13. Z.-B. Li, Z. Wu, K. Chen, F.T. Chin, X. Chen, Click chemistry for 18F-labeling of RGD
peptides and microPET imaging of tumor integrin avb3 expression. Bioconjug. Chem. 18(6),
1987–1994 (2007)
14. T. Ramenda, R. Bergmann, F. Wuest, Synthesis of
18
F-labeled neurotensin(8-13) via
copper-mediated 1,3-dipolar [3+2] cycloaddition reaction. Lett. Drug Des. Discov. 4(4), 279–
285 (2007)
15. M. Glaser, E. Årstad, “Click labeling” with 2-[
18
F] fluoroethylazide for positron emission
tomography. Bioconjug Chem. 18(3), 989–993 (2007)
16. T. Ramenda, T. Kniess, R. Bergmann, J. Steinbach, F. Wuest, Radiolabeling of proteins with
fluorine-18 via click chemistry. Chem. Commun (Camb) 48, 7521–7523 (2009)
17. T. Ramenda, J. Steinbach, F. Wuest, 4-[18F] Fluoro-N-methyl-N-(propyl-2-yn-1-yl)
benzenesulfonamide ([
18
F] F-SA): a versatile building block for labeling of peptides, proteins
and oligonucleotides with fluorine-18 via Cu(I)-mediated click chemistry. Amino Acids 44
(4), 1167–1180 (2013)
18. N.K. Devaraj, E.J. Keliher, G.M. Thurber, M. Nahrendorf, R. Weissleder,
18
F labeled
nanoparticles for in vivo PET-CT imaging. Bioconjug. Chem. 20(2), 397–401 (2009)
19. C.M. Lee, H.J. Jeong, D.W. Kim, M.H. Sohn, S.T. Lim, The effect of fluorination of zinc
oxide nanoparticles on evaluation of their biodistribution after oral administration.
Nanotechnology 23(20), 205102 (2012)
20. C.D. Hein, X.-M. Liu, D. Wang, Click chemistry, a powerful tool for pharmaceutical
sciences. Pharm. Res. 25(10), 2216–2230 (2008)
21. T. Wang, Z. Guo. Copper in Medicine: Homeostasis, chelation therapy and antitumor drug
design. Curr. Med. Chem. 13(5), 525–537 (2006)
22. K.D. Held, F.C. Sylvester, K.L. Hopcia, J.E. Biaglow, Role of fenton chemistry in
thiol-induced toxicity and apoptosis. Radiat. Res. 145(5), 542–553 (1996)
23. N.J. Agard, J.A. Prescher, C.R. Bertozzi, A strain-promoted [3+2] azide–alkyne cycloaddition
for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126(46),
15046–15047 (2004)
24. G. Wittig, A. Krebs, Zur existenz niedergliedriger cycloalkine I. Chem. Ber. 94(12), 3260–
3275 (1961)
25. M.F. Debets, S.S. van Berkel, J. Dommerholt, A.J. Dirks, F.P.J.T. Rutjes, F.L. van Delft,
Bioconjugation with strained alkenes and alkynes. Acc. Chem. Res. 44(9), 805–815 (2011)
26. E.M. Sletten, C.R. Bertozzi, From mechanism to mouse: a tale of two bioorthogonal reactions.
Acc. Chem. Res. 44(9), 666–676 (2011)
27. C.R. Becer, R. Hoogenboom, U.S. Schubert, Click chemistry beyond metal-catalyzed
cycloaddition. Angew. Chem. Int. Ed. Engl. 48(27), 4900–4908 (2009)
