dc.contributor.author | Blázquez Moraleja, Alberto | |
dc.contributor.author | Maierhofer, Larissa | |
dc.contributor.author | Mann, Enrique | |
dc.contributor.author | Prieto Montero, Ruth | |
dc.contributor.author | Oliden Sánchez, Ainhoa | |
dc.contributor.author | Celada, Lucía | |
dc.contributor.author | Martínez Martínez, Virginia | |
dc.contributor.author | Chiara, María Dolores | |
dc.contributor.author | Chiara, José Luis | |
dc.date.accessioned | 2022-11-11T17:56:12Z | |
dc.date.available | 2022-11-11T17:56:12Z | |
dc.date.issued | 2022 | |
dc.identifier.citation | Organic Chemistry Frontiers 9(21) : 5774-5789 (2022) | es_ES |
dc.identifier.issn | 2052-4129 | |
dc.identifier.uri | http://hdl.handle.net/10810/58328 | |
dc.description.abstract | Current methods for the preparation of functional small-molecule fluorophores generally require labor-intensive, multi-step synthetic routes for all the major chromophoric groups. In spite of recent significant contributions from numerous laboratories, the paucity of rapid, straightforward and wide-scope synthetic strategies in this field is limiting the development of advanced probes for bioimaging, sensing and therapeutic applications. We describe herein a general and robust methodology for the one-step fluorescent labeling of a wide variety of molecules having C-, N-, P-, O-, S-, or halide-nucleophilic centers, using stable and readily available acetoxymethyl-BODIPYs as reagents in the presence of an acid catalyst. This modular methodology allows a very facile preparation of mono- and di-functional probes incorporating a broad assortment of biomolecules, enzyme cofactors, natural products, and other chromophores, as well as chemical functionalities for a wide range of applications including bioorthogonal conjugation, polymerization, and supramolecular chemistry, among others. The photophysical properties and preliminary applications of the new probes in live-cell imaging were also studied. The described strategy enables the high-throughput engineering of novel BODIPY dyes with diverse functionalities for basic and applied science with potential for innovative technological applications. | es_ES |
dc.description.sponsorship | We gratefully acknowledge financial support from Instituto de Salud Carlos III/FEDER "A way to make Europe/Investing in your future" (project FIS 20/01754), MCIN/AEI/10.13039/501100011033 (projects PID2020-114347RB-C31 and PID2020114347RB-C32), and Gobierno Vasco-Eusko Jaurlaritza (project IT1639-22). A. B.-M. and L. C. thank MCIN for a FPI (BES-2015073571) and a FPU (FPU2017-01317) predoctoral contract, respectively. R. P. M. thanks MIU and NGEU for a postdoctoral contract (MARSA21/71). A. O. S. thanks UPV-EHU for a predoctoral fellowship. The authors thank the technical and human support provided by SGIker (UPV/EHU/ERDF, EU), X-rays: Molecules and Materials Unit, for the XRD structure of compound 9. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Royal Society of Chemistry | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2020-114347RB-C31 | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2020114347RB-C32 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es/ | * |
dc.subject | cross coupling reactions | es_ES |
dc.subject | f-bodipys | es_ES |
dc.subject | building blocks | es_ES |
dc.subject | regioselective functionalization | es_ES |
dc.subject | efficient preparation | es_ES |
dc.subject | laser dyes | es_ES |
dc.subject | derivatives | es_ES |
dc.subject | fluorophore | es_ES |
dc.subject | deprotection | es_ES |
dc.subject | access | es_ES |
dc.title | Acetoxymethyl-BODIPY dyes: a universal platform for the fluorescent labeling of nucleophiles | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © the Partner Organisations 2022.
This article is licensed under a Creative Commons Attribution 3.0 unported licence | es_ES |
dc.rights.holder | Atribución 3.0 España | * |
dc.relation.publisherversion | https://pubs.rsc.org/en/content/articlelanding/2022/QO/D2QO01099B | es_ES |
dc.identifier.doi | 10.1039/d2qo01099b | |
dc.departamentoes | Química física | es_ES |
dc.departamentoeu | Kimika fisikoa | es_ES |