Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups

Lipophilic fluorescent groups with a chain-like linear conformation emitting in the visible range and with high photostability are presently unavailable. These structures would be of great interest as labels for long-chain fatty acids and phospholipids lacking intrinsic fluorescent groups. With this...

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Autores: Quesada, Ernesto, Delgado, Javier, Hornillos, Valentín, Acuña, A. Ulises, Amat-Guerri, Francisco
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2007
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/11501
Acceso en línea:http://hdl.handle.net/10261/11501
Access Level:acceso abierto
Palabra clave:Amphiphiles
Polyenes
Cross-coupling
Enynes
Fluorescent probes
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spelling Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent GroupsQuesada, ErnestoDelgado, JavierHornillos, ValentínAcuña, A. UlisesAmat-Guerri, FranciscoAmphiphilesPolyenesCross-couplingEnynesFluorescent probesLipophilic fluorescent groups with a chain-like linear conformation emitting in the visible range and with high photostability are presently unavailable. These structures would be of great interest as labels for long-chain fatty acids and phospholipids lacking intrinsic fluorescent groups. With this aim in mind, we report the synthesis and the spectroscopic characterization of a series of emitting amphiphilic lipids that may approach that ideal fluorescent tag. Each lipid was constructed by attaching a linear, all-(E) conjugated pentaene, tetraenyne, -phenyltetraene, or -phenyltrienyne chromophore to a hydrophilic head-group through a polymethylene chain spacer. The key steps of the synthesis were the Pd0-mediated cross-coupling reaction between bromopolyenes and terminal acetylenic compounds, yielding tetraenynes or -phenyltrienynes, and the subsequent triple-bond partial reduction, producing the corresponding pentaenes or -phenyltetraenes in good overall yields. This method represents a further successful example of the so-called acetylenic approach to the indirect high-yield synthesis of polyene systems. In the case of -phenyltrienynes, a higher proportion of the all-(E) isomer was obtained using an alternative method based on the reaction of an -phenyldienylphosphonate with an -acetylenic aldehyde. Some of the resulting compounds exhibit spectral and photochemical properties that warrant their use as emitting lipophilic tags. Thus, the -phenyltetraene and -phenyltrienyne members of the series show intense absorption bands in the 320-370 nm range with fluorescence emission centered at 475 nm and quantum yields up to 0.25. These parameters are appropriate for the applications noted above.This work was supported by the Spanish Ministerio de Educación y Ciencia (MEC) (Projects BQU2000-1500 and BQU2003/04413). E. Q., J. D. and V. H. acknowledge predoctoral grants from the same source.Peer reviewedJohn Wiley & SonsConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]200920092007info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionapplication/pdf4085 bytesimage/gifhttp://hdl.handle.net/10261/11501reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1002/ejoc.200600954Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/115012026-05-22T06:33:51Z
dc.title.none.fl_str_mv Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
title Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
spellingShingle Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
Quesada, Ernesto
Amphiphiles
Polyenes
Cross-coupling
Enynes
Fluorescent probes
title_short Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
title_full Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
title_fullStr Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
title_full_unstemmed Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
title_sort Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups
dc.creator.none.fl_str_mv Quesada, Ernesto
Delgado, Javier
Hornillos, Valentín
Acuña, A. Ulises
Amat-Guerri, Francisco
author Quesada, Ernesto
author_facet Quesada, Ernesto
Delgado, Javier
Hornillos, Valentín
Acuña, A. Ulises
Amat-Guerri, Francisco
author_role author
author2 Delgado, Javier
Hornillos, Valentín
Acuña, A. Ulises
Amat-Guerri, Francisco
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Amphiphiles
Polyenes
Cross-coupling
Enynes
Fluorescent probes
topic Amphiphiles
Polyenes
Cross-coupling
Enynes
Fluorescent probes
description Lipophilic fluorescent groups with a chain-like linear conformation emitting in the visible range and with high photostability are presently unavailable. These structures would be of great interest as labels for long-chain fatty acids and phospholipids lacking intrinsic fluorescent groups. With this aim in mind, we report the synthesis and the spectroscopic characterization of a series of emitting amphiphilic lipids that may approach that ideal fluorescent tag. Each lipid was constructed by attaching a linear, all-(E) conjugated pentaene, tetraenyne, -phenyltetraene, or -phenyltrienyne chromophore to a hydrophilic head-group through a polymethylene chain spacer. The key steps of the synthesis were the Pd0-mediated cross-coupling reaction between bromopolyenes and terminal acetylenic compounds, yielding tetraenynes or -phenyltrienynes, and the subsequent triple-bond partial reduction, producing the corresponding pentaenes or -phenyltetraenes in good overall yields. This method represents a further successful example of the so-called acetylenic approach to the indirect high-yield synthesis of polyene systems. In the case of -phenyltrienynes, a higher proportion of the all-(E) isomer was obtained using an alternative method based on the reaction of an -phenyldienylphosphonate with an -acetylenic aldehyde. Some of the resulting compounds exhibit spectral and photochemical properties that warrant their use as emitting lipophilic tags. Thus, the -phenyltetraene and -phenyltrienyne members of the series show intense absorption bands in the 320-370 nm range with fluorescence emission centered at 475 nm and quantum yields up to 0.25. These parameters are appropriate for the applications noted above.
publishDate 2007
dc.date.none.fl_str_mv 2007
2009
2009
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/10261/11501
url http://hdl.handle.net/10261/11501
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1002/ejoc.200600954
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
4085 bytes
image/gif
dc.publisher.none.fl_str_mv John Wiley & Sons
publisher.none.fl_str_mv John Wiley & Sons
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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