Specific DNA adducts induced by some mono-substitued epoxides in vitro and in vivo

Chemico-Biological Interactions

Volumn 129, Issue 3, 2000, Pages 209-229

  Koskinen, Mikko ^a   Plná, Kamila ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Biomarkers; DNA adducts; Epoxides; Mutagenicity

Indexed keywords

1,3 BUTADIENE; ADENINE DERIVATIVE; ALKENE DERIVATIVE; CYTOSINE DERIVATIVE; DNA BASE; EPICHLOROHYDRIN; EPOXIDE; GUANINE DERIVATIVE; PROPYLENE OXIDE; STYRENE; URACIL DERIVATIVE;

BIOLOGICAL MONITORING; CHEMICAL INDUSTRY; DETOXIFICATION; DNA ADDUCT; DNA BINDING; GENOTOXICITY; MUTAGENICITY; SHORT SURVEY;

ANIMALS; BINDING SITES; DNA; DNA ADDUCTS; ENVIRONMENTAL MONITORING; EPOXY COMPOUNDS; HUMANS; MUTAGENS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034671702     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(00)00206-4     Document Type: Short Survey

References (120)

1. DNA adducts, mutations and cancer
2. Genetic toxicity of some important epoxides
3. Nucleic acid adducts of chemical carcinogens and mutagens
4. Catalytic selectivity of human cytochrome P450 enzymes: Relevance to drug metabolism and toxicity
5. Genetic polymorphism of P450 IAI, 2D6 and 2E1: Regulation and toxicological significance
6. Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: Evidence of major role by cytochromes P450 2A6 and 2E1
7. Hepatic microsomal metabolism of 1,3-butadiene
8. Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats
9. Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats, and mice
10. High concentration of butadiene epoxides in livers and lungs of mice compared with rats exposed to 1,3-butadiene
11. Dosimetry of glycidyl ethers in mice by quantification of haemoglobin adducts
12. Continuous spectrophotometric assays for cytosolic epoxide hydrolase
13. Urinary metabolite profile of phenyl and o-cresyl glycidyl ether in rats: Identification of a novel pathway leading to N-acetylserine O-conjugates
14. Human peripheral lymphocytes as indicators of microsomal epoxide hydrolase activity in liver and lung
15. Human microsomal epoxide hydrolase genetic polymorphism and functional expression in vitro of amino acid variants
16. Enzymes and transport systems involved in the formation and disposition of glutathione S-conjugates. Role in bioactivation and detoxication mechanisms of xenobiotics
17. Identification and quantitative determination of 3-chloro-2-hydroxypropylmercapturic acid and alpha-chlorohydrin in urine of rats treated with epichlorohydrin
18. DNA-protein cross-links and sister chromatid exchange frequencies in lymphocytes and hydroxyethyl mercapturic acid in urine of ethylene oxide-exposed hospital workers
19. Polymorphism of xenobiotic-metabolizing enzymes and susceptibility to cancer
20. Aralkylation of guanosine with para-substituted styrene oxides
21. Styrene oxide as a stereochemical probe for the mechanism of aralkylation at different sites on guanosine
22. 6-positions
23. 3-deoxyuridine adducts of butadiene monoxide
24. Formation of deaminated products in styrene oxide reactions with deoxycytidine
25. Styrene oxide-induced 2′-deoxycytidine adducts: Implication on the mutagenicity
26. In vitro reaction of ethylene oxide with DNA and characterization of DNA adducts
27. Reaction products in hemoglobin and DNA after in vitro treatment with ethylene oxide and N-(2-hydroxyethyl)-N-nitrosourea
28. Reactions of propylene oxide with 2′-deoxynucleosides and in vitro with calf thymus DNA
29. 6-substituted adenine and 3-substituted cytosine/uracil of propylene oxide. Formation and persistence in vitro and in vivo
30. Reaction of epichlorohydrin with 2′-deoxynucleosides: Characterization of adducts
31. Quantitative analysis of DNA adducts formed by some epoxides of industrial importance
32. DNA adduct formation by allyl glycidyl ether
33. Reaction products of styrene oxide with guanosine in aqueous media
34. The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: Synthesis and characterization of the main adducts
35. 7-guanosine adducts of butadiene monoxide
36. 1-adenosine adducts as major initial products
37. Characterization of four N-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide
38. 6 adducts
39. 7-position
40. Identification and quantitation of DNA adducts from calf thymus DNA exposed to 3,4-epoxy-1-butene
41. Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane
42. Adenine adducts with diepoxybutane: Isolation and analysis in exposed calf thymus DNA
43. Butadiene diolepoxide- and diepoxybutane-derived DNA adducts at N7-guanine: A high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure
44. 32P-postlabelling analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro
45. 32P]-postlabelling and four-sector tandem mass spectrometry: Anticipated adducts formed upon treatment of DNA with styrene 7,8-oxide
46. Alkylation of anionic DNA bases by styrene 7,8-oxide
47. In vitro reactions of 2-cyanoethylene oxide with calf thymus DNA
48. Effect of ionic state of 2′-deoxyguanosine and solvent on its aralkylation by benzyl bromide
49. In vitro reactions of butadiene monoxide with single- and double-stranded DNA: Characterization and quantitation of several purine and pyrimidine adducts
50. Identification of alkylation products of styrene oxide in single- and double-stranded DNA
51. Characterization of reaction products between styrene and deoxynucleosides and DNA
