Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase

Autores
Giorgi, María Eugenia; Piuselli, Damian; Agusti, Rosalia; Muchnik, Rosa
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. Crystallographic studies showed two sites in the catalytic region of TcTS, one binding the sialic acid donor and the other involved in binding terminal β-D-galactopyranosyl-containing compounds. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. On the other hand, oseltamivir is a sialic acid mimetic effective against some types of influenza virus. In this paper we report covalent conjugation of oseltamivir with lactose and lactobionolactone with the aim to obtain a bi-substrate potential inhibitor. The behavior of the new compounds in the TcTS reaction was studied.
Fil: Giorgi, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Piuselli, Damian. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Agusti, Rosalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Muchnik, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
INHIBITORS
LACTOSE DERIVATIVES
OSELTAMIVIR
TRANS-SIALIDASE
TRYPANOSOMA CRUZI
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/68834
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidaseGiorgi, María EugeniaPiuselli, DamianAgusti, RosaliaMuchnik, RosaINHIBITORSLACTOSE DERIVATIVESOSELTAMIVIRTRANS-SIALIDASETRYPANOSOMA CRUZIhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. Crystallographic studies showed two sites in the catalytic region of TcTS, one binding the sialic acid donor and the other involved in binding terminal β-D-galactopyranosyl-containing compounds. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. On the other hand, oseltamivir is a sialic acid mimetic effective against some types of influenza virus. In this paper we report covalent conjugation of oseltamivir with lactose and lactobionolactone with the aim to obtain a bi-substrate potential inhibitor. The behavior of the new compounds in the TcTS reaction was studied.Fil: Giorgi, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Piuselli, Damian. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Agusti, Rosalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Muchnik, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaArkat USA2011-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/68834Giorgi, María Eugenia; Piuselli, Damian; Agusti, Rosalia; Muchnik, Rosa; Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase; Arkat USA; Arkivoc - Archive for Organic Chemistry; 2011; 7; 3-2011; 260-2711551-70121551-7004CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2011/7/info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.722info:eu-repo/semantics/altIdentifier/url/https://quod.lib.umich.edu/a/ark/5550190.0012.722/1info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:15:29Zoai:ri.conicet.gov.ar:11336/68834instacron: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:34982025-09-29 10:15:29.779CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
title Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
spellingShingle Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
Giorgi, María Eugenia
INHIBITORS
LACTOSE DERIVATIVES
OSELTAMIVIR
TRANS-SIALIDASE
TRYPANOSOMA CRUZI
title_short Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
title_full Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
title_fullStr Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
title_full_unstemmed Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
title_sort Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase
dc.creator.none.fl_str_mv Giorgi, María Eugenia
Piuselli, Damian
Agusti, Rosalia
Muchnik, Rosa
author Giorgi, María Eugenia
author_facet Giorgi, María Eugenia
Piuselli, Damian
Agusti, Rosalia
Muchnik, Rosa
author_role author
author2 Piuselli, Damian
Agusti, Rosalia
Muchnik, Rosa
author2_role author
author
author
dc.subject.none.fl_str_mv INHIBITORS
LACTOSE DERIVATIVES
OSELTAMIVIR
TRANS-SIALIDASE
TRYPANOSOMA CRUZI
topic INHIBITORS
LACTOSE DERIVATIVES
OSELTAMIVIR
TRANS-SIALIDASE
TRYPANOSOMA CRUZI
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. Crystallographic studies showed two sites in the catalytic region of TcTS, one binding the sialic acid donor and the other involved in binding terminal β-D-galactopyranosyl-containing compounds. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. On the other hand, oseltamivir is a sialic acid mimetic effective against some types of influenza virus. In this paper we report covalent conjugation of oseltamivir with lactose and lactobionolactone with the aim to obtain a bi-substrate potential inhibitor. The behavior of the new compounds in the TcTS reaction was studied.
Fil: Giorgi, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Piuselli, Damian. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Agusti, Rosalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Muchnik, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
description Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. Crystallographic studies showed two sites in the catalytic region of TcTS, one binding the sialic acid donor and the other involved in binding terminal β-D-galactopyranosyl-containing compounds. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. On the other hand, oseltamivir is a sialic acid mimetic effective against some types of influenza virus. In this paper we report covalent conjugation of oseltamivir with lactose and lactobionolactone with the aim to obtain a bi-substrate potential inhibitor. The behavior of the new compounds in the TcTS reaction was studied.
publishDate 2011
dc.date.none.fl_str_mv 2011-03
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/11336/68834
Giorgi, María Eugenia; Piuselli, Damian; Agusti, Rosalia; Muchnik, Rosa; Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase; Arkat USA; Arkivoc - Archive for Organic Chemistry; 2011; 7; 3-2011; 260-271
1551-7012
1551-7004
CONICET Digital
CONICET
url http://hdl.handle.net/11336/68834
identifier_str_mv Giorgi, María Eugenia; Piuselli, Damian; Agusti, Rosalia; Muchnik, Rosa; Synthesis of oseltamivir conjugates with lactose analogs for inhibition studies on Trypanosoma cruzi trans-sialidase; Arkat USA; Arkivoc - Archive for Organic Chemistry; 2011; 7; 3-2011; 260-271
1551-7012
1551-7004
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2011/7/
info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.722
info:eu-repo/semantics/altIdentifier/url/https://quod.lib.umich.edu/a/ark/5550190.0012.722/1
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
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
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score 13.069144

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