154044-78-7Relevant academic research and scientific papers
Click Cchemistry with O-dimethylpropargylcarbamate for preparation of pH-sensitive functional groups. A case study
Bertrand, Philippe,Gesson, Jean Pierre
, p. 3596 - 3599 (2007)
(Chemical Equation Presented) Click chemistry has became an important tool for molecular constructs such as biopolymers. During the development of biodegradable multifunctional poly(ethylene oxide) (PEO) polymers suitable for click chemistry in water, an
Copper-Triggered Bioorthogonal Cleavage Reactions for Reversible Protein and Cell Surface Modifications
Wang, Xin,Liu, Yanjun,Fan, Xinyuan,Wang, Jie,Ngai, William Shu Ching,Zhang, Heng,Li, Jiaofeng,Zhang, Gong,Lin, Jian,Chen, Peng R.
, p. 17133 - 17141 (2019)
Temporal and reversible control over protein and cell conjugations holds great potential for traceless release of antibody-drug conjugates (ADCs) on tumor sites as well as on-demand altering or removal of targeting elements on cell surface. We herein developed a bioorthogonal and traceless releasable reaction on proteins and intact cells to fulfill such purposes. A systematic survey of transition metals in catalyzing the bioorthogonal cleavage reactions revealed that copper complexes such as Cu(I)-BTTAA and dual-substituted propargyl (dsPra) or propargyloxycarbonyl (dsProc) moieties offered a bioorthogonal releasable pair for reversible blockage and rescue of primary amines and phenol alcohols on small molecule drugs, protein side chains, as well as intact cell surface. For proof-of-concept, we employed such Cu(I)-BTTAA/dsProc and Cu(I)-BTTAA/dsPra pairs as a "traceless linker" strategy to construct cleavable ADCs to unleash cytotoxic compounds on cancer cells in situ and as a "reversible modification" strategy for cell surface engineering. Furthermore, by coupling with the genetic code expansion strategy, we site-specifically modulated ligand-receptor interactions on live cell membranes. Together, our work expanded the transition-metal-mediated bioorthogonal cleavage tool kit from terminal decaging to internal-linker breakage, which offered a temporal and reversible conjugation strategy on therapeutic proteins and cells.
O-ALKYL TRIAZOLYL CARBAMATES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE (FAAH)
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Page/Page column 49; 54; 55, (2015/02/02)
The present invention provides compounds of formula I and pharmaceutical compositions for inhibiting fatty acid amide hydrolase (FAAH). Inhibition of FAAH is contemplated as a method to sustain the levels of the fatty acid ethanolamides arachidonoylethanolamide (AEA), palmitoylethanolamide (PEA), and oleoylethanolamide (OEA), three substrates of FAAH, in conditions characterized byreduced concentrations of AEA, PEA and OEA. The invention also provides methods for treating disorders in which decreased levels of AEA, PEA and OEA are associated with the disorder.
Novel triazolyl derivatives for acidic release of amines
Delatouche, Regis,Mondon, Martine,Gil, Adri,Frapper, Gilles,Bachmann, Christian,Bertrand, Philippe
scheme or table, p. 401 - 407 (2011/03/18)
Triazolyl derivatives of amines were prepared using click chemistry and evaluated as releasing systems in mildly acidic environments. Triazolylcarbamates and alkylamines were obtained, depending on the reactivity of the propargylic intermediates used for the Huisgen cycloaddition. A fast hydrolysis of some derivatives in mildly acidic conditions was achieved. The relative rates were correlated to a proposed mechanism highlighting the complementary role of the triazole ring and carbocation reactivity/stability. Copyright
