Biological Reactive Intermediates III: Mechanisms of Action in Animal Models and Human Disease

Front Matter....Pages i-xv
Years with Elizabeth and James Miller: in Appreciation....Pages 1-9
Reactivity and Tumorigenicity of Bay-Region Diol Epoxides Derived from Polycyclic Aromatic Hydrocarbons....Pages 11-30
Chemistry of Covalent Binding: Studies with Bromobenzene and Thiobenzamide....Pages 31-40
Role of Thiols in Protection Against Biological Reactive Intermediates....Pages 41-51
Role of Parenchymal Versus Non-Parenchymal Cells on the Control of Biologically Reactive Intermediates....Pages 53-61
Significance of Covalent Binding of Chemically Reactive Metabolites of Foreign Compounds to Proteins and Lipids....Pages 63-82
Structure and Function of Cytochrome P-450....Pages 83-94
Antibodies as Probes of Cytochrome P450 Isozymes....Pages 95-106
Age and Sex Differences in Constitutive Forms of Cytochrome P-450 of Rat Liver Microsomes....Pages 107-117
Identification of Intratissue Sites for Xenobiotic Activation and Detoxication....Pages 119-144
Monoclonal Antibody-Directed Analysis of Cytochrome P-450....Pages 145-154
Drug Interactions with Macrolide Antibiotics: Specificity of Pseudo-Suicide Inhibition and Induction of Cytochrome P-450....Pages 155-162
Isomeric Composition of N -Alkylated Protoporphyrins Produced by Substituted Dihydropyridines in Vivo and in Vitro ....Pages 163-170
UDP-Glucuronyltransferases and Their Toxicological Significance....Pages 171-184
Expression and Sequence Analysis of Rat Liver Glutathione S-Transferase Genes....Pages 185-193
Rat Cytosolic Epoxide Hydrolase....Pages 195-201
Multiplicity of Cytochrome P-450 in Morris Hepatoma....Pages 203-212
The Metabolism of Benzene and Phenol by a Reconstituted Purified Phenobarbital-Induced Rat Liver Mixed Function Oxidase System....Pages 213-222
Comparison of the Metabolism of Benzene and Its Metabolite Phenol in Rat Liver Microsomes....Pages 223-235
Further Evidence for a Role of Isozymes of P450 in the Metabolism and Toxicity of Carbon Disulfide (CS 2 )....Pages 237-242
Effect of a Suicide Substrate on the Metabolism of Steroids and Xenobiotics and on Cytochrome P-450 Apoproteins....Pages 243-251
Activation of Cytochrome P-450 Heme in Vivo ....Pages 253-261
The FAD-Containing Monooxygenase of Lung and Liver Tissue from Rabbit, Mouse and Pig: Species and Tissue Differences....Pages 263-272
Oxygen Radical Formation During Redox Cycling of Bleomycin-Fe(III) Catalyzed by NADPH-Cytochrome P-450 Reductase of Liver Microsomes and Nuclei....Pages 273-280
Superoxide Dismutase Modification and Genotoxicity of Transition-Metal Ion Chelators....Pages 281-290
Toxicologic Implications of the Iron-Dependent Activation of Bleomycin A 2 by Mouse Lung Microsomes....Pages 291-300
The Peroxidative Activation of Butylated Hydroxytoluene to BHT-Quinone Methide and Stilbenequinone....Pages 301-309
Activation of Xenobiotics by Human Polymorphonuclear Leukocytes via Reactive Oxygen-Dependent Reactions....Pages 311-321
Metabolism of Diehtylstilbestrol by Horseradish Peroxidase and Prostaglandin Synthase — Evidence for a Free Radical Intermediate....Pages 323-328
Thiyl Radicals--Their Generation and Further Reactions....Pages 329-335
Mechanism of the Cytochrome P-450 Catalyzed Isomerization of Hydroperoxides....Pages 337-346
Indole-3-carbinol Inhibits Lipid Peroxidation in Cell-Free Systems....Pages 347-356
Glutathione Peroxidase and Reactive Oxygen Species in TCDD-Induced Lipid Peroxidation....Pages 357-365
