Toxic Phosphorus Esters

Toxic Phosphorus Esters

Chemistry, Metabolism, and Biological Effects

1st Edition - January 1, 1960

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  • Author: Richard D. O'Brien
  • eBook ISBN: 9781483270937

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Description

Toxic Phosphorus Esters: Chemistry, Metabolism, and Biological Effects aims to become a source book on organophosphate research and show how the understanding of the events following organophosphate poisoning of animals can be understood in terms of events at the molecular level. The manuscript first offers information on nonenzymic reactions and the reaction with cholinesterase in vitro. Discussions focus on hydrolysis, isomerization, oxidation, phosphorylation of the enzyme, and selectivity for different cholinesterases. The text then examines enzymic degradation and activation in vitro, effects in mammals, and effects on isolated whole tissues. The publication ponders on the effects in insects and plants, including results of poisoning, metabolism, resistance, antagonism and synergism, and phytotoxicity. The text also reviews selective toxicity, as well as excretion and storage, metabolism, design of new selective compounds, and nature of the target. The manuscript is a dependable reference for readers interested in the composition, reactions, and effects of toxic phosphorus esters.

Table of Contents


  • Preface

    1. Introduction

    Plan of this Book

    History

    Nomenclature of Esterases and Organophosphates

    Structure of Cholinesterase

    Biological Significance of Cholinesterase

    References

    2. Nonenzymic Reactions

    Hydrolysis

    Effect of Substituents

    Site of Cleavage

    Secondary Hydrolysis

    Catalysis

    Isomerization

    Thiono-Thiolo Isomerization

    Cis-Trans Isomerism

    Methodology

    Transalkylation

    Oxidation

    Dehydrohalogenation

    Effects of Light

    References

    3. The Reaction with Cholinesterase in Vitro

    Phosphorylation of the Enzyme

    Kinetics

    Site

    The Relationship between Structure and Anticholinesterase Activity

    Protection from Inhibition

    Reversal of Inhibition (Reactivation)

    Spontaneous

    Induced

    "Aging"

    Selectivity for Different Cholinesterases

    Conclusion

    References

    4. Enzymic Degradation and Activation in Vitro

    Degradation

    Phosphatase Action

    Esterase and Amidase Action

    Insect Hydrolases

    Oxidative Degradation

    Activation

    Phosphoramidate Oxidation by Mammalian Tissues

    Phosphoramidate Oxidation by Insect Tissues

    Phosphorothionate Oxidation by Mammalian Tissues

    Phosphorothionate Oxidation by Insect Tissues

    Thioether Oxidation

    Triphenyl Phosphate Activation by Liver

    References

    5. Effects on Isolated Whole Tissues

    Ion Permeability

    Muscle Contraction

    Nerve Transmission

    Animals Other than Insects

    Insects

    References

    6. Effects in Mammals

    Results of Poisoning

    Symptoms

    Cause of Death

    Cholinesterase after Poisoning

    Acetylcholine after Poisoning

    Demyelination

    Mode of Administration

    Degrading Enzymes

    Protection and Therapy

    Antagonism to Acetylcholine

    Reversal of Inhibited Cholinesterase

    Raising of Esterase Levels

    Blockade of Cholinesterase

    Antagonism of Activating Enzymes

    Synergism ("Potentiation")

    Metabolism and Residues in Intact Animals

    Co-ral

    Diazinon

    Delnav

    Dimethoate

    Dipterex

    Malathion

    Parathion

    Phosdrin

    Ronnel (Viozene, Trolene, Dow ET14, Dow ET57)

    Systox

    Influence of Rumen Microorganisms

    References

    7. Effects in Insects

    Results of Poisoning

    Symptoms

    Inhibition of Cholinesterase

    Accumulation of Acetylcholine

    Other Effects; the Cause of Death

    Ovicidal Action

    Differential Toxicity

    Distribution

    Metabolism

    Hydrolysis

    Oxidation

    Dehydrochlorination

    Resistance

    Occurrence

    Cross Resistance

    Mechanisms of Resistance

    Antagonism and Synergism

    Antagonism

    Synergism

    References

    8. Effects in Plants

    Systemic Activity

    Metabolism

    Schradan

    Thioethers

    Sulfinylphenates

    Dimethoate

    Phosdrin

    Residues

    Phytotoxicity

    Dimefox

    Guthion

    Malathion

    Parathion

    Schradan

    TEPP

    References

    9. Selective Toxicity

    Absorption

    Excretion and Storage

    Metabolism

    Carboxyesters

    Other Selective Organophosphates

    Penetration to the Target

    Nature of the Target

    Design of New Selective Compounds

    References

    10. Techniques

    Radio Tracer Synthesis

    Exchange

    Preparation of the Intermediate

    Coupling

    Purification

    Product

    Analysis

    Extraction of Metabolites from Homogenates

    Separation and Identification of Solvent-Extractable Metabolites

    Separation of Solvent-Unextractable Metabolites

    Spectroscopy

    Ultraviolet Spectroscopy

    Infrared Spectroscopy

    Nuclear Magnetic Resonance

    Refractive Index

    Esterase Determinations

    Manometric Techniques

    Potentiometric Methods

    Spectrophotometric Methods

    References

    Appendix 1. Electronic Interpretations

    The Underlying Concepts

    The Inductive Effect

    Polarity

    Acidity and Basicity

    Reaction Rates

    The Field Effect

    The Mesomeric Effect

    Appendix 2. Structure of Organophosphates

    Author Index

    Subject Index

Product details

  • No. of pages: 446
  • Language: English
  • Copyright: © Academic Press 1960
  • Published: January 1, 1960
  • Imprint: Academic Press
  • eBook ISBN: 9781483270937

About the Author

Richard D. O'Brien

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