A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor

The synthesis of a series of vinylated analogues of sphingosine-1-phosphate together with their unambiguous configurational assignment by VCD methods is reported. Among them, compound RBM10-8 can irreversibly inhibit human sphingosine-1-phosphate lyase (hS1PL) while behaving also as an enzyme substr...

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Autores: Pons, Guillem, Riba, Daniel, Casasampere, Mireia, Izquierdo, Eduardo, Abad, José Luis, Fabriàs, Gemma, Rodríguez Ortega, Pilar G., Montejo, Manuel, López González, Juan J., Casas, Josefina, Delgado Cirilo, Antonio
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:dnet:digitalcsic_::139a60067f4540c3f91e693db31bcebd
Acceso en línea:http://hdl.handle.net/10261/212234
Access Level:acceso abierto
Palabra clave:Sphingosines
Alkanolamines
Enzyme substrates
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spelling A Mechanism-Based Sphingosine-1-phosphate Lyase InhibitorPons, GuillemRiba, DanielCasasampere, MireiaIzquierdo, EduardoAbad, José LuisFabriàs, GemmaRodríguez Ortega, Pilar G.Montejo, ManuelLópez González, Juan J.Casas, JosefinaDelgado Cirilo, AntonioSphingosinesAlkanolaminesEnzyme substratesThe synthesis of a series of vinylated analogues of sphingosine-1-phosphate together with their unambiguous configurational assignment by VCD methods is reported. Among them, compound RBM10-8 can irreversibly inhibit human sphingosine-1-phosphate lyase (hS1PL) while behaving also as an enzyme substrate. These findings, together with the postulated mechanism for S1PL activity, reinforce the role of RBM10-8 as a new mechanism-based hS1PL inhibitor. Copyright © 2019 American Chemical Society.Peer reviewedAmerican Chemical SocietyAbad, José Luís [0000-0002-8343-9611]Fabriàs, Gemma [0000-0001-7162-3772]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202020202020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/212234reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés10.1021/acs.joc.9b02420Síinfo:eu-repo/semantics/openAccessoai:dnet:digitalcsic_::139a60067f4540c3f91e693db31bcebd2026-05-22T06:33:51Z
dc.title.none.fl_str_mv A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
title A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
spellingShingle A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
Pons, Guillem
Sphingosines
Alkanolamines
Enzyme substrates
title_short A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
title_full A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
title_fullStr A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
title_full_unstemmed A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
title_sort A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor
dc.creator.none.fl_str_mv Pons, Guillem
Riba, Daniel
Casasampere, Mireia
Izquierdo, Eduardo
Abad, José Luis
Fabriàs, Gemma
Rodríguez Ortega, Pilar G.
Montejo, Manuel
López González, Juan J.
Casas, Josefina
Delgado Cirilo, Antonio
author Pons, Guillem
author_facet Pons, Guillem
Riba, Daniel
Casasampere, Mireia
Izquierdo, Eduardo
Abad, José Luis
Fabriàs, Gemma
Rodríguez Ortega, Pilar G.
Montejo, Manuel
López González, Juan J.
Casas, Josefina
Delgado Cirilo, Antonio
author_role author
author2 Riba, Daniel
Casasampere, Mireia
Izquierdo, Eduardo
Abad, José Luis
Fabriàs, Gemma
Rodríguez Ortega, Pilar G.
Montejo, Manuel
López González, Juan J.
Casas, Josefina
Delgado Cirilo, Antonio
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Abad, José Luís [0000-0002-8343-9611]
Fabriàs, Gemma [0000-0001-7162-3772]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Sphingosines
Alkanolamines
Enzyme substrates
topic Sphingosines
Alkanolamines
Enzyme substrates
description The synthesis of a series of vinylated analogues of sphingosine-1-phosphate together with their unambiguous configurational assignment by VCD methods is reported. Among them, compound RBM10-8 can irreversibly inhibit human sphingosine-1-phosphate lyase (hS1PL) while behaving also as an enzyme substrate. These findings, together with the postulated mechanism for S1PL activity, reinforce the role of RBM10-8 as a new mechanism-based hS1PL inhibitor. Copyright © 2019 American Chemical Society.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/212234
url http://hdl.handle.net/10261/212234
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv 10.1021/acs.joc.9b02420
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
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score 15.811543

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