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).
The reaction of the (+)- and (-)-enantiomers of BDPE trans-7,8-dihydroxy-anti-9,10-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 exocyclic 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 for this 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.
Cosman
M
M
Department of Chemistry, New York University, NY 10003.
Ibanez
V
V
Geacintov
N E
NE
Harvey
R G
RG
D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide; D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D004101:Dihydroxydihydrobenzopyrenes; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004101:Dihydroxydihydrobenzopyrenes; D009838:Oligodeoxyribonucleotides; D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide