Mechanisms of carcinogenicity of aryl hydrazines, aryl hydrazides, and arenediazonium ions

Journal of Environmental Pathology, Toxicology and Oncology

Volumn 21, Issue 1, 2002, Pages 1-31

  Powell, Jeannine H ^a   Gannett, Peter M ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

Arenediazonium ion; Aryl hydrazines; Carcinogenesis; DNA adducts; DNA damage; DNA repair; ESR; Free radicals; Genotoxicity; Mutagenicity

Indexed keywords

DIAZONIUM COMPOUND; FREE RADICAL; HYDRAZIDE; HYDRAZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; BIOCHEMISTRY; CARCINOGENESIS; CARCINOGENICITY; CHEMISTRY; DNA ADDUCT; DNA DAMAGE; DNA REPAIR; ELECTRON SPIN RESONANCE; ENZYME ACTIVATION; GENOTOXICITY; METABOLISM; MUTAGENICITY; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL;

EID: 0036206954     PISSN: 07318898     EISSN: None     Source Type: Journal    
DOI: 10.1615/jenvironpatholtoxicoloncol.v21.i1.10     Document Type: Article

References (147)

1. Chemical carcinogenesis: Mechanisms and approaches to its control
2. Theory of tumour initiation by chemical carcinogens: Dependence of activity on structure of ultimate carcinogen
3. Organotropic carcinogenic effects of 65 various N-nitroso-compounds on BD rats
4. The relationship between mutagenicity and carcinogenicity of some nitrosoamines
5. Genotoxicity of a variety of hydrazine derivatives in the hepatocyte primary culture/DNA repair test using rat and mouse hepatocytes
6. Synthetic and naturally occurring hydrazines as possible cancer causative agents
7. 2-γ-glutamyl-4-carboxyphenylhydrazine of Agaricus bisporus in mice
8. The relationship of isoniazid (INH) and allied compounds to carcinogenesis in some species of small laboratory animals: A review
9. Genetic effects of hydralazine
10. Biochemical toxicology of hydrazines
11. A new way to carcinogenicity of azo dyes: The benzenediazonium ion formed from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomal enzymes binds to deoxyguanosine residues of DNA
12. A review of the natural occurrence, synthetic production and use of carcinogenic hydrazines and related chemicals
13. Unusual occupational toxins
14. Early intermediates in hydrazine oxidations, hydrazine cation radicals, hydrazyls, diazenium cations
15. In vivo formation of sigma-methyl and sigma-phenylferric complexes of hemoglobin and liver-cytochrome P-450 upon treatment of rats with methyl and phenylhydrazine
16. The reaction of phenylhydrazine with microsomal cytochrome P-450
17. Effect of 2-chloroethylnitrosoureas on plasmid DNA including formation of strand breaks and interstrand cross-links
18. Aryl radical formation during the metabolism of arylhydrazines by microsomes
19. 2-by the interaction of the hemolytic agent, phenylhydrazine, with human hemoglobin
20. Phenyl radical production during the oxidation of phenylhydrazine and in phenylhydrazine-induced haemolysis
21. The mechanism of superoxide anion generation by the interaction of phenylhydrazine with hemoglobin
22. Irreversible inhibition of soybean lipoxygenase by phenyldiazene, autoxidizing phenylhydrazine and related materials
23. Different patterns of mutagenicity of arenediazonium ions in V79 cells and Salmonella typhimurium TA 102: Evidence for different mechanisms of action
24. Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical
25. Reductive arylation of electron-deficient olefins: 4-(4-chlorophenyl)butan-2-one
26. Reactions of aryl diazonium salts and arylazo alkyl ethers in basic alcoholic solvents. Steric and mechanistic studies
27. Polycondensation of mercaptobenzenediazonium salts
28. 1-Aryl-3,3-dialkyltriazenes as tumor inhibitors
29. Reactions of benzenediazonium ions with guanine and its derivatives
30. Reactions of benzenediazonium ions with adenine and its derivatives
31. 8-Arylguanine adducts from arenediazonium ions and DNA
