Triggered reactivation of the self-immolative reactivity from the gated CB-SIE2 complex was investigated using a competitive guest molecule 1-adamantylamine (Figure ). 1-adamantylamine is known for its high binding affinity with CB (Ka > 10 11 M -1 ) and its excellent safety profile as evidenced by its approval by the Food and Drug Administration (FDA) as a prophylactic for influenza A and to treat Parkinson's disease. We added 200 µM adamantane into a solution of the 10×CB/SIE2 complex (pH 6.5 MES, [SIE2]0 = 10 µM). The introduction of adamantane essentially restored the rate of coumarin release as shown by fluorescence measurements (Figure , blue). The adamantane-triggered reactivation of self-immolative release in phosphate buffer conditions was also confirmed by NMR measurements (Figure ). Further, the supramolecular regulation of release is reversible (Figure ): alternating addition of excess CB and adamantane turned the self-immolation off and on, respectively, enabling temporal control of the release on demand.