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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/68834
Ver los metadatos del registro completo
id |
CONICETDig_3f8c60be11aaddbc99b3753749dc23c7 |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/68834 |
network_acronym_str |
CONICETDig |
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 Técnicas2025-09-03T10:01:34Zoai: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:34982025-09-03 10:01:34.45CONICET 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 |
_version_ |
1842269704367898624 |
score |
13.13397 |