Link to glow - iEDDA conjugation of a Ruthenium(II) tetrazine complex leading to dihydropyrazine and pyrazine complexes with improved 1O2 formation ability

Müller, Carolin; Wintergerst, Pascal; Nair, Shruthi S.; Meitinger, Nicolas; Rau, Sven; Dietzek‐Ivanšić, Benjamin

doi:10.1016/j.jpap.2022.100130

“…1276 nm. The tetrazine complexes 1 – 3 displayed low 1 O 2 generation yields ( Φ Δ =0.02–0.19; Table S3), which should result from the strong quenching capability of the tetrazine unit [17] . In contrast, the pyridazine complexes 1‐BCN – 3‐BCN displayed higher 1 O 2 generation efficiencies ( Φ Δ =0.19–0.66; Table S3), demonstrating the controllable 1 O 2 ‐photosensitization properties of the ruthenium(II) complexes via the IEDDA reaction.…”

Section: Resultsmentioning

confidence: 99%

A Concerted Enzymatic and Bioorthogonal Approach for Extra‐ and Intracellular Activation of Environment‐Sensitive Ruthenium(II)‐Based Imaging Probes and Photosensitizers

Shum

¹

,

Lee

²

,

Chiang

³

et al. 2023

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In this article, we report a novel targeting strategy involving the combination of an enzymeinstructed self-assembly (EISA) moiety and a strained cycloalkyne to generate large accumulation of bioorthogonal sites in cancer cells. These bioorthogonal sites can serve as activation triggers in different regions for transition metal-based probes, which are new ruthenium(II) complexes carrying a tetrazine unit for controllable phosphorescence and singlet oxygen generation. Importantly, the environment-sensitive emission of the complexes can be further enhanced in the hydrophobic regions offered by the large supramolecular assemblies, which is highly advantageous to biological imaging.Additionally, the (photo)cytotoxicity of the large supramolecular assemblies containing the complexes was investigated, and the results illustrate that cellular localization (extracellular and intracellular) imposes a profound impact on the efficiencies of photosensitizers.

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“…8 Our group showed that the 1,2,4-triazine Ir( iii ) complexes react with BCN approximately 200 times faster than the corresponding uncoordinated ligands. 9 More recently, the boost of the reaction rates in Ru( ii ) 10,11 and Re( i ) 12 complexes of tetrazines has also been demonstrated. Metal complexation not only facilitates the click reaction but also brings many opportunities for further modification of the structures and designing new methodologies in chemical biology.…”

Section: Introductionmentioning

confidence: 98%

Catching up with tetrazines: coordination of Re(i) to 1,2,4-triazine facilitates an inverse electron demand Diels–Alder reaction with strained alkynes to a greater extent than in corresponding 1,2,4,5-tetrazines

Sims¹,

Kyriakou²,

Matthews³

et al. 2023

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show abstract

A Concerted Enzymatic and Bioorthogonal Approach for Extra‐ and Intracellular Activation of Environment‐Sensitive Ruthenium(II)‐Based Imaging Probes and Photosensitizers

Shum

¹

,

Lee

²

,

Chiang

³

et al. 2023

Angew Chem Int Ed

3

0

View full text Add to dashboard Cite

In this article, we report a novel targeting strategy involving the combination of an enzymeinstructed self-assembly (EISA) moiety and a strained cycloalkyne to generate large accumulation of bioorthogonal sites in cancer cells. These bioorthogonal sites can serve as activation triggers in different regions for transition metal-based probes, which are new ruthenium(II) complexes carrying a tetrazine unit for controllable phosphorescence and singlet oxygen generation. Importantly, the environment-sensitive emission of the complexes can be further enhanced in the hydrophobic regions offered by the large supramolecular assemblies, which is highly advantageous to biological imaging.Additionally, the (photo)cytotoxicity of the large supramolecular assemblies containing the complexes was investigated, and the results illustrate that cellular localization (extracellular and intracellular) imposes a profound impact on the efficiencies of photosensitizers.

show abstract

Link to glow - iEDDA conjugation of a Ruthenium(II) tetrazine complex leading to dihydropyrazine and pyrazine complexes with improved 1O2 formation ability

Cited by 3 publications

References 71 publications

A Concerted Enzymatic and Bioorthogonal Approach for Extra‐ and Intracellular Activation of Environment‐Sensitive Ruthenium(II)‐Based Imaging Probes and Photosensitizers

A Concerted Enzymatic and Bioorthogonal Approach for Extra‐ and Intracellular Activation of Environment‐Sensitive Ruthenium(II)‐Based Imaging Probes and Photosensitizers

Catching up with tetrazines: coordination of Re(i) to 1,2,4-triazine facilitates an inverse electron demand Diels–Alder reaction with strained alkynes to a greater extent than in corresponding 1,2,4,5-tetrazines

A Concerted Enzymatic and Bioorthogonal Approach for Extra‐ and Intracellular Activation of Environment‐Sensitive Ruthenium(II)‐Based Imaging Probes and Photosensitizers

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