77089-07-7Relevant academic research and scientific papers
Vinylboronic acid-caged prodrug activation using click-to-release tetrazine ligation
Lelieveldt, Lianne P.W.M.,Eising, Selma,Wijen, Abel,Bonger, Kimberly M.
, p. 8816 - 8821 (2019/10/22)
Bioorthogonal reactions can be performed selectively in the presence of any biological functional group and are widely used to achieve site-selective chemical modifications of biomolecules. The click-to-release reaction is a bioorthogonal bond-cleavage variant that has gained much interest over the last few years. The bioorthogonal reaction between tetrazines and trans-cyclooctenes or vinyl ethers, for example, initiates the release of a small molecule immediately after the cycloaddition with tetrazines. Recently, our group reported that vinylboronic acids (VBAs) give exceptionally high reaction rates in the bioorthogonal inverse electron-demand Diels-Alder reaction with tetrazines that are substituted with boron-coordinating ligands. In the present study, we show that VBAs can be used in a click-to-release variant and demonstrate its bioorthogonality with a VBA-protected doxorubicin prodrug. We show that the cytotoxicity of doxorubicin is silenced by the attachment of the VBA, and activity can be largely restored upon the reaction with a tetrazine, inducing cell death.
Aromatic vinyl ether as well as a synthesis method and application thereof
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Paragraph 0052; 0053; 0057, (2019/01/05)
The invention belongs to the technical field of chemical engineering, and particularly relates to aromatic vinyl ether as well as a synthesis method and application thereof. The first synthesis methoddisclosed by the invention is characterized in that phe
Visualization of mercury(ii) accumulation: In vivo using bioluminescence imaging with a highly selective probe
Ke, Bowen,Chen, Hui,Ma, Lin,Zingales, Sarah,Gong, Deying,Hu, Die,Du, Lupei,Li, Minyong
, p. 2388 - 2392 (2018/04/12)
Mercury is a highly toxic environmental pollutant that negatively affects human health. Thus, an in vivo method for noninvasive imaging of mercury(ii) and visualization of its accumulation within living systems would be advantageous. Herein, we describe a reaction-based bioluminescent probe for detection of mercury(ii) in vitro and accumulation in vivo. The application of this probe would help to shed light on the intricate contributions of mercury(ii) to various physiological and pathological processes.
A Tetrazine-Labile Vinyl Ether Benzyloxycarbonyl Protecting Group (VeZ): An Orthogonal Tool for Solid-Phase Peptide Chemistry
Staderini, Matteo,Gambardella, Alessia,Lilienkampf, Annamaria,Bradley, Mark
, p. 3170 - 3173 (2018/06/11)
The vinyl ether benzyloxycarbonyl (VeZ) protecting group is selectively cleaved by treatment with tetrazines via an inverse electron-demand Diels-Alder reaction. This represents a new orthogonal protecting group for solid-phase peptide synthesis, with Fmoc-Lys(VeZ)-OH as a versatile alternative to Fmoc-Lys(Alloc)-OH and Fmoc-Lys(Dde)-OH, as demonstrated by the synthesis of two biologically relevant cyclic peptides.
A sensitive colorimetric and ratiometric fluorescent probe for mercury species in aqueous solution and living cells
Jiang, Jie,Liu, Wei,Cheng, Ju,Yang, Lizi,Jiang, Huie,Bai, Decheng,Liu, Weisheng
, p. 8371 - 8373 (2012/10/29)
A highly sensitive and selective fluorescent probe for inorganic and organic mercury species displays colorimetric and ratiometric response in a buffer solution via mercury promoted cleavage reaction. The probe is demonstrated to detect CH3HgCl
