Novel Platinum(II) Tetrazine Complex Capable of Live‐Cell IEDDA Reaction

The development of the first Pt(II) tetrazine complex, trans-[Pt(II)Cl<sub>2</sub>(dmso)(CH<sub>3</sub>-Tz-Bz-NH<sub>2</sub>)] (1), is reported, which exhibits good in vitro cytotoxicity against MDA-MB-231 cells and succesfully undergoes inverse electron demand Diels-Alder (IEDDA) reactions with trans-cyclooctene (TCO) and bicyclononyne (BCN) derivates in solution. We demonstrate a live-cell IEDDA reaction of 1 with a BF<sub>2</sub>-azadipyrromethene fluorophore (NIR-AZA) posessing a BCN handle. A live-cell bioorthogonal reaction is established using fluorescence lifetime imaging microscopy (FLIM), through a fluorescence lifetime change of 0.3 ns from BF<sub>2</sub>-azadipyrromethene fluorophore starting material to IEDDA Pt fluorophore reaction product. As there is a distinct difference in fluorescence lifetimes between starting material and product, this approach removes the necessity for designing challenging off to on fluorogenic Pt probes and washing steps when developing bioorthogonal cell-imaging strategies for Pt complexes.

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Publication Details

Journal
ChemBioChem
Published
2025-08-29
DOI
https://doi.org/10.1002/cbic.202500376
Primary Topic
Click Chemistry and Applications
Type
article
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article

Novel Platinum(II) Tetrazine Complex Capable of Live‐Cell IEDDA Reaction

Alby Benny, Darren M. Griffith, Brendan Twamley, Ellen King et al.
ChemBioChem
Click Chemistry and Applications
article

Novel Platinum(II) Tetrazine Complex Capable of Live‐Cell IEDDA Reaction

Alby Benny, Darren M. Griffith, Brendan Twamley, Ellen King, Olga Piskareva, Donal F. O’Shea, Paul O'Dowd, Dan Wu, Alice Harford
article en

Abstract

The development of the first Pt(II) tetrazine complex, trans-[Pt(II)Cl<sub>2</sub>(dmso)(CH<sub>3</sub>-Tz-Bz-NH<sub>2</sub>)] (1), is reported, which exhibits good in vitro cytotoxicity against MDA-MB-231 cells and succesfully undergoes inverse electron demand Diels-Alder (IEDDA) reactions with trans-cyclooctene (TCO) and bicyclononyne (BCN) derivates in solution. We demonstrate a live-cell IEDDA reaction of 1 with a BF<sub>2</sub>-azadipyrromethene fluorophore (NIR-AZA) posessing a BCN handle. A live-cell bioorthogonal reaction is established using fluorescence lifetime imaging microscopy (FLIM), through a fluorescence lifetime change of 0.3 ns from BF<sub>2</sub>-azadipyrromethene fluorophore starting material to IEDDA Pt fluorophore reaction product. As there is a distinct difference in fluorescence lifetimes between starting material and product, this approach removes the necessity for designing challenging off to on fluorogenic Pt probes and washing steps when developing bioorthogonal cell-imaging strategies for Pt complexes.

ChemBioChemVol. 26(18)
Royal College of Surgeons in Ireland (IE), Science Foundation Ireland (IE), Trinity College Dublin (IE), Cancer Trials Ireland (IE), Advanced Materials and BioEngineering Research (IE), Technological University Dublin (IE), Dublin City University (IE)
Openalex Percentile: Top 83%
Click Chemistry and Applications
DOIOpen Access PDFOpenAlex
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Novel Platinum(II) Tetrazine Complex Capable of Live‐Cell IEDDA Reaction — Alby Benny, Darren M. Griffith, et al. · ChemBioChem (2025) | TGRS Research Map | TGRS