대한방사성의약품학회지 (Journal of Radiopharmaceuticals and Molecular Probes)

  • 제7권2호
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  • Pages.153-159
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  • 2021
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  • 2384-1583(pISSN)
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  • 2508-3848(eISSN)
대한방사성의약품학회 (Korean Society of Radiopharmaceuticals and Molecular Probes)
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Synthesis of 18F-labeled 2-cyanobenzothiazole derivative for efficient radiolabeling of N-terminal cysteine-bearing biomolecules

  • Jung Eun Park (Department of Applied Chemistry, College of Engineering, Kyungpook National University) ;
  • Jongho Jeon (Department of Applied Chemistry, College of Engineering, Kyungpook National University)
  • 투고 : 2021.12.21
  • 심사 : 2021.12.28
  • 발행 : 2021.12.30
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초록

This article provides an efficient 18F-labeling protocol based on a rapid condensation reaction between 2-cyanobenzothiazole (CBT) and N-terminal cysteine-containing biomolecules. The 18F-labeled CBT (18F-1) was prepared by radiofluorination of the tosylated precursor 4 with 18-crown-6/K+/[18F]F- complex. Using the purified 18F-1, 18F-labeled peptide (18F-7) and protein (18F-8) could be synthesized efficiently under mild conditions. This strategy would provide a convenient approach for rapid and site-specific 18F-labeling of various peptides and proteins for in vivo imaging and biomedical applications.

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과제정보

This research was funded by the National Research Foundation of Korea (Grant number:2019R1F1A1061596).

참고문헌

  1. Devaraj NK. The Future of Bioorthogonal Chemistry. ACS Cent Sci 2018;4:952-959. https://doi.org/10.1021/acscentsci.8b00251
  2. Smeenk MLWJ, Agramunt J, Bonger KM. Recent developments in bioorthogonal chemistry and the orthogonality within. Curr Opin Chem Biol 2021;60:79-88. https://doi.org/10.1016/j.cbpa.2020.09.002
  3. McKay CS, Finn MG. Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation. Chem Biol 2014;21:1075-1101. https://doi.org/10.1016/j.chembiol.2014.09.002
  4. Bird RE, Lemmel SA, Yu X, Zhou QA. Bioorthogonal Chemistry and Its Applications. Bioconjugate Chem 2021;32:2457-2479. https://doi.org/10.1021/acs.bioconjchem.1c00461
  5. Lee B, Choi JY. Click Reaction: An Applicable Radiolabeling Method for Molecular Imaging. Nucl Med Mol Imaging 2015;49:258-267. https://doi.org/10.1007/s13139-015-0377-6
  6. Dubost E, McErlain H, Babin V, Sutherland A, Cailly T. Recent Advances in Synthetic Methods for Radioiodination. J Org Chem 2020;85:8300-8310. https://doi.org/10.1021/acs.joc.0c00644
  7. Mushtaq S, Yun SJ, Jeon J. Recent Advances in Bioorthogonal Click Chemistry for Efficient Synthesis of Radiotracers and Radiopharmaceuticals. Molecules 2019;24:3567.
  8. Lee W, Sarkar S, Pal R, Kim JY, Park H, Huynh PT, Bhise A, Bobba KN, Kim KI, Ha YS, Soni N, Kim W, Lee K, Jung JM, Rajkumar S, Lee KC, Yoo J. ACS Appl Bio Mater 2021;4:2544-2557. https://doi.org/10.1021/acsabm.0c01555
  9. Mushtaq S, Jeon J. Synthesis of PET and SPECT Radiotracers Using Inverse Electron-demand Diels-Alder Reaction. Appl Chem Eng 2017;28:141-152.
  10. Cui L, Rao J. 2-Cyanobenzothiazole (CBT) condensation for site-specific labeling of proteins at the terminal cysteine residues. Methods Mol Biol 2015;1266:81-92. https://doi.org/10.1007/978-1-4939-2272-7_5
  11. Wang HC, Yu CC, Liang CF, Huang LD, Hwu JR, Lin CC. Site-selective protein immobilization through 2-cyanobenzothiazole-cysteine condensation. Chembiochem 2014;15:829-835. https://doi.org/10.1002/cbic.201300800
  12. Mushtaq S, Choi DS, Jeon J. Radiosynthesis of 125I-labeled-2-cyanobenzothiazole: A new prosthetic group for efficient radioiodination reaction. J Radiopharm Mol Probes 2017;1:44-51.
  13. Wang C, Du W, Wu C, Dan S, Sun M, Zhang T, Wang B, Yuan Yue, Liang G. Cathespin B-Initiated Cypate Nanoparticle Formation for Tumor Photoacoustic Imaging. Angew Chem Int Ed 2021:e202114766.
  14. Ren H, Xiao F, Zhan K, Kim, YP, Xie H, Xia Z, Rao J. A biocompatible condensation reaction for the labeling of terminal cysteine residues on proteins. Angew Chem Int Ed 2009;48:9658-9662. https://doi.org/10.1002/anie.200903627
  15. Liang G, Ren H, Rao J.A biocompatible condensation reaction for controlled assembly of nanostructures in living cells. Nat Chem 2010;2:54-60. https://doi.org/10.1038/nchem.480
  16. Jeon J, Shen B, Xiong L, Miao Z, Lee KH, Rao J, Chin FT. Efficient Method for Site-Specific 18F-Labeling of Biomolecules Using the Rapid 1. Condensation Reaction between 2-Cyanobenzothiazole and Cysteine. Bioconjugate Chem 2012;23:1902-1908. https://doi.org/10.1021/bc300273m