Fig. 3
|
Tetrazine-mediated release of pyridine from the isocyanopropyl (ICPr) groups. (a) Synthesis of ICPr-modified pyridine by reacting pyridine with isocyanopropyl tosylate. (b) Concept of pyridine release from the ICPr group by reaction with tetrazine. (c) 1H NMR analysis of release of pyridine from the ICPr precursor ICPr-Py (6 mM ICPr-Py, 18 mM tBu2Tz, DMSO-d6/PBS-d, 9/1, pH = 7.4, 37 °C). (d) HPLC analysis of release of naphthalamide probe of pyridine (Py-NA) from ICPr precursor (ICPr-Py-NA) (2 mM ICPr-Py-NA, 20 mM PEG-Tz (see Chart 1 in the Supporting Information), DMSO/PBS, 1/9, pH = 7.4, 37 °C). (e) Time dependence of pyridine release by HPLC (2 mM ICPr-Py-NA, 20 mM PEG-Tz, DMSO/PBS, 1/9, pH = 7.4, 37 °C). |