Click chemistry: a transformative technology in nuclear medicine

Samantha M. Sarrett, Brian M. Zeglis, David Bauer, Jason S. Lewis

Published: 2023-04-25 DOI: 10.1038/s41596-023-00825-8

click chemistry

nuclear medicine

radiopharmaceutical chemistry

azide-alkyne cycloaddition

copper-catalyzed reaction

AI 解读

Efficient and safe single-cell cloning of human pluripotent stem cells using the CEPT cocktail

Profiling native pulmonary basement membrane stiffness using atomic force microscopy

Genetic circuit design automation with Cello 2.0

Synthesis of siRNA nanoparticles to silence plaque-destabilizing gene in atherosclerotic lesional macrophages

Scalable dual-omics profiling with single-nucleus chromatin accessibility and mRNA expression sequencing 2 (SNARE-seq2)

A practical guide to scanning light-field microscopy with digital adaptive optics

Effective high-throughput isolation of fully human antibodies targeting infectious pathogens

Improved sampling and DNA extraction procedures for microbiome analysis in food-processing environments

MOF-derived nanoporous carbons with diverse tunable nanoarchitectures

Tutorial: a statistical genetics guide to identifying HLA alleles driving complex disease

查看全部

Sections

Figures

References

The 2022 Nobel Prize in Chemistry was awarded to Professors K. Barry Sharpless, Morten Meldal and Carolyn Bertozzi for their pioneering roles in the advent of click chemistry. Sharpless and Meldal worked to develop the canonical click reaction—the copper-
The CuAAC reaction
The SPAAC reaction
‘Next-generation’ click reactions
- Outlook
References
ACKNOWLEDGMENTS

