35. J. Dommerholt, F.P.J.T. Rutjes, F.L. van Delft, Strain-promoted 1,3-dipolar cycloaddition of
cycloalkynes and organic azides. Top. Curr. Chem. 374(2), 16 (2016)
36. 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)
37. D. Zeng, N.S. Lee, Y. Liu, D. Zhou, C.S. Dence, K.L. Wooley et al.,
64
Cu core-labeled
nanoparticles with high specific activity via metal-free click chemistry. ACS Nano 6(6),
5209–5219 (2012)
38. C. Pérez-Medina, D. Abdel-Atti, Y. Zhang, V.A. Longo, C.P. Irwin, T. Binderup et al., A
modular labeling strategy for in vivo PET and near-infrared fluorescence imaging of
nanoparticle tumor targeting. J. Nucl. Med. 55(10), 1706–1711 (2014)
39. J. Schoch, M. Staudt, A. Samanta, M. Wiessler, A. Jäschke, Site-specific one-pot dual
labeling of DNA by orthogonal cycloaddition chemistry. Bioconjug. Chem. 23(7), 1382–1386
(2012)
40. M.R. Karver, R. Weissleder, S.A. Hilderbrand, Synthesis and evaluation of a series of
1,2,4,5-tetrazines for bioorthogonal conjugation. Bioconjug. Chem. 22(11), 2263–2270
(2011)
41. K. Lang, L. Davis, S. Wallace, M. Mahesh, D.J. Cox, M.L. Blackman et al., Genetic encoding
of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live
mammalian cells via rapid fluorogenic Diels-Alder reactions. J. Am. Chem. Soc. 134(25),
10317–10320 (2012)
42. M.L. Blackman, M. Royzen, J.M. Fox, Tetrazine ligation: fast bioconjugation based on
inverse-electron-demand Diels–Alder reactivity. J. Am. Chem. Soc. 130(41), 13518–13519
(2008)
43. M.T. Taylor, M.L. Blackman, O. Dmitrenko, J.M. Fox, Design and synthesis of highly
reactive dienophiles for the tetrazine-trans-cyclooctene ligation. J. Am. Chem. Soc. 133(25),
9646–9649 (2011)
44. A.-C. Knall, C. Slugovc, Inverse electron demand Diels-Alder (iEDDA)-initiated conjugation:
a (high) potential click chemistry scheme. Chem. Soc. Rev. 42(12), 5131–5142 (2013)
45. J. Sauer, D.K. Heldmann, J. Hetzenegger, J. Krauthan, H. Sichert, J. Schuster,
1,2,4,5-Tetrazine: synthesis and reactivity in [4+2] cycloadditions. Euro. J. Org. Chem.
1998(12), 2885–2896 (1998)
46. Z. Li, H. Cai, M. Hassink, M.L. Blackman, R.C.D. Brown, P.S. Conti et al.,
Tetrazine-trans-cyclooctene ligation for the rapid construction of
18
F labeled probes. Chem.
Commun. 46(42), 8043–8045 (2010)
47. E.J. Keliher, T. Reiner, A. Turetsky, S.A. Hilderbrand, R. Weissleder, High-yielding,
two-step
18
F labeling strategy for
18
F-PARP1 inhibitors. Chem. Med. Chem. 6(3), 424–427
(2011)
48. T. Reiner, J. Lacy, E.J. Keliher, K.S. Yang, A. Ullal, R.H. Kohler et al., Imaging therapeutic
PARP inhibition in vivo through bioorthogonally developed companion imaging agents.
Neoplasia 14, 169–177 (2012)
49. R. Selvaraj, S. Liu, M. Hassink, C. Huang, L. Yap, R. Park et al., Tetrazine-trans-cyclooctene
ligation for the rapid construction of integrin avb3 targeted PET tracer based on a cyclic RGD
peptide. Bioorg. Med. Chem. Lett. 21(17), 5011–5014 (2011)
50. S. Liu, M. Hassink, R. Selvaraj, L.-P. Yap, R. Park, H. Wang et al., Efficient
18
F labeling of
cysteine-containing peptides and proteins using tetrazine–trans-cyclooctene ligation. Mol.
