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• W2797029176 abstract "Bioorthogonal chemistry has found increased application in living systems over the past decade. In particular, tetrazine bioorthogonal chemistry has become a powerful tool for imaging, detection, and diagnostic purposes, as reflected in the increased number of examples reported in the literature. The popularity of tetrazine ligations are likely due to rapid and tunable kinetics, the existence of high quality fluorogenic probes, and the selectivity of reaction. In this Account, we summarize our recent efforts to advance tetrazine bioorthogonal chemistry through improvements in synthetic methodology, with an emphasis on developing new routes to tetrazines and expanding the range of useful dienophiles. These efforts have removed specific barriers that previously limited tetrazine ligations and have broadened their potential applications. Among other advances, this Account describes how our group discovered new methodology for tetrazine synthesis by developing a Lewis acid-promoted, one-pot method for generating diverse symmetric and asymmetric alkyl tetrazines with functional substituents in satisfactory yields. We attached these tetrazines to microelectrodes and succeeded in controlling tetrazine ligation by changing the redox state of the reactants. Using this electrochemical control process, we were able to modify an electrode surface with redox probes and enzymes in a site-selective fashion. This Account also describes how our group improved the ability of tetrazines to act as fluorogenic probes by developing a novel elimination-Heck cascade reaction to synthesize alkenyl tetrazine derivatives. In this approach, tetrazine was conjugated to fluorophores to produce strongly quenched probes that, after bioorthogonal reaction, are turned on to enhance fluorescence, in many cases by >100-fold. These probes have allowed no-wash fluorescence imaging in living cells and intact animals. Finally, this Account reviews our efforts to expand the range of dienophile substrates to make tetrazine bioorthogonal chemistry compatible with specific biochemical and biomedical applications. We found that methylcyclopropene is sufficiently stable and reactive in the biological milieu to act as an efficient dienophile. The small size of the reactive tag minimizes steric hindrance, allowing cyclopropene to serve as a metabolic reporter group to reveal biological dynamics and function. We also used norbornadiene derivatives as strained dienophiles to undergo tetrazine-mediated transfer (TMT) reactions involving tetrazine ligation followed by a retro-Diels-Alder process. This TMT reaction generates a pair of nonligating products. Using nucleic acid-templated chemistry, we have combined the TMT reaction with our fluorogenic tetrazine probes to detect endogenous oncogenic microRNA at picomolar concentrations. In a further display of dienophile versatility, we used a novel vinyl ether to cage a near-infrared fluorophore in a nonfluorescent form. Then we opened the cage in a click to release tetrazine bioorthogonal reaction, restoring the fluorescent form of the fluorophore. Combining this label with a corresponding nucleic acid probe allowed fluorogenic detection of target mRNA. In summary, this Account describes improvements in tetrazine and dienophile synthesis and application to advance tetrazine bioorthogonal chemistry. These advances have further enabled application of tetrazine ligation chemistry, not only in fundamental research but also in diagnostic studies." @default.
• W2797029176 created "2018-04-24" @default.
• W2797029176 creator A5018498392 @default.
• W2797029176 creator A5020075025 @default.
• W2797029176 date "2018-04-11" @default.
• W2797029176 modified "2023-09-29" @default.
• W2797029176 title "Advances in Tetrazine Bioorthogonal Chemistry Driven by the Synthesis of Novel Tetrazines and Dienophiles" @default.
• W2797029176 cites W1963598974 @default.
• W2797029176 cites W1970345429 @default.
• W2797029176 cites W1971433224 @default.
• W2797029176 cites W1974563432 @default.
• W2797029176 cites W1978407833 @default.
• W2797029176 cites W1980232662 @default.
• W2797029176 cites W1981659539 @default.
• W2797029176 cites W1982925953 @default.
• W2797029176 cites W1989293702 @default.
• W2797029176 cites W1996896173 @default.
• W2797029176 cites W1998277890 @default.
• W2797029176 cites W2004041567 @default.
• W2797029176 cites W2007785341 @default.
• W2797029176 cites W2011871947 @default.
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• W2797029176 cites W2051320086 @default.
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• W2797029176 cites W2069977295 @default.
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• W2797029176 cites W2101967466 @default.
• W2797029176 cites W2103182846 @default.
• W2797029176 cites W2104312767 @default.
• W2797029176 cites W2116548502 @default.
• W2797029176 cites W2141731346 @default.
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• W2797029176 cites W2283105825 @default.
• W2797029176 cites W2321291727 @default.
• W2797029176 cites W2322302718 @default.
• W2797029176 cites W2322691084 @default.
• W2797029176 cites W2325940861 @default.
• W2797029176 cites W2332024781 @default.
• W2797029176 cites W2332754533 @default.
• W2797029176 cites W2399274946 @default.
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• W2797029176 doi "https://doi.org/10.1021/acs.accounts.8b00062" @default.
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• W2797029176 hasPublicationYear "2018" @default.
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