Forging the links between metabolism and carcinogenesis

Mutation Research - Reviews in Mutation Research

Volumn 488, Issue 3, 2001, Pages 195-209

  Guengerich, F Peter ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Carcinogens; Cytochrome P450; Metabolism; Mutagenesis

Indexed keywords

AFLATOXIN B1; CARCINOGEN; CYTOCHROME P450; DNA; PROTEIN;

CARCINOGENICITY; CHEMICAL CARCINOGENESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMOPROPHYLAXIS; CONJUGATION; DETOXIFICATION; DNA ADDUCT; ENZYME INDUCTION; GENETICS; HALF LIFE TIME; HUMAN; METABOLISM; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW;

AFLATOXIN B1; ANIMALS; AUTOBIOGRAPHY; BIOTRANSFORMATION; CARCINOGENS; CELL TRANSFORMATION, NEOPLASTIC; CYTOCHROME P-450 ENZYME SYSTEM; DNA; DNA ADDUCTS; DNA DAMAGE; GENETIC PREDISPOSITION TO DISEASE; HISTORY, 20TH CENTURY; HUMANS; ISOENZYMES; MICROSOMES, LIVER; MOLECULAR BIOLOGY; MUTAGENESIS; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP;

ACRONICTA LEPORINA;

EID: 0035005384     PISSN: 13835742     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5742(01)00059-X     Document Type: Review

References (172)

