One-pot solvent free synthesis and DNA binding studies of thieno[2,3-b]-1,8-naphthyridines

Prep Biochem Biotechnol. 2008;38(1):115-28. doi: 10.1080/10826060701774445.

Abstract

With the aim of evaluating interaction between double-stranded calf thymus (ds)DNA and sulphur containing fused planar rings, the derivatives of 1,8-naphthyridine containing thiono groups were synthesized by the condensation of 2-mercapto-3-formyl[1,8]naphthyridines using 1-chloroacetone, 2-chloroacetamide, chloroaceticacid, and 2-chloro-1-phenylethanone in the presence of anhydrous potassium carbonate as s catalyst under solvent free microwave irradiation. The structures of the compounds were elucidated on the basis of elemental analysis, IR, (1)H NMR, and mass spectra. The interaction of thieno[2,3-b]-1,8-naphthyridine-2-carboxylic acid (TNC) (3a) with ct-DNA was studied by UV-Vis spectrophotometry, viscosity, thermal denaturation, as well as cyclic voltammetry experiments. On binding to DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. Binding parameters, determined from spectrophotometric measurements indicated a binding constant of Kb=2.1 x 10(6) M(-1). The thieno[2,3-b]-1,8-naphthyridine-2-carboxylic acid (3a) increases the viscosity of sonicated rod-like DNA fragments. The binding of TNC to DNA increased the melting temperature by about 4 degrees C. The decrease in peak current heights and shifts of peak potential values are observed by the addition of calf thymus DNA in cyclic voltammetry studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Carbonates / chemistry
  • Catalysis
  • DNA / chemistry
  • DNA / metabolism*
  • Electrochemistry
  • Humans
  • Magnetic Resonance Spectroscopy
  • Microwaves
  • Models, Chemical
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / metabolism
  • Nucleic Acid Denaturation
  • Potassium / chemistry
  • Solvents / chemistry*
  • Spectrophotometry, Ultraviolet
  • Temperature
  • Viscosity

Substances

  • Carbonates
  • Naphthyridines
  • Solvents
  • DNA
  • calf thymus DNA
  • potassium carbonate
  • Potassium