BIOREDUCTIVE ACTIVATION OF QUINONES - REDOX PROPERTIES AND THIOL REACTIVITY

被引:95
作者
WARDMAN, P
机构
[1] Cancer Research Campaign, Gray Luboratory, Mount Vernon Hospital, Northwood, Middx HA6 ZJR
来源
FREE RADICAL RESEARCH COMMUNICATIONS | 1990年 / 8卷 / 4-6期
关键词
Glutathione; Quinones; Radicals; Semiquinone radicals; Superoxide; Thiols;
D O I
10.3109/10715769009053355
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Redox properties and thiol reactivity are central to the therapeutic and toxicological properties of qui-nones. The use of other physicochemical parameters to establish predictive relationships for redox properties of quinones is discussed. and attention drawn to situations where such relationships may be unreliable. The rates of reaction of semiquinone radicals with oxygen, including those of chemotherapeutic agents such as mitomycin and the anthracyclines. can be predicted with reasonable confidence from the redox properties. The reactions of quinones with thiols such as glutathione produces reduced quinones and radicals. but the reactions are complex and all the features are not well understood © 1990 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted.
引用
收藏
页码:219 / 229
页数:11
相关论文
共 42 条
[1]  
ASHNAGAR A, 1984, BIOCHIM BIOPHYS ACTA, V801, P351, DOI 10.1016/0304-4165(84)90138-7
[2]   THE FORMATION CONSTANT OF DUROSEMIQUINONE [J].
BAXENDALE, JH ;
HARDY, HR .
TRANSACTIONS OF THE FARADAY SOCIETY, 1953, 49 (12) :1433-1437
[3]   EQUILIBRIA OF SUBSTITUTED SEMIQUINONES AT HIGH PH [J].
BISHOP, CA ;
TONG, LKJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (03) :501-&
[5]  
BUTLER J, 1987, British Journal of Cancer, V55, P53
[6]   REACTIONS OF THE SEMIQUINONE FREE-RADICALS OF ANTI-TUMOR AGENTS WITH OXYGEN AND IRON COMPLEXES [J].
BUTLER, J ;
HOEY, BM ;
SWALLOW, AJ .
FEBS LETTERS, 1985, 182 (01) :95-98
[7]  
BUTLER J, 1986, Journal of Free Radicals in Biology and Medicine, V2, P77, DOI 10.1016/0748-5514(86)90127-3
[8]   CIS-TRANS ISOMERIZATION OF THE (5-NITRO-2-FURYL)ACRYLAMIDE, AF-2, INITIATED BY ASCORBATE, GLUTATHIONE, FE(II) AND OH- [J].
CLARKE, ED ;
WARDMAN, P ;
WILSON, I .
BIOCHEMICAL PHARMACOLOGY, 1984, 33 (01) :83-87
[9]   THE SPONTANEOUS AND ENZYMATIC-REACTION OF N-ACETYL-PARA-BENZOQUINONIMINE WITH GLUTATHIONE - A STOPPED-FLOW KINETIC-STUDY [J].
COLES, B ;
WILSON, I ;
WARDMAN, P ;
HINSON, JA ;
NELSON, SD ;
KETTERER, B .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1988, 264 (01) :253-260
[10]   REDOX CYCLING AND SULFHYDRYL ARYLATION - THEIR RELATIVE IMPORTANCE IN THE MECHANISM OF QUINONE CYTO-TOXICITY TO ISOLATED HEPATOCYTES [J].
GANT, TW ;
RAO, DNR ;
MASON, RP ;
COHEN, GM .
CHEMICO-BIOLOGICAL INTERACTIONS, 1988, 65 (02) :157-173