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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/193021
Amino acids with fluorescent tetrazine ethers as bioorthogonal handles for peptide modification
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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.
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ROS, Enric, BELLIDO, Marina, MATARIN, Joan a., GALLEN ORTIZ, Albert, MARTÍNEZ LÓPEZ, Manuel, RODRÍGUEZ RAURELL, Laura, VERDAGUER I ESPAULELLA, Xavier, RIBAS DE POUPLANA, Lluís, RIERA I ESCALÉ, Antoni. Amino acids with fluorescent tetrazine ethers as bioorthogonal handles for peptide modification. _RSC Advances_. 2022. Vol. 12, núm. 23, pàgs. 14321-14327. [consulta: 20 de gener de 2026]. ISSN: 2046-2069. [Disponible a: https://hdl.handle.net/2445/193021]