1. Carcinogenesis by chemicals: An overview. G.H.A. Clowes Memorial Lecture
2. The role of metabolism in chemical mutagenesis and chemical carcinogenesis
3. Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules
4. Activated metabolites of carcinogenic hydrocarbons
5. Metabolism of chemical carcinogens
6. Mutagens as carcinogens: Development of current concepts
7. Brief history of chemical carcinogenesis
8. The metabolism of xenobiotics to reactive electrophiles in chemical carcinogenesis and mutagenesis: A collaboration with Elizabeth Cavert Miller and our associates
9. Ueber blasentumoren bei fuchsinarbeitern
10. Experimentelle studie über die pathogenese der epithelialgeschwulste
11. Carcinogenic substances and their fluorescence spectra
12. The isolation of a cancer-producing hydrocarbon from coal tar, Parts I, II, and III
13. Experimental production of bladder tumors in dogs by administration of beta-naphthylamine
14. Apparition de cancers de la mamelle chez la souris male, soumise a des injections de folliculine
15. The presence and significance of bound amino azodyes in the livers of rats fed p-dimethylaminoazobenzene
16. The carcinogenicity of certain azo dyes related to p-dimethylaminoazobenzene
17. Studies on the formation of protein-bound derivatives of 3,4-benzpyrene in the epidermal fraction of mouse skin
18. Studies on the chemical nature of the substance inducing transformation of pnuemococcal types. I. Induction of transformation by a desoxyribonucleic acid fraction isolated from pneumonococcus type III
19. 14
20. Accelerator mass spectrometry in biomedical dosimetry: Relationship between low-level exposure and covalent binding of heterocyclic amine carcinogens to DNA
21. Chemical production of mutations
22. Effect of nitrogen mustards on the ultraviolet absorption spectrum of thymonucleate, uracil and purines
23. Genetical implications of the structure of deoxyribonucleic acid
24. Complementary base pairing and the origin of substitution mutations
25. Identification by UV resonance Raman spectroscopy of an imino tautomer of 5-hydroxy-2′-deoxycytidine, a powerful base analog transition mutagen with a much higher unfavored tautomer frequency than that of the natural residue 2′-deoxycytidine
26. Production of mutations in mice by 1:2:5:5-dibenzanthracene
27. Different types of chemical carcinogen and their mode of action: A review
28. Metabolism of polycyclic compounds, 5. Formation of 1,2-dihydroxy-1,2-dihyronaphthalenes
29. Mutations and decreases in density of transforming DNA produced by derivative of the carcinogens 2-acetylaminoflourene and N-methyl-4-aminoazobenzene
30. The detection of chemical mutagens with enteric bacteria
31. Carcinogens are mutagens: A simple test system combining liver homogenates for activation and bacteria for detection
32. Identifying environmental chemicals causing mutations and cancer
33. Ranking possible carcinogenic hazards
34. Chemical characterization of 465 known or suspected carcinogens and their correlation with mutagenic activity in the Salmonella typhimurium system
35. Chemical structure, Salmonella mutagenicity and extent of carcinogenicity as indicators of genotoxic carcinogenesis among 222 chemicals tested in rodents by the US NCI/NTP
36. Do short-term tests predict rodent carcinogenicity?
37. The metabolism of 4,4-dimethylaminoazobenzene by rat liver homogenates
38. Liver tumor inhibition and adrenal histologic responses in rats to which 3′-methyl-4,4-dimethylaminoazobenzene and 20-methylcholanthrene were simultaneously administered
39. The metabolism of methylated aminoazo dyes. IV. Dietary factors enhancing demthylation in vitro
40. The acceleration of evipan oxidation and the demethylation of methylaminopyrine by barbiturates
41. The metabolism of methylated aminoazo dyes. V. Evidence for induction of enzyme synthesis in the rat by 3-methylcholanthrene
42. Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. II. Cellular responses during enzyme induction
43. Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase
44. Genetic variation of aryl hydrocarbon hydroxylase in human lymphocytes
45. Aryl hydrocarbon hydroxylase inducibility and bronchogenic carcinoma
46. Variations in aryl hydrocarbon hydroxylase activities in mitogen-activated human and nonhuman primate lymphocytes
47. Expression of CYP1A1 gene in patients with lung cancer: Evidence for cigarette smoke-induced gene expression in normal lung tissue and for altered gene regulation in primary pulmonary carcinomas
48. A new cytochrome in liver microsomes
49. The light reversible carbon monoxide inhibition of the steroid C21-hydroxylase system of the adrenal cortex
50. Microsomal N-oxidation of the hepatocarcinogen N-methyl-4-aminoazobenzene and the reactivity of N-hydroxy-N-methyl-4-aminoazobenzene
51. Cytochrome P-450 and flavin-containing monooxygenase-catalyzed formation of the carcinogen N-hydroxy-2-aminofluorene, and its covalent binding to nuclear DNA
52. Role of hemoprotein P-450 in fatty acid w-hydroxylation in a soluble enzyme system from liver microsomes
53. Effects of inducers and epoxide hydrolase on the metabolism of benzo[a]pyrene by liver microsomes and a reconstituted system: Analysis by high pressure liquid chromatography
54. Position-specific oxygenation of benzo[a]pyrene by different forms of purified cytochrome P-450 from rabbit liver
55. Separation and purification of multiple forms of microsomal cytochrome P-450. Activities of different forms of cytochrome P-450 towards several compounds of environmental interest
