Bioorthogonal Click of Colloidal Gold Nanoparticles to Antibodies In vivo

Poulie, Christian B. M.; Sporer, Emanuel; Hvass, Lars; Jørgensen, Jesper Tranekjær; Kempen, Paul; Broek, Sara Lopes van den; Shalgunov, Vladimir; Kjær, Andreas; Jensen, Andreas Tue Ingemann; Herth, Matthias M.

doi:10.1002/chem.202201847

Cited by 6 publications

(3 citation statements)

References 65 publications

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“…Equatorial TCO-PNB ester[ 45 ] (29 mg, 0.11 mmol) was dissolved in DMF (1 mL) and added dropwise to a premixed solution of sodium alendronate trihydrate (32 mg, 0.1 mmol) and Et 3 N (181 μL, 1.3 mmol) in H 2 O (1 mL), and the mixture stirred overnight in the dark. The reaction mixture was diluted to 7 mL with H 2 O (containing 0.5% TFA) and was submitted to preparative HPLC.…”

Section: Methodsmentioning

confidence: 99%

Development of a 99mTc-labeled tetrazine for pretargeted SPECT imaging using an alendronic acid-based bone targeting model

Bohrmann,

Poulie,

Rodríguez-Rodríguez

et al. 2024

PLoS ONE

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Pretargeting, which is the separation of target accumulation and the administration of a secondary imaging agent into two sequential steps, offers the potential to improve image contrast and reduce radiation burden for nuclear imaging. In recent years, the tetrazine ligation has emerged as a promising approach to facilitate covalent pretargeted imaging due to its unprecedented kinetics and bioorthogonality. Pretargeted bone imaging with TCO-modified alendronic acid (Aln-TCO) is an attractive model that allows the evaluation of tetrazines in healthy animals without the need for complex disease models or targeting regimens. Recent structure-activity relationship studies of tetrazines evaluated important parameters for the design of potent tetrazine-radiotracers for pretargeted imaging. However, limited information is available for 99mTc-labeled tetrazines. In this study, four tetrazines intended for labeling with fac-[99mTc(OH2)3 (CO)3]+ were synthesized and evaluated using an Aln-TCO mouse model. 3,6-bis(2-pyridyl)-1,2,4,5-Tz without additional linker showed higher pretargeted bone uptake and less background activity compared to the same scaffold with a PEG8 linker or 3-phenyl-1,2,4,5-Tz-based compounds. Additionally, improved bone/blood ratios were observed in pretargeted animals compared to animals receiving directly labeled Aln-TCO. The results of this study implicate 3,6-bis(2-pyridyl)-1,2,4,5-Tz as a promising scaffold for potential 99mTc-labeled tetrazines.

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Section: Methodsmentioning

confidence: 99%

Development of a 99mTc-labeled tetrazine for pretargeted SPECT imaging using an alendronic acid-based bone targeting model

Bohrmann,

Poulie,

Rodríguez-Rodríguez

et al. 2024

PLoS ONE

Self Cite

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“…For example, platinum prodrugs are developed and activated by photoswitches in vivo . Rhodamine B (RhB) was coupled with carboplatin- and oxaliplatin-based Pt(IV) complexes to decrease the distance between the photoswitch and the Pt(IV) center ( 64 ). Rhodaplatin was combined with sodium ascorbate in a physiological environment for photoreduction under visible-light irradiation to generate Pt(II) and free RhB ligands ( Figure 5B ).…”

Section: Major Transition Metal-mediated Bioorthogonal Reactionsmentioning

confidence: 99%

A narrative review: progress in transition metal-mediated bioorthogonal catalysis for the treatment of solid tumors

Wan,

Zhang,

Nie

et al. 2023

Transl Cancer Res

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Background and Objective Transition metals are commonly used catalysts in bioorthogonal chemistry and have attracted extensive attention in biochemistry because of their efficient catalytic performance. In recent years, transition metal-mediated cycloaddition reactions, bond cleavage, and formation reactions are being actively explored for tumor treatment. However, the direct application of transition metals in complex biological environments has several problems, including poor solubility, toxicity, and easy inactivation. The combination of transition metals and nanomaterials can solve those problems by playing a bioorthogonal catalytic role in tumor treatment. In this review, we summarize some research on the application of transition metals modified by nanomaterials in tumor therapy and discuss the potential and challenges of transition metal-mediated bioorthogonal therapy in comprehensive tumor therapy. Methods English literature on transition metal in cancer treatment was searched in PubMed and Web of Science. The main search terms were “cancer treatment”, “bioorthogonal reaction”, “transition metal”, “bioorthogonal catalysis”, etc. Key Content and Findings This review summarizes research on several major transition metals that can be used for bioorthogonal catalysis with the assistance of nanomaterials in anti-tumor therapy. In addition, bioorthogonal catalysis is a new supplement to antitumor therapy. We have compiled the potential challenges of the clinical application of transition metal-based nanocatalysts, which lays the foundation for future research related to medicinal chemistry and targeted cancer therapy. Conclusions Most of the transition metals still have a lot of room for exploration in cancer treatment research. We still need more research to confirm the feasibility of in vivo and clinical trials.

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“…Bioorthogonal chemistry realizes the pretargeting approach [ 24 , 25 , 26 , 27 , 28 ]. B8I-2 was discovered by Smith Mark A. et al to be able to attach to VirB8’s surface groove close to the dimerization site and prevent the assembly of the T4SS system [ 29 , 30 , 31 , 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

Click Triazole as a Linker for Pretargeting Strategies: Synthesis, Docking Investigations, Fluorescence Diagnosis, and Antibacterial Action Studies

Liu

Zhao²,

Song

et al. 2023

Molecules

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In this study, three compounds A1, A2, and A3 and fluorescent probes T1, T2, T3, and T4 were designed and synthesized. 1H NMR, 13C NMR, and MS characterization and elemental analysis were used to confirm A1–A3 and T1–T4. A1–A3 and T1–T4 formed diagnostic molecules by “click” reactions. A1–A3 and T1–T4 did not significantly increase cell death at concentrations of 80 μmol/L. Preliminary screening of the compounds for antibacterial activity revealed that A2 has better antibacterial activity against Agrobacterium tumefaciens. The synthesized compounds and fluorescent probes can be targeted and combined in the physiological condition to form diagnostic molecules for fluorescence detection of Agrobacterium tumefaciens. The binding sites of A1–A3 were deduced theoretically using the AutoDock Vina software docking tool. Further study of the mechanism of the antibacterial action of these compounds is likely to identify new agents against resistant bacterial strains.

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Bioorthogonal Click of Colloidal Gold Nanoparticles to Antibodies In vivo

Cited by 6 publications

References 65 publications

Development of a 99mTc-labeled tetrazine for pretargeted SPECT imaging using an alendronic acid-based bone targeting model

Development of a 99mTc-labeled tetrazine for pretargeted SPECT imaging using an alendronic acid-based bone targeting model

A narrative review: progress in transition metal-mediated bioorthogonal catalysis for the treatment of solid tumors

Click Triazole as a Linker for Pretargeting Strategies: Synthesis, Docking Investigations, Fluorescence Diagnosis, and Antibacterial Action Studies

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