Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/32435 |
Resumo: | We have proposed recently that the DO3A-N-alfa-(amino)propionate chelator and its amide conjugates are leads to targeted, high relaxivity, safe Contrast Agents for Magnetic Resonance Imaging. In this work we illustrate further the expeditious nature and robustness of the synthetic methodologies developed by preparing the DO3A-N-(alfa-pyrenebutanamido)propionate chelator. Its Gd3+ chelate retains the optimized water exchange, high stability and inertness of the parent complex. The pyrene moiety imparts concentration-dependent self-assembly properties and aggregation-sensitive fluorescence emission to the Gd3+ complex. The Gd3+ complex displays pyrene-centred fluorescence whilst the Yb3+ and Nd3+ complexes exhibit sensitized lanthanide-centred near-infrared luminescence. The aggregated form of the complex displays high relaxivity (32 mM-1s-1, 20 MHz, 25 ºC) thanks to simultaneous optimization of the rotational correlation time and of the water exchange rate. The relaxivity is however still limited by chelate flexibility. This report demonstrates that the DO3A-N-(alfa-amino)propionate chelator is a valuable platform for constructing high relaxivity CA using simple design principles and robust chemistries accessible to most chemistry labs. |
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Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical propertiesCiências Naturais::Ciências QuímicasScience & TechnologyWe have proposed recently that the DO3A-N-alfa-(amino)propionate chelator and its amide conjugates are leads to targeted, high relaxivity, safe Contrast Agents for Magnetic Resonance Imaging. In this work we illustrate further the expeditious nature and robustness of the synthetic methodologies developed by preparing the DO3A-N-(alfa-pyrenebutanamido)propionate chelator. Its Gd3+ chelate retains the optimized water exchange, high stability and inertness of the parent complex. The pyrene moiety imparts concentration-dependent self-assembly properties and aggregation-sensitive fluorescence emission to the Gd3+ complex. The Gd3+ complex displays pyrene-centred fluorescence whilst the Yb3+ and Nd3+ complexes exhibit sensitized lanthanide-centred near-infrared luminescence. The aggregated form of the complex displays high relaxivity (32 mM-1s-1, 20 MHz, 25 ºC) thanks to simultaneous optimization of the rotational correlation time and of the water exchange rate. The relaxivity is however still limited by chelate flexibility. This report demonstrates that the DO3A-N-(alfa-amino)propionate chelator is a valuable platform for constructing high relaxivity CA using simple design principles and robust chemistries accessible to most chemistry labs.This work was financially supported by Fundação para a Ciência e Tecnologia, Portugal: PEst-C/QUI/UI0686/2013; FCOMP-01-0124-FEDER-037302; PTDC/QUI/70063/2006; grant SFRH/BD/63994/2009 to Miguel Ferreira and sabbatical grant SFRH/BSAB/1328/2013 to J. A. Martins; Rede Nacional de RMN (REDE/1517/RMN/2005) for the acquisition of the Varian VNMRS 600 NMR spectrometer at the University of Coimbra and the Bruker Avance-3 400 Plus at the University of Minho in Braga. The work in France was supported by La Ligue contre le Cancer. S. Petoud acknowledges support from the Institut National de la Santé́ et de la Recherche Médicale (INSERM). This work was carried out in the framework of the COST Actions D38 “Metal Based Systems for Molecular Imaging”, TD1004 “Theragnostic Imaging” and CM1006 “EUFEN: European F-Element Network”.Royal Society of ChemistryUniversidade do MinhoFerreira, Miguel F.Pereira, GoretiMartins, A. F.Martins, Catarina I. O.Prata, M. I. M.Petoud, S.Toth, E.Ferreira, Paula M. T.Martins, J. A.Geraldes, Carlos F. G. C.20142014-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/32435engFerreira, M. F.; Pereira, G.; Martins, A. F.; Martins, C. I. O.; Prata, M. I. M.; Petoud, S.; Toth, E.; Ferreira, P. M. T.; Martins, J. A.; Geraldes. C. F. G. C. Ln[DO3A-N-α-(pyrenebutanamido)propionate] complexes: optimized relaxivity and NIR optical properties. Dalton Trans., 2014, 43, 3162-3173. DOI: 10.1039/C3DT52958D1477-922610.1039/C3DT52958D24343660info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:49:24ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties |
title |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties |
spellingShingle |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties Ferreira, Miguel F. Ciências Naturais::Ciências Químicas Science & Technology |
title_short |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties |
title_full |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties |
title_fullStr |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties |
title_full_unstemmed |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties |
title_sort |
Ln[DO3A-N-alfa-(pyrenebutanamido)propionate] complexes : optimized relaxivity and NIR optical properties |
author |
Ferreira, Miguel F. |
author_facet |
Ferreira, Miguel F. Pereira, Goreti Martins, A. F. Martins, Catarina I. O. Prata, M. I. M. Petoud, S. Toth, E. Ferreira, Paula M. T. Martins, J. A. Geraldes, Carlos F. G. C. |
author_role |
author |
author2 |
Pereira, Goreti Martins, A. F. Martins, Catarina I. O. Prata, M. I. M. Petoud, S. Toth, E. Ferreira, Paula M. T. Martins, J. A. Geraldes, Carlos F. G. C. |
author2_role |
author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Ferreira, Miguel F. Pereira, Goreti Martins, A. F. Martins, Catarina I. O. Prata, M. I. M. Petoud, S. Toth, E. Ferreira, Paula M. T. Martins, J. A. Geraldes, Carlos F. G. C. |
dc.subject.por.fl_str_mv |
Ciências Naturais::Ciências Químicas Science & Technology |
topic |
Ciências Naturais::Ciências Químicas Science & Technology |
description |
We have proposed recently that the DO3A-N-alfa-(amino)propionate chelator and its amide conjugates are leads to targeted, high relaxivity, safe Contrast Agents for Magnetic Resonance Imaging. In this work we illustrate further the expeditious nature and robustness of the synthetic methodologies developed by preparing the DO3A-N-(alfa-pyrenebutanamido)propionate chelator. Its Gd3+ chelate retains the optimized water exchange, high stability and inertness of the parent complex. The pyrene moiety imparts concentration-dependent self-assembly properties and aggregation-sensitive fluorescence emission to the Gd3+ complex. The Gd3+ complex displays pyrene-centred fluorescence whilst the Yb3+ and Nd3+ complexes exhibit sensitized lanthanide-centred near-infrared luminescence. The aggregated form of the complex displays high relaxivity (32 mM-1s-1, 20 MHz, 25 ºC) thanks to simultaneous optimization of the rotational correlation time and of the water exchange rate. The relaxivity is however still limited by chelate flexibility. This report demonstrates that the DO3A-N-(alfa-amino)propionate chelator is a valuable platform for constructing high relaxivity CA using simple design principles and robust chemistries accessible to most chemistry labs. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014 2014-01-01T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/1822/32435 |
url |
http://hdl.handle.net/1822/32435 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Ferreira, M. F.; Pereira, G.; Martins, A. F.; Martins, C. I. O.; Prata, M. I. M.; Petoud, S.; Toth, E.; Ferreira, P. M. T.; Martins, J. A.; Geraldes. C. F. G. C. Ln[DO3A-N-α-(pyrenebutanamido)propionate] complexes: optimized relaxivity and NIR optical properties. Dalton Trans., 2014, 43, 3162-3173. DOI: 10.1039/C3DT52958D 1477-9226 10.1039/C3DT52958D 24343660 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
dc.source.none.fl_str_mv |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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