56. Separation and purification of multiple forms of microsomal cytochrome P-450. Partial characterization of three apparently homogeneous cytochromes P-450 prepared from livers of phenobarbital- and 3-methylcholanthrene-treated rats
57. Purification and characterization of liver microsomal cytochromes P-450: Electrophoretic, spectral, catalytic, and immunochemical properties and inducibility of eight isozymes isolated from rats treated with phenobarbital or β-naphthoflavone
58. Highly purified cytochrome P-448 and P-450 from rat liver microsomes
59. Separation and characterization of highly purified forms of liver microsomal cytochrome P-450 from rats treated with polychlorinated biphenyls, phenobarbital, and 3-methylcholanthrene
60. Metabolism of benzo[a]pyrene and benzo[a]pyrene derivatives to mutagenic products by highly purified hepatic microsomal enzymes
61. Purification and characterization of the rat liver microsomal cytochrome P-450 involved in the 4-hydroxylation of debrisoquine, a prototype for genetic variation in oxidative drug metabolism
62. Purification of human liver cytochrome P-450 and comparison to the enzyme isolated from rat liver
63. Purification and characterization of six cytochrome P-450 isozymes from human liver microsomes
64. Polymorphic hydroxylation of debrisoquine in man
65. Purification and characterization of the human liver cytochromes P-450 involved in debrisoquine 4-hydroxylation and phenacetin O-deethylation, two prototypes for genetic polymorphism in oxidative drug metabolism
66. Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Purification and characterization of two similar forms involved in the reaction
67. Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism
68. Purification and characterization of human liver microsomal cytochrome P-450 2A6
69. Characterization of cytochrome P450 2B6 in human liver microsomes
70. Oxidation of quinidine by human liver cytochrome P-450
71. Estimation of isozymes of microsomal cytochrome P-450 in rats, rabbits, and humans using immunochemical staining coupled with sodium dodecyl sulfate-polyacrylamide gel electrophoresis
72. Accessibility of cytochrome P450 in microsomal membranes: Inhibition of metabolism by antibodies to cytochrome P450
73. Molecular genetics of the P-450 superfamily
74. SOS function tests for studies of chemical carcinogenesis in Salmonella typhimurium TA 1535/pSK1002, NM2009, and NM3009
75. Evidence for cytochrome P-450NF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver
76. Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA1535/pSK1002
77. Roles of individual human cytochrome P-450 enzymes in the bioactivation of benzo[a]pyrene, 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene, and other dihydrodiol derivatives of polycyclic aromatic hydrocarbons
78. 1
79. Metabolic deactivation of furylfuramide by cytochrome P450 in human and rat liver microsomes
80. Inactivation of 1,3-, 1,6-, and 1,8-dinitropyrene by human and rat microsomes
81. Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae
82. Activation of amino-α-carboline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and a copper phthalocyanine cellulose extract of cigarette smoke condensate by cytochrome P-450 enzymes in rat and human liver microsomes
83. Participation of rat liver cytochrome P450 2E1 in the activation of N-nitrosodimethylamine and N-diethylnitrosamine to products genotoxic in Salmonella typhimurium NM2009
84. Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes
85. Activation of procarcinogens by human cytochrome P450 enzymes expressed in Escherichia coli. Simplified bacterial systems for genotoxicity assays
86. Procarcinogen activation by cytochrome P450 3A4 and 3A5 expressed in Escherichia coli and by human liver microsomes
87. Activation of chemically diverse procarcinogens by human cytochrome P450 1B1
88. Human cytochrome P-450PA (P-450IA2), the phenacetin O-deethylase is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines
89. Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats, and mice
90. Oxidation of benzo[a]pyrene by recombinant human cytochrome P450 enzymes
91. 1 by bacterial recombinant human cytochrome P450 enzymes
92. Cooperativity in oxidations catalyzed by cytochrome P450 3A4
93. 3+, in N-oxygenation of amines by cytochrome P450 enzymes
94. Development of a human lymphoblastoid cell line constitutively expressing human CYP1A1 cDNA: Substrate specificity with model substrates and promutagens
95. Baculovirus expression of bovine cytochrome P450c17 in Sf9 cells and comparison with expression in yesat, mammalian cells, and E. coli
96. New applications of bacterial systems to problems in toxicology
97. Coexpression of a human P450 (CYP3A4) and P450 reductase generates a highly functional monooxygenase system in Escherichia coli
98. Drug metabolism by Escherichia coli expressing human cytochromes P450
99. Establishment of a Salmonella tester strain highly sensitive to mutagenic heterocyclic amines
100. Bioactivation of aromatic amines by recombinant human cytochrome P450 1A2 expressed in bacteria: A substitute for mammalian tissue preparations in mutagenicity testing
101. Metabolic activation of aromatic amine mutagens by simultaneous expression of human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and N-acetyltransferase in Escherichia coli
102. Plasmid-mediated expression of the UmuCD mutagenesis proteins in Escherichia coli engineered for cytochrome P450-catalyzed activation of aromatic amines
103. A set of lacZ mutations in Escherichia coli that allow rapid detection of specific frameshift mutations
104. Development of a new genotoxicity test system with Salmonella typhimurium OY1001/1A2 expressing human cytochrome P450 1A2 and NADPH-cytochrome P450 reductase
