Disease relevance of dioxetane

• A chemiluminescence in situ hybridization method was developed for the search of B19 parvovirus DNA in bone marrow cells, employing digoxigenin-labeled B19 DNA probes, immunoenzymatically detected with a highly sensitive 1,2-dioxetane phosphate as chemiluminescent substrate [1].
• The reaction of beta-galactosidase enzyme from E. coli with the dioxetane substrate generated light at 530 nm [2].

High impact information on dioxetane

• Our findings also show that the formation of dioxetane intermediates through peroxyradical cyclization is not required to achieve oxidative fragmentation of PUFAs [3].
• Neither an endoperoxide nor a dioxetane intermediate was detected by low-temperature NMR even at -78 degrees C. A product (A) with an oxidized imidazole ring was the only major product detected at room temperature; this compound could be isolated by low-temperature column chromatography and was characterized by (1)H and (13)C and mass spectroscopy [4].
• This radical reacts with molecular oxygen, producing a peroxyl intermediate radical that, via a putative dioxetane intermediate, promotes formation of benzophenone as the main final product of this reaction, detected by high-performance liquid chromatography coupled with tandem mass spectrometry [5].
• C-525 sensitized CL only in the systems where peroxyl radical and/or triplet excited carbonyls are produced, the mechanism of CL sensitization apparently is energy transfer from the excited triplet carbonyls formed in the peroxyl radical self-reaction via Russell's mechanism or by dioxetane decomposition [6].
• It was found that a chemiluminescent detection system employing an alkaline phosphatase activated dioxetane in the presence of chemiluminescent enhancers provides a high degree of sensitivity in hybridization protocols with a significant savings in overall filter processing time [7].

Biological context of dioxetane

• Applications of dioxetane chemiluminescent probes to molecular biology [8].
• A model based on dioxetane chemiluminescence is proposed to explain the observed kinetics [9].
• The difference in light-emission kinetics between the Ca(2+)-triggered bioluminescent reaction of the photoprotein aequorin (AEQ) and the alkaline phosphatase (ALP)-catalyzed chemiluminescent hydrolysis of dioxetane aryl phosphate substrates was exploited for the analysis of both alleles of biallelic polymorphisms in a single microtiter well [10].
• Formation of 7,8-dihydro-8-oxoguanine in the 1,2-dioxetane-induced oxidation of calf thymus DNA: evidence for photosensitized DNA damage by thermally generated triplet ketones in the dark [11].
• The varieties of 1,2-dioxetane substrates available provides assay versatility, allowing optimization of assay formats with the available instrumentation, and are ideal for use in gene expression assays performed in both biomedical and pharmaceutical research [12].

Anatomical context of dioxetane

• The psoralen dioxetane (2a) or PsD bound photochemically to calf thymus DNA at the alpha-pyrone ring of psoralen (fluorescence measurements) [13].

Associations of dioxetane with other chemical compounds

• Chemiluminescent enzyme immunoassay of alpha-fetoprotein based on an adamantyl dioxetane phenyl phosphate substrate [14].
• It is postulated that IBAL- or MP-generated triplet carbonyls are produced by the thermolysis of dioxetane intermediates, which are formed by the cyclization of alpha-hydroperoxide intermediates produced by insertion of dioxygen into the IBAL or MP enolyl radicals, followed by their reduction [15].
• Improved quality of nonradioactive detection was obtained by the use of digoxigenin-labeled nucleotides in combination with dioxetane substrates which are decomposed by the hydrolysis of alkaline phosphatase [16].
• To monitor quantitatively the formation of the mutagenic oxidation product 7,8-dihydro-8-oxoguanine (8-oxoGua), a sensitive and selective HPLC electrochemical assay was used after acidic hydrolysis (HF/pyridine) of the dioxetane-treated DNA [11].
• A computer model, based on homology, of the catalytic antibody 7F11 that catalyses the decomposition of the benzoate ester of a dioxetane resulting in chemiluminescence is reported [17].

Gene context of dioxetane

• The spectroscopic profile of the light emission is distinguishable from (a) singlet oxygen, (b) triplet carbonyls from dioxetane and alpha-hydroxyperoxyl radicals, and (c) biacyl triplet formed by the coupling of two acyl radicals [18].
• BGR was evaluated using the chemiluminescent substrate, AMPGD (3-¿4-Methoxyspiro[1,2-dioxetane-3, 2'-tricyclo(3.3.1.1(3,7))decan]-yl¿phenyl-b-D-galactopyra nos ide), a phenylgalactose-substituted 1,2-dioxetane compound [19].
• The assay was based on the reaction of beta-galactosidase enzyme from E. coli with a phenylgalactosidase-substituted dioxetane substrate [20].
• Effects of some trivalent metal ions on the fluoride-induced chemiluminescence from a phenylphosphate-substituted dioxetane Lumigen PPD [21].

Analytical, diagnostic and therapeutic context of dioxetane

• The substrate in the chemiluminescent assay is a derivative of adamantyl 1,2-dioxetane phosphate [22].
• Detection of alkaline phosphatase is by autoradiography of the chemiluminescence produced during enzymatic dephosphorylation of a dioxetane substrate [23].
• Dual labelled amplicons were bound, treated with anti-digoxigenin antibody conjugated to alkaline phosphatase to complete the two-site sandwich immunoassay configuration, and detected by the chemiluminescence generated upon hydrolysis of a phosphate substituted dioxetane substrate, AMPPD [24].

References