(a) Strategies for cell labeling with azides using metabolic expression of non-natural sugars, followed by Cu-catalyzed click chemistry labeling [21]. (b) Cu-free methods of cell labeling with strained cyclooctynes [23]. Reproduced with permission from: Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Copper-Free Click Chemistry for Dynamic in Vivo Imaging. Proc. Natl. Acad. Sci. U. S. A.
2007, 104 (43), 16793–16797. (c) Comparison of Jurkat cell labeling with a biarylazacyclooctyne (BARAC), fluorinated cyclooctyne (DIFO), and non-fluorinated cyclooctyne (DBCO) [26].