Ebook: Biological Reactive Intermediates VI: Chemical and Biological Mechanisms in Susceptibility to and Prevention of Environmental Diseases

This volume presents a discussion of the biological effects produced following the metabolism of xenobiotic chemicals to chemically reactive metabolites, i.e., toxic and carcinogenic effects, which have been the basis of all five earlier volumes in this series. In particular, this volume devotes sections to structure-activity relationships, recent advances in the understanding of the chemistry of reactive metabolites, and the generation and activity of reactive oxygen species with special emphasis on nitric oxide. There are also segments on DNA damage by reactive metabolites and DNA repair, tissue specific responses to BRIs, and human health effects of BRIs. The papers that comprise this volume were submitted by world class scientists who were in attendance at The Symposium on Biological Reactive Intermediates VI at the Université René Descartes, July 16-20, 2000.

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Content:
Front Matter....Pages i-xv
Biological Reactive Intermediates and Mechanisms of Cell Death....Pages 1-10
Structure Activity Relationships for the Chemical Behaviour and Toxicity of Electrophilic Quinones/Quinone Methides....Pages 11-21
Use of Structure-Activity Relationships for Probing Biochemical Mechanisms: Glutathione Transferase Zeta Conjugation of Haloacids....Pages 23-31
Structure Toxicity Relationships - How Useful Are They in Predicting Toxicities of New Drugs?....Pages 33-43
Biological Reactive Intermediates in Drug Discovery and Development....Pages 45-51
Bioactivation of Toxicants by Cytochrome P450-Mediated Dehydrogenation Mechanisms....Pages 53-62
New Aspects of DNA Adduct Formation by the Carcinogens Crotonaldehyde and Acetaldehyde....Pages 63-71
Mechanisms of Ovotoxicity Induced by Environmental Chemicals: 4-Vinylcyclohexene Diepoxide as a Model Chemical....Pages 73-81
Mutagenicity and Carcinogenicity of Biological Reactive Intermediate’s Derived from a “Non-Genotoxic” Carcinogen....Pages 83-92
Reactive Metabolites of 1,3-Butadiene: DNA and Hemoglobin Adduct Formation and Potential Roles in Carcinogenicity....Pages 93-103
Chemistry and Biological Activity of Novel Selenium-Containing Compounds....Pages 105-112
Formation and Fate of Reactive Intermediates of Haloalkanes, Haloalkenes, and ?-Haloacids....Pages 113-120
Human Epoxide Hydrolase is the Target of Germander Autoantibodies on the Surface of Human Hepatocytes: Enzymatic Implications....Pages 121-124
Structural Characterisation Of the Main Epichlorohydringuanosine Adducts....Pages 125-128
Adducts of the Chloroform Metabolite Phosgene....Pages 129-132
Oxygenation of Arachidonic Acid by Cyclooxygenases Generates Reactive Intermediates That Form Adducts with Proteins....Pages 133-137
Use of Isotopes and LC-MS-ESI-TOF for Mechanistic Studies of Tienilic Acid Metabolic Activation....Pages 139-144
Inhibition by Ticlopidine and Its Derivatives of Human Liver Cytochrome P450. Mechanism-Based Inactivation of CYP 2C19 by Ticlopidine....Pages 145-148
Microperoxidase 8 (MP8) as a Convenient Model for Hemoproteins: Formation and Characterisation of New Iron(II)-Nitrosoalkane Complexes of Biological Relevance....Pages 149-152
Hemoglobin Adducts in Rats Chronically Exposed to Room-Aged Cigarette Sidestream Smoke and Diesel Engine Exhaust....Pages 153-156
DNA Microarray Reveals Increased Expression of Thioredoxin Peroxidase in Thioredoxin-1 Transfected Cells and Its Functional Consequences....Pages 157-168
Reactive Nitrogen Species and Proteins: Biological Significance and Clinical Relevance....Pages 169-174
Bicarbonate Enhances Nitration and Oxidation Reactions in Biological Systems—Role of Reactive Oxygen and Nitrogen Species....Pages 175-182
Nitric Oxide and Peroxynitrite in Ozone-Induced Lung Injury....Pages 183-190
Antioxidant Reactions of Green Tea Catechins and Soy Isoflavones....Pages 191-197
Reactive Oxygen Species Analysis in Gastritis Patients and P53 Methylation Analysis in Gastric Tumor Cell Line Ags Infected by Helicobacter Pylori....Pages 199-202
Biological Reactive Intermediates that Mediate Chromium (VI) Toxicity....Pages 203-207
Involvement of Peroxynitrite on the Early Loss of P450 in Short-Term Hepatocyte Cultures....Pages 209-212
Lack of Correlation Between CYP2A6 Genotype and Smoking Habits....Pages 213-215
Free Radical Lipid Peroxidation and Monooxygenase Activity in Experimental Influenza Virus Infection after Treatment with Rimantadine....Pages 217-220
