Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups

Bioorg Med Chem Lett. 2013 Feb 1;23(3):776-8. doi: 10.1016/j.bmcl.2012.11.079. Epub 2012 Dec 1.

Abstract

The consecutive arrangement of 2'-deoxy-6-thioguanosines (s(6)Gs) and 4-thiothymidines (s(4)Ts) in antiparallel triplex-forming oligonucleotides (TFOs) considerably stabilized the resulting antiparallel triplexes with high base recognition ability by the strong stacking effects of thiocarbonyl groups. This result was remarkable because chemical modifications of the sugar moieties and nucleobases of antiparallel TFOs generally destabilize triplex structures. Moreover, in comparison with unmodified TFOs, it was found that TFOs containing s(6)Gs and s(4)Ts could selectively bind to the complementary DNA duplex but not to mismatched DNA duplexes or single-stranded RNA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Pairing
  • Base Sequence
  • Computer Simulation
  • DNA / chemistry*
  • Models, Molecular*
  • Molecular Sequence Data
  • Sulfhydryl Compounds / chemistry*

Substances

  • Sulfhydryl Compounds
  • triplex DNA
  • DNA