A new ligand binding to G-G mismatch having improved thermal and alkaline stability

Bioorg Med Chem Lett. 2005 Jan 17;15(2):259-62. doi: 10.1016/j.bmcl.2004.11.003.

Abstract

Naphthyridine dimer (ND) specially binds to guanine-guanine (G-G) mismatch in duplex DNA. In order to improve the thermal and alkaline stability and binding ability of the ligand, we have examined structural modification of the linker. A new ligand (NNC) possessing 2-amino-1,8-naphthyridines and a carbamate linker is much more thermally stable than ND. The half-life of NNC is 2.5 times longer than that of ND at 80 degrees C. NNC is also much more stable than ND under alkaline conditions. In addition, NNC binds to G-G mismatch more strongly than ND. The improved stability and the binding of NNC to the G-G mismatch would be suitable for the practical use of NNC-immobilized sensor.

MeSH terms

  • Base Pair Mismatch*
  • Biosensing Techniques*
  • Carbamates / chemistry
  • DNA / chemistry
  • DNA / drug effects*
  • Dimerization
  • Guanine / chemistry*
  • Half-Life
  • Hydrogen-Ion Concentration
  • Ligands
  • Naphthyridines / chemical synthesis*
  • Nucleic Acid Conformation
  • Nucleic Acid Denaturation
  • Temperature

Substances

  • Carbamates
  • Ligands
  • Naphthyridines
  • Guanine
  • DNA