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Environment, Chemistry, and metabolism

1st Edition - January 1, 1978

Editor: Harry Gelboin

Hardback ISBN:

9 7 8 - 0 - 1 2 - 2 7 9 2 0 1 - 4

eBook ISBN:

9 7 8 - 0 - 3 2 3 - 1 5 0 5 6 - 9

Polycyclic Hydrocarbons and Cancer, Volume 1: Environment, Chemistry, and Metabolism brings together information from many diverse disciplines in the environmental, chemical,… Read more

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Polycyclic Hydrocarbons and Cancer, Volume 1: Environment, Chemistry, and Metabolism brings together information from many diverse disciplines in the environmental, chemical, biological, and medical sciences to provide a comprehensive account of the link between polycyclic aromatic hydrocarbons (PAHs) and cancer. This volume consists of 19 chapters divided into seven sections based on the following themes: Energy Sources; Environmental Occurrence and Monitoring; Tobacco Carcinogenesis; Chemistry, Carcinogenicity, and Theory; Metabolism and Activation; Enzymology; and Pharmacokinetics. The first three chapters focus on the energy sources, occurrence and surveillance, and environmental monitoring of PAHs. The discussion then turns to the link between smoking and cancer; the carcinogenicity of 5-methylchrysene; synthesis and reactions of diol epoxides and related metabolites of carcinogenic hydrocarbons; and enzymes of oxygenation. The final chapter is devoted to the pharmacokinetics of chemically reactive metabolites. This book will be of interest to investigators and educators concerned with scientific aspects of PAH research; government officials and elected representatives as well as industry leaders who must confront and solve the problems related to PAHs; and others in various fields such as chemistry, environmental science, biochemistry and enzymology, pharmacology, molecular and cell biology, and genetics.

