© 1990 Oxford University Press
other |
Preparation and isolation of adducts in high yield derived from the binding of two benzo[a]pyrene-7,8-dihydroxy-9,10-oxide stereoisomers to the oligonucleotide d(ATATGTATA)
Department of Chemistry, New York University New York, NY 10003
1Ben May Institute, University of Chicago Chicago, IL 60637, USA
The reaction of the (+)- and (–)-enantlomers of BDPE (trans-7,8-dihydroxy-anti-9,1O-epoxy-7,8,9,10-tetrahydrobenzo-[a]pyrene) with the oligodeoxynucleotide d(ATATGTATA) in aqueous buffer solutions gives rise predominantly to trans and cis addition products at the exocydlic amino group of the single deoxyguanosine residue. The trans/cis ratios are 7:1 in the case of (+)-BPDE, and 2:1 in the case of (–)-BPDE, while the reaction yields correspond to 34 and 15% respectively, of modified strands. These relatively high reaction efficiencies, at least forthis particular type of oligonucleotide sequence, offer the possibilities of synthesizing relatively large amounts of well-defined covalent BPDE-oligonucleotide adducts (with different sequences of nucleotides flanking the modified base) for detailed spectroscopic and biochemical studies.
CiteULike 
Connotea 
Del.icio.us What's this?
This article has been cited by other articles:
|
|
 |
|
  F. A. Rodriguez, Y. Cai, C. Lin, Y. Tang, A. Kolbanovskiy, S. Amin, D. J. Patel, S. Broyde, and N. E. Geacintov Exocyclic amino groups of flanking guanines govern sequence-dependent adduct conformations and local structural distortions for minor groove-aligned benzo[a]pyrenyl-guanine lesions in a GG mutation hotspot context Nucleic Acids Res., March 12, 2007; 35(5): 1555 - 1568. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
B. Zhao, J. Wang, N. E. Geacintov, and Z. Wang Pol{eta}, Pol{zeta} and Rev1 together are required for G to T transversion mutations induced by the (+)- and (-)-trans-anti-BPDE-N2-dG DNA adducts in yeast cells Nucleic Acids Res., January 13, 2006; 34(2): 417 - 425. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 K.-Y. Seo, A. Nagalingam, M. Tiffany, and E. L. Loechler Mutagenesis studies with four stereoisomeric N2-dG benzo[a]pyrene adducts in the identical 5'-CGC sequence used in NMR studies: G->T mutations dominate in each case Mutagenesis, November 1, 2005; 20(6): 441 - 448. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 Y. Zhang, X. Wu, D. Guo, O. Rechkoblit, J.-S. Taylor, N. E. Geacintov, and Z. Wang Lesion Bypass Activities of Human DNA Polymerase {micro} J. Biol. Chem., November 8, 2002; 277(46): 44582 - 44587. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
O. Rechkoblit, Y. Zhang, D. Guo, Z. Wang, S. Amin, J. Krzeminsky, N. Louneva, and N. E. Geacintov trans-Lesion Synthesis Past Bulky Benzo[a]pyrene Diol Epoxide N2-dG and N6-dA Lesions Catalyzed by DNA Bypass Polymerases J. Biol. Chem., August 16, 2002; 277(34): 30488 - 30494. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
Y. Zhang, X. Wu, O. Rechkoblit, N. E. Geacintov, J.-S. Taylor, and Z. Wang Response of human REV1 to different DNA damage: preferential dCMP insertion opposite the lesion Nucleic Acids Res., April 1, 2002; 30(7): 1630 - 1638. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
Y. Zhang, F. Yuan, X. Wu, O. Rechkoblit, J.-S. Taylor, N. E. Geacintov, and Z. Wang Error-prone lesion bypass by human DNA polymerase {eta} Nucleic Acids Res., December 1, 2000; 28(23): 4717 - 4724. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
Y. Zhang, F. Yuan, X. Wu, M. Wang, O. Rechkoblit, J.-S. Taylor, N. E. Geacintov, and Z. Wang Error-free and error-prone lesion bypass by human DNA polymerase {kappa} in vitro Nucleic Acids Res., November 1, 2000; 28(21): 4138 - 4146. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 R. Shukla, N. E. Geacintov, and E. L. Loechler The major, N2-dG adduct of (+)-anti-B[a]PDE induces G->A mutations in a 5'-AGA-3' sequence context Carcinogenesis, February 1, 1999; 20(2): 261 - 268. [Abstract] [Full Text] [PDF]
|
|