52. Deamination and Dimroth rearragement of deoxyadenosine-styrene oxide adducts in DNA
53. Effects of some chemical mutagens and carcinogens on nucleic acids
54. Relevance of urinary DNA adducts as markers of carcinogen exposure
55. 32P-postlabelling of 7-(3-chloro-2-hydroxypropyl)guanine in white blood cells of workers occupationally exposed to epichlorohydrin
56. Adenine N3 is a main alkylation site of styrene oxide in double-stranded DNA
57. 32P-postlabelling/HPLC analysis of various styrene-induced DNA adducts in mice
58. Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry
59. Crystal structure of a carcinogen: Nucleoside adduct
60. Hemoglobin adducts for in vivo dose monitoring and cancer risk estimation
61. Comparison of ethylene, propylene and styrene 7,8-oxide in vitro adduct formation on N-terminal valine in human haemoglobin and on N-7-guanine in human DNA
62. 32P-postlabelling method for the detection of 7-alkylguanine adducts formed by the reaction of different 1,2-alkyl epoxides with DNA
63. Reaction kinetics of alkyl epoxides with DNA and other nucleophiles
64. Dosimetry of ethylene oxide in the rat by quantitation of alkylated histidine in hemoglobin
65. In vivo tissue dosimetry of propylene oxide as a basis for cross-species extrapolation in cancer risk assessment
66. 32P-Postlabelling of DNA adducts formed by allyl glycidyl ether in vitro and in vivo
67. Adducts with haemoglobin and with DNA in epichlorohydrin-exposed rats
68. Adduct formation on DNA and haemoglobin in mice intraperitoneally administred with styrene
69. Dose-response relationships for carcinogens
70. DNA adducts: Biological markers of exposure and potential applications to risk assessment
71. Carcinogen DNA and protein adducts as biomarkers of human exposure in environmental cancer epidemiology
72. DNA adduct measurements and tumor incidence during chronic carcinogen exposure in animal models: Implications for DNA adduct-based human cancer risk assessment
73. High levels of dipyrimidine dimers are induced in human skin by solar-simulating UV radiation
74. Molecular dosimetry of ethylene oxide: Formation and persistence of 7-(2-hydroxymethyl)guanine in DNA following repeated exposures of rats and mice
75. 32P-postlabelling
76. Molecular dosimetry of N-7 guanine adduct formation in mice and rats exposed to 1,3-butadiene
77. Regio- and stereospecific DNA adduct formation in mouse lung at N6 and N7 position of adenine and guanine after 1,3-butadiene inhalation exposure
78. 7-(2,3,4-trihydroxybutyl)guanine adducts in the livers of mice and rats exposed to 1,3-butadiene
79. Molecular dosimetry of DNA and hemoglobin adducts in mice and rats exposed to ethylene oxide
80. 6-adenine adducts of epoxybutanediol in vivo after 1,3-butadiene exposure
81. Haemoglobin adducts of epoxybutanediol from exposure to 1,3-butadiene or butadiene epoxides
82. 6-position of guanine
83. 32P-postlabeling of DNA adducts of styrene-exposed lamination workers
84. 32P-postlabelling
85. An evaluation of styrene genotoxicity using several biomarkers in a 3-year follow-up study of hand-lamination workers
86. 32P-Post-labeling detection of DNA adducts in mononuclear cells of workers occupationally exposed to styrene
87. Human DNA adducts of 1,3-butadiene, an important environmental carcinogen
88. Measurement of 7-methyl- and 7-(2-hydroxyethyl)-guanine DNA adducts in white blood cells of smokers and non-smokers
89. Endogenous and background DNA adducts by methylating and 2-hydroxyethylating agents
90. 6-methylguanine built into a unique site in a viral genome
91. 6-methylthymine in Escherichia coli
92. Methylation-induced blocks to in vitro DNA replication
93. Mutagenesis by apurinic/apyrimidic sites
94. Molecular analysis of styrene oxide-induced hprt mutations in human T-lymphocytes
95. Mutagenic activity and specificities of biologically and environmentally significant epoxides
96. Mutagenicity of butadiene and its epoxide metabolites: II Mutational spectra of butadiene, 1,2-epoxybutene and diepoxybutane at the hprt locus in splenic T Cells from exposed B6C3F1 mice
97. Endogenous apurinic/apyrimidinic sites in genomic DNA of mammalian tissues
98. Molecular analysis of lacI mutants from bone marrow of B6C3F1 transgenic mice following inhalation exposure to 1,3-butadiene
99. Increased frequency of mutations at A:T base pairs in the bone marrow of B6C3F1 lac1 transgenic mice exposed to 1,3-butadiene
100. Mutagenicity and mutational spectra of 1,3-butadiene in the bone marrow of B6C3F1 lacI transgenic mice
101. Characterization of hprt mutations following 1, 2-epoxy-3-butene exposure of human TK6 cells
102. The replication fate of R- and S-strene oxide adducts on adenine N6 is dependent on both the chirality of the lesion and the local sequence context
103. 6 adducts of monoepoxide and diolepoxide derivatives of butadiene
104. Mutagenicity of butadiene and its epoxide metabolites: I Mutagenic potential of butadiene, 1,2-epoxybutene and diepoxybutane in cultured human lymphoplasts
105. Detection of diepoxybutane-induced DNA-DNA crosslinks by cesium trifluoroacetate (CsTFA) density-gradient centrifugation
106. Diepoxybutane cross-links DNA at 5′-GNC sequences
107. 2 adducts of butadiene mono- and diolepoxide
108. Propylene oxide mutagenesis at template cytosine residues
109. 4-ethano-2′-deoxycytidine, and 3-(2-hydroxyethyl)-2′-deoxyuridine
110. The role of 3-hydroxyethyldeoxyuridine in mutagenesis by ethylene oxide