TMPD.- 22.6 Autoxidation of DMPD and TMPD and the influence of superoxide radicals.- 22.7 Reactions of the TMPD radical cation with GSH.- 22.8 Reactions of TMPD with red cells.- 22.9 Arylamine-induced ferrihaemoglobin formation from oxyhaemoglobin: possible reaction mechanisms.- 22.10 Reactions of arylaminyl radical cations with sulphydryl groups.- 22.11 Conclusions.- References.- 23 Relevance of primary and secondary nitroxide radicals in biological oxidations.- 23.1 Introduction.- 23.2 Primary aromatic nitroxides.- 23.3 Secondary aromatic nitroxides.- 23.4 Conclusions.- References.- 24 Molecular approaches to evaluation of the risk of aromatic amineinduced bladder cancer: smoking related carcinogen-DNA adducts in biopsied samples of human urinary bladder.- 24.1 Introduction.- 24.2 32P-postlabelling.- 24.3 Sampling of human bladder for 32P-postlabeIling analysis.- 24.4 Carcinogen-DNA adducts in human urinary bladder.- 24.5 Conclusions.- References.- 25 The role of N-oxidation by leukocytes in drug-induced agranulocytosis and other drug hypersensitivity reactions.- 25.1 Introduction.- 25.2 Metabolism of drugs by leukocytes and adverse reactions.- 25.3 Conclusions.- References.- 26 Phototoxic effects of N-oxidized drugs and related compounds.- 26.1 Introduction.- 26.2 Photobiological reactions of nitroarenes.- 26.3 Photobiological reactions of imino-N-oxides.- 26.4 Conclusions.- References.
Text of Note
One Analysis of N-Oxidized Products.- 1 Formation of aromatic amine free radicals by prostaglandin hydroperoxidase and peroxyl radicals: analysis by ESR and stable end products.- 1.1 Introduction.- 1.2 Metabolism of aromatic amines.- 1.3 Mechanism for the N-dealkylation of N-substituted amines.- 1.4 A new mechanism for the oxidation of amines.- 1.5 Conclusions.- References.- 2 The application of 15N-NMR in the analysis of N-oxygenated amidines and guanidines.- 2.1 Introduction.- 2.2 Technical aspects of measuring 15N-NMR spectra.- 2.3 Analysis of various classes of N-oxidized compounds.- 2.4 Conclusions.- References.- 3 Radioimmunoassay and other methods for trace analysis of N-oxide compounds.- 3.1 Introduction.- 3.2 Defining the problem.- 3.3 Techniques available for the qualitative and quantitative analysis of intact N-oxides.- 3.4 Conclusions.- References.- Two Enzymology of N-Oxidation.- 4 Mechanism, multiple forms and substrate specificities of flavincontaining mono-oxygenases.- 4.1 Introduction.- 4.2 Multiple forms.- 4.3 Mechanism.- 4.4 Specificity.- 4.5 Inhibitors.- References.- 5 On the genetic polymorphism of the flavin-containing monooxygenase.- 5.1 Introduction.- 5.2 Factors providing indirect evidence of the existence of multiple FMO forms.- 5.3 Factors providing direct evidence of the existence of multiple FMO forms.- 5.4 Conclusions.- References.- 6 Factors regulating the activity of the rabbit lung flavincontaining mono-oxygenase.- 6.1 Introduction.- 6.2 Purification and distinct properties of rabbit lung FMO.- 6.3 Regulation of maternal and fetal rabbit lung FMO during pregnancy.- 6.4 Diurnal regulation of rabbit FMO.- 6.5 Phospholipid binding to lung FMO and modulation of activity.- 6.6 Inhibition of FMO by tannic acid.- 6.7 Conclusions.- References.- 7 Human pharmacogenetics of nitrogen oxidations.- 7.1 Introduction.- 7.2 Human pharmacogenetics.- 7.3 Nitrogen oxidations.- 7.4 Primary trimethylaminuria: a pharmacogenetic phenomenon of nitrogen oxidation.- 7.5 Secondary trimethylaminurias: the consequence of reduced N-oxidation capacity.- 7.6 Implications of reduced N-oxidation capacity on the metabolism of other xenobiotics.- References.- 8 Microbial N-hydroxylases.- 8.1 Introduction.- 8.2 Studies on Aerobacter aerogenes 62-1.- 8.3 Studies on aerobactin biosynthesis encoded on pCoIV plasmids.- 8.4 Studies with Gram-positive bacteria.- 8.5 Studies on fungi.- References.- 9 Roles of aminium radical intermediates in the biotransformation of dihydropyridines, cycloalkylamines, and N,N-dimethylanilines by cytochrome P-450 enzymes.- 9.1 Introduction.- 9.2 Formation of N-O compounds.- 9.3 Ring expansion of a cyclobutylamine.- 9.4 Oxidation of dihydropyridines.- 9.5 Estimation of the oxidation potential of the active oxygenating species of P-450.- References.- 10 The role of cytochrome P-450 in the biological nuclear N-oxidation of aminoazaheterocyclic drugs and related compounds.- 10.1 Introduction.- 10.2 Observations of metabolic N-oxidation of aminoazaheterocycles.- 10.3 Enzymology of nuclear N-oxidation of aminoazaheterocycles.- 10.4 Factors involved in the N-oxidation of aminoazaheterocycles.- 10.5 Substrate-enzyme complex formation.- 10.6 Conclusions.- References.- 11 New aspects of the microsomal N-hydroxylation of benzamidines.