List of Contributors

Preface

In Memoriam, Madame Pascaline Daudel

Contents of Volume 2

Part I Energy Sources

1 Energy Sources of Polycyclic Aromatic Hydrocarbons

I. Introduction

II. Petroleum

III. Coal

IV. Oil Shale

V. Conclusions, Comparisons, Comments

References

Part II Environment: Occurrence and Monitoring

2 Occurrence and Surveillance of Polycyclic Aromatic Hydrocarbons

I. Introduction

II. Occurrence of Polycyclic Aromatic Hydrocarbons

III. Contamination of Food and Water Supplies

IV. Surveillance Methods

V. Conclusion

References

3 Analytical Methods for Monitoring Polycyclic Aromatic Hydrocarbons in the Environment

I. Introduction

II. Multiple PAH Analysis

III. Major Component Analysis

IV. Benzo[a]pyrene Analysis

V. Application of the Analytical Methods to Environmental Survey

References

Part III Tobacco Carcinogenesis

4 Tobacco Carcinogenesis

I. Introduction

II. Some Epidemiological Observations

III. Characteristics of Tobacco Smoke

IV. Bioassays

V. Identification of Tumorigenic Agents

VI. Reduction of Tumorigenicity

VII. The Less Harmful Cigarette

VIII. Summary

References

5 On the Carcinogenicity of 5-Methylchrysene: Structure-Activity Studies and Metabolism

I. Introduction

II. Results and Discussion

III. Summary

References

Note Added in Proof

Part IV Chemistry, Carcinogenicity, and Theory

6 Synthesis and Reactions of Diol Epoxides and Related Metabolites of Carcinogenic Hydrocarbons

I. Introduction

II. Synthesis of Arene Dihydrodiols

III. Synthesis of Arene Tetrahydrodiols

IV. Synthesis and Characterization of Arene Diol Epoxides

V. Specific Synthetic Procedures

VI. Resolution of Dihydrodiols and the Synthesis of Optically Active Diol Epoxides

VII. Reactions of Arene Diol Epoxides

References

Note Added in Proof

7 Synthesis of Carbon-13-Labeled Benzo[a]pyrene Derivatives

Text

References

8 The Bay-Region Theory of Carcinogenesis by Polycyclic Aromatic Hydrocarbons

I. Introduction

II. Formulation of the Bay-Region Theory

III. A Quantum Mechanical Basis for the Bay-Region Theory

IV. Evidence in Support of the Bay-Region Theory

V. Conclusion

References

Note Added in Proof

9 Mutagenicity and Carcinogenicity of Benzo[a]Pyrene and Benzo[a]Pyrene Derivatives

I. Introduction

II. Mutagenesis

III. Carcinogenesis

References

Note Added in Proof

Part V Metabolism and Activation

10 Benzoftfjpyrene Metabolism: Activation and Detoxification

I. Introduction

II. Benzo[a]Pyrene Metabolism

III. Enzymes of Polycyclic Aromatic Hydrocarbon Metabolism

IV. Assays for Polycyclic Aromatic Hydrocarbon Metabolism

References

11 Distribution and Excretion of the Hydrocarbon 3-Methylcholanthrene in the Animal Body

I. Introduction

II. Distribution of 3-Methylcholanthrene in Mice

III. Metabolism of 3-Methylcholanthrene in Organs

IV. Metabolism of 3-Methylcholanthrene in Perfused Rat Liver

V. 3-Methylcholanthrene Metabolites in the Excreta

VI. Distribution and Metabolism of 3-Methylcholanthrene in Fetal Mice

VII. Tissue Susceptibility and Accumulation of 3-Methylcholanthrene

References

12 Electron Spin Resonance Study of the Binding of the 6-Oxybenzo[a]Pyrene Radical and Benzo[a]Pyrene-Semiquinone Radicals with DNA and Polynucleotides

I. Introduction

II. Binding of 6-Oxy-BP Radical with DNA and Polynucleotides

III. Binding of BP-Semiquinone Radicals with DNA and Polynucleotides

IV. Summary

References

13 Benzo[a]Pyrene Metabolism: One-Electron Pathways and the Role of Nuclear Enzymes

I. One-Electron Redox Cycles Involving Benzo[a]Pyrene Quinone Metabolites

II. Benzo[a]Pyrene Metabolism in Liver Nuclei from Female Rats

References

14 Hydrocarbon-Nitrosamine Pulmonary Syncarcinogenesis: Reciprocal Effects on Metabolism

I. Introduction

II. Working Hypothesis

III. Materials and Methods

IV. Results

V. Conclusions

References

Part VI Enzymology

15 The Role of Cytochrome P-450 and the Microsomal Electron Transport System: The Oxidative Metabolism of Benzo[a]Pyrene

I. Introduction

II. Microsomes

III. Microsomal Electron Transport Reactions

IV. Studies Related to the Organization of Microsomal Electron Transport Carriers within the Microsomal Membrane

V. The Cyclic Function of Cytochrome Ρ-450

VI. The Oxidative Metabolism of Benzo[a]Pyrene

VII. Substrate Orientation: A General Hypothesis

VIII. Conclusion

References

16 Enzymes of Oxygenation

I. Introduction

II. Classification of Oxygenases

III. Dioxygenases

IV. Monooxygenases

V. Electronic Structure of Cytochrome Ρ-450

References

17 Biochemical Studies on Chemical Carcinogenesis: Role of Multiple Forms of Liver Microsomal Cytochrome P-450 in the Metabolism of Benzo[a]pyrene and Other Foreign Compounds

I. Introduction

II. Experimental Procedures

III. Results and Discussion

IV. Summary

References

18 Affinity Chromatography of Microsomal Enzymes and Interaction of Activated Estrogens with Nucleic Acids

I. Introduction

II. Materials and Methods

III. Results and Discussion

References

Part VII Pharmacokinetics

19 Pharmacokinetic Aspects of the Formation and Inactivation of Chemically Reactive Metabolites

I. Introduction

II. Pharmacokinetics of a Single Reactive Metabolite Reacting with a Single Pool of DNA

ΠΙ. Pharmacokinetics of Covalent Binding of Reactive Metabolites in Several Tissues

IV. Application of Pharmacokinetic Principles to in Vitro Experiments

References

Subject Index