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Chemical name: N-[2-[2-[(6-chlorohexyl)oxy]ethoxy]ethyl]-gamma-oxo-dibenz[b,f]azocine-5(6H)-butanamide // Synonyms: Haloalkane dehalogenase ligand; HaloTag ligand
|Molecular weight:||511,06 g/mol|
A clickable HaloTag ligand. HaloTag is a modified bacterial haloalkane dehalogenase that reacts with chloralkane-containing ligands to form a covalent HaloTag-ligand conjugate. The reaction between the chloralkane linker and HaloTag is fast and irreversible under physiological conditions and the system has been used extensively to measure protein-protein interactions in cells.
The DBCO moiety shows enhanced kinetics in Click reactions due to its increased strain energy of the cyclooctyne moiety = strain-promoted azide-alkyne cycloaddition. Furthermore, this reaction benefits of increased biocompatibility as there is no requirement for cytotoxic Cu(I) as catalyst.
Preparation of coelenterazine compounds as nanoluc suicide substrates; B. Binkowski, M. P. Hall, T. Machleidt, J. Walkr, W. Zhou; 2019; WO 2019213119 A1.
Systemic Evaluation of Biorthogonal Reactions in Live Cells with Clickable HaloTag Ligands: Implications for Intracellular Imaging. H. E. Murrey, J. C. Judkins, C. W. am Ende, T. E. Ballard, Y. Fang, K. Riccardi, L. Di, E. R. Guilmette, J. W. Schwartz, J. M. Fox, D. S. Johnson; JACS 2015; 137(35): 11461-11475. https://doi.org/10.1021/jacs.5b06847.
NanoClick: A High Throughput, Target-Agnostic Peptide Cell Permeability Assay; A. Peier, L. Ge, N. Boyer, J. Frost, R. Duggal, K. Biswas, S. Edmondson, J. D. Hermes, L. Yan, C. Zimprich, A. Sadruddin, H. Y. K. Kaan, A. Chandramohan, C. J. Brown, D. Thean, X. E. Lee, T. Y. Yuen, F. J. Ferrer-Gago, C. W. Johannes, D. P. Lane, B. Sherborne, C. Corona, M. B. Robers, T. K. Sawyer, A. P. Partridge; ACX Chem. Biol. 2021; 16(2): 293-309. https://doi.org/10.1021/acschembio.0c00804.
HaloTag technology: a versatile platform for biomedical applications; C. G. England, H. Luo and W. Cai; Bioconjug Chem 2015; 26: 975-86. https://doi.org/10.1021/acs.bioconjchem.5b00191.
HaloTag: a novel protein labeling technology for cell imaging and protein analysis; G. V. Los, L. P. Encell, M. G. McDougall, D. D. Hartzell, N. Karassina, C. Zimprich, M. G. Wood, R. Learish, R. F. Ohana, M. Urh, D. Simpson, J. Mendez, K. Zimmerman, P. Otto, G. Vidugiris, J. Zhu, A. Darzins, D. H. Klaubert, R. F. Bulleit and K. V. Wood; ACS Chem Biol 2008; 3: 373-382. https://doi.org/10.1021/cb800025k.
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