Chemi-luminescence as a Diagnostic Feature of Heterolytic Reactions which Produce Oxygen

McKeown, E.; Waters, William A.

doi:10.1038/2031063b0

Cited by 24 publications

(8 citation statements)

References 3 publications

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“…The 'Ag state is extremely long-lived (it is known to survive more than 10s collisions in the vapor).12 The 7 8+ state is shorter lived, and is rapidly quenched by water vapor. [7][8][9][10][11][12][13] We previously reported in preliminary form that an oxidizing species (probably zAg oxygen) produced in the reaction of sodium hypochlorite and hydrogen peroxide oxygenates many compounds to give products identical with those of the dye-sensitized photooxygenation.14 Similar observations were made by Corey and Taylor, using singlet oxygen produced by radiofrequency discharge in gaseous oxygen.16 Since these reports, several investigators have described oxygenations using these methods or similar ones.8-12b-18 In this paper, the chemical oxygenation of a number of organic substrates which , yield a single product on photooxygenation is described from a mainly preparative standpoint, with attention to the effect of certain reaction variables on product yield. A series of papers in preparation will present detailed comparisons of the photooxygenation and hypochlorite-hydrogen peroxide oxygenation in regard to stereoselectivity, substrate reactivity, substituent effects, and mechanism.…”

mentioning

confidence: 99%

Chemistry of singlet oxygen. IV. Oxygenations with hypochlorite-hydrogen peroxide

Foote¹,

Wexler²,

Andō³

et al. 1968

J. Am. Chem. Soc.

232

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mentioning

confidence: 99%

Chemistry of singlet oxygen. IV. Oxygenations with hypochlorite-hydrogen peroxide

Foote¹,

Wexler²,

Andō³

et al. 1968

J. Am. Chem. Soc.

232

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“…As suggested by McKeown et al [15], singlet oxygen produced by reaction between KCN and H 2 O 2 in basic alkaline solution is responsible for luminol CL. Indeed, the addition of a singlet oxygen quencher, e.g.…”

Section: Resultsmentioning

confidence: 87%

Controlled kinetics of non-enzymatic chemiluminescence reactions for simple imaging of DNA and protein

Lau

Yamaguchi

et al. 2002

Analytical and Bioanalytical Chemistry

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A robust and sensitive non-enzymatic chemiluminescence (CL) imaging method is presented. In the method a fast-emitting CL reaction is tuned to furnish a slower-emitting reaction suitable for simple CL imaging. Typically, non-enzymatic CL reactions between luminol or fluorescein and oxygen species generated by KCN as catalyst, were rather fast and unsuitable for CL imaging; the speed of the reactions could, however, be reduced substantially by changing KCN for CH(3)CN or benzonitrile. Light emission from the tuned CL reaction was intense and long-lived, and even with a simple arrangement high sensitivity could be achieved. The maximum CL peak was reached after approximately 1.5 min in the presence of 25% acetonitrile, and as little as 16 fmol commercial isoluminol-labeled streptavidin was detected and visualized on either microplate or membrane. The approach was further illustrated by imaging of DNA on a membrane and of antibody on a microplate by use of biotin-streptavidin chemistry. Overall, this simple, economical, and sensitive CL imaging system is expected to be very useful in biochemical analysis, and greatly complements currently used enzyme-based CL imaging methods, especially in routine applications.

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“…One of the mechanisms is that singlet oxygen, 15 produced from the reaction of H2O2 and CH3CN, reacts with 2, and the product then emits light via decomposition of dioxetane formed at the 2-and 3-positions of the indole ring (Fig. 2a).…”

Section: Resultsmentioning

confidence: 99%

Lasting Chemiluminescence of 3-Indoleglyoxylyl Chloride and Its Enhancement

2003

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The chemiluminescence (CL) intensities of various indole derivatives substituted with a glyoxylyl group at the 3-position and a hydroxyl group at the 5-position of the indole ring were compared upon the addition of H2O2 in alkaline media. The CL intensities of 3-indoleglyoxylyl chloride, 3-indoleglyoxylic acid, 5-hydroxyindole and 5-benzyloxyindole in CH3CN were 5.9-, 48-, 5.9-and 3.3-fold stronger than that of 3-methylindole. A lasting CL of 3-indoleglyoxylyl chloride was found. Under appropriate conditions, the CL emission reached a maximum within 10 min after the addition of H2O2 in the presence of NaOH, and the intensity was retained for 25 min. One of the final products via the CL reaction of 3-indoleglyoxylyl chloride was indole-3-carboxylic acid. 3-Indoleglyoxylyl chloride emitted light by decompositions via both dioxetane and dioxetanedione. An enhancement effect of β-cyclodextrin and bovine serum albumin on the CL of 3-indoleglyoxylyl chloride was also found.

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Chemi-luminescence as a Diagnostic Feature of Heterolytic Reactions which Produce Oxygen

Cited by 24 publications

References 3 publications

Chemistry of singlet oxygen. IV. Oxygenations with hypochlorite-hydrogen peroxide

Chemistry of singlet oxygen. IV. Oxygenations with hypochlorite-hydrogen peroxide

Controlled kinetics of non-enzymatic chemiluminescence reactions for simple imaging of DNA and protein

Lasting Chemiluminescence of 3-Indoleglyoxylyl Chloride and Its Enhancement

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