Conformational determinants of structures in stereoisomeric cis-opened anti-benzo[a]pyrene diol epoxide adducts to adenine in DNA

Chemical Research in Toxicology

Volumn 13, Issue 9, 2000, Pages 811-822

  Tan, J ^a   Geacintov, N E ^a   Broyde, S ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; ANTINEOPLASTIC AGENT; CARCINOGEN; DIHYDROXYBENZO[A]PYRENE OXIDE; DOUBLE STRANDED DNA;

ARTICLE; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CONFORMATION; DNA ADDUCT; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ADENINE; BENZOPYRENES; DNA ADDUCTS; DNA DAMAGE; ISOMERISM; MATHEMATICAL COMPUTING; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEIC ACID CONFORMATION; NUCLEIC ACID HETERODUPLEXES; THERMODYNAMICS;

EID: 0033796107     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx000094q     Document Type: Article

References (42)

1. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons
2. Double stranded DNA stereo-selectively binds benzo[a]pyrene diol epoxides
3. DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide
4. Benzo[a]pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo
5. Benzo[a]pyrene-nucleic acid derivative found in vivo: Structure of benzo[a]pyrenetetrahydrodiol epoxide-guanine adduct
6. The reaction of (+)-7α,8β-dihydroxy-9β,10β-epoxy-7,8,9,-10-tetrahydrobenzo[a]pyrene with DNA
7. 6-amino group to (-)-(7R,8S,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
8. 6-amino group to (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene : An unusual syn glycosidic torsion angle at the modified dA
9. Solution structure of the minor conformer of a DNA duplex containing a dG mismatch opposite a benzo[a]pyrene diol epoxide/ dA adduct: Glycosidic rotation syn to anti at modified deoxyadenosine
10. 1H NMR
11. 6-amino group to (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
12. Solution structure of the (+)-cis-anti-benzo[a]pyrene-dA ([BP]dA) adduct opposite dT in a DNA duplex
13. Dose-dependent differences in the profile of mutations induced by an ultimate carcinogen from benzo[a]pyrene
14. Dose-dependent differences in the profile of mutations induced by (+)-7R,8S-dihydroxy-9S,10R-epoxy-7,8,9,10-tetrahy-drobenzo[a]pyrene in the coding region of the hypoxanthine (guanine) phosphoribosyltransferase gene in Chinese hamster V-79 cells. Cancer Res
15. The ratio of deoxyadenosine to deoxyguanosine adducts formed by (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in purified calf thymus DNA and DNA in V-79 cells is independent of dose
16. Mutagenic replication in a human cell extract of DNAs containing site-specific and stereospecific benzo[a]pyrene-7,8-diol-9,10-epoxide DNA adducts placed on the leading and lagging strands
17. Mutational consequences of replication of M13mp7L2 constructs containing cis-opened benzo[a]pyrene 7,8-diol 9,10-epoxide-deoxyadenosine adducts
18. 6 at the second position of N-ras codon 61
19. Primer extension by various polymerases using oligonucleotide templates containing stereoisomeric benzo- [a]pyrene-deoxyadenosine adducts
20. In vitro replication by prokaryotic and eukaryotic polymerases on DNA templates containing site-specific and stereospecific benzo[a]pyrene-7,8-dihydrodiol-9,-10-epoxide adducts
21. Impact of the stereochemistry of benzo[a]pyrene 7,8-dihydrodiol 9,10-epoxide-deoxyadenosine adducts on resistance to digestion by phosphodiesterases I and II and translesion synthesis with HIV-1 reverse transcriptase
22. NMR solution structures of stereoisomeric covalent polycyclic aromatic carcinogen-DNA adduct: Principles, patterns, and diversity
23. Solution conformation of the major adduct between the carcinogen (+)-anti-benzo[a]pyrene diol epoxide and DNA
24. Influence of benzo[a]pyrene diol epoxide chirality on solution conformations of DNA covalent adducts: (-)-trans-anti- [BP]G·C adduct structure and comparison with (+)-trans-anti- [BP]G·C enantiomer
25. Structural characterization of a (+)-trans-anti-benzo[a]pyrene-DNA adduct using NMR, restrained energy minimization and molecular dynamics
26. Solution conformation of the (+)-cis-anti-[BP]dG adduct in a DNA duplex: Intercalation of covalently attached benzo[a]pyrenyl ring into helix and displacement of modified deoxyguanosine
27. Solution conformation of the (+)-trans-anti-[BP]dG adduct opposite a deletion site in a DNA duplex: Intercalation of the covalently attached benzo[a]pyrene into the helix with base displacement of the modified deoxyguanosine into the major groove
28. Solution conformation of the (+)-cis-anti-[BP]dG adduct opposite a deletion site in a DNA duplex: Intercalation of the covalently attached benzo[a]pyrene into the helix with base displacement of the modified deoxyguanosine into the minor groove
29. Solution conformation of the (-)-cis-anti-benzo[a]pyrenyl-dG adduct opposite dC in a DNA duplex: Intercalation of covalently attached BP ring into the helix with base displacement of modified deoxyguanosine into major groove
30. Solution conformation of the (-)-cis-anti-benzo[a]pyrenyl-dG adduct opposite dC in a DNA duplex: Intercalation of covalently attached BP ring into the helix with base displacement of modified deoxyguanosine into major groove
31. Solution conformation of the (-)-trans-anti-[BP]dG adduct opposite a deletion site in a DNA duplex: Intercalation of the covalently attached benzo[a]-pyrene into the helix with base displacement of the modified deoxyguanosine into the minor groove
32. Principles governing conformations in stereoisomeric adducts of bay region benzo[a]pyrene diol epoxides to adenine in DNA: Steric and hydrophobic effects are dominant
33. A second generation force field for the simulation of proteins and nucleic acids
34. Dielectric effects in biopolymers: The theory of ionic saturation revisited
35. The electrostatic contribution to DNA base-stacking interactions
36. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model
37. Stereochemical origin of opposite orientations in DNA adducts derived from enantiomeric anti-benzo[a]pyrene diol epoxides with different tumorigenic potentials
38. Origins of conformation differences between cis and trans DNA adducts derived from enantiomeric anti-benzo[a]pyrene diol epoxides