Toxic Phosphorus Esters - 1st Edition - ISBN: 9781483227740, 9781483270937

Toxic Phosphorus Esters

1st Edition

Chemistry, Metabolism, and Biological Effects

Authors: Richard D. O'Brien
eBook ISBN: 9781483270937
Imprint: Academic Press
Published Date: 1st January 1960
Page Count: 446
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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

Details

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

About the Author

Richard D. O'Brien