Polyaza Crown Ether as Non-Nucleosidic Building Blocks in DNA-Conjugates

Abstract

The synthesis of amphiphilic polyaza crown ether monomers X (palmityl-substituted), Y (cholesteryl-substituted) and Z (dipalmityl-subtituted) and their incorporation into oligonucleotides are described. Their effects on thermal duplex stability were investigated by UV melting curve analysis. Thermal denaturation experiments showed remarkable stabilization of dsDNA by polyaza crown ether monomers when incorporated in opposite positions. The series of polyaza crown ether monomers (X, Y, and Z) with different lipophilicity showed a trend of increased stability of the corresponding dsDNA with increasing lipophilicity of the polyaza crown ether monomer.

Keywords:

• Polyaza crown ether
• amphiphilic DNA
• DNA-conjugates

Notes

^a10 mM sodium phosphate, 100 mM NaCl, 0.1 mM EDTA, adjusted to pH 7.0, concentration of 1 μM for each DNA strand.

^a10 mM sodium phosphate, 100 mM NaCl, 0.1 mM EDTA, adjusted to pH 7.0, concentration of 1 μM for each DNA strand.