Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphoge...

Autores
Rabinovich, Gabriel A.; Cumashi, Albana; Bianco, German Ariel; Ciavardelli, Domenico; Iurisci, Ida; D’Egidio, Maurizia; Piccolo, Enza; Tinari, Nicola; Nifantiev, Nikolay; Iacobelli, Stefano
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Galectins, a family of structurally related carbohydrate-binding proteins, contribute to different events associated with cancer biology, including apoptosis, homotypic cell aggregation, angiogenesis and tumor-immune escape. To interfere with galectin-carbohydrate interactions during tumor progression, a current challenge is the design of specific galectin inhibitors for therapeutic purposes. Here, we report the synthesis of three novel low molecular weight synthetic lactulose amines (SLA): (1) N-lactulose-octamethylenediamine (LDO), (2) N,N´-dilactulose-octamethylenediamine (D-LDO), and (3) N,N´-dilactulose-dodecamethylenediamine (D-LDD). These compounds showed a differential ability to inhibit binding of galectin-1 and/or galectin-3 to the highly glycosylated protein 90K in solid-phase assays. In addition, each compound demonstrated selective regulatory effects in different events linked to tumor progression including tumor-cell apoptosis, homotypic cell aggregation, and endothelial cell morphogenesis. Our results suggest that galectin inhibitors with subtle differences in their carbohydrate structures may be potentially used to specifically block different steps of tumor growth and metastasis
Fil: Rabinovich, Gabriel A.. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina. Universidad de Buenos Aires. Facultad de Medicina. Hospital de Clínicas General San Martín; Argentina
Fil: Cumashi, Albana. Università degli Studi G. D´Annunzio; Italia
Fil: Bianco, German Ariel. Universidad de Buenos Aires. Facultad de Medicina. Hospital de Clínicas General San Martín; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina
Fil: Ciavardelli, Domenico. Università degli Studi G. D´Annunzio; Italia
Fil: Iurisci, Ida. Università degli Studi G. D´Annunzio; Italia
Fil: D’Egidio, Maurizia. Università degli Studi G. D´Annunzio; Italia
Fil: Piccolo, Enza. Università degli Studi G. D´Annunzio; Italia
Fil: Tinari, Nicola. Università degli Studi G. D´Annunzio; Italia
Fil: Nifantiev, Nikolay. Academia de Ciencias Rusa; Rusia
Fil: Iacobelli, Stefano. Università degli Studi G. D´Annunzio; Italia
Materia
Antineoplastic Agents
Apoptosis
Endothelial Cells
Galectin
Glycosylation
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:11336/28531
Acceder
id CONICETDig_80a63b19a9a0f99a64b24e7607cacebf
oai_identifier_str oai:ri.conicet.gov.ar:11336/28531
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesisRabinovich, Gabriel A.Cumashi, AlbanaBianco, German ArielCiavardelli, DomenicoIurisci, IdaD’Egidio, MauriziaPiccolo, EnzaTinari, NicolaNifantiev, NikolayIacobelli, StefanoAntineoplastic AgentsApoptosisEndothelial CellsGalectinGlycosylationhttps://purl.org/becyt/ford/3.1https://purl.org/becyt/ford/3Galectins, a family of structurally related carbohydrate-binding proteins, contribute to different events associated with cancer biology, including apoptosis, homotypic cell aggregation, angiogenesis and tumor-immune escape. To interfere with galectin-carbohydrate interactions during tumor progression, a current challenge is the design of specific galectin inhibitors for therapeutic purposes. Here, we report the synthesis of three novel low molecular weight synthetic lactulose amines (SLA): (1) N-lactulose-octamethylenediamine (LDO), (2) N,N´-dilactulose-octamethylenediamine (D-LDO), and (3) N,N´-dilactulose-dodecamethylenediamine (D-LDD). These compounds showed a differential ability to inhibit binding of galectin-1 and/or galectin-3 to the highly glycosylated protein 90K in solid-phase assays. In addition, each compound demonstrated selective regulatory effects in different events linked to tumor progression including tumor-cell apoptosis, homotypic cell aggregation, and endothelial cell morphogenesis. Our results suggest that galectin inhibitors with subtle differences in their carbohydrate structures may be potentially used to specifically block different steps of tumor growth and metastasisFil: Rabinovich, Gabriel A.. