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Annealing 1,2,4-triazine to iridium(iii) complexes induces luminogenic behaviour in bioorthogonal reactions with strained alkynes

Lookup NU author(s): Katie Gristwood, Dr Antony Antoniou, Dr Hannah Walden, Dr James KnightORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).


Abstract

© 2024 The Royal Society of ChemistryA phenanthroline-type ligand containing an annealed 1,2,4-triazine ring was used to prepare novel Ir(iii) complexes 3 and 4. The complexes are non-luminescent but show luminogenic behaviour following the inverse electron demand Diels-Alder (IEDDA) reaction with bicyclononyne (BCN) derivatives. It was observed that the complexes react with BCN-C10 faster than the corresponding free ligands. The magnitude of this accelerating metal-coordination effect, however, is less profound than in previously reported Ir(iii) complexes of 1,2,4-triazines, in which the triazine was directly coordinated to the Ir(iii) metal centre. Nevertheless, luminogenic behaviour opens prospects for the use of such complexes in bioimaging applications, which was demonstrated by developing a convenient methodology using the “chemistry on the complex” concept for labelling antibodies with luminescent Ir(iii) complexes. The bioorthogonal reactivity of complex 4 was demonstrated by metabolically labelling live cells with BCN groups, followed by a luminogenic IEDDA reaction with the triazine iridium complex.


Publication metadata

Author(s): Cooke L, Gristwood K, Adamson K, Sims MT, Deary ME, Bruce D, Antoniou AN, Walden HR, Knight JC, Antoine-Brunet T, Joly M, Goyard D, Lanoë P-H, Berthet N, Kozhevnikov VN

Publication type: Article

Publication status: Published

Journal: Dalton Transactions

Year: 2024

Volume: 53

Issue: 37

Print publication date: 07/10/2024

Online publication date: 28/08/2024

Acceptance date: 26/08/2024

Date deposited: 30/08/2024

ISSN (print): 1477-9226

ISSN (electronic): 1477-9234

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/d4dt01499e

DOI: 10.1039/d4dt01499e

Data Access Statement: The authors declare that the data supporting the findings of this study are available within the paper and its ESI files.† Should any raw data files be needed in another format they are available from the corresponding author upon reasonable request. https://pubs.rsc.org/en/content/articlelanding/2024/dt/d4dt01499e#fn1


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