8. D.C. Kennedy, C.S. McKay, M.C. Legault, D.C. Danielson, J.A. Blake, A.F. Pegoraro et al.,
Cellular consequences of copper complexes used to catalyze bioorthogonal click reactions.
J. Am. Chem. Soc. 133(44), 17993–18001 (2011)
9. M. Pretze, D. Pietzsch, C. Mamat, Recent trends in bioorthogonal click-radiolabeling
reactions using fluorine-18. Molecules 18(7), 8618–8665 (2013)
10. J.C. Jewett, C.R. Bertozzi, Cu-free click cycloaddition reactions in chemical biology. Chem.
Soc. Rev. 39(4), 1272–1279 (2010)
11. E.M. Sletten, C.R. Bertozzi, From mechanism to mouse: a tale of two bioorthogonal reactions.
Acc. Chem. Res. 44(9), 666–676 (2011)
12. M.F. Debets, S.S. van Berkel, J. Dommerholt, A.T. Dirks, F.P. Rutjes, F.L. van Delft,
Bioconjugation with strained alkenes and alkynes. Acc. Chem. Res. 44(9), 805–815 (2011)
13. E.M. Sletten, C.R. Bertozzi, Bioorthogonal chemistry: fishing for selectivity in a sea of
functionality. Angew. Chem. Int. Ed. Engl. 48(38), 6974–6998 (2009)
14. S.T. Laughlin, J.M. Baskin, S.L. Amacher, C.R. Bertozzi, In vivo imaging of
membrane-associated glycans in developing zebrafish. Science 320(5876), 664–667 (2008)
15. J.C. Jewett, E.M. Sletten, C.R. Bertozzi, Rapid Cu-free click chemistry with readily
synthesized biarylazacyclooctynones. J. Am. Chem. Soc. 132(11), 3688–3690 (2010)
16. Y. Jiang, J. Chen, C. Deng, E.J. Suuronen, Z. Zhong, Click hydrogels, microgels and
nanogels: emerging platforms for drug delivery and tissue engineering. Biomaterials 35(18),
4969–4985 (2014)
17. L. Carroll, H.L. Evans, E.O. Aboagye, A.C. Spivey, Bioorthogonal chemistry for pre-targeted
molecular imaging–progress and prospects. Org. Biomol. Chem. 11(35), 5772–5781 (2013)
18. V. Bouvet, M. Wuest, F. Wuest, Copper-free click chemistry with the short-lived positron
emitter fluorine-18. Org. Biomol. Chem. 9(21), 7393–7399 (2011)
19. P. Ostrovskis, C.M.R. Volla, M. Turks, D. Markovic, Application of metal free click
chemistry in biological studies. Curr. Org. Chem. 17, 610–640 (2013)
20. J.M. Baskin, C.R. Bertozzi, Copper-free click chemistry: Bioorthogonal reagents for tagging
azides. Aldrichimica Acta. 43, 15–23 (2010)
21. X. Ning, J. Guo, M.A. Wolfert, G.J. Boons, Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast Huisgen cycloadditions. Angew. Chem. Int. Ed.
Engl. 47(12), 2253–2255 (2008)
22. A.A. Poloukhtine, N.E. Mbua, M.A. Wolfert, G.J. Boons, V.V. Popik, Selective labeling of
living cells by a photo-triggered click reaction. J. Am. Chem. Soc. 131(43), 15769–15776
(2009)
23. M.F. Debets, S.S. van Berkel, S. Schoffelen, F.P. Rutjes, J.C. van Hest, F.L. van Delft,
Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3 + 2)
cycloaddition. Chem. Commun. (Camb.) 46(1), 97–99 (2010)
24. N.K. Devaraj, R. Weissleder, Biomedical applications of tetrazine cycloadditions. Acc. Chem.
Res. 44(9), 816–827 (2011)
25. M.E. Phelps, Positron emission tomography provides molecular imaging of biological
processes. Proc. Natl. Acad. Sci. U.S.A. 97, 9226–9233 (2000)
26. T.F. Massoud, S.S. Gambhir, Molecular imaging in living subjects: seeing fundamental
biological processes in a new light. Genes Dev. 17(5), 545–580 (2003)
27. S. Vallabhajosula, Molecular Imaging: Radiopharmaceuticals for PET and SPECT, 1st edn.
(Springer, New York, 2009), pp. 133–193
28. S.M. Ametamey, M. Honer, P.A. Schubiger, Molecular imaging with PET. Chem. Rev. 108,
1501–1516 (2008)
29. S.S. Gambhir, Molecular imaging of cancer with positron emission tomography. Nat. Rev.
Cancer 2, 683–693 (2002)
30. R. Schirrmacher, C. Wängler, E. Schirrmacher, Recent developments and trends in
18F-radiochemistry: syntheses and applications. Mini Rev. Org. Chem. 4, 317–329 (2007)
31. D.W. Kim, D.S. Ahn, Y.H. Oh, S. Lee, H.S. Kil, S.J. Oh et al., A new class of SN2 reactions
catalyzed by protic solvents: Facile fluorination for isotopic labeling of diagnostic molecules.