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina. Universidad de Buenos Aires. Facultad de Medicina. Hospital de Clínicas General San Martín; ArgentinaFil: Cumashi, Albana. Università degli Studi G. D´Annunzio; ItaliaFil: Bianco, German Ariel. Universidad de Buenos Aires. Facultad de Medicina. Hospital de Clínicas General San Martín; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; ArgentinaFil: Ciavardelli, Domenico. Università degli Studi G. D´Annunzio; ItaliaFil: Iurisci, Ida. Università degli Studi G. D´Annunzio; ItaliaFil: D’Egidio, Maurizia. Università degli Studi G. D´Annunzio; ItaliaFil: Piccolo, Enza. Università degli Studi G. D´Annunzio; ItaliaFil: Tinari, Nicola. Università degli Studi G. D´Annunzio; ItaliaFil: Nifantiev, Nikolay. Academia de Ciencias Rusa; RusiaFil: Iacobelli, Stefano. Università degli Studi G. D´Annunzio; ItaliaOxford Univ Press Inc2006-03info: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/11336/28531Rabinovich, Gabriel A.; Cumashi, Albana; Bianco, German Ariel; Ciavardelli, Domenico; Iurisci, Ida; et al.; Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis; Oxford Univ Press Inc; Glycobiology; 16; 3; 3-2006; 210-2200959-66581460-2423CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://academic.oup.com/glycob/article/16/3/210/716073info:eu-repo/semantics/altIdentifier/doi/10.1093/glycob/cwj056info:eu-repo/semantics/altIdentifier/pmid/16282605info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:09:07Zoai:ri.conicet.gov.ar:11336/28531instacron: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 10:09:07.324CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
title Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
spellingShingle Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
Rabinovich, Gabriel A.
Antineoplastic Agents
Apoptosis
Endothelial Cells
Galectin
Glycosylation
title_short Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
title_full Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
title_fullStr Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
title_full_unstemmed Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
title_sort Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis
dc.creator.none.fl_str_mv Rabinovich, Gabriel A.
Cumashi, Albana
Bianco, German Ariel
Ciavardelli, Domenico
Iurisci, Ida
D’Egidio, Maurizia
Piccolo, Enza
Tinari, Nicola
Nifantiev, Nikolay
Iacobelli, Stefano
author Rabinovich, Gabriel A.
author_facet Rabinovich, Gabriel A.
Cumashi, Albana
Bianco, German Ariel
Ciavardelli, Domenico
Iurisci, Ida
D’Egidio, Maurizia
Piccolo, Enza
Tinari, Nicola
Nifantiev, Nikolay
Iacobelli, Stefano
author_role author
author2 Cumashi, Albana
Bianco, German Ariel
Ciavardelli, Domenico
Iurisci, Ida
D’Egidio, Maurizia
Piccolo, Enza
Tinari, Nicola
Nifantiev, Nikolay
Iacobelli, Stefano
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Antineoplastic Agents
Apoptosis
Endothelial Cells
Galectin
Glycosylation
topic Antineoplastic Agents
Apoptosis
Endothelial Cells
Galectin
Glycosylation
purl_subject.fl_str_mv https://purl.org/becyt/ford/3.1
https://purl.org/becyt/ford/3
dc.description.none.fl_txt_mv Galectins, a family of structurally related carbohydrate-binding proteins, contribute to different events associated with cancer biology, including apoptosis, homotypic cell aggregation, angiogenesis and tumor-immune escape. To interfere with galectin-carbohydrate interactions during tumor progression, a current challenge is the design of specific galectin inhibitors for therapeutic purposes. Here, we report the synthesis of three novel low molecular weight synthetic lactulose amines (SLA): (1) N-lactulose-octamethylenediamine (LDO), (2) N,N´-dilactulose-octamethylenediamine (D-LDO), and (3) N,N´-dilactulose-dodecamethylenediamine (D-LDD). These compounds showed a differential ability to inhibit binding of galectin-1 and/or galectin-3 to the highly glycosylated protein 90K in solid-phase assays. In addition, each compound demonstrated selective regulatory effects in different events linked to tumor progression including tumor-cell apoptosis, homotypic cell aggregation, and endothelial cell morphogenesis. Our results suggest that galectin inhibitors with subtle differences in their carbohydrate structures may be potentially used to specifically block different steps of tumor growth and metastasis
