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Selective Toxicity
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Table of Contents

One: Topics of General Interest.- 1 Selectivity in the service of man.- 1.0 What is `Selectivity'?.- 1.1 Beneficial results from the use of selectivity toxic agents.- 1.2 The physical basis of selectivity: the three principles.- Steps in the correlation of structure with biological action.- 2.0 The earliest correlations.- 2.1 The concept of `receptors'. The receptor as part of an enzyme, permease, or other protein.- 2.2 The receptor as part of a nucleic acid.- 2.3 The receptor as a coenzyme or other small molecule.- 2.4 Reversibility, and other aspects of receptors.- 2.5 How a small change in a molecule can lead to a large change in biological properties.- 2.6 Correlations: Today's perspective.- 3 Comparative distribution: the first principle of selectivity.- 3.0 Examples of selectivity through distribution.- 3.1 How drugs are absorbed, distributed, and eliminated.- 3.2 The permeability of natural membranes.- 3.3 The significance of partition coefficients.- 3.4 Mechanisms that produce loss. Storage and elimination.- 3.5 Metabolic change as an early step in excretion. Synergism and antagonism.- 3.6 Metabolic change as an early step in activation. Pro-drugs.- 3.7 Quantitative aspects of distribution. Pharmacokinetics. 97 Sustained release.- Sustained release.- 4 Comparative biochemistry: the second principle of selectivity.- 4.0 Nucleic acids.- 4.1 Proteins.- 4.2 Analogous enzymes and coenzymes.- 4.3 Nitrogen and phosphorus metabolism.- 4.4 Carbohydrate and lipid metabolism.- 4.5 The tricarboxylic acid cycle, and electron transport.- 4.6 Photosynthesis.- 4.7 Hormones and pheromones.- 4.8 Metabolism of foreign substances.- 4.9 Quantitative aspects of comparative biochemistry.- 5 Comparative cytology: the third principle of selectivity.- 5.0 The variations of cell architecture.- 5.1 Cytological aspects of cancer therapy.- 5.2 Cytological aspects of immunotherapy.- 5.3 The cell wall.- 5.4 Sub-cellular architecture.- 5.5 Viruses.- 6 Chemotherapy: history and principles.- 6.0 The early history of chemotherapy.- 6.1 Ehrlich's fundamental contributions.- 6.2 Chemotherapeutic drugs available before 1935. The chemotherapeutic index.- 6.3 1935 and afterwards.- 6.4 Parallel developments in crop-protecting agents: agrochemicals.- 6.5 Resistance to drugs and other agents.- 6.6 Therapeutic interference.- 7 Pharmacodynamics.- 7.0 Pharmacodynamics and chemotherapy compared.- 7.1 Early history of the use of synthesis to find new drugs.- 7.2 Some common molecular patterns in pharmacodynamic drugs.- 7.3 Simplification of the structure of natural products.- 7.4 Recognition of the importance of measurement.- 7.5 How agonists and antagonists act on receptors.- 7.6 The natural divisions of pharmacodynamics.- The forces available for binding an agent. Chemical bonds. Adsorption.- 8.0 Types of chemical bonds.- 8.1 Adsorption.- 8.2 Non-biological aspects of selectivity.- Two: Studies, in Depth, of Topics from Part One.- 9 Anti-metabolites: antagonistic analogues of coenzymes and enzymic substrates.- 9.0 Enzymes.- 9.1 Anti-metabolites (antagonistic analogues): definition, derivation, and mode of action.- 9.2 History of analogue antagonism prior to 1940.- 9.3 The folic acid antagonists.- 9.4 Other metabolite analogues of proven value in prophylaxis and therapy.- 9.5 `Transition-state' inhibitors.- 9.6 Sequential blocking.- 9.7 Analogues that form a covalent bond.- 9.8 Special relationships between agonists and antagonists.- 9.9 Pharmacogenetics.- 10 Ionization.- 10.0 The nature of ionization.- 10.1 The ionization constant (Ka).- 10.2 Differences in ionization that can bring about selectivity.- 10.3 Substances that are more biologically active when ionized.- 10.4 Substances that appear to be less active when ionized.- 10.5 Substances of which both ion and molecule play a part in the biological action.- 10.6 The ionization of receptors.- 10.7 Conclusions.- 11 Metal-binding substances.- 11.0 Metals in the living cell.- 11.1 Biochemical differences that can assist selectivity.- 11.2 The chemistry of chelation.- 11.3 Quantitative treatment of metal binding.- 11.4 Chemical differences that can assist selectivity.- 11.5 The various modes of biological action of chelating agents (an introduction).- 11.6 Diminution, by chelation, of the toxic effect of a metal.- 11.7 Augmentation, by chelation, of the toxic effect of a metal.- 11.8 The tetracyclines.- 11.9 Substances whose biological action is at least partly due to chelation.- 11.10 The special case of robust complexes.- 11.11 Fundamental considerations in designing new chelating agents. Promising avenues of application.- 12 Steric factors.- 12.0 Some fundamental considerations.- 12.1 Optical isomerism.- 12.2 Geometrical isomerism.- 12.3 Conformational behaviour.- 12.4 Catecholamine receptors.- 12.5 Acetylcholinesterase.- 12.6 Acetylcholine receptors.- 12.7 The GABA receptor and the benzodiazepines.- 12.8 Morphine and the opioid receptors.- 12.9 Psychotherapeutic agents.- 12.10 Conclusion.- 13 The covalent bond in selective toxicity.- 13.0 Arsenicals, antimonials, and mercurials.- 13.1 The penicillins.- 13.2 Cephalosporins. Other ss-lactam inhibitors of the formation of new cell walls.- 13.3 Organic phosphates and carbamates.- 13.4 Alkylating agents.- 13.5 Lethal synthesis.- 13.6 Miscellaneous examples.- 14 Surface chemistry. The modification of membranes by surface-active agents.- 14.0 Surface phenomena in vitro.- 14.1 Surface phenomena and drug action. Diuretics. Cardiac glycosides.- 14.2 Ionophores.- 14.3 The injury of membranes by biologically active agents.- 14.4 The preservation of membranes by biologically active agents.- 15 Biological activity unrelated to structure.- 15.0 General biological depressants (hypnotics, general anaesthetics, and volatile insecticides).- 15.1 Mitotic disorganizers.- 16 The perfection of a discovery.- 15.0 Multiple regression analysis.- 15.1 Alternative methods.- 15.2 Steric considerations.- 17 Some numerical assistance.- 17.0 Table: Calculation of percentage ionized, given pH and pKa.- 17.1 Table and discussion: Fragmental constants and partition coefficients.- 17.2 Table and discussion: Electronic effects in molecules (Hammett and Taft sigma values).- 17.3 Table and discussion: Nuclear magnetic resonance.- 17.4 Searching the literature.- References.- Formula index.

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