Issue 10, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Nov. 2018
Accepted
12 Janv. 2019
First published
16 Janv. 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 2945-2955

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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