J. Am. Chem. Soc. 128(50), 16394–16397 (2006)
14 Bioorthogonal Reaction for Fluorine-18 Labeling
273
Cellular consequences of copper complexes used to catalyze bioorthogonal click reactions.
J. Am. Chem. Soc. 133(44), 17993–18001 (2011)
9. M. Pretze, D. Pietzsch, C. Mamat, Recent trends in bioorthogonal click-radiolabeling
reactions using fluorine-18. Molecules 18(7), 8618–8665 (2013)
10. J.C. Jewett, C.R. Bertozzi, Cu-free click cycloaddition reactions in chemical biology. Chem.
Soc. Rev. 39(4), 1272–1279 (2010)
11. E.M. Sletten, C.R. Bertozzi, From mechanism to mouse: a tale of two bioorthogonal reactions.
Acc. Chem. Res. 44(9), 666–676 (2011)
12. M.F. Debets, S.S. van Berkel, J. Dommerholt, A.T. Dirks, F.P. Rutjes, F.L. van Delft,
Bioconjugation with strained alkenes and alkynes. Acc. Chem. Res. 44(9), 805–815 (2011)
13. E.M. Sletten, C.R. Bertozzi, Bioorthogonal chemistry: fishing for selectivity in a sea of
functionality. Angew. Chem. Int. Ed. Engl. 48(38), 6974–6998 (2009)
14. S.T. Laughlin, J.M. Baskin, S.L. Amacher, C.R. Bertozzi, In vivo imaging of
membrane-associated glycans in developing zebrafish. Science 320(5876), 664–667 (2008)
15. J.C. Jewett, E.M. Sletten, C.R. Bertozzi, Rapid Cu-free click chemistry with readily
synthesized biarylazacyclooctynones. J. Am. Chem. Soc. 132(11), 3688–3690 (2010)
16. Y. Jiang, J. Chen, C. Deng, E.J. Suuronen, Z. Zhong, Click hydrogels, microgels and
nanogels: emerging platforms for drug delivery and tissue engineering. Biomaterials 35(18),
4969–4985 (2014)
17. L. Carroll, H.L. Evans, E.O. Aboagye, A.C. Spivey, Bioorthogonal chemistry for pre-targeted
molecular imaging–progress and prospects. Org. Biomol. Chem. 11(35), 5772–5781 (2013)
18. V. Bouvet, M. Wuest, F. Wuest, Copper-free click chemistry with the short-lived positron
emitter fluorine-18. Org. Biomol. Chem. 9(21), 7393–7399 (2011)
19. P. Ostrovskis, C.M.R. Volla, M. Turks, D. Markovic, Application of metal free click
chemistry in biological studies. Curr. Org. Chem. 17, 610–640 (2013)
20. J.M. Baskin, C.R. Bertozzi, Copper-free click chemistry: Bioorthogonal reagents for tagging
azides. Aldrichimica Acta. 43, 15–23 (2010)
21. X. Ning, J. Guo, M.A. Wolfert, G.J. Boons, Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast Huisgen cycloadditions. Angew. Chem. Int. Ed.
Engl. 47(12), 2253–2255 (2008)
22. A.A. Poloukhtine, N.E. Mbua, M.A. Wolfert, G.J. Boons, V.V. Popik, Selective labeling of
living cells by a photo-triggered click reaction. J. Am. Chem. Soc. 131(43), 15769–15776
(2009)
23. M.F. Debets, S.S. van Berkel, S. Schoffelen, F.P. Rutjes, J.C. van Hest, F.L. van Delft,
Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3 + 2)
cycloaddition. Chem. Commun. (Camb.) 46(1), 97–99 (2010)
24. N.K. Devaraj, R. Weissleder, Biomedical applications of tetrazine cycloadditions. Acc. Chem.
Res. 44(9), 816–827 (2011)
25. M.E. Phelps, Positron emission tomography provides molecular imaging of biological
processes. Proc. Natl. Acad. Sci. U.S.A. 97, 9226–9233 (2000)
26. T.F. Massoud, S.S. Gambhir, Molecular imaging in living subjects: seeing fundamental
biological processes in a new light. Genes Dev. 17(5), 545–580 (2003)
27. S. Vallabhajosula, Molecular Imaging: Radiopharmaceuticals for PET and SPECT, 1st edn.
(Springer, New York, 2009), pp. 133–193
28. S.M. Ametamey, M. Honer, P.A. Schubiger, Molecular imaging with PET. Chem. Rev. 108,
1501–1516 (2008)
29. S.S. Gambhir, Molecular imaging of cancer with positron emission tomography. Nat. Rev.
Cancer 2, 683–693 (2002)
30. R. Schirrmacher, C. Wängler, E. Schirrmacher, Recent developments and trends in
18F-radiochemistry: syntheses and applications. Mini Rev. Org. Chem. 4, 317–329 (2007)
31. D.W. Kim, D.S. Ahn, Y.H. Oh, S. Lee, H.S. Kil, S.J. Oh et al., A new class of SN2 reactions
catalyzed by protic solvents: Facile fluorination for isotopic labeling of diagnostic molecules.
J. Am. Chem. Soc. 128(50), 16394–16397 (2006)
14 Bioorthogonal Reaction for Fluorine-18 Labeling
273