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Issue 10, 2019
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Light emission enhancement by supramolecular complexation of chemiluminescence probes designed for bioimaging

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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.

Graphical abstract: Light emission enhancement by supramolecular complexation of chemiluminescence probes designed for bioimaging

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Publication details

The article was received on 20 Nov 2018, accepted on 12 Jan 2019 and first published on 16 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05174G
Citation: Chem. Sci., 2019,10, 2945-2955
  • Open access: Creative Commons BY license
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    Light emission enhancement by supramolecular complexation of chemiluminescence probes designed for bioimaging

    S. Gnaim, A. Scomparin, A. Eldar-Boock, C. R. Bauer, R. Satchi-Fainaro and D. Shabat, Chem. Sci., 2019, 10, 2945
    DOI: 10.1039/C8SC05174G

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