Role of hydrophobic effects in the reaction of a polynuclear aromatic diol epoxide with oligodeoxynucleotides in aqueous solutions

Chemical Research in Toxicology
N PirogovN E Geacintov

Abstract

The need for large-scale direct synthesis of stereochemically defined and site-specific benzo[alpha]pyrenediol epoxide-oligodeoxyribonucleotide adducts for detailed NMR and other biochemical and physicochemical studies has necessitated a better understanding of variables that lead to an enhancement of the reaction yields. It is shown that, in aqueous solution, the formation of noncovalent hydrophobic complexes between 7r, 8t-dihydroxy-9t,10t-epoxy-7,8,9,10-tetrahydrobenzo[alpha] pyrene (BPDE) and the single-stranded oligonucleotide 5'-d(CCATCGCTACC) precedes the covalent binding reaction of BPDE with the single deoxyguanosine residue. The yield of covalent reaction products (involving reaction of BPDE at the C10 position with the exocyclic amino group of the dG residue) increases with increasing DNA concentration and tends toward saturation at oligonucleotide single-strand concentrations above approximately 3 mM. The addition of NaCl (0.3 M) also tends to enhance the adduct reaction yields. However, organic solvents such as tetrahydrofuran in the reaction mixtures (10-40%) decrease the stabilities of the noncovalent complexes, which in turn leads to reductions in the yields of covalent BPDE-dG oligonucleotide adducts. The effic...Continue Reading

References

Aug 1, 1979·International Journal of Cancer. Journal International Du Cancer·R F NewboldR G Harvey

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Citations

Jan 19, 2012·Environmental Health Perspectives·Julie B HerbstmanFrederica P Perera
Nov 24, 1999·Molecular and Cellular Biology·J WuG M Li
Jun 10, 2011·Chembiochem : a European Journal of Chemical Biology·Young-Ae LeeVladimir Shafirovich
Nov 19, 2004·The Journal of Biological Chemistry·Gerald W HsuLorena S Beese
Dec 14, 2001·Journal of Medicinal Chemistry·M B LylesH R Rawls

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