2.50
Hdl Handle:
http://hdl.handle.net/10541/95633
Title:
The autoxidation of the reduced forms of EO9.
Authors:
Butler, John; Spanswick, V J; Cummings, J
Abstract:
The properties of the semiquinone radical from [3-hydroxy-5-aziridinyl-1-methyl-2-(1H-indole-4,7-indi one)-prop-beta-en-alpha-ol], EO9, have been studied using pulse-radiolysis techniques. The reduction potential of the semiquinone of EO9 at pH7.4, E(EO9/EO9-), is -253 +/- 6 mV and hence this quinone can be readily reduced by one-electron reducing enzymes such as cytochrome P450 reductase and xanthine oxidase. However, the radical is unstable in the presence of oxygen (k = 1.3 +/- 0.15 x 10(8) M-1 s-1). The semiquinone radicals and the hydroquinone are in equilibrium although the formation of the hydroquinone is favoured t physiologically relevant pH. The hydroquinone of EO9 is also unstable in the presence of oxygen and it is predicted that in fully aerated solutions, its half life is 1.5 +/- 0.3 seconds. These results are discussed in view of the selective cytotoxicity of EO9 and its ability to undergo bioreductive activation by one-electron reducing enzymes and DT-diaphorase.
Affiliation:
CRC Department of Biophysical Chemistry, Paterson Institute for Cancer Research, Christie Hospital, Manchester, UK.
Citation:
The autoxidation of the reduced forms of EO9. 1996, 25 (2):141-8 Free Radic. Res.
Journal:
Free Radical Research
Issue Date:
Aug-1996
URI:
http://hdl.handle.net/10541/95633
DOI:
10.3109/10715769609149919
PubMed ID:
8885332
Type:
Article
Language:
en
ISSN:
1071-5762
Appears in Collections:
All Paterson Institute for Cancer Research

Full metadata record

DC FieldValue Language
dc.contributor.authorButler, Johnen
dc.contributor.authorSpanswick, V Jen
dc.contributor.authorCummings, Jen
dc.date.accessioned2010-04-06T09:55:55Z-
dc.date.available2010-04-06T09:55:55Z-
dc.date.issued1996-08-
dc.identifier.citationThe autoxidation of the reduced forms of EO9. 1996, 25 (2):141-8 Free Radic. Res.en
dc.identifier.issn1071-5762-
dc.identifier.pmid8885332-
dc.identifier.doi10.3109/10715769609149919-
dc.identifier.urihttp://hdl.handle.net/10541/95633-
dc.description.abstractThe properties of the semiquinone radical from [3-hydroxy-5-aziridinyl-1-methyl-2-(1H-indole-4,7-indi one)-prop-beta-en-alpha-ol], EO9, have been studied using pulse-radiolysis techniques. The reduction potential of the semiquinone of EO9 at pH7.4, E(EO9/EO9-), is -253 +/- 6 mV and hence this quinone can be readily reduced by one-electron reducing enzymes such as cytochrome P450 reductase and xanthine oxidase. However, the radical is unstable in the presence of oxygen (k = 1.3 +/- 0.15 x 10(8) M-1 s-1). The semiquinone radicals and the hydroquinone are in equilibrium although the formation of the hydroquinone is favoured t physiologically relevant pH. The hydroquinone of EO9 is also unstable in the presence of oxygen and it is predicted that in fully aerated solutions, its half life is 1.5 +/- 0.3 seconds. These results are discussed in view of the selective cytotoxicity of EO9 and its ability to undergo bioreductive activation by one-electron reducing enzymes and DT-diaphorase.en
dc.language.isoenen
dc.subject.meshAntineoplastic Agents-
dc.subject.meshAziridines-
dc.subject.meshDrug Stability-
dc.subject.meshFree Radicals-
dc.subject.meshHalf-Life-
dc.subject.meshHydrogen-Ion Concentration-
dc.subject.meshHydroquinones-
dc.subject.meshIndolequinones-
dc.subject.meshIndoles-
dc.subject.meshOxidation-Reduction-
dc.subject.meshOxygen-
dc.subject.meshPulse Radiolysis-
dc.subject.meshSpectrophotometry-
dc.titleThe autoxidation of the reduced forms of EO9.en
dc.typeArticleen
dc.contributor.departmentCRC Department of Biophysical Chemistry, Paterson Institute for Cancer Research, Christie Hospital, Manchester, UK.en
dc.identifier.journalFree Radical Researchen

Related articles on PubMed

All Items in Christie are protected by copyright, with all rights reserved, unless otherwise indicated.