Zeglis, B. M. & Lewis, J. S. Click here for better chemistry. N. Engl. J. Med. http://doi.org/10.1056/NEJMcibr2213596 (2022).
Nevelius, E. The Nobel Prize in Chemistry 2022; http://www.nobelprize.org/prizes/chemistry/2022/press-release/ (2023)
Meldal, M. & Tornoe, C. W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 108, 2952–3015 (2008).
Huisgen, R. Centenary lecture—1,3-dipolar cycloadditions. Proc. Chem. Soc., 357–396, (1961).
Jewett, J. C. & Bertozzi, C. R. Cu-free click cycloaddition reactions in chemical biology. Chem. Soc. Rev. 39, 1272–1279 (2010).
Devaraj, N. K. The future of bioorthogonal chemistry. ACS Cent. Sci. 4, 952–959 (2018).
Blackman, M. L., Royzen, M. & Fox, J. M. Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity. J. Am. Chem. Soc. 130, 13518–13519 (2008).
Meyer, J. P., Adumeau, P., Lewis, J. S. & Zeglis, B. M. Click chemistry and radiochemistry: the first 10 years. Bioconjug. Chem. 27, 2791–2807 (2016).
Zeng, D., Zeglis, B. M., Lewis, J. S. & Anderson, C. J. The growing impact of bioorthogonal click chemistry on the development of radiopharmaceuticals. J. Nucl. Med. 54, 829–832 (2013).
Wangler, C., Schirrmacher, R., Bartenstein, P. & Wangler, B. Click-chemistry reactions in radiopharmaceutical chemistry: fast & easy introduction of radiolabels into biomolecules for in vivo imaging. Curr. Med. Chem. 17, 1092–1116 (2010).
Mamat, C., Ramenda, T. & Wuest, F. Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging. Mini Rev. Org. Chem. 6, 21–34 (2009).
Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004–2021 (2001).
Marik, J. & Sutcliffe, J. L. Click for PET: rapid preparation of [18F]fluoropeptides using CuI catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett. 47, 6681–6684 (2006).
Glaser, M. & Arstad, E. “Click labeling” with 2-[18F]fluoroethylazide for positron emission tomography. Bioconjug. Chem. 18, 989–993 (2007).
Wang, Y., Weng, J., Lin, J., Ye, D. & Zhang, Y. NIR scaffold bearing three handles for biocompatible sequential click installation of multiple functional arms. J. Am. Chem. Soc. 142, 2787–2794 (2020).
Pisaneschi, F. et al. Automated, resin-based method to enhance the specific activity of fluorine-18 clicked PET radiotracers. Bioconjug. Chem. 28, 583–589 (2017).
Kluba, C. A. & Mindt, T. L. Click-to-chelate: development of technetium and rhenium-tricarbonyl labeled radiopharmaceuticals. Molecules 18, 3206–3226 (2013).
Yan, R. et al. A one-pot three-component radiochemical reaction for rapid assembly of 125I-labeled molecular probes. J. Am. Chem. Soc. 135, 703–709 (2013).
Denk, C. et al. Multifunctional clickable reagents for rapid bioorthogonal astatination and radio-crosslinking. ChemPlusChem 84, 774 (2019).
Doss, M. et al. Biodistribution and radiation dosimetry of the integrin marker 18F-RGD-K5 determined from whole-body PET/CT in monkeys and humans. J. Nucl. Med. 53, 787–795 (2012).
Dubash, S. R. et al. Clinical translation of a click-labeled 18F-octreotate radioligand for imaging neuroendocrine tumors. J. Nucl. Med. 57, 1207–1213 (2016).
Quigley, N. G. et al. PET/CT imaging of head-and-neck and pancreatic cancer in humans by targeting the “Cancer Integrin” alphavbeta6 with Ga-68-Trivehexin. Eur. J. Nucl. Med. Mol. Imaging 49, 1136–1147 (2022).
Agard, N. J., Prescher, J. A. & Bertozzi, C. R. A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046–15047 (2004).
Campbell-Verduyn, L. S. et al. Strain-promoted copper-free “click” chemistry for 18F radiolabeling of bombesin. Angew. Chem. Int. Ed. 50, 11117–11120 (2011).
Zeng, D. et al. 64Cu core-labeled nanoparticles with high specific activity via metal-free click chemistry. ACS Nano 6, 5209–5219 (2012).
Cai, Z. et al. 64Cu-labeled somatostatin analogues conjugated with cross-bridged phosphonate-based chelators via strain-promoted click chemistry for PET imaging: in silico through in vivo studies. J. Med. Chem. 57, 6019–6029 (2014).
Agarwal, P. & Bertozzi, C. R. Site-specific antibody–drug conjugates: the nexus of bioorthogonal chemistry, protein engineering, and drug development. Bioconjug. Chem. 26, 176–192 (2015).
Wu, Y. et al. Synthesis of site-specific radiolabeled antibodies for radioimmunotherapy via genetic code expansion. Bioconjug. Chem. 27, 2460–2468 (2016).
Ahn, S. H. et al. Site-specific 89Zr- and 111In-radiolabeling and in vivo evaluation of glycan-free antibodies by azide-alkyne cycloaddition with a non-natural amino acid. Bioconjug. Chem. 31, 1177–1187 (2020).
Vivier, D. et al. The influence of glycans-specific bioconjugation on the Fcgamma RI binding and in vivo performance of 89Zr-DFO-pertuzumab. Theranostics 10, 1746–1757 (2020).
Sarrett, S. M. et al. Lysine-directed site-selective bioconjugation for the creation of radioimmunoconjugates. Bioconjug. Chem. 33, 1750–1760 (2022).
Mamat, C., Gott, M. & Steinbach, J. Recent progress using the Staudinger ligation for radiolabeling applications. J. Label. Comp. Radiopharm. 61, 165–178 (2018).
Narayanam, M. K. et al. Positron emission tomography tracer design of targeted synthetic peptides via 18F-sydnone alkyne cycloaddition. Bioconjug. Chem. 32, 2073–2082 (2021).
Steinkopf, W. Über aromatische sulfofluoride. J. Prakt. Chem. 117, 1–82 (1927).
Zheng, Q. et al. Sulfur [18F]fluoride exchange click chemistry enabled ultrafast late-stage radiosynthesis. J. Am. Chem. Soc. 143, 3753–3763 (2021).
Nakamoto, Y. et al. Expanding the applicability of the metal labeling of biomolecules by the RIKEN click reaction: a case study with gallium-68 positron emission tomography. ChemBioChem 19, 2055–2060 (2018).
Zeglis, B. M. et al. Modular strategy for the construction of radiometalated antibodies for positron emission tomography based on inverse electron demand Diels–Alder click chemistry. Bioconjug. Chem. 22, 2048–2059 (2011).
Li, Z. et al. Tetrazine-trans-cyclooctene ligation for the rapid construction of 18F labeled probes. Chem. Commun. 46, 8043–8045 (2010).
Rashidian, M. et al. The use of 18F-2-fluorodeoxyglucose (FDG) to label antibody fragments for immuno-PET of pancreatic cancer. ACS Cent. Sci. 1, 142–147 (2015).
Patra, M., Zarschler, K., Pietzsch, H. J., Stephan, H. & Gasser, G. New insights into the pretargeting approach to image and treat tumours. Chem. Soc. Rev. 45, 6415–6431 (2016).
Rossin, R. et al. In vivo chemistry for pretargeted tumor imaging in live mice. Angew. Chem. Int. Ed. 49, 3375–3378 (2010).
Edem, P. E. et al. Evaluation of a 68Ga-labeled DOTA-tetrazine as a PEt alternative to 111In-SPECT pretargeted imaging. Molecules http://doi.org/10.3390/molecules25030463 (2020).
Meyer, J. P. et al. 18F-based pretargeted PET imaging based on bioorthogonal Diels–Alder click chemistry. Bioconjug. Chem. 27, 298–301 (2016).
Cook, B. E. et al. Pretargeted PET imaging using a site-specifically labeled immunoconjugate. Bioconjug. Chem. 27, 1789–1795 (2016).
Poty, S. et al. Leveraging bioorthogonal click chemistry to improve 225Ac-radioimmunotherapy of pancreatic ductal adenocarcinoma. Clin. Cancer Res. 25, 868–880 (2019).
Keinanen, O. et al. Harnessing 64Cu/67Cu for a theranostic approach to pretargeted radioimmunotherapy. Proc. Natl Acad. Sci. USA 117, 28316–28327 (2020).
Maitz, C. A. et al. Pretargeted PET of osteodestructive lesions in dogs. Mol. Pharm. 19, 3153–3162 (2022).

Click chemistry: a transformative technology in nuclear medicine

推荐阅读