Characterization of DNA adducts derived from syn-benzo[ghi]fluoranthene- 3,4-dihydrodiol-5,5a-epoxide and comparative DNA binding studies with structurally-related anti-diolepoxides of benzo[ghi]fluoranthene and benzo[c]phenanthrene

Chemical Research in Toxicology

Volumn 15, Issue 2, 2002, Pages 198-208

  Chang, Hui Fang ^a   Huffer, Duane M ^b   Chiarelli, M Paul ^b   Blankenship, Lonnie R ^c   Culp, Sandra J ^c   Cho, Bongsup P ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

^b LOYOLA UNIVERSITY CHICAGO   (United States)

^c NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[C]PHENANTHRENE 11,12 DIHYDRODIOL 13,14 EPOXIDE; BENZO[C]PHENANTHRENE 3,4 DIHYDRODIOL 1,2 EPOXIDE; BENZO[GHI]FLUORANTHENE 3,4 DIHYDRODIOL 5,5A EPOXIDE; DEOXYADENOSINE; DEOXYCYTIDINE; DEOXYGUANOSINE; DNA; EPOXIDE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CONFORMATION; CONTROLLED STUDY; DNA ADDUCT; DNA BINDING; DNA DENATURATION; DNA STRUCTURE; ELECTRICITY; ISOMER; MOLECULAR INTERACTION; MOLECULAR MODEL; MUTAGENICITY; NONHUMAN; SALMONELLA TYPHIMURIUM; SPECTROSCOPY; STRUCTURE ANALYSIS;

ANIMALS; BINDING SITES; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; DOSE-RESPONSE RELATIONSHIP, DRUG; EPOXY COMPOUNDS; FLUORENES; ISOMERISM; MOLECULAR CONFORMATION; MUTAGENICITY TESTS; MUTAGENS; PHENANTHRENES; SALMONELLA TYPHIMURIUM;

SALMONELLA TYPHIMURIUM; STAPHYLOCOCCUS PHAGE 187;

EID: 0036173569     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0101346     Document Type: Article

References (50)

