Benzene-glycol nucleic acid (BGNA)–DNA chimeras: synthesis, binding properties, and ability to elicit human RNase H activity

Abstract

This paper describes the synthesis and properties of benzene-glycol nucleic acid (BGNA)–DNA chimeras containing four nucleoside analogs – thymidine, cytidine, adenosine, and guanosine – with a base-benzene-glycol structure. We found that the BGNA–DNA chimeras are able to form thermally and thermodynamically stable duplexes with complementary RNAs, and have base-discriminating abilities. The BGNA–DNA chimeras were 20-fold more stable in a buffer containing 30% bovine serum than unmodified DNA. Furthermore, BGNA–DNA chimera/RNA duplexes were found to be good substrates for human RNase H. Thus, BGNA–DNA chimeras are good candidates for the development of therapeutic antisense molecules.