Anti-tumour activity of fatty acid maltotriose esters

The anti-tumour properties of two fatty acid esters of maltotriose, 6’’-O-lauroylmaltotriose and 6’’-O-palmitoylmaltotriose, in which the 6-OH at the non-reducing end of the maltotriose has been regioselectively acylated, were studied. Both compounds were synthesised by transesterification of vinyl...

Descripción completa

Detalles Bibliográficos
Autores: Ferrer, Manuel, Pérez, Gabriela, Plou Gasca, Francisco José, Castell, José V.
Tipo de recurso: artículo
Fecha de publicación:2005
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/23349
Acceso en línea:http://hdl.handle.net/10261/23349
Access Level:acceso abierto
Palabra clave:Anti-cancer agents
Carbohydrate esters
Cytotoxicity
Lipases
Maltotriose laurate
Maltotriose palmitate
id ES_2beb79f20dcb7fc963d91c8499ab2dd4
oai_identifier_str oai:digital.csic.es:10261/23349
network_acronym_str ES
network_name_str España
repository_id_str
spelling Anti-tumour activity of fatty acid maltotriose estersFerrer, ManuelPérez, GabrielaPlou Gasca, Francisco JoséCastell, José V.Anti-cancer agentsCarbohydrate estersCytotoxicityLipasesMaltotriose laurateMaltotriose palmitateThe anti-tumour properties of two fatty acid esters of maltotriose, 6’’-O-lauroylmaltotriose and 6’’-O-palmitoylmaltotriose, in which the 6-OH at the non-reducing end of the maltotriose has been regioselectively acylated, were studied. Both compounds were synthesised by transesterification of vinyl laurate or vinyl palmitate with maltotriose, in presence of immobilized lipase from Thermomyces lanuginosus. A mixture formed by 2-methyl-2-butanol and dimethylsulfoxide (80:20 v/v) was the reaction medium. Their cytotoxic activities against two human cancer cell lines, Hep-G2 and HeLa, were studied. 6’’-O-palmitoylmaltotriose showed 50% inhibition values (IC50) of 2.3 M (1.7 g/ml) for Hep-G2 and 3.6 M (2.7 g/ml) for HeLa cells, whereas 6’’-O-lauroylmaltotriose displayed a lower inhibitory effect. 6’’-O-palmitoylmaltotriose showed a marginal cytotoxicity to rat hepatocytes, confirming its potential as a new anti-tumour agent.We thank Prof. Manuel Bernabé (Instituto de Química Orgánica, CSIC, Madrid) for help with NMR analysis. This work was supported by European Union (project MERG-CT-2004-505242) and the Spanish CICYT (Project BIO2002-00337).Peer reviewed201020102005info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501250248 bytesapplication/pdfhttp://hdl.handle.net/10261/23349reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)InglésDOI: 10.1042/BA20040122info:eu-repo/semantics/openAccessoai:digital.csic.es:10261/233492026-05-22T06:33:51Z
dc.title.none.fl_str_mv Anti-tumour activity of fatty acid maltotriose esters
title Anti-tumour activity of fatty acid maltotriose esters
spellingShingle Anti-tumour activity of fatty acid maltotriose esters
Ferrer, Manuel
Anti-cancer agents
Carbohydrate esters
Cytotoxicity
Lipases
Maltotriose laurate
Maltotriose palmitate
title_short Anti-tumour activity of fatty acid maltotriose esters
title_full Anti-tumour activity of fatty acid maltotriose esters
title_fullStr Anti-tumour activity of fatty acid maltotriose esters
title_full_unstemmed Anti-tumour activity of fatty acid maltotriose esters
title_sort Anti-tumour activity of fatty acid maltotriose esters
dc.creator.none.fl_str_mv Ferrer, Manuel
Pérez, Gabriela
Plou Gasca, Francisco José
Castell, José V.
author Ferrer, Manuel
author_facet Ferrer, Manuel
Pérez, Gabriela
Plou Gasca, Francisco José
Castell, José V.
author_role author
author2 Pérez, Gabriela
Plou Gasca, Francisco José
Castell, José V.
author2_role author
author
author
dc.subject.none.fl_str_mv Anti-cancer agents
Carbohydrate esters
Cytotoxicity
Lipases
Maltotriose laurate
Maltotriose palmitate
topic Anti-cancer agents
Carbohydrate esters
Cytotoxicity
Lipases
Maltotriose laurate
Maltotriose palmitate
description The anti-tumour properties of two fatty acid esters of maltotriose, 6’’-O-lauroylmaltotriose and 6’’-O-palmitoylmaltotriose, in which the 6-OH at the non-reducing end of the maltotriose has been regioselectively acylated, were studied. Both compounds were synthesised by transesterification of vinyl laurate or vinyl palmitate with maltotriose, in presence of immobilized lipase from Thermomyces lanuginosus. A mixture formed by 2-methyl-2-butanol and dimethylsulfoxide (80:20 v/v) was the reaction medium. Their cytotoxic activities against two human cancer cell lines, Hep-G2 and HeLa, were studied. 6’’-O-palmitoylmaltotriose showed 50% inhibition values (IC50) of 2.3 M (1.7 g/ml) for Hep-G2 and 3.6 M (2.7 g/ml) for HeLa cells, whereas 6’’-O-lauroylmaltotriose displayed a lower inhibitory effect. 6’’-O-palmitoylmaltotriose showed a marginal cytotoxicity to rat hepatocytes, confirming its potential as a new anti-tumour agent.
publishDate 2005
dc.date.none.fl_str_mv 2005
2010
2010
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/23349
url http://hdl.handle.net/10261/23349
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv DOI: 10.1042/BA20040122
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 250248 bytes
application/pdf
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869405193985064960
score 15,811543

Similares en LA Referencia