Fil: Rabinovich, Gabriel A.. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina. Universidad de Buenos Aires. Facultad de Medicina. Hospital de Clínicas General San Martín; Argentina
Fil: Cumashi, Albana. Università degli Studi G. D´Annunzio; Italia
Fil: Bianco, German Ariel. Universidad de Buenos Aires. Facultad de Medicina. Hospital de Clínicas General San Martín; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Biología y Medicina Experimental. Fundación de Instituto de Biología y Medicina Experimental. Instituto de Biología y Medicina Experimental; Argentina
Fil: Ciavardelli, Domenico. Università degli Studi G. D´Annunzio; Italia
Fil: Iurisci, Ida. Università degli Studi G. D´Annunzio; Italia
Fil: D’Egidio, Maurizia. Università degli Studi G. D´Annunzio; Italia
Fil: Piccolo, Enza. Università degli Studi G. D´Annunzio; Italia
Fil: Tinari, Nicola. Università degli Studi G. D´Annunzio; Italia
Fil: Nifantiev, Nikolay. Academia de Ciencias Rusa; Rusia
Fil: Iacobelli, Stefano. Università degli Studi G. D´Annunzio; Italia
description Galectins, a family of structurally related carbohydrate-binding proteins, contribute to different events associated with cancer biology, including apoptosis, homotypic cell aggregation, angiogenesis and tumor-immune escape. To interfere with galectin-carbohydrate interactions during tumor progression, a current challenge is the design of specific galectin inhibitors for therapeutic purposes. Here, we report the synthesis of three novel low molecular weight synthetic lactulose amines (SLA): (1) N-lactulose-octamethylenediamine (LDO), (2) N,N´-dilactulose-octamethylenediamine (D-LDO), and (3) N,N´-dilactulose-dodecamethylenediamine (D-LDD). These compounds showed a differential ability to inhibit binding of galectin-1 and/or galectin-3 to the highly glycosylated protein 90K in solid-phase assays. In addition, each compound demonstrated selective regulatory effects in different events linked to tumor progression including tumor-cell apoptosis, homotypic cell aggregation, and endothelial cell morphogenesis. Our results suggest that galectin inhibitors with subtle differences in their carbohydrate structures may be potentially used to specifically block different steps of tumor growth and metastasis
publishDate 2006
dc.date.none.fl_str_mv 2006-03
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/11336/28531
Rabinovich, Gabriel A.; Cumashi, Albana; Bianco, German Ariel; Ciavardelli, Domenico; Iurisci, Ida; et al.; Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis; Oxford Univ Press Inc; Glycobiology; 16; 3; 3-2006; 210-220
0959-6658
1460-2423
CONICET Digital
CONICET
url http://hdl.handle.net/11336/28531
identifier_str_mv Rabinovich, Gabriel A.; Cumashi, Albana; Bianco, German Ariel; Ciavardelli, Domenico; Iurisci, Ida; et al.; Synthetic lactulose amines: novel class of anticancer agents that induce tumor-cell apoptosis and inhibit galectin-mediated homotypic cell aggregation and endothelial cell morphogenesis; Oxford Univ Press Inc; Glycobiology; 16; 3; 3-2006; 210-220
0959-6658
1460-2423
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://academic.oup.com/glycob/article/16/3/210/716073
info:eu-repo/semantics/altIdentifier/doi/10.1093/glycob/cwj056
info:eu-repo/semantics/altIdentifier/pmid/16282605
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 Oxford Univ Press Inc
publisher.none.fl_str_mv Oxford Univ Press Inc
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 12.885934

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