Activation of Nitrosamines to Mutagens by Rat and Rabbit Nasal, Lung and Liver S-9 Homogenates....Pages 367-372
Structure of the Adduct of Glutathione and Activated 3-Mathylindole....Pages 373-380
Studies on the Mechanism of S -Cysteine Conjugate Metabolism and Toxicity in Rat Liver, Kidney, and a Cell Culture Model....Pages 381-390
Formation and Identification of Naphthoquinone Glutathione Conjugates Following Microsomal Metabolism of 1-Naphthol....Pages 391-397
The Formation of N-Glucuronides Catalyzed by Purified Hepatic 17β-Hydroxysteroid and 3α-Hydroxysteroid UDP-Glucuronyltransferases....Pages 399-405
Improved Method for Determination of Cellular Thiols, Disulfides and Protein Mixed Disulfides Using HPLC with Electrochemical Detection....Pages 407-413
Arylsulfotransferase IV Catalyzed Sulfation of 1-Naphthalenemethanol....Pages 415-422
Activated Phase II Metabolites: Comparison of Alkylation by 1-0-Acyl Glucuronides and Acyl Sulfates....Pages 423-429
Reactions of Oxaprozin-1-0-Acyl Glucuronide in Solutions of Human Plasma and Albumin....Pages 431-441
Nephrotoxic Amino Acid and Glutathione S -Conjugates: Formation and Renal Activation....Pages 443-455
The Role of Glutathione in the Toxicity of Xenobiotic Compounds: Metabolic Activation of 1,2-Dibromoethane by Glutathione....Pages 457-467
A Comparison of the Alkylating Capabilities of the Cysteinyl and Glutathionyl Conjugates of 1,2-Dichloroethane....Pages 469-475
Covalent Reactions in the Toxicity of SO 2 and Sulfite....Pages 477-492
One- and Two-Electron Oxidation of Reduced Glutathione by Peroxidases....Pages 493-503
Reactive Oxygen Species Formed in Vitro and in Cells: Role of Thiols(GSH). Model Studies with Xanthine Oxidase and Horseradish Peroxidase....Pages 505-512
Active Oxygen and Toxicity....Pages 513-526
Studies on the Mechanism of Activation and the Mutagenicity of Ronidazole, a 5-Nitroimidazole....Pages 527-535
Carcinogen-DNA Adduct Formation as a Predictor of Metabolic Activation Pathways and Reactive Intermediates in Benzidine Carcinogenesis....Pages 537-549
Purification, Properties and Function of N-Hydroxyarylamine O- Acetyltransferase....Pages 551-561
Metabolism and Carcinogenicity of Nitrotoluenes....Pages 563-571
Hydroxylamines and Hemolytic Anemia....Pages 573-582
Electrophilic Sulfuric Acid Ester Metabolites as Ultimate Carcinogens....Pages 583-595
Biological Reactive Intermediates of Mycotoxins....Pages 597-610
Biological Reactive Intermediates of Pyrrolizidine Alkaloids....Pages 611-620
Mutagens and Carcinogens Formed During Cooking....Pages 621-629
Quinone Imines as Biological Reactive Intermediates....Pages 631-644
The Role of Reactive Intermediates in Sulfhydryl-Dependent Immunotoxicity: Interference with Microtubule Assembly and Microtubule-dependent Cell Function....Pages 645-655
Investigation of the Immunological Basis of Halothane-Induced Hepatotoxicity....Pages 657-673
Inhibition of RNA Synthesis in Mouse Macrophages and Lymphocytes by Benzene and Its Metabolites....Pages 675-690
p-Nitrosophenetole: A Reactive Intermediate of Phenacetin that Binds to Protein....Pages 691-696
Mechanism of Fasting-Induced Suppression of Acetaminophen Glucuronidation in the Rat....Pages 697-706
Effect of Diethyl Ether on the Bioactivation, Detoxification, and Hepatotoxicity of Acetaminophen in Vitro and in Vivo....Pages 707-715
Piperonyl Butoxide Reduces Salicylate-Induced Nephrotoxicity and Covalent Binding in Male Rats....Pages 717-726