1. Mechanisms of carcinogenesis of polycyclic aromatic hydrocarbons
2. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture
3. NMR solution structures of stereoisomeric covalent polycyclic aromatic carcinogen-DNA adducts: Principles, patterns, and diversity
4. DNA reactions, mutagenic action and stealth properties of polycyclic hydrocarbon carcinogens
5. The approach to understanding aromatic hydrocarbon carcinogenesis; the central role of radical cations in metabolic activation
6. Unrepaired fjord region polycyclic aromatic hydrocarbons-DNA adducts in ras codon 61 mutational hot spots
7. Glutathione conjugation of bay- and fjord-region diol epoxides of polycyclic aromatic hydrocarbons by glutathione transfereases M1-1 and P1-1
8. Molecular topology of polycyclic aromatic carcinogens determines DNA adduct conformation: A link to tumorigenic activity
9. Fjord- and bay-region diol-epoxides investigated for stability, SOS induction in Escherichia coli, and mutagenicity in Salmonella typhymurium and mammalian cells
10. Relationship between mutagenicity and DNA adduct formation in mammalian cells for fjord and bay-region diol-epoxides of polycyclic aromatic hydrocarbons
11. Stereoselective activation of dibenzo[a,l]pyrene to (-)-anti(11R, 12S, 13S, 14R)- and (+)-syn (11S, 12R, 13S, 14R)-11,12-diol-13,14-epoxides which bind extensively to deoxyadenosine residues of DNA in the human carcinoma cell line MCF-7
12. Stereoselective activation of dibenzo-[a,l]pyrene and its trans-11,12-dihydrodiol to fjord-region 11,12-diol-13,14-epoxides in a human mammary carcinoma MCF-7 cell-mediated V79 cell mutation assay
13. Tumorigenicity in newborn mice of fjord-region and other sterically hindered diolepoxides of benzo[g]chrysene, dibenzo[a,l]-pyrene (dibenzo[def,p]chrysene), 4H-cyclopenta[def]chrysene and fluoranthene
14. Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene
15. Benzo[c]phenanthrene-DNA adducts in mouse epidermis in relation to the tumorigenicities of four configurationally isomeric 3,4-dihydrodiol 1,2-epoxides
16. Mammary carcinogenicity in female CD rats of fjord region diolepoxides of benzo[c]phenanthrene, benzo[g]chrysene and dibenzo[a,l]pyrene
17. Marked differences in base selectivity between DNA and the free nucleotides upon adduct formation from bay- and fjord-region diol epoxides
18. Reactions of dihydrodiol epoxides of 5-methylchrysene and 5, 6-dimethylchrysene with DNA and deoxyribonucleotides
19. DNA adduct formation by polycyclic aromatic hydrocarbon dihydrodiol epoxides
20. Synthesis of anti- and syn-diol epoxides of trans-3,4-dihydroxy-3,4-dihydrobenzo[ghi]-fluoranthene: Model planar diol epoxides
21. Determination of polycyclic aromatic hydrocarbons in a coal tar standard reference material
22. Exceptionally high tumor-initiating activity of benzo[c]phenanthrene bay-region diol-epoxides in mouse skin
23. Novel bay-region diolepoxides from benzo[c]phenanthrene
24. Optically active benzo[c]phenanthrene diolepoxides bind extensively to adenine in DNA
25. Tumorigenicity of optical isomer of the diastereomeric bay-region 3,4-diol-1,2-epoxides of benzo(c)phenanthrene in murine tumor models
26. Stereo-selective metabolism of the (+)-(S,S)- and (-)-(R,R)-enantiomers of trans-3,4-dihydroxy-3,4-dihydrobenzo[c]phenanthrene by rat and mouse liver microsomes and by a purified and reconstituted cytochrome P-450 system
27. Chemical characterization of DNA adducts derived from the configurationally isomeric benzo[c]phenanthrene-3,4-diol 1,2-epoxides
28. Tumor-initiating activity on mouse skin of bay-region diol-epoxides of 5,6-dimethyl and benzo[c]phenanthrene
29. Mutagenicity of the enantiomers of the diastereomeric bay-region benzo[c]-phenanthrene 3,4-diol-1,2-epoxides in bacterial and mammalian cells
30. Mutagenic specificities of four steroisomeric benzo[c]-phenanthrene dihydrodiol epoxides
31. Matrix-assisted laser desorption ionization and time-of-flight mass spectrometry for the sensitive determination of arylamide-deoxy-nucleoside adducts
32. Product ion studies of diastereomeric benzo[ghi]-fluoranthene tetraols by matrix-assisted laser desorption ionization time-of-flight mass spectrometry and post-source decay
33. Revised methods for the Salmanella mutagenicity test
34. Structures of covalent nucleoside adducts formed from adenine, guanine, and cytosine bases of DNA and the optically active bay-region 3,4-diol 1,2-epoxides of benz[a]anthracene
35. Structures of covalent nucleoside adducts formed from adenine, guanine, and cytosine bases in DNA and the optically active bay-region 3,4-diol 1,2-epoxides of dibenz[a,j]anthracene
36. Fluoranthene metabolism: Human and rat liver microsomes display different stereoselective formation of the trans-2,3-dihydrodiol
37. Reactive metabolites of carcinogens and their interaction with DNA
38. Characterization of DNA adducts formed by anti-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide
39. Reactian with DNA and mutagenic specificity for syn-Benzog]chrysene 11,12-Dihydrodiol 13,14-Epoxide
40. Benzo-[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide adducts in native and denatured DNA
41. Quantum mechanical studies of the structure and reactivities of the diol epoxides of benzo[c]phenanthrene
42. Solution conformation of the (+)-trans-anti-[BPh]dA adduct opposite dT in a DNA duplex: Interaction of the covalently attached benzo[c]phenanthrenyl ring to the 5′-side of the adduct site without disruption of the modified base pair
43. Solution conformation of the (-)-trans-anti-Benzo[c]phenanthrene-dA ([BPh]-dA) adduct opposite dT in a DNA duplex: Interaction of the covalently attached benzo[c]phenanthrenyl ring to the 3′-side of the adduct site and comparison with the (+)-trans-anti-[BPh]dA opposite dT stereoisomer
44. Solution conformation of the (+)-trans-anti-benzo[g]-chrysene-dA adduct opposite dT in a DNA duplex
45. Mutagenicity of the dihydrodiols and bay-region diol-epoxides of benzo[c]phenanthrene in bacterial and mammalian cells
46. 2-deoxyguanosine adduct
47. Detection of the major DNA Adducts of benzo[j]fluoranthene in mouse skin: Nonclassical dihydrodiol epoxides