Catechol ortho-quinones: The electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases

Carcinogenesis

Volumn 23, Issue 6, 2002, Pages 1071-1077

  Cavalieri, Ercole L ^a   Li, Kai Ming ^a   Balu, Narayanan ^a   Saeed, Muhammad ^a   Devanesan, Prabu ^a   Higginbotham, Sheila ^a   Zhao, John ^b   Gross, Michael L ^b   Rogan, Eleanor G ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; CATECHOL; CATECHOL DERIVATIVE; CATECHOL ESTROGEN; CATECHOLAMINE; DEOXYGUANOSINE; DNA; DOPAMINE; GUANINE; HORSERADISH PEROXIDASE; MONOPHENOL MONOOXYGENASE; PHENOBARBITAL; PURINE; QUINONE DERIVATIVE;

ANIMAL CELL; ANIMAL TISSUE; APURINIC SITE; ARTICLE; CARCINOGENESIS; CONTROLLED STUDY; DEGENERATIVE DISEASE; DNA ADDUCT; ENZYME METABOLISM; ENZYME SYNTHESIS; GENE MUTATION; HYPOTHESIS; LEUKEMOGENESIS; LIVER MICROSOME; METABOLISM; MOLECULAR MECHANICS; NONHUMAN; OXIDATION; PARKINSON DISEASE; PATHOGENESIS; PRIORITY JOURNAL; RAT;

EID: 0036309549     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/23.6.1071     Document Type: Article

References (61)

1. Free radical generation by redox cycling of estrogens
2. The key role of catechol estrogen 3,4-quinones in tumor initiation
3. Quinones: The present state of addition and substitution chemistry
4. Molecular origin of cancer: Catechol estrogen-3,4-quinones as endogenous tumor initiators
5. Estrogens as endogenous genotoxic agents: DNA adducts and mutations
6. Relating aromatic hydrocarbon-induced DNA adducts and c-Harvey-ras mutations in mouse skin papillomas: The role of apurinic sites
7. Evidence that error-prone DNA repair converts dibenzo[a,l]pyrene-induced depurinating lesions into mutations: Formation, clonal proliferation and regression of initiated cells carrying H-ras oncogene mutations in early preneoplasia
8. Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and forms mutations in the H-ras gene
9. Carcinogenicity of catecholestrogens in Syrian hamsters
10. Estrogen carcinogenesis in Syrian hamster tissue: Role of metabolism
11. 2-3,4-quinone with DNA
12. Hematotoxicity and carcinogenicity of inhaled benzene
13. Benzene: An experimental multipotential carcinogen: Results of the long-term bioassays performed at the Bologna Institute of Oncology
14. 1 mice
15. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans
16. Benzene and leukemia. An epidemiologic risk assessment
17. 3H] benzene
18. Partial hepatectomy reduces both metabolism and toxicity of benzene
19. Recent advances in the metabolism and toxicity of benzene
20. A perspective on benzene leukemogenesis
21. Differences in quinone reductase activity in primary bone marrow stromal cells derived from C57BL/6 and DBA/2 mice
22. Identification of ethanol-inducible P450 isozyme 3a. P450 II E1 as a benzene and phenol hydroxylase
23. Role of human cytochrome P-450 II E1 in the oxidation of many low molecular weight cancer suspects
24. 1 mice
25. Formation of muconaldehyde, an open ring metabolite of benzene in mouse liver microsomes: An additional pathway for toxic metabolites
26. Benzene and phenol metabolism by mouse and rat liver microsomes
27. Benzene absorption in rats after inhalation exposure
28. 14C-labeled benzene metabolites in the rat
29. Metabolic activation of phenol by human myeloperoxidase and horseradish peroxidase
30. Metabolism of hydroquinone by human myeloperoxidase: Mechanism of stimulation by other phenolic compounds
31. Oxidation of catechol by horseradish peroxidase and human leukocyte peroxidase: Reactions of o-benzoquinone and o-benzosemiquinone
32. Prostaglandin H synthase catalyzed oxidation of hydroquinone to a sulfhydryl-binding and DNA damaging metabolite
33. 32P-postlabeling
34. Potentiation of DNA adduct formation in HL-60 cells by combination of benzene metabolites
35. Peroxidase activation of hydroquinone results in the formation of DNA adducts in HL-60 cells, mouse bone marrow macrophages and human bone marrow
36. Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro
37. Role of oxidation in the neurotoxic effects of intrastriatal dopamine injections
38. Pre- and postsynaptic neurotoxic effects of dopamine demonstrated by intrastitial injection
39. 3H]dopamine: Impact of ascorbic acid and glutathione
40. Detection of dopamine-DNA adducts: Potential role in Parkinson's disease
41. Formation of DNA adducts and oxidative base damage by copper-mediated oxidation of dopamine and 6-hydroxydopamine
42. Enzymatic oxidation of dopamine: The role of prostaglandin H synthase
43. Prostaglandin H synthease-mediated metabolism of dopamine: Implication for Parkinson's disease
44. Semiquinone anion radicals of catechol(amine)s, catechol estrogens, and their metal ion complexes
45. Peroxidatic oxidation of catecholamines: A kinetic electron spin resonance investigation using the spin stabilization approach
46. Dependence of benzo[a]pyrene metabolic profile on the concentration of cumene hydroperoxide with uninduced and induced rat liver microsomes
47. 32P-Postlabeling analysis of benzo[a]pyrene-DNA adducts formed in vitro and in vivo
48. Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides
49. Metabolic activation and formation of DNA adducts of hexestrol, a synthetic non-steroidal carcinogenic estrogen
50. New role for estrogen in cancer?
51. DT diaphorase - A quinone reductase with special functions in cell metabolism and detoxication
52. Temporary decrease in renal quinone reductase activity induced by chronic administration of estradiol to male Syrian hamsters
53. Synthesis and characterization of estrogen 2,3- and 3,4-quinones. Comparison of DNA adducts formed by the quinones versus horseradish peroxidase-activated catechol estrogens
54. Relative carcinogenic activity of various synthetic and natural estrogens in the Syrian hamster kidney
55. Carcinogenicity and metabolic activation of hexestrol
56. Oxidative metabolism of the synthetic estrogens hexestrol and dienestrol indicates reactive intermediates
57. 1 mice
58. Two benzene metabolites, catechol and hydroquinone, produce a synergistic genotoxic response in cultured human lymphocytes
59. The mechanism of benzene-induced leukemia: A hypothesis and speculations on the causes of leukemia
60. Mechanisms of control of the cytotoxicity of orthoquinone intermediates of melanogenesis
61. Kinetics and mechanism of oxidation pathways of some catecholamines with periodic acid