The chemiluminescence of riboflavin

Strehler, Bernard L.; Shoup, Charles S.

doi:10.1016/0003-9861(53)90433-0

Cited by 32 publications

(16 citation statements)

References 10 publications

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“…The luminescence obtained on the electrochemical oxidation of H 2 0 2 in the presence of flavin (pathways B and C, Scheme 1) may be similar to the light reaction shown by the chemical system of flavin/H,02/Fe' ' which has been known for a long time (Strehler and Shoup, 1953) but has never been well-formulated mechanistically. We now propose that the hydroxyl radicals, produced in the reduction of H202 by Fe'' react with the flavin to give 7 [Eq.…”

Section: ' "mentioning

confidence: 68%

Electrochemical Superoxidation of Flavins: Generation of Active Precursors in Luminescent Model Systems

Mager¹,

Tu²,

Liu

et al. 1990

Photochem & Photobiology

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Using 3-methyllumiflavin and tetraacetyliriboflavin as examples, we have shown that the socalled "fully oxidized" flavins can be "superoxidized" at an anodic potential of 1.8 to 1.9 V giving flavin radical cation transients which are rapidly transformed in subsequent chemical reactions. An attack by H2O subsequent to the superoxidation of 3-methyllumiflavin provides a route for the formation of 4a-hydroxy-3-methyllumiflavin radical cation, as evident from the subsequent decomposition to the protonated form of the starting flavin. When 3-methyllumiflavin is superoxidized in the presence of a base, a recycling process occurs, allowing superoxidized flavin to be trapped in a slower, competitive conversion. The relatively more stable trapped product is active in reacting with H2O2 to emit chemiluminescence. Electrochemical oxidation of H2O2 in acetonitrile at 1.30 V in the presence of an oxidized flavin results in a direct protonation of the flavin by H+ generated from the electrolysis of H2O2. Minor reactions presumably provide alternative formations of the 4a-hydroperoxy- and 4a-hydroxy-flavin radical cation transients by the direct addition of HOO. and HO. radicals, which also arise in the oxidation of H2O2, to protonated flavin. Under such conditions the superoxidized flavin radical cation is apparently also formed, either directly or by process(es) such as decomposition of the flavin 4a-adduct radical cations. Subsequent reductions of either the superoxidized flavin or the flavin 4a-adduct radical cations lead to an almost steady level of luminescence.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: ' "mentioning

confidence: 68%

Electrochemical Superoxidation of Flavins: Generation of Active Precursors in Luminescent Model Systems

Mager¹,

Tu²,

Liu

et al. 1990

Photochem & Photobiology

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“…A reaction volume of 1.3 ml contained 1.01 x 10" H riboflavin, 1.75 x I0"4 M OsC13-3H20, and 0.679 M H 2 0 2 . The spectrum represents a number of reaction emissions at intermittent wavelengths using the same concentration of reactants for each point (9). The in vitro system contained 0.1 ml of partially purified luciferase that mixed with dodecyl aldehyde in a 10:1 enzyme/aldehyde ratio.…”

Section: Imentioning

confidence: 99%

“…Strehler and Shoup, 9 in their paper on riboflavin luminescence, produced data that indicated that the maximum wavelength of riboflavin chemiluminescence was identical to the fluorescence maximum for riboflavin. We present data in this paper that place the maximum wavelength of riboflavin chemiluminescence not at 535 mii, which is the fluorescence maximum, but at 495 mq, which is close to the maximum wavelength of the emission from several luminescent bacteria.…”

Section: Introduction*mentioning

confidence: 99%

Some characteristics of riboflavin chemiluminescence

Towner¹,

Neufeld²,

Shevlin³

1970

Archives of Biochemistry and Biophysics

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“…We believe that the chemiluminesce~~ce of zinc tetraphenyl porphine and of riboflavin report,ed by Linschitz (76) and by Strehler and Shoup (144), respectively, fall into the class of sensitized chemiluminescence, while in the case of firefly bioluminescence the quantum yield and the kinetic data point to the light emission being a direct chemi-W . I).…”

Section: Mechanisms Of Chemiluminescent Reactionsmentioning

confidence: 99%

“…In 1951, Shoup and Strehler (144) found that an acetonized preparation from Achromobacter fischeri would luminesce brightly for some tirne after being suspended in water. Following these observations, Strehler (136) observed that the duration of luminescence depended upon the concentration of the extracts and that a luciferin-luciferase reaction was obtainable if sufficiently concentrated materials were employed.…”

Section: B Bacteriamentioning

confidence: 99%