SELF-COMPLEMENTARY OLIGODEOXYRIBONUCLEOTIDES CONTAINING 2'-O-(ANTHRAQUINONE-2-METHYL) ADENOSINE

Incorporation of an intercalating agent into an oligodeoxynucleotide ( ODN) has the potential to enhance binding affinity upon duplex formati on, to increase ODN hydrophobicity, and to enhance resistance to nucle ase hydrolysis. Site-specific intercalation has been achieved through the synthesis of 2'-O-(anthraquinone-2-methyl)adenosine(rA ) and its incorporation into the palindromic dodecanucleotide d(CGCrACATGTGCG). Melting temperature, CD spectra, 1D and 2D (DQF-COSY and NOESY) NMR s pectra, and molecular models were obtained and compared with the unmod ified dodecamer. The data clearly establish that intercalation of the anthraquinone ring into a predominantly B-type helix occurs between th e A4-T9 and C5-G8 base pairs, significantly stabilizing the duplex and enhancing the hydrophobicity of the ODN.