28. J.C. Jewett, C.R. Bertozzi, Cu-free click cycloaddition reactions in chemical biology. Chem.
Soc. Rev. 39(4), 1272–1279 (2010)
29. J.M. Baskin, C.R. Bertozzi, Bioorthogonal click chemistry: covalent labeling in living
systems. QSAR Comb. Sci. 26(11–12), 1211–1219 (2007)
30. 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)
31. J.M. Baskin, C.R. Bertozzi, Copper-free click chemistry: bioorthogonal reagents for tagging
azides. Aldrichimica Acta 43(1), 15–23 (2010)
32. J.A. Codelli, J.M. Baskin, N.J. Agard, C.R. Bertozzi, Second-generation difluorinated
cyclooctynes for copper-free click chemistry. J. Am. Chem. Soc. 130(34), 11486–11493
(2008)
33. C.G. Gordon, J.L. Mackey, J.C. Jewett, E.M. Sletten, K.N. Houk, C.R. Bertozzi, Reactivity of
biarylazacyclooctynones in copper-free click chemistry. J. Am. Chem. Soc. 134(22), 9199–
9208 (2012)
34. J. Dommerholt, O. Van Rooijen, A. Borrmann, C.F. Guerra, F.M. Bickelhaupt, F.L. Van
Delft, Highly accelerated inverse electron-demand cycloaddition of electron-deficient azides
with aliphatic cyclooctynes. Nat. Commun. 5, 5378 (2014)
260
J. C. Knight and B. Cornelissen
peptides and microPET imaging of tumor integrin avb3 expression. Bioconjug. Chem. 18(6),
1987–1994 (2007)
14. T. Ramenda, R. Bergmann, F. Wuest, Synthesis of
18
F-labeled neurotensin(8-13) via
copper-mediated 1,3-dipolar [3+2] cycloaddition reaction. Lett. Drug Des. Discov. 4(4), 279–
285 (2007)
15. M. Glaser, E. Årstad, “Click labeling” with 2-[
18
F] fluoroethylazide for positron emission
tomography. Bioconjug Chem. 18(3), 989–993 (2007)
16. T. Ramenda, T. Kniess, R. Bergmann, J. Steinbach, F. Wuest, Radiolabeling of proteins with
fluorine-18 via click chemistry. Chem. Commun (Camb) 48, 7521–7523 (2009)
17. T. Ramenda, J. Steinbach, F. Wuest, 4-[18F] Fluoro-N-methyl-N-(propyl-2-yn-1-yl)
benzenesulfonamide ([
18
F] F-SA): a versatile building block for labeling of peptides, proteins
and oligonucleotides with fluorine-18 via Cu(I)-mediated click chemistry. Amino Acids 44
(4), 1167–1180 (2013)
18. N.K. Devaraj, E.J. Keliher, G.M. Thurber, M. Nahrendorf, R. Weissleder,
18
F labeled
nanoparticles for in vivo PET-CT imaging. Bioconjug. Chem. 20(2), 397–401 (2009)
19. C.M. Lee, H.J. Jeong, D.W. Kim, M.H. Sohn, S.T. Lim, The effect of fluorination of zinc
oxide nanoparticles on evaluation of their biodistribution after oral administration.
Nanotechnology 23(20), 205102 (2012)
20. C.D. Hein, X.-M. Liu, D. Wang, Click chemistry, a powerful tool for pharmaceutical
sciences. Pharm. Res. 25(10), 2216–2230 (2008)
21. T. Wang, Z. Guo. Copper in Medicine: Homeostasis, chelation therapy and antitumor drug
design. Curr. Med. Chem. 13(5), 525–537 (2006)
22. K.D. Held, F.C. Sylvester, K.L. Hopcia, J.E. Biaglow, Role of fenton chemistry in
thiol-induced toxicity and apoptosis. Radiat. Res. 145(5), 542–553 (1996)
23. N.J. Agard, J.A. Prescher, C.R. Bertozzi, A strain-promoted [3+2] azide–alkyne cycloaddition
for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126(46),
15046–15047 (2004)
24. G. Wittig, A. Krebs, Zur existenz niedergliedriger cycloalkine I. Chem. Ber. 94(12), 3260–
3275 (1961)
25. M.F. Debets, S.S. van Berkel, J. Dommerholt, A.J. Dirks, F.P.J.T. Rutjes, F.L. van Delft,
Bioconjugation with strained alkenes and alkynes. Acc. Chem. Res. 44(9), 805–815 (2011)
26. E.M. Sletten, C.R. Bertozzi, From mechanism to mouse: a tale of two bioorthogonal reactions.
Acc. Chem. Res. 44(9), 666–676 (2011)
27. C.R. Becer, R. Hoogenboom, U.S. Schubert, Click chemistry beyond metal-catalyzed
cycloaddition. Angew. Chem. Int. Ed. Engl. 48(27), 4900–4908 (2009)
28. J.C. Jewett, C.R. Bertozzi, Cu-free click cycloaddition reactions in chemical biology. Chem.
Soc. Rev. 39(4), 1272–1279 (2010)
29. J.M. Baskin, C.R. Bertozzi, Bioorthogonal click chemistry: covalent labeling in living
systems. QSAR Comb. Sci. 26(11–12), 1211–1219 (2007)
30. 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)
31. J.M. Baskin, C.R. Bertozzi, Copper-free click chemistry: bioorthogonal reagents for tagging
azides. Aldrichimica Acta 43(1), 15–23 (2010)
32. J.A. Codelli, J.M. Baskin, N.J. Agard, C.R. Bertozzi, Second-generation difluorinated
cyclooctynes for copper-free click chemistry. J. Am. Chem. Soc. 130(34), 11486–11493
(2008)
33. C.G. Gordon, J.L. Mackey, J.C. Jewett, E.M. Sletten, K.N. Houk, C.R. Bertozzi, Reactivity of
biarylazacyclooctynones in copper-free click chemistry. J. Am. Chem. Soc. 134(22), 9199–
9208 (2012)
34. J. Dommerholt, O. Van Rooijen, A. Borrmann, C.F. Guerra, F.M. Bickelhaupt, F.L. Van
Delft, Highly accelerated inverse electron-demand cycloaddition of electron-deficient azides
with aliphatic cyclooctynes. Nat. Commun. 5, 5378 (2014)
260
J. C. Knight and B. Cornelissen