Imaging 12, 121–128 (2013)
51. Z. Wu, S. Liu, M. Hassink, I. Nair, R. Park, L. Li et al., Development and evaluation of
18
F-TTCO-Cys40-Exendin-4: a PET probe for imaging transplanted islets. J. Nucl. Med. 54
(2), 244–251 (2013)
52. E.J. Keliher, T. Reiner, G.M. Thurber, R. Upadhyay, R. Weissleder, Efficient
18
F-labeling of
synthetic exendin-4 analogues for imaging beta cells. ChemistryOpen. 1(4), 177–183 (2012)
53. J.C. Knight, B. Cornelissen, Bioorthogonal chemistry: implications for pretargeted nuclear
(PET/SPECT) imaging and therapy. Am. J. Nucl. Med. Mol. Imaging 4(2), 96–113 (2014)
13 Preservation of Ligand Functionality by Click Chemistry
261
cycloalkynes and organic azides. Top. Curr. Chem. 374(2), 16 (2016)
36. 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)
37. D. Zeng, N.S. Lee, Y. Liu, D. Zhou, C.S. Dence, K.L. Wooley et al.,
64
Cu core-labeled
nanoparticles with high specific activity via metal-free click chemistry. ACS Nano 6(6),
5209–5219 (2012)
38. C. Pérez-Medina, D. Abdel-Atti, Y. Zhang, V.A. Longo, C.P. Irwin, T. Binderup et al., A
modular labeling strategy for in vivo PET and near-infrared fluorescence imaging of
nanoparticle tumor targeting. J. Nucl. Med. 55(10), 1706–1711 (2014)
39. J. Schoch, M. Staudt, A. Samanta, M. Wiessler, A. Jäschke, Site-specific one-pot dual
labeling of DNA by orthogonal cycloaddition chemistry. Bioconjug. Chem. 23(7), 1382–1386
(2012)
40. M.R. Karver, R. Weissleder, S.A. Hilderbrand, Synthesis and evaluation of a series of
1,2,4,5-tetrazines for bioorthogonal conjugation. Bioconjug. Chem. 22(11), 2263–2270
(2011)
41. K. Lang, L. Davis, S. Wallace, M. Mahesh, D.J. Cox, M.L. Blackman et al., Genetic encoding
of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live
mammalian cells via rapid fluorogenic Diels-Alder reactions. J. Am. Chem. Soc. 134(25),
10317–10320 (2012)
42. M.L. Blackman, M. Royzen, J.M. Fox, Tetrazine ligation: fast bioconjugation based on
inverse-electron-demand Diels–Alder reactivity. J. Am. Chem. Soc. 130(41), 13518–13519
(2008)
43. M.T. Taylor, M.L. Blackman, O. Dmitrenko, J.M. Fox, Design and synthesis of highly
reactive dienophiles for the tetrazine-trans-cyclooctene ligation. J. Am. Chem. Soc. 133(25),
9646–9649 (2011)
44. A.-C. Knall, C. Slugovc, Inverse electron demand Diels-Alder (iEDDA)-initiated conjugation:
a (high) potential click chemistry scheme. Chem. Soc. Rev. 42(12), 5131–5142 (2013)
45. J. Sauer, D.K. Heldmann, J. Hetzenegger, J. Krauthan, H. Sichert, J. Schuster,
1,2,4,5-Tetrazine: synthesis and reactivity in [4+2] cycloadditions. Euro. J. Org. Chem.
1998(12), 2885–2896 (1998)
46. Z. Li, H. Cai, M. Hassink, M.L. Blackman, R.C.D. Brown, P.S. Conti et al.,
Tetrazine-trans-cyclooctene ligation for the rapid construction of
18
F labeled probes. Chem.
Commun. 46(42), 8043–8045 (2010)
47. E.J. Keliher, T. Reiner, A. Turetsky, S.A. Hilderbrand, R. Weissleder, High-yielding,
two-step
18
F labeling strategy for
18
F-PARP1 inhibitors. Chem. Med. Chem. 6(3), 424–427
(2011)
48. T. Reiner, J. Lacy, E.J. Keliher, K.S. Yang, A. Ullal, R.H. Kohler et al., Imaging therapeutic
PARP inhibition in vivo through bioorthogonally developed companion imaging agents.
Neoplasia 14, 169–177 (2012)
49. R. Selvaraj, S. Liu, M. Hassink, C. Huang, L. Yap, R. Park et al., Tetrazine-trans-cyclooctene
ligation for the rapid construction of integrin avb3 targeted PET tracer based on a cyclic RGD
peptide. Bioorg. Med. Chem. Lett. 21(17), 5011–5014 (2011)
50. S. Liu, M. Hassink, R. Selvaraj, L.-P. Yap, R. Park, H. Wang et al., Efficient
18
F labeling of
cysteine-containing peptides and proteins using tetrazine–trans-cyclooctene ligation. Mol.
Imaging 12, 121–128 (2013)
51. Z. Wu, S. Liu, M. Hassink, I. Nair, R. Park, L. Li et al., Development and evaluation of
18
F-TTCO-Cys40-Exendin-4: a PET probe for imaging transplanted islets. J. Nucl. Med. 54
(2), 244–251 (2013)
52. E.J. Keliher, T. Reiner, G.M. Thurber, R. Upadhyay, R. Weissleder, Efficient
18
F-labeling of
synthetic exendin-4 analogues for imaging beta cells. ChemistryOpen. 1(4), 177–183 (2012)
53. J.C. Knight, B. Cornelissen, Bioorthogonal chemistry: implications for pretargeted nuclear
(PET/SPECT) imaging and therapy. Am. J. Nucl. Med. Mol. Imaging 4(2), 96–113 (2014)
13 Preservation of Ligand Functionality by Click Chemistry
261