Oxidative Stress and the Structure/Activity Relationships of Ergopeptide Alkaloids....Pages 221-224
Multiple Oxidative Stress Parameters are Modulated in Vitro by Oxygenated Polycyclic Aromatic Hydrocarbons Identified in River Sediments....Pages 225-228
Hydrogen Peroxide Supports Hepatocyte P450 Catalysed Xenobiotic/Drug Metabolic Activation to form Cytotoxic Reactive Intermediates....Pages 229-232
NAD(P)H:Quinone Oxidoreductase (NQO1) Protects Astroglial Cells Against L-Dopa Toxicity....Pages 233-236
GSH-Dependent Redox Regulation and Antioxidant Enzymes in the Formation of Resistance to Doxorubicin in K562 Human Erythroleukemia Cells....Pages 237-240
Opposite Effects of Oxidative Stress on Endothelial Cell Lines (ECV 304 and Eahy 926) Interaction With Extracellular Matrix....Pages 241-244
Hepatocyte Lysis Induced by Environmental Metal Toxins May Involve Apoptotic Death Signals Initiated by Mitochondrial Injury....Pages 245-248
Quantification of F-Ring and D-/E-Ring Isoprostanes and Neuroprostanes in Alzheimer’s Disease....Pages 249-252
Preventive Effect of Vitamin E on the Processes of Free Radical Lipid Peroxidation and Monooxygenase Enzyme Activity in Experimental Influenza Virus Infection....Pages 253-256
Lysosomal Oxidative Stress Cytotoxicity Induced by Nitrofurantoin Redox Cycling in Hepatocytes....Pages 257-260
Scavenging and Antioxidant Effects of Estrogen Derivatives in Cholesterol-Fed Rabbits....Pages 261-265
Inhibition of Oxidative Damage of Red Blood Cells and Liver Tissue by Genistein-8C-Glucoside....Pages 267-270
Effects of Several Wine Polyphenols on Lipid Peroxidation and Oxygen Activation in Rat Liver Microsomes....Pages 271-274
Chromosome Damage from Biological Reactive Intermediates of Benzene and 1,3-Butadiene in Leukemia....Pages 275-278
The Antitumor Agent Ecteinascidin 743: Characterization of Its Covalent Dna Adducts and Chemical Stability....Pages 279-287
Design of DNA Damaging Agents that Hijack Transcription Factors and Block DNA Repair....Pages 289-299
The Potential Role of Topoisomerase II Inhibition in Hydroquinone-Induced Alterations in the Maturation of Mouse Myeloblasts....Pages 301-313
Design and Characterization of a Novel « Family-Shuffling » Technology Adapted to Membrane Enzyme: Application to P450s Involved in Xenobiotic Metabolism....Pages 315-318
One-Electron Reduction of Quinones by the Neuronal Nitric-Oxide Synthase Reductase Domain....Pages 319-322
Purification, Biochemical Characterization and Comparative Enzyme Kinetics of Recombinant Human CYP2D6 1 and CYP2D6 2 Variants....Pages 323-326
Inhibitory Effects of Roquefortine on Hepatic Cytochromes P450....Pages 327-330
Association of Cytochromes P450 1A2 and 2B4: are the Interactions between Different p450 Species Involved in the Control of the Monooxygenase Activity and Coupling?....Pages 331-334
Inactivation of Polymorphic Variants of Human Glutathione Transferase Zeta (hGSTZ1-1) by Maleylacetone and Fumarylacetone....Pages 335-338
Structure-Activity Relationships of Cyclotetrapeptides: Interaction of Tentoxin Derivatives with Three Membrane Proteins....Pages 339-342
Triazolam Substrate Inhibition....Pages 343-346
Effect of the Microsomal System on Quinone Redox Cycling, Oxygen Activation, and Lipid Peroxidation....Pages 347-350
Reaction of Nucleic Acids with Triformylmethane; A Novel Dna-Modifying Agent....Pages 351-354
Are Blood-brain Interfaces Efficient in Protecting the Brain from Reactive Molecules ?....Pages 355-358
The Roles of P-Glycoprotein and MRP1 in the Blood-Brain and Blood-Cerebrospinal Fluid Barriers....Pages 359-364
Are Dopamine, Norepinephrine, and Serotonin Precursors of Biologically Reactive Intermediates Involved in the Pathogenesis of Neurodegenerative Brain Disorders?....Pages 365-372
Serotonergic Neurotoxicity of Methylenedioxyamphetamine and Methylenedioxymetamphetamine....Pages 373-396
Caspase Cascades in Chemically-Induced Apoptosis....Pages 397-406
Spermatogenesis by Sisyphus: Proliferating Stem Germ Cells Fail to Repopulate the Testis after ‘Irreversible’ Injury....Pages 407-420
The Interaction of 1,4-Benzoquinone, a Bioreactive Intermediate of Benzene, with Three Proteins Essential for Differentiation/ Maturation of the Mouse Myeloid Stem Cell....Pages 421-428
Hematopoietic Stem and Progenitor Cells as Targets for Biological Reactive Intermediates....Pages 429-439
Metabolism of 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone (Nnk) in A/J Mouse Lung And Effect of Cigarette Smoke Exposure on in Vivo Metabolism to Biological Reactive Intermediates....Pages 441-449
