Abstract
Chemiluminescence offers advantages over fluorescence for bioimaging, since an external light source is unnecessary with chemiluminescent agents. This report demonstrates the first encapsulation of chemiluminescence phenoxy-adamantyl-1,2-dioxetane probes with trimethyl β-cyclodextrin. Clear proof for the formation of a 1 : 1 host-guest complex between the adamantyl-1,2-dioxetane probe and trimethyl β-cyclodextrin was provided by mass spectroscopy and NMR experiments. The calculated association constant of this host-guest system, 253 M-1, indicates the formation of a stable inclusion complex. The inclusion complex significantly amplified the light emission intensity relative to the noncomplexed probe under physiological conditions. Complexation of adamantyl-dioxetane with fluorogenic dye-tethered cyclodextrin resulted in light emission through energy transfer to a wavelength that corresponds to the fluorescent emission of the conjugated dye. Remarkably, the light emission intensity of this inclusion complex was approximately 1500-fold higher than that of the non-complexed adamantyl-dioxetane guest. We present the first demonstration of microscopic cell images obtained using a chemiluminescence supramolecular dioxetane probe and demonstrate the utility of these supramolecular complexes by imaging of enzymatic activity and bio-analytes in vitro and in vivo. We anticipate that the described chemiluminescence supramolecular dioxetane probes will find use in various biological applications.
Highlights
Non-invasive acquisition of biomedical images at tissue and cellular levels is considered as a major challenge.[1,2] A common bioimaging modality used today is based on optical uorescence.[3]
Clear proof for the formation of a 1 : 1 host–guest complex between the adamantyl-1,2-dioxetane probe and trimethyl b-cyclodextrin was provided by mass spectroscopy and NMR experiments
Complexation of adamantyl-dioxetane with fluorogenic dye-tethered cyclodextrin resulted in light emission through energy transfer to a wavelength that corresponds to the fluorescent emission of the conjugated dye
Summary
Non-invasive acquisition of biomedical images at tissue and cellular levels is considered as a major challenge.[1,2] A common bioimaging modality used today is based on optical uorescence.[3]. Bioimaging using a chemiluminescence modality offers attractive advantages over uorescence imaging, mainly due to the fact that an external light source is unnecessary with chemiluminescent agents.[12] Further, chemiluminescent assays are among the most sensitive methods for determination of enzymatic activity and analyte concentrations.[13,14,15] Most known chemiluminescence probes emit light following a reaction with an oxidizing agent. Such probes usually undergo oxidation to form unstable strained peroxides that rapidly decompose to generate excited state intermediates that decay to the ground state through emission of light. This oxidation-based mechanism is widely utilized for activation of common chemiluminescent substrates such as luminol and oxalate esters.[16]
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