Free Radicals in Biology and Medicine
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1 Free Radicals in Biology and Medicine 0 \ Second Edition BARRY HALLIWELL Professor of Medical Biochemistry, University of London King's College and JOHN M.C. GUTTERIDGE Senior Scientist, National Institute for Biological Standards and Control and Visiting Professor, Oklahoma Medical Research Foundation Q0 CLARENDON PRESS 1989 OXFORD
2 Contents 1 Oxygen is poisonous an introduction to oxygen toxicity and free radicals Oxygen and the Earth Oxygen and anaerobic organisms Oxygen and aerobes What causes the toxic effects of oxygen? What is a free radical? Oxygen and its derivatives Ozone and oxides of nitrogen Transition metals Other free radicals Further reading 20 2 The chemistry of oxygen radicals and other oxygen-derived species Reaction rates and rate constants Measurement of reaction rates for radical reactions Pulse radiolysis Stopped-flow methods Reactions of the hydroxyl radical Production of hydroxyl radicals in living systems Ionizing radiation Ultrasound, lithotripsy, and freeze-drying Reaction of metal ions with hydrogen peroxide Formation of hydroxyl radicals from ozone Ethanol metabolism Detection of hydroxyl radicals in biological systems Electron spin resonance and spin-trapping Aromatic hydroxylation Measurement of products of radical attack upon DNA Conversion of methional and related compounds into ethene (ethylene) gas (C 2 H 4 ) Other methods Production of singlet oxygen Reactions of singlet oxygen Detection of singlet oxygen in biological systems Use of scavengers 70
3 xii Contents Deuterium oxide Light emission Reactions of the superoxide radical Hydrogen peroxide in biological systems Further reading 81 3 Protection against oxidants in biological systems: the superoxide theory of oxygen toxicity Protection by enzymes 86 $ Protection against hydrogen peroxide by catalase and peroxidases Superoxide dismutase Protection by small molecules Ascorbic acid (vitamin C) Glutathione Uric acid Protection by sequestration of metal ions Metallothioneins Repair systems Methionine sulphoxide reductase DNA repair Degradation of abnormal proteins The superoxide theory of oxygen toxicity Is superoxide formed in vivo} Is the true function of superoxide dismutase that of removing superoxide radicals? Evidence bearing on the superoxide theory of oxygen toxicity Is superoxide a damaging species? Challenges to the superoxide theory Regulation of bacterial SOD synthesis by metal ions Oxygen radicals and radiation damage Food irradiation Further reading Lipid peroxidation: a radical chain reaction 188 o 4.1 Membrane structure 189 * 4.2 The peroxidation process Initiation and propagation The importance of iron in lipid peroxidation Products of the reaction of metal complexes with lipid peroxides 204
4 Contents xiii * 4.3 Enzymic and non-enzymic lipid peroxidation Acceleration of lipid peroxidation by species other than oxygen radicals Singlet oxygen 'A g Ozone Halogen radicals Peroxidation of other molecules Measurement of lipid peroxidation Uptake of oxygen Measurement of peroxides Diene conjugation Measurement of hydrocarbon gases Loss of fatty acids Light emission Measurement of fluorescence 225 tf The thiobarbituric acid (TBA) test Measurement of aldehydes other than MDA Summary which is the method of choice? Protection against lipid peroxidation 234 ' Protection by structural organization of the lipids 234, Protection by 'antioxidants': general principles 236, Vitamin E Synthetic antioxidants Glutathione peroxidase, a peroxide-decomposing antioxidant Antioxidants of extracellular fluids Erythrocyte lipid peroxidation The biomedical significance of lipid peroxidation Further reading Protection against radical damage: systems with problems The chloroplasts of higher plants The problems The solutions The eye Diabetic cataract Further reading Free radicals and toxicology Bipyridyl herbicides Paraquat toxicity to plants Toxicity to bacteria 305
5 xiv Contents Toxicity to animals Paraquat, lipid peroxidation, and hydroxyl radical formation Alloxan and streptozotocin Substituted dihydroxyphenylalanines and other phenolic compounds Cigarette smoke Lung defences against cigarette smoke Other air pollutants Haemolytic and anti-malarial drugs Hydrazines Sulphur-containing haemolytic drugs Quinones Oxidant stress, favism, and malaria Ethanol Paracetamol and phenacetin Halogenated hydrocarbons Carbon tetrachloride and chloroform Other halogenated hydrocarbons Hypoxic cell sensitizers and related compounds Antibiotics MPTP and Parkinson's disease Aluminium and Alzheimer's disease Aluminium and lipid peroxidation Toxicity of other metals Sporidesmin The 'Spanish cooking-oil' syndrome Ultraviolet light Further reading Free radicals as useful species Reduction of ribonucleosides Oxidation, carboxylation, and hydroxylation reactions Dioxygenases Pyruvate-metabolizing enzymes Hydroxylases Carboxylation of glutamic acid Phagocytosis The bacterial killing mechanism Significance of extracellular oxidant production by phagocytes Peroxidase and NADH oxidase enzymes Fruit ripening and the'wound response'of plant tissues 394
6 Contents xv 7.6 Eicosanoids: prostaglandins and leukotrienes Prostaglandins and thromboxanes Leukotrienes and other lipoxygenase products Endothelial-derived relaxing factor (EDRF) Further reading 408 Free radicals, ageing, and disease General principles Atherosclerosis Chronic inflammation and the autoimmune diseases Autoimmune diseases and phagocyte action Oxidants and human rheumatoid disease Are oxidants important in autoimmune diseases? Anti-inflammatory drugs and oxidant damage Ischaemia/reoxygenation injury Intestinal injury Cardiac injury Cerebral injury Preservation of organs for transplantation: kidney, liver, and skin Rheumatoid arthritis Pancreas Limb ischaemia Lung damage and the adult respiratory distress syndrome Exercise-induced oxidant damage Ageing 450 e Programmed ageing 451 «8.7.2 Damage accumulation ageing 454 t Free-radical theory of ageing Fluorescent tissue pigments Progeroid syndromes Neuronal ceroid lipofuscinosis (NCL) Amyloid Model systems Cancer Oxidants and carcinogenesis Immune surveillance Mechanism of action of carcinogens Antitumour drugs and oxidant production Footprinting of DNA by using hydroxyl radical and other active complexes Further reading 494
7 xvi Contents Appendix I: A consideration of atomic structure and bonding 509 A. 1 Atomic structure 509 A.2 Bonding between atoms 517 A.2.1 Ionic binding 517 A.2.2 Covalent bonding 518 A.2.3 Non-ideal character of bonds 521 A.2.4 Hydrocarbons and electron delocalization 522 A.3 Further reading 524 Appendix II: A simple guide to lymphocytes 525 Index 527
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