gisele Emilse; Albesa, Inés; Mazzieri, Maria Rosa; Becerra, María Cecilia; Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles; Pharmaceutical Soc Japan; Chem. Pharm. Bull.; 64; 2; 1-2016; 135-141
0009-2363
1347-5223
CONICET Digital
CONICET
url http://hdl.handle.net/11336/22607
identifier_str_mv Martinez, Sol Romina; Miana, Gisele Emilse; Albesa, Inés; Mazzieri, Maria Rosa; Becerra, María Cecilia; Evaluation of antibacterial activity and reactive species generation of N-benzenesulfonyl derivatives of heterocycles; Pharmaceutical Soc Japan; Chem. Pharm. Bull.; 64; 2; 1-2016; 135-141
0009-2363
1347-5223
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1248/cpb.c15-00682
info:eu-repo/semantics/altIdentifier/url/https://www.jstage.jst.go.jp/article/cpb/64/2/64_c15-00682/_article
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pharmaceutical Soc Japan
publisher.none.fl_str_mv Pharmaceutical Soc Japan
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.22299

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