Document Detail


Reduction of antitumour mitosenes in non-aqueous and aqueous environment. An electron spin resonance and cyclic voltammetry study.
MedLine Citation:
PMID:  7704182     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Chemical reduction of mitosenes under aerobic conditions in DMSO showed characteristic ESR signals of the mitosene derived semiquinone free radicals. However, these signals diminished strongly upon addition of water to the reaction mixture, indicating a short lifetime of the mitosene semiquinone free radicals under aqueous conditions. In addition, enzymatic one-electron reduction of these mitosenes with either xanthine oxidase or purified NADPH cytochrome P450 reductase under anaerobic conditions showed no signals of the mitosene semiquinone free radicals. Subsequent cyclic voltammetry measurements demonstrated facilitation of the further one-electron reduction of the mitosene semiquinone free radicals in the presence of water in comparison with non-aqueous conditions. The present results strongly suggest that in the presence of water relatively stable hydroquinones are formed upon reduction of mitosenes. Consequently, the steady state concentrations of mitosene semiquinone free radicals will be lowered substantially in aqueous environment. Thus under physiological conditions, two-electron reduction and formation of the mitosene hydroquinone might be important in processes leading to DNA alkylation by these mitosenes.
Authors:
M Maliepaard; N J De Mol; L H Janssen; A R Goeptar; J M Te Koppele; N P Vermeulen; W Verboom; D N Reinhoudt
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Free radical research     Volume:  22     ISSN:  1071-5762     ISO Abbreviation:  Free Radic. Res.     Publication Date:  1995 Feb 
Date Detail:
Created Date:  1995-05-05     Completed Date:  1995-05-05     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  9423872     Medline TA:  Free Radic Res     Country:  SWITZERLAND    
Other Details:
Languages:  eng     Pagination:  109-21     Citation Subset:  IM    
Affiliation:
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Utrecht University, The Netherlands.
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MeSH Terms
Descriptor/Qualifier:
Alkylation
Animals
Antineoplastic Agents / chemistry*,  metabolism
Borohydrides / chemistry
DNA / chemistry
Dimethyl Sulfoxide
Electron Spin Resonance Spectroscopy*
Free Radicals
Mitomycins / chemistry*,  metabolism
NADPH-Ferrihemoprotein Reductase / metabolism
Oxidation-Reduction
Quinones / chemistry
Rats
Solutions
Water*
Xanthine Oxidase / metabolism
Chemical
Reg. No./Substance:
0/Antineoplastic Agents; 0/Borohydrides; 0/Free Radicals; 0/Mitomycins; 0/Quinones; 0/Solutions; 16940-66-2/sodium borohydride; 3567-35-9/mitosene; 67-68-5/Dimethyl Sulfoxide; 7732-18-5/Water; 9007-49-2/DNA; EC 1.17.3.2/Xanthine Oxidase; EC 1.6.2.4/NADPH-Ferrihemoprotein Reductase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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