32. Formation of C8-aryladenine adducts from arenediazonium ions and DNA
33. 8-aryladenine formation in calf thymus DNA from arenediazonium ions
34. In vivo rat hemoglobin thiyl free radical formation following administration of phenylhydrazine and hydrazine based drugs
35. Detection of free radical metabolite formation using in vivo EPR spectroscopy: Evidence of rat hemoglobin thiyl radical formation following administration of phenylhydrazine
36. Activation of AP-1 through the MAP kinase pathway: A potential mechanism of the carcinogenic effect of arenediazonium ions
37. Determination of base sequence in nucleic acids with the electron microscope. II. The reaction of a guanine-selective marker with the mononucleotides
38. Substitution of pand o-hydroxyphenyl radicals at the 8 position of purine nucleosides by reaction with mutagenic pand o-diazoquinones
39. A free radical mediated cooxidation of tetramethylhydrazine by prostaglandin hydroperoxidase
40. An electron spin resonance study of a novel radical cation produced during the horseradish peroxidase-catalyzed oxidation of tetramethylhydrazine
41. Isolation of 9,9′-bis-9-azabicyclo[3.3.1]nonane radical cation hexafluorophosphate and its reversible oxidation to the dication
42. The electron spin resonance study of free radicals formed during the arachidonic acid cascade and cooxidation of xenobiotics by prostaglandin synthase
43. Free radical metabolism of hydralazine. Binding and degradation of nucleic acids
44. Enzymatic activation of hydrazine derivatives. A spin-trapping study
45. The in vitro metabolism of hydralazine
46. The oxidative metabolism of hydralazine by rat liver microsomes
47. Monosubstituted diazenes (diimides). Surprising intermediates
48. The interactions of hydrazine derivatives with rat-hepatic cytochrome P-450
49. Structure and absolute stereochemistry of the four N-phenylprotoporphyrin IX regioisomers isolated from phenylhydrazine-treated myoglobin
50. Nitrogen-15 nuclear magnetic resonance studies of benzenediazonium ions. Effects of solvent, substituent, anion and 18-crown-6
51. Evidence of a hydrazinereactive group at the active site of the nonheme portion of horseradish peroxidase
52. Inactivation of catalase byphenylhydrazine
53. Possible role of free radical intermediates in hepatotoxicity of hydrazine derivatives
54. Generation of superoxide radicals by hydrazine. Its role in phenylhydrazine-induced hemolytic anemia
55. Metabolism of arylhydrazines by cytochrome P-450 mixed function oxidases and prostaglandin(H)synthase from mouse lungs
56. Metabolism of arylhydrazines by mouse liver mixed-function oxidases in vitro
57. Substituent effects in the polarography of aromatic diazonium salts
58. Isolation and structure of agaritine, a (gamma)-glutamyl-substituted arylhydrazine derivative from Agaricaceae
59. Structure and enzymatic cleavage of agaritine, a phenylhydrazide of L-glutamic acid isolated from Agaricaceae
60. Antibiotics from Basidiomycetes evidence for the occurrence of the 4-hydroxybenzenediazonium ion in the extracts of Agaricus xanthodermus Genevier (Agaricales)
61. Tumorigenicity of tetramethylhydrazine hydrochloride in Swiss mice
62. Diazenes. I. Decarboxylation of phenyldiazenecarboxylic acid
63. Diazenes. II. Preparation of phenyldiazene
64. Diazenes. III. Properties of phenyldiazene
65. DNA strand scission by the carbon radical derived from 2-phenylethylhydrazine metabolism
66. DNA alterations induced by the carbon-centered radical derived from the oxidation of 2-phenylethylhydrazine
67. Mechanism of site-specific DNA damage induced by methylhydrazines in the presence of copper (II) or manganese (III)
68. DNA strand breakage by hydroxyphenyl radicals generated from mutagenic diazoquinone compounds
69. Synthesis and reaction of 4′-hydroperoxynucleosides. A model for oxidative degradation of DNA by action of bleomycins