Pharmacokinetics of Benzene Following an Oral or Intradermal Dose in FVB and Tg.AC Mice....Pages 451-454
Metabolism of the Food Mutagen 2-Amino-3,8-Dimethylimidazo[4,5-f]Quinoxaline in Human Hepatocytes....Pages 455-458
Preventive Effect of Selenium on T-2 Toxin Membrane Toxicity....Pages 459-462
Modulation Influence of p-Chloromercuribenzoate on Plasma Membrane Na+-Ca2+Exchanger of the Secretory Cells of Chironomus Larvae Salivary Gland....Pages 463-466
Tobacco Toxicology Revisited....Pages 467-470
Functional Genomics of Oxidant-Induced Lung Injury....Pages 471-478
Mitochondrial-Derived Oxidants and Quartz Activation of Chemokine Gene Expression....Pages 479-487
Quinoids as Reactive Intermediates in Estrogen Carcinogenesis....Pages 489-496
Assessing Underlying Mechanisms of Quinoid-Induced Hematopoietic Cell Toxicity....Pages 497-507
Structure of the Malondialdehyde Deoxyguanosine Adduct M1G When Placed Opposite a Two-Base Deletion in the (CpG)3 Frameshift Hotspot of the Salmonella Typhimurium hisd3052 Gene....Pages 509-512
A Sensitive Procedure for the Determination of Protein Bound 3,4-Dihydroxyphenyl-Alanine as a Marker for Posttranslational Protein Hydroxylation in Human Frontal Cortex, Liver, and Red Blood Cells....Pages 513-516
Reactive Metabolite Screen for Reducing Candidate Attrition in Drug Discovery....Pages 517-519
Metabolism of R,S Enantiomers of 3-Phenylamino-1,2-Propanediol, a Compound Associated with the Toxic Oil Syndrome, in C57BL/6- and A/J-Strain Mice....Pages 521-524
Cytochrome P450-Catalysed Irreversible Binding Examined in Precision-Cut Adrenal Slice Culture....Pages 525-529
Elevation of Glutathione Levels by Coffee Components and Its Potential Mechanisms....Pages 531-534
Inhibition of Carcinogenesis and Toxicity by Dietary Constituents....Pages 535-539
Modelling the Responses to Biological Reactive Intermediates....Pages 541-550
Interindividual Differences in Response to Chemoprotection Against Aflatoxin-Induced Hepatocarcinogenesis: Implications for Human Biotransformation Enzyme Polymorphisms....Pages 551-558
Sequestration of Biological Reactive Intermediates by Trapping as Covalent Enzyme-Intermediate Complex....Pages 559-576
Chemoprotection and Interindividual Differences in Response to Biological Reactive Intermediates....Pages 577-586
Oxidative Stress, Glucose-6-Phosphate Dehydrogenase and the Red Cell....Pages 587-594
Hepatocarcinogenesis in the Context of Strain Differences in Energy Metabolism Between Inbred Strains of Mice (C57BL/6J and C3H/He)....Pages 595-605
Characterization of hOGG1 Promoter Structure, Expression During Cell Cycle and Overexpression in Mammalian Cells....Pages 607-611
Proinflammatory Cytokines mRNA Expression in Dependence of Suppressive Epitope of Retroviral Transmembrane p15E Peptide Activation at Multiple Sclerosis Patients....Pages 613-616
Determination of Nucleotide Excision Repair Capacity of Liver Cells in Vivo and in Vitro by a Cell-Free Assay....Pages 617-620
Dietary Induction of Phase II Enzymes: A Promising Strategy for Protection Against DNA-Reactive Intermediates in Man?....Pages 621-624
Concurrent Flavin-Containing Monooxygenase Down Regulation and Cytochrome P450 Induction by Dietary Indoles in the Rat: Implication for Drug-Drug Interactions....Pages 625-628
Reactive Intermediates in Biological Systems: What Have We Learned and Where Are We Going?....Pages 629-633
The Role of Toxicological Science in Risk Assessment and Risk Management....Pages 635-638
Covalent Binding of Chemical Residues: Health Impact....Pages 639-650
Identification of Hepatic Protein Targets of the Reactive Metabolites of the Non-hepatotoxic Regioisomer of Acetaminophen, 3’-Hydroxyacetanilide, in the Mouse in Vivo Using Two-Dimensional Gel Electrophoresis and Mass Spectrometry....Pages 651-656
Exocyclic DNA Adducts as Secondary Markers for Oxidative Stress: Applications in Human Cancer Etiology and Risk Assessment....Pages 657-661
Dose Dependent Induction of DNA Adducts, Gene Mutations, and Cell Proliferation by the Antiandrogenic Drug Cyproterone Acetate in Rat Liver....Pages 663-673
Dose-Dependent Differences in the Profile of Mutations Induced by Carcinogenic (R,S,S,R) Bay-and Fjord-Region Diol Epoxides of Polycyclic Aromatic Hydrocarbons....Pages 675-686
Nucleic Acid Microarray Technology For Toxicology: Promise And Practicalities....Pages 687-696
Use of Covalent Binding in Risk Assessment....Pages 697-707
Back Matter....Pages 709-714
....Pages 715-722