A Cleavable C2-Symmetric trans-Cyclooctene Enables Fast and Complete Bioorthogonal Disassembly of Molecular Probes
نویسندگان
چکیده
منابع مشابه
Conformationally Strained trans-Cyclooctene (sTCO) Enables the Rapid Construction of (18)F-PET Probes via Tetrazine Ligation.
The bioorthogonal reaction between tetrazines and trans-cyclooctenes is a method for the rapid construction of F-18 probes for PET imaging. Described here is a second generation (18)F-labeling system based on a conformationally strained trans-cyclooctene (sTCO)-a dienophile that is approximately 2 orders of magnitude more reactive than conventional TCO dienophiles. Starting from a readily prepa...
متن کاملA 99mTc-Labelled Tetrazine for Bioorthogonal Chemistry. Synthesis and Biodistribution Studies with Small Molecule trans-Cyclooctene Derivatives
A convenient strategy to radiolabel a hydrazinonicotonic acid (HYNIC)-derived tetrazine with 99mTc was developed, and its utility for creating probes to image bone metabolism and bacterial infection using both active and pretargeting strategies was demonstrated. The 99mTc-labelled HYNIC-tetrazine was synthesized in 75% yield and exhibited high stability in vitro and in vivo. A trans-cyclooctene...
متن کاملCorrection: A 99mTc-Labelled Tetrazine for Bioorthogonal Chemistry. Synthesis and Biodistribution Studies with Small Molecule trans-Cyclooctene Derivatives
[This corrects the article DOI: 10.1371/journal.pone.0167425.].
متن کاملFast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition.
There is considerable interest in the use of bioorthogonal covalent chemistry, such as “click” reactions, to label small molecules located on live or fixed cells. Such labeling has been used for the visualization of glycans, activity-based protein profiling, the site-specific tagging of proteins, the detection of DNA and RNA synthesis, investigation of the fate of small molecules in plants, and...
متن کاملAzide and trans-cyclooctene dUTPs: incorporation into DNA probes and fluorescent click-labelling.
5-Azidomethyl dUTP and two 5-trans-cyclooctene dUTPs with different linkers between the TCO and the uracil base have been incorporated into DNA by primer extension, reverse-transcription and PCR amplification. For azidomethyl dUTP the PCR reaction was successful even when the modified dUTP was not supplemented with dTTP. In one case 335 azidomethyl dU residues were incorporated into the 523 bas...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2020
ISSN: 0002-7863,1520-5126
DOI: 10.1021/jacs.0c07922