70. Cleavage of DNA resulting from exposure to phenyl radicals
71. DNA strand breaking by the carbon-centered radical generated from 4-(hydroxymethyl)benzene diazonium salt, a carcinogen in mushroom Agaricus bisporus
72. Free radical production and site-specific DNA damage induced by hydralazine in the presence of metal ions or peroxidase/hydrogen peroxide
73. Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines: Non-Fenton-type hydroxyl radical formation
74. Novak RE Hydrazine mediated DNA damage: Role of hemoprotein, electron transport, and organic free radicals
75. On the reaction of mononucleotides with diazonium salts
76. Selective deamination of nucleosides by 2,4-dinitrophenylhydrazine
77. Calf thymus DNA with hydrazine and 2,4-dinitrophenylhydrazine
78. Chemical determination of free radical-induced damage to DNA
79. Evidence for an unstable DNA adduct from N-nitroso-N-methylaniline
80. Influences of alkyl groups on the rates of decomposition of N-nitrosoureas in basic aqueous solutions
81. Synthesis and miscoding specificity of oligodeoxynucleotide containing 8-phenyl-2′-deoxyguanosine
82. 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G → T and A → C substitutions
83. Mutagenicity of a unique 8-oxoguanine in a human Ha-ras sequence in mammalian cells
84. All three SOS-inducible DNA polymerases (Pol II, Pol IV and Pol V) are involved in induced mutagenesis
85. Strong sequence dependent polymorphism in adduct-induced DNA structure: Analysis of single N-2-acetylaminofluorene residues bound within the NarI mutation hot spot
86. Accumulation of premutagenic DNA lesions in mice defective in removal of oxidative base damage
87. The yeast 8-oxoguanine DNA glycosylase (OGG1) contains a DNA deoxyribophosphodiesterase (dRpase) activity
88. Miscoding and misincorporation of 8-oxo-guanine during leading and lagging strand synthesis in Escherichia coli
89. Detection of carcinogens as mutagens in the Salmonell/microsome test: Assay of 300 chemicals
90. Detection of carcinogens as mutagens in the Salmonella/microsome test: Assay of 300 chemicals: Discussion
91. DNA-damaging activity in vivo and bacterial mutagenicity of sixteen hydrazine derivatives as related quantitatively to their carcinogenicity
92. Comparative carcinogenicity of N-isopropyl-alpha-(2-methylhydrazino)-ptoluamide-HC1(procarbazine hydrochloride), its degradation products, other hydrazines, and isonicootinic acid hydrazide
93. Collaborative study of mutagenicity with Salmonella typhimurium TA102
94. Detection of oxidative mutagenesis by isoniazid, other hydrazine derivatives in Escherichia coli WP2 tester strain IC203, deficient in OxyR: Strong protective effects of rat liver S9
95. Mutagenic and alkylating activities of 3-methyl-1-phenyltriazenes and their possible role as carcinogenic metabolites of the parent dimethyl compounds
96. Microbial mutagenicity of selected hydrazines
97. The mutagenic activity of agaritine - A constituent of the cultivated mushroom Agaricus bisporus - And its derivatives detected with the Salmonella/mammalian microsome assay (Ames test)
98. Mutagens in larger fungi: I. Forty-eight species screened for mutagenic activity in the Salmonella/microsome assay
99. Interactions of histidine-containing test substances and extraction methods with the Ames mutagenicity test
100. The mutagenicity of edible mushrooms in a histidine-independent bacterial test system
101. Bioactivation of the mushroom hydrazine, agaritine, to intermediates that bind covalently to proteins and induce mutations in the Ames test
102. Phenethyl alcohol 1. Effect on macromolecular synthesis of Escherichia coli
103. Hydrazine antidepressants and isoniazid: Potential carcinogens
104. An evaluation of tests using DNA repair-deficient bacteria for predicting genotoxicity and carcinogenicity