Cross-Linking of Protein Molecules by the Reactive Metabolite of Acetaminophen, N -Acetyl- p -Benzoquinone Imine, and Related Quinoid Compounds....Pages 727-737
Acetaminophen as a Cosubstrate and Inhibitor of Prostaglandin H Synthase....Pages 739-747
The Fate of 4-Cyanoacetanilide in Rats and Mice: The Mechanism of Formation of a Novel Electrophilic Metabolite....Pages 749-753
Mechanistic Studies of Acetamide Hepatocarcinogenicity....Pages 755-762
Reactions of Glutathione with Oxidative Intermediates of Acetaminophen....Pages 763-772
Flavin-Containing Monooxygenase Activity in Human Liver Microsomes....Pages 773-779
S9-Dependent Activation of 1-Nitropyrene and 3-Nitrofluoranthene in Bacterial Mutagenicity Assays....Pages 781-788
Formation of a Ring-Opened Product from Benzene in a Hydroxyl Radical Generating System....Pages 789-795
H-2 Modulation of Aryl Hydrocarbon Hydroxylase Induction and the Mutagenicity of Benzo(a)Pyrene after 3-Methylcholanthrene Treatment....Pages 797-807
Stereoselectivity of Rat Liver Cytochrome P-450 Isozymes: Direct Determination of Enantiomeric Composition of K-Region Epoxides Formed in the Metabolism of Benz[A]Anthracene and 7,12-Dimethylbenz[A]Anthracene....Pages 809-818
Induction of Unscheduled DNA Synthesis in Human Mononuclear Leukocytes by Oxidative Stress....Pages 819-823
Deoxyguanosine Adducts Formed from Benzoquinone and Hydroquinone....Pages 825-832
3-Hydroxy- Trans -7,8-Dihydro-7,8-Dihydroxy-Benzo(a)Pyrene, a Metabolite of 3-Hydroxybenzo(a)Pyrene....Pages 833-842
Time Course of the Effect of 4-Hydroperoxycyclophosphamide on Limb Differentiation in Vitro....Pages 843-852
Hepatic Pathological Changes Due to Hydroxyalkenals....Pages 853-860
Clofibrate Selectively Induces Azoreduction of Dimethylaminoazobenzene (DAB) by Rat Liver Microsomes....Pages 861-870
Intracellular Dissipative Structures (IDS) as Ultimate Targets of Chemical Cytotoxicity....Pages 871-889
Helenalin: Mechanism of Toxic Action....Pages 891-896
Evidence for Stereoselective Production of Phenytoin (5,5-Diphenylhydantoin) Arene Oxides in Man....Pages 897-902
Tissue Distribution and Covalent Binding of [ 14 C]1,1-Dichloroethylene in Mice: In vivo and in vitro Studies....Pages 903-910
Inhibition of Respiration in Rabbit Proximal Tubules by Bromophenols and 2-Bromohydroquinone....Pages 911-917
 In Vitro Covalent Binding of 14 C-Mibolerone to Rat Liver Microsomes....Pages 919-924
Chemistry of Metabolites of Thioureas....Pages 925-929
Conversion of Phenytoin to Reactive Metabolites in Rat Liver Microsomes....Pages 931-939
Comparison of N-Methylformamide-Induced Hepatotoxicity and Metabolism in Rats and Mice....Pages 941-950
Epoxidation of 1,3-Butadiene in Liver and Lung Tissue of Mouse, Rat, Monkey and Man....Pages 951-957
Enzyme Catalysed Cleavage of the N-N Bond of N-Nitrosamines....Pages 959-970
Use of the Chemiluminigenic Probes Luminol and Lucigenin for the Detection of Active Oxygen Species in Hepatic Microsomes and in Intact Hepatocytes....Pages 971-980
Altered Expression of Oncogenes in Mouse Epidermis Following Exposure to Benzo(A)Pyrene Diol Epoxides....Pages 981-992
Acetaminophen Toxicity in Isolated Hepatocytes....Pages 993-1003
Mechanism of Organ Specificity in Nitrosamine Carcinogenesis....Pages 1005-1011
Biological Reactive Metabolites in Human Toxicity....Pages 1013-1016
Metabolic Host Factors as Modifiers of Reactive Intermediates Possibly Involved in Human Cancer....Pages 1017-1027
Closing Remarks....Pages 1029-1037
Back Matter....Pages 1039-1059