Effect of gamma-hydroxypropano deoxyguanosine, the major acrolein-derived adduct, on monomolecular quadruplex structure of telomeric repeat d(TTAGGG)(4)

Bioorg Med Chem Lett. 2004 Nov 1;14(21):5417-21. doi: 10.1016/j.bmcl.2004.07.074.

Abstract

The three oligodeoxyribonucleotides (ODNs) a-c, having the telomeric repeat d(TTAGGG)(4) sequence and incorporating gamma-hydroxypropano deoxyguanosine at different positions, were synthesized. Gel electrophoresis and CD analyses indicated that the ODNs assume monomolecular quadruplex structures in Na+ and in K+ buffers. The T(m) values, obtained by CD melting experiments, showed that the presence of the acrolein-dG adduct into the ODN b decreases the thermal stability of the monomolecular quadruplex structure in Na+ solution, whereas for a and c no significant effect could be detected in the same experimental conditions. On the contrary, all ODNs a-d show the same behaviour in K+ buffer. These findings are briefly discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrolein / chemistry*
  • Buffers
  • Circular Dichroism
  • DNA Adducts / chemistry*
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemistry*
  • Electrophoresis, Polyacrylamide Gel
  • Humans
  • Nucleic Acid Conformation
  • Oligodeoxyribonucleotides
  • Potassium / chemistry
  • Repetitive Sequences, Nucleic Acid
  • Sodium / chemistry
  • Temperature

Substances

  • Buffers
  • DNA Adducts
  • Oligodeoxyribonucleotides
  • alpha-hydroxypropanodeoxyguanosine
  • Acrolein
  • Sodium
  • Deoxyguanosine
  • Potassium