105. Mutagenicity testing with TA97 and TA102 of 30 DNA-damaging compounds, negative with other Salmonella strains
106. SOS chromotest, a direct assay of induction of an SOS function in Escherichia coli K-12 to measure genotoxicity
107. SOS induction in Escherichia coli and Salmonella mutagenicity: A comparison using 330 compounds
108. SOS chromotest and mutagenicity in Salmonella: Evidence for mechanistic differences
109. Studies on the mechanism of hydralazine induced mutagenicity and genotoxicity
110. Studies on the mechanism of mutagenicity and genotoxicity induced by dihydralazine
111. Acetylation and its role in the mutagenicity of the antihypertensive agent hydralazine
112. Electron transfer in the heme pocket of hemoglobin
113. Outer-sphere one-electron reductions of arenediazonium salts
114. Comparative mutagenicity of hydrazine and 3 methylated derivatives in L5178Y lymphoma cells
115. Determination of the activity of 16 hydrazine derivatives in the bioluminescence test for genotoxic agents
116. Nitroxyls; VII. Synthesis and reactions of highly reactive 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-ylmethyl sulfonates
117. Prophage λ induction in Escherichia coli K12 envA uvrB: A highly sensitive test for potential carcinogens
118. Phorbol ester-inducible genes contain a common cis element recognized by a TPA-modulate trans-acting factor
119. 1 Transition in Mouse
120. The role of jun, fos and the AP1 complex in cell-proliferation and transformation
121. Study of gene regulatin by NF-κB and AP-1 in response to reactive oxygen intermediates
122. AP1/jun function is differentially induced in promotion-sensitive and resistant JB6 cells
123. Stromelysin in tumor progression and metastasis
124. Cancer induction studies using different administrations of benzenediazonium sulfate in mice
125. Carcinogenesis by the cultivated baked Agaricus bisporus mushroom in mice
126. Genotoxicity of agaritine in the lacI transgenic mouse mutation assay: Evaluation of the health risk of mushroom consumption
127. Actual new cancer-causing hydrazines, hydrazides, and hydrazones
128. Agaricus bisporus: An assessment of its carcinogenic potency
129. The induction of pulmonary tumours in Balb/Cb/Se mice by derivatives of hydrazine
130. Tumorigenic effect of 4-methylphenylhydrazine hydrochloride in Swiss mice
131. Tumor induction with the N′-acetyl derivative of 4-hydroxymethylphenylhydrazine
132. N-nitroso-N-methylaniline: Possible mode of DNA modification
133. Mutagenic activity and specificity of N-nitrosomethylaniline and N nitrosodiphenylamine in Salmonell
134. The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomes of rat livers
135. Triazene drug metabolites: Part 15. Synthesis and plasma hydrolysis of anticancer triazenes containing amino acid carriers
136. Relating aromatic hydrocarbon-induced DNA adducts and c-H-ras mutations in mouse skin papillomas: The role of apurinic sites
137. Regulation of CSF1 promoterbythe SWI/SNF like BAF complex
138. Mechanism-based inactivation of lacrimal-gland peroxidase by phenylhydrazine: A suicidal substrate to probe the active site
139. Phenyl radical production during the oxidation of phenylhydrazine and in phenylhydrazine-induced haemolysis
140. 1-Acetyl-2-phenylhydrazine carcinogenesis in mice
141. The gumorigenic effect of 1-hydrazinoph thalazine hydrochloride in mice
142. Carcinogenesis by benzenediazonium sulfate in mice
143. Tumor induction by 4-(methyl)benzenediazonium sulfate in mice
144. Carcinogenesis of 4-(hydroxymethyl)benzenediazonium ion (tetrafluoroborate) of Agaricus bisporus
145. Cancer induction by the sulfate form of 4-(hydroxymethyl) benzenediazonium ion of Agaricus bisporus
146. Cancer induction in mice by 4-hydroxybenzenediazonium sulfate of the Agaricus xanthodermus mushroom