A chemiluminescent catalytic antibody†

Stevenson, James D.; Dietel, Anja; Thomas, Neil R.

doi:10.1039/a906566k

Cited by 13 publications

(5 citation statements)

References 15 publications

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“…Over the past 30 years or so, numerous examples of chemiluminescence probes based on Schaap’s dioxetane have been reported in the literature. ,− In addition, Matsumoto has also explored other triggerable dioxetane probes with alternative groups in place of the phenols . These probes were designed to release benzoate upon activation; such benzoate is a weakly emissive species under aqueous conditions.…”

Section: Resultsmentioning

confidence: 99%

Opening a Gateway for Chemiluminescence Cell Imaging: Distinctive Methodology for Design of Bright Chemiluminescent Dioxetane Probes

et al. 2017

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Chemiluminescence probes are considered to be among the most sensitive diagnostic tools that provide high signal-to-noise ratio for various applications such as DNA detection and immunoassays. We have developed a new molecular methodology to design and foresee light-emission properties of turn-ON chemiluminescence dioxetane probes suitable for use under physiological conditions. The methodology is based on incorporation of a substituent on the benzoate species obtained during the chemiexcitation pathway of Schaap’s adamantylidene–dioxetane probe. The substituent effect was initially evaluated on the fluorescence emission generated by the benzoate species and then on the chemiluminescence of the dioxetane luminophores. A striking substituent effect on the chemiluminescence efficiency of the probes was obtained when acrylate and acrylonitrile electron-withdrawing groups were installed. The chemiluminescence quantum yield of the best probe was more than 3 orders of magnitude higher than that of a standard, commercially available adamantylidene–dioxetane probe. These are the most powerful chemiluminescence dioxetane probes synthesized to date that are suitable for use under aqueous conditions. One of our probes was capable of providing high-quality chemiluminescence cell images based on endogenous activity of β-galactosidase. This is the first demonstration of cell imaging achieved by a non-luciferin small-molecule probe with direct chemiluminescence mode of emission. We anticipate that the strategy presented here will lead to development of efficient chemiluminescence probes for various applications in the field of sensing and imaging.

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Section: Resultsmentioning

confidence: 99%

Opening a Gateway for Chemiluminescence Cell Imaging: Distinctive Methodology for Design of Bright Chemiluminescent Dioxetane Probes

et al. 2017

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“…357 Chemical modification to introduce a thiazolium group converted 38C2 into a catalyst for oxidative decarboxylation with a rate enhancement of 370-fold. 358 Several interesting examples have appeared in the last few years including systems that catalyse sulfoxide-sulfenate rearrangement, 359 chemiluminescent dioxetane cleavage, 360 S N 1-norbornyl displacement via a carbocation rather than via non-classsical ion, 361 and 1,3-dipolar cycloadditions. 362 Use of an N-methylpiperidinium hapten allowed the raising of an antibody capable of catalysing a 6-ring closure of an epoxide to form a pyran, whereas the corresponding chemical transformation yields the 5-ring furan.…”

Section: Catalytic Antibodiesmentioning

confidence: 99%

2 Synthetic methods : Part (v) Enzyme methods

Davis

2002

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

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“…130 Thomas and co-workers chose to adapt the hydroxyaryl substituted adamantyl-1,2-dioxetanes, developed by Schaap et al 131 to screen for hydrolytic catalytic activity. 132 These are a highly versatile class of chemiluminescent substrates, which undergo Chemically Initiated Electron Exchange Luminescence (CIEEL) following cleavage of a triggering group (Scheme 40). This triggering group, at the key 3-hydroxyaryl position, can be varied according to the desired enzyme activity (ester, carbamate, or phosphate or glycoside hydrolysis).…”

Section: Chemiluminescent Substratesmentioning

confidence: 99%