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Chemical name: 4-((2-(2-((6-chlorohexyl)oxy)ethoxy)ethyl)amino)-4-oxobutanoic acid // Synonyms: Haloalkane Dehalogenase Ligand
|Molecular weight:||323,81 g/mol|
This chloroalkane linker is a ligand for a specific modified bacterial haloalkane dehalogenase, also known as HaloTag®. The linker can be used for the chloroalkane penetration assay (CAPA), a quantitative and compartment-specific cell penetration assay for peptides and other potential biotherapeutics.
Further applications of the HaloTag® technology include cellular imaging as well as protein immobilization. Those applications can be accessed via an appropriate modification of the linker's carboxyl terminus, e.g. with an amine-functionalized fluorophore.
Oligomers of Cyclic Oligochalcogenides for Enhanced Cellular Uptake; R. Martinent, D. Du, J. López-Andaria, N. Sakai, S. Matile; ChemBioChem 2021; 22: 253-259. https://doi.org/10.1002/cbic.202000630.
Macropinocytosis as a Key Determinant of Peptidomimetic Uptake in Cancer Cells; D. Y. Yoo, S. A. Barros, G. C. Brown, C. Rabot, D. Bar-Sagi, P. S. Arora; J. Am. Chem. Soc. 2020; 142(34): 14461-14471. https://doi.org/10.1021/jacs.0c02109.
Covalently Tethered Rhodamine Voltage Reporters for High Speed Functional Imaging in Brain Tissue; P. E. Deal, P. Liu, S. H. Al-Abdullatif, V. R. Muller, K. Shamardani, H. Adesnik, E. W. Miller; J. Am. Chem. Soc. 2020; 142(1): 614-622. https://doi.org/10.1021/jacs.9b12265.
Multifunctionalization of Cells with a Self-Assembling Molecule to Enhance Cell Engraftment; I. Takashima, K. Kusamori, H. Hakariya, M. Takashima, T. H. Vu, Y. Mizukami, N. Noda, Y. Takayama, Y. Katsuda, S.-I. Sato, Y. Takakura, M. Nishikawa, M. Uesugi; ACS Chem. Biol. 2019; 14(4): 775-783. https://doi.org/10.1021/acschembio.9b00109.
Cell Penetration Profiling Using the Chloroalkane Penetration Assay; L. Peraro, K. L. Deprey, M. K. Moser, Z. Zou, H. L. Ball, B. Levine, J. A. Kritzer; J. Am. Chem. Soc. 2018; 140(36): 11360-11369. https://doi.org/10.1021/jacs.8b06144.
Diversity-Oriented Stapling Yields Intrinsically Cell-Penetrant Inducers of Autophagy; L. Peraro, Z. Zou, K. M. Makwana, A. E. Cummings, H. L. Ball, H. Yu, Y.-S. Lin, B. Levine, J. A. Kritzer; J. Am. Chem. Soc. 2017; 139(23): 7792-7802. https://doi.org/10.1021/jacs.7b01698.
Optogenetic control of kinetochore function; H. Zhang, C. Aonbangkhen, E. V. Tarasovetc, E. R. Ballister, D. M. Chenoweth, M. A. Lampson; Nat. Chem. Biol. 2017; 13(10): 1096-1101. https://doi.org/10.1038/nchembio.2456.
Targeted delivery of gold nanoparticle contrast agents for reporting gene detection by magnetic resonance imaging; Chem. Commun. 2016; 52: 160-163. https://doi.org/10.1039/C5CC06565H.
Bifunctional Molecules beyond PROTACs; S. J. Conway; Journal of medicinal chemistry 2020; 63: 2802-2806. doi: https://doi.org/10.1021/acs.jmedchem.0c00293
Cell Penetration Profiling Using the Chloroalkane Penetration Assay; L. Peraro, K. L. Deprey, M. K. Moser, Z. Zou, H. L. Ball, B. Levine and J. A. Kritzer; J Am Chem Soc 2018; 140: 11360-11369. doi: https://doi.org/10.1021/jacs.8b06144
HaloTag technology: a versatile platform for biomedical applications; C. G. England, H. Luo and W. Cai; Bioconjug Chem 2015; 26: 975-86. doi: 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. doi: https://doi.org/10.1021/cb800025k
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