105. Use of genetically engineered Salmonella typhimurium OY1002/1A2 strain co-expressing human cytochrome P450 1A2 and NADPH-cytochrome P450 1A2 reductase and bacterial O-acetyltransferase in SOS/umu assay
106. Über verwandlung der benzoesäure in hippursäure
107. Über die nach einführing von brombenzol und chlorbenzol im organismus entstehenden schwefelthaltigen säuren
108. Introduction and historical perspective
109. An enzyme from rat liver catalysing conjugations with glutathione
110. Mechanisms of chemical carcinogenesis: Nature of proximate carcinogens and interactions with macromolecules
111. Activation and detoxification of N-2-fluorenylacetamide in man
112. Inhibition by pentachlorophenol of the initiating and promoting activites of 1′-hydroxysafrole for the formation of enzyme-altered foci and tumors in rat liver
113. Induction of stomach cancer in rats and mice by halogenated aliphatic fumigants
114. The mutagenic effect of 1,2-dichloroethane on Salmonella typhimurium. I. Activation through conjugation with glutathione in vitro
115. 7-guanyl)ethyl]glutathione adduct in glutathione-mediated binding of 1,2-dibromoethane to DNA
116. Mechanisms of mutagenicity of DNA adducts derived from alkyl and vinyl halides
117. 7-guanyl)ethyl]glutathione as a mutagenic lesion formed from ethylene dibromide
118. 6-guanyl)ethyl]glutathione
119. 7-guanyl thioether derivatives of d(TGCTG*CAAG) with potential complements
120. Expression of mammalian glutathione S-transferase 5-5 in Salmonella typhimurium TA1535 leads to base-pair mutations upon exposure to dihalomethanes
121. Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S-transferase
122. A new Salmonella typhimurium NM5004 strain expressing rat glutathione S-transferase 5-5: Use in detection of genotoxicity of dihaloalkanes using an SOS/umu test system
123. Metabolism of polycyclic aromatic hydrocarbon derivatives to ultimate carcinogens during lipid peroxidation
124. Aflatoxins
125. Aflatoxins as risk factors for hepatocellular carcinoma in humans
126. 1 in vitro
127. 1-DNA or -ribosomal RNA adducts formed in hepatic microsome-mediated reactions and in rat liver in vivo
128. 1 exo-8,9-epoxide and relevance to toxicity and detoxication
129. 1 exo and endo epoxides by rat and human glutathione S-transferases
130. 1: Mechanistic studies
131. 1 exo-8,9-oxide and rearrangement of the dihydrodiol
132. 1 8,9-exo-epoxide catalyzed by rat and human glutathione transferases: Estimation of kinetic parameters
133. 1 8,9-epoxide
134. 1 exo-8,9-epoxide with DNA: Kinetic analysis of covalent binding and DNA-induced hydrolysis
135. 1 by glutathione and glutathione transferases in vitro
136. 1: The ultimate carcinogenic species
137. Mutagenicity of the enantiomers of the diastereomeric bay-region benzo[c]phenanthrene 3,4-diol-1,2-epoxides in bacterial and mammalian cells
138. 1 in vivo in rats
139. 1 is expressed in rat liver during carcinogenesis and following the administration of an anti-oxidant
140. Expression of cytochrome P450 1A1/2 and 3A4 in liver tissues of hepatocellular carcinoma cases and controls from Taiwan and their relationship to hepatitis B virus and aflatoxin B-1- and 4-aminobiphenyl-DNA adducts
141. 1 metabolism in human hepatocytes in primary culture
142. 1
143. Chronic hepatitis B carriers with null genotypes of glutathione S-transferase M1 and T1 polymorphisms who are exposed to aflatoxin are at increased risk of hepatocellular carcinoma
144. 2u-globulin nephropathy
145. p53 mutations in human cancers
146. Ras genes
147. Mutations in the p53 tumor suppressor gene: Clues to cancer etiology and molecular pathogenesis
148. Vinyl carbamate as a promutagen and a more carcinogenic analog of ethyl carbamate
149. 6-Ethenoadenosine formation, mutagenicity and murine tumor induction as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethane) and vinyl carbamate
150. Comparative carcinogenicities and mutagenicities of vinyl carbamate, ethyl carbamate, and ethyl N-hydroxycarbamate
151. 6-ethenoadenosine
152. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes
153. Differences in activation of heterocyclic aromatic amines by rat and human liver microsomes and by rat and human cytochromes P450 1A2
154. Sex steroid induced changes in hepatic enzymes
155. Regulation of rat hepatic cytochrome P-450: Age-dependent expression, hormonal imprinting, and xenobiotic inducibility of sex-specific isoenzymes
156. Growth hormone regulates expression of rat liver cytochrome P-45015β at a pretranslational level
157. STAT5b-deficient mice are growth hormone pulse-resistant
158. Enzymatic activation of chemicals to toxic metabolites
159. Metabolism of benzo[a]pyrene by isolated hepatocytes and factors affecting covalent binding of benzo[a]pyrene metabolites to DNA in hepatocyte and microsomal systems
160. Characterization of electron transport enzymes in the envelope of rat liver nuclei
161. Differences in the functional interaction of two purified cytochrome P-450 isozymes with epoxide hydrolase
162. Differential stereoselectivity of cytochromes P-450b and P-450c in the formation of naphthalene and anthracene 1,2-oxides: The role of epoxide hydrolase in determining the enantiomer composition of the 1,2-dihydrodiols formed
163. Detoxication enzymes
164. Role of CYP2E1 in the hepatotoxicity of acetaminophen
165. Role of CYP1A2 in the toxicity of long-term phenacetin feeding in mice
166. The Ah locus: Genetic differences in toxicity, cancer, mutation, and birth defects
167. Roles of cytochrome P-450 enzymes in chemical carcinogenesis and cancer chemotherapy