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

Samer Gnaim, Anna Scomparin, Anat Eldar-Boock, Christoph R. Bauer, Ronit Satchi-Fainaro, Doron Shabat*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

55 Scopus citations


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.

Original languageEnglish
Pages (from-to)2945-2955
Number of pages11
JournalChemical Science
Issue number10
StatePublished - 2019


FundersFunder number
European Union's Seventh Framework Programme/ERC
German Israeli Foundation
Israeli Ministry of Science and Technology
Seventh Framework Programme617445
European Research Council
United States-Israel Binational Science Foundation
Israel Science Foundation
Council for Higher Education


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