Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry

Autores
Testero, Sebastian Andres; Llarrull, Leticia Irene; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT 1 was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless copper-catalyzed Huisgen dipolar cycloaddition of an azide and a terminal alkyne. While these triazole derivatives possessed fair activity as gelatinase inhibitors, an intermediate used in the dipolar cycloaddition, 4-(propargyloxy)phenyl derivative 2, showed very good activity (<50% inhibitory activity following a 3 h pre-incubation of 2 at a concentration of 3 μM) as an inhibitor of human matrix metalloproteinase-2.
Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Llarrull, Leticia Irene. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Fisher, Jed F.. University of Notre Dame; Estados Unidos
Fil: Chang, Mayland. University of Notre Dame; Estados Unidos
Fil: Mobashery, Shahriar. University of Notre Dame; Estados Unidos
Materia
CUAAC CLICK CHEMISTRY
GELATINASE INHIBITOR
MMP
THIIRANE
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:11336/129195
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistryTestero, Sebastian AndresLlarrull, Leticia IreneFisher, Jed F.Chang, MaylandMobashery, ShahriarCUAAC CLICK CHEMISTRYGELATINASE INHIBITORMMPTHIIRANEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT 1 was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless copper-catalyzed Huisgen dipolar cycloaddition of an azide and a terminal alkyne. While these triazole derivatives possessed fair activity as gelatinase inhibitors, an intermediate used in the dipolar cycloaddition, 4-(propargyloxy)phenyl derivative 2, showed very good activity (<50% inhibitory activity following a 3 h pre-incubation of 2 at a concentration of 3 μM) as an inhibitor of human matrix metalloproteinase-2.Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Llarrull, Leticia Irene. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; ArgentinaFil: Fisher, Jed F.. University of Notre Dame; Estados UnidosFil: Chang, Mayland. University of Notre Dame; Estados UnidosFil: Mobashery, Shahriar. University of Notre Dame; Estados UnidosArkat USA2011-02info: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/11336/129195Testero, Sebastian Andres; Llarrull, Leticia Irene; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar; Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry; Arkat USA; Arkivoc; 2011; 7; 2-2011; 221-2361551-70041551-7012CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/ark.5550190.0012.719info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.719info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:00:15Zoai:ri.conicet.gov.ar:11336/129195instacron: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:34982025-09-03 10:00:15.645CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
title Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
spellingShingle Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
Testero, Sebastian Andres
CUAAC CLICK CHEMISTRY
GELATINASE INHIBITOR
MMP
THIIRANE
title_short Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
title_full Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
title_fullStr Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
title_full_unstemmed Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
title_sort Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry
dc.creator.none.fl_str_mv Testero, Sebastian Andres
Llarrull, Leticia Irene
Fisher, Jed F.
Chang, Mayland
Mobashery, Shahriar
author Testero, Sebastian Andres
author_facet Testero, Sebastian Andres
Llarrull, Leticia Irene
Fisher, Jed F.
Chang, Mayland
Mobashery, Shahriar
author_role author
author2 Llarrull, Leticia Irene
Fisher, Jed F.
Chang, Mayland
Mobashery, Shahriar
author2_role author
author
author
author
dc.subject.none.fl_str_mv CUAAC CLICK CHEMISTRY
GELATINASE INHIBITOR
MMP
THIIRANE
topic CUAAC CLICK CHEMISTRY
GELATINASE INHIBITOR
MMP
THIIRANE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT 1 was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless copper-catalyzed Huisgen dipolar cycloaddition of an azide and a terminal alkyne. While these triazole derivatives possessed fair activity as gelatinase inhibitors, an intermediate used in the dipolar cycloaddition, 4-(propargyloxy)phenyl derivative 2, showed very good activity (<50% inhibitory activity following a 3 h pre-incubation of 2 at a concentration of 3 μM) as an inhibitor of human matrix metalloproteinase-2.
Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Llarrull, Leticia Irene. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Fisher, Jed F.. University of Notre Dame; Estados Unidos
Fil: Chang, Mayland. University of Notre Dame; Estados Unidos
Fil: Mobashery, Shahriar. University of Notre Dame; Estados Unidos
description A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT 1 was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless copper-catalyzed Huisgen dipolar cycloaddition of an azide and a terminal alkyne. While these triazole derivatives possessed fair activity as gelatinase inhibitors, an intermediate used in the dipolar cycloaddition, 4-(propargyloxy)phenyl derivative 2, showed very good activity (<50% inhibitory activity following a 3 h pre-incubation of 2 at a concentration of 3 μM) as an inhibitor of human matrix metalloproteinase-2.
publishDate 2011
dc.date.none.fl_str_mv 2011-02
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/11336/129195
Testero, Sebastian Andres; Llarrull, Leticia Irene; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar; Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry; Arkat USA; Arkivoc; 2011; 7; 2-2011; 221-236
1551-7004
1551-7012
CONICET Digital
CONICET
url http://hdl.handle.net/11336/129195
identifier_str_mv Testero, Sebastian Andres; Llarrull, Leticia Irene; Fisher, Jed F.; Chang, Mayland; Mobashery, Shahriar; Exploring the functional space of thiiranes as gelatinase inhibitors using click chemistry; Arkat USA; Arkivoc; 2011; 7; 2-2011; 221-236
1551-7004
1551-7012
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/ark.5550190.0012.719
info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.719
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 Arkat USA
publisher.none.fl_str_mv Arkat USA
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
_version_ 1842269627639398400
score 13.13397

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