- 11.1 Introduction.- 11.2 Aspects of metabolic investigations with amidines.- 11.3 Microsomal N-hydroxylation of N,N-unsubstituted benzamidines.- 11.4 Structure-activity relationships and mechanisms of the N-oxidative metabolism of amidines.- 11.5 Predictability of N-oxygenations by cytochrome P-450 derived from studies on amidines.- 11.6 Further transformations of benzamidoxime and benzamidine.- 11.7 Pharmacological properties of N-oxygenated metabolites.- 11.8 Genotoxic activities of benzamidoxime.- References.- 12 Studies on the N-oxidation of phentermine: evidence for an indirect pathway of N-oxidation mediated by cytochrome P-450.- 12.1 Introduction.- 12.2 Biochemical studies with microsomes.- 12.3 Biochemical studies with reconstituted systems.- 12.4 Superoxide-mediated reactions: possible mechanisms.- 12.5 Conclusions.- References.- 13 Molecular activation mechanisms involved in arylamine cytotoxicity: peroxidase products.- 13.1 Introduction.- 13.2 Enzymic mechanisms of acetaminophen bioactivation and cytotoxicity.- 13.3 Bioactivation of acetaminophen and aminophenol in hepatocytes in the presence of halides.- 13.4 Conclusions.- References.- Three Reductions and Conjugations of N-Oxygenated Compounds.- 14 Reduction and conjugation reactions of N-oxides.- 14.1 Introduction.- 14.2 Further transformations of N-oxides.- 14.3 Conclusions.- References.- 15 In vivo metabolism of N-oxides.- 15.1 Introduction.- 15.2 In vivo metabolism of tricyclic antidepressant N-oxides.- 15.3 In vivo metabolism of chlorpromazine N-oxide.- 15.4 Comparison of studies involving amitriptyline N-oxide and chlorpromazine N-oxide.- 15.5 Conclusions.- References.- 16 Purification and characterization of rat hepatic acetyltransferase.- 16.1 Introduction.- 16.2 Enzymes responsible for formation of reactive N-acetoxyarylamine metabolites.- 16.3 Conclusion.- References.- Four Bioactivation of Nitrogenous Compounds and Cell Toxicity.- 17 Metabolism and activation of nitrosamines catalysed by cytochrome P-450 isoenzymes.- 17.1 Introduction.- 17.2 Enzymology of NDMA metabolism.- 17.3 Kinetics and mechanisms of NDMA metabolism.- 17.4 The role of cytochrome P450IIE1 in the activation of NDMA.- 17.5 Regulation and functions of cytochrome P450IIE1.- 17.6 Substrate specificity and alkyl group selectivity in the metabolism of other nitrosamines.- 17.7 Metabolism of 4-(N-nitrosomethylamino)-1-(3-pyridyl)- 1-butanone (NHK).- 17.8 Organ specificity in nitrosamine metabolism and carcinogenesis.- References.- 18 Cytochrome P-450-catalysed activation of carcinogenic aromatic amines and amides.- 18.1 Introduction.- 18.2 AAF N-hydroxylation by liver microsomes.- 18.3 N-Hydroxylation of various aromatic amides.- 18.4 N-Oxidation of aromatic amines.- 18.5 Kinetic studies with microsomal preparations.- 18.6 Resolution and reconstitution of the cytochrome P-450 enzyme system.- 18.7 Conclusions.- References.- 19 Comparative biochemistry of cytochrome P-450 species responsible for the activation of mutagenic food-derived heterocyclic amines.- 19.1 Introduction.- 19.2 Activation of mutagenic food-derived heterocyclic amines by liver microsomes.- 19.3 Activation of mutagenic heterocyclic amines by human fetal liver cytochrome P-450.- 19.4 Purification and properties of P-450-D2 and P-450-D3 from liver microsomes of PCB (KC-500) treated dogs.- 19.5 Molecular cloning and expression of dog liver cytochrome P-450.- 19.6 Molecular cloning and expression of monkey liver cytochrome P-450.- 19.7 Conclusions.- References.- 20 Specificity and inducibility of cytochrome P-450 catalysing the activation of food-derived mutagenic heterocyclic amines.- 20.1 Introduction.- 20.2 The role of the P-450IA subfamily in the activation of food mutagens and other aromatic amines in various species.- 20.3 Conclusions.- References.- 21 Monoamine oxidase-mediated activation of MPTP and related compounds.- 21.1 Introduction.- 21.2 MPTP and Parkinson's disease.- 21.3 MAO B and MPTP.- 21.4 The mechanism of MPTP toxicity.- 21.5 Analogues of MPTP as substrates for MAO A and B.- 21.6 Other routes of MPTP metabolism.- 21.7 MAO B in human brain and platelets.- 21.8 Isatin, an endogenosus MAO B inhibitor.- 21.9 Effects of (-)deprenyl on longevity and Parkinson's disease.- References.- 22 Activation of aromatic amines by oxyhaemoglobin.- 22.1 Introduction.- 22.2 Formation of ferrihaemoglobin by aromatic amines.- 22.3 Fate of TMPD in the reaction with haemoglobin.- 22.4 Formation of ferrihaemoglobin by the N,N-dimethyl- and N,N,N' ,N'-tetramethyl-p-phenylenediamine radical cations.- 22.5 Influence of superoxide radicals and hydrogen peroxide on ferrihaemoglobin formation by DMPD and