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http://hdl.handle.net/2445/193021
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DC Field | Value | Language |
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dc.contributor.author | Ros, Enric | - |
dc.contributor.author | Bellido, Marina | - |
dc.contributor.author | Matarin, Joan A. | - |
dc.contributor.author | Gallen Ortiz, Albert | - |
dc.contributor.author | Martínez López, Manuel, 1957- | - |
dc.contributor.author | Rodríguez Raurell, Laura | - |
dc.contributor.author | Verdaguer i Espaulella, Xavier | - |
dc.contributor.author | Ribas de Pouplana, Lluis | - |
dc.contributor.author | Riera i Escalé, Antoni | - |
dc.date.accessioned | 2023-02-03T09:06:51Z | - |
dc.date.available | 2023-02-03T09:06:51Z | - |
dc.date.issued | 2022-05-12 | - |
dc.identifier.issn | 2046-2069 | - |
dc.identifier.uri | http://hdl.handle.net/2445/193021 | - |
dc.description.abstract | A set of 3-bromo-1,2,4,5-tetrazines with three distinct substitutions have been used as reagents for late-stage functionalization of small molecules through nucleophilic aromatic substitution. Spectroscopic studies of the products obtained proved that tetrazine ethers are intrinsically fluorescent. This fluorescence is lost upon inverse Electron-Demand Diels-Alder (iEDDA) cycloaddition with strained alkenes. Tetrazine-phenol ethers are rather interesting because they can undergo rapid iEDDA reactions with a second order rate constant (k2) compatible with bioorthogonal ligations. As a showcase, L-tyrosine was derivatized with 3-bromo-6-methyl-1,2,4,5-tetrazine and coupled to the peptide drug octreotide. This peptide was detected in cellular flow cytometry, and its fluorescence turned off through a bioorthogonal iEDDA cycloaddition with a strained alkene, showing for the first time the detection and reactivity of intrinsically fluorescent tetrazines in a biologically relevant context. The synthesis and characterization of fluorescent tetrazine ethers with bioorthogonal applicability pave the way for the generation of useful compounds for both detection and bioconjugation in vivo. | - |
dc.format.extent | 7 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Royal Society of Chemistry | - |
dc.relation.isformatof | Reproducció del document publicat a: https://doi.org/10.1039/D2RA02531K | - |
dc.relation.ispartof | RSC Advances, 2022, vol. 12, num. 23, p. 14321-14327 | - |
dc.relation.uri | https://doi.org/10.1039/D2RA02531K | - |
dc.rights | cc-by (c) Ros, Enric et al., 2022 | - |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Aminoàcids | - |
dc.subject.classification | Fluorescència | - |
dc.subject.other | Amino acids | - |
dc.subject.other | Fluorescence | - |
dc.title | Amino acids with fluorescent tetrazine ethers as bioorthogonal handles for peptide modification | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/publishedVersion | - |
dc.identifier.idgrec | 723402 | - |
dc.date.updated | 2023-02-03T09:06:51Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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