Nucleosides and nucleotides. 208. Alternate-strand triple-helix formation by the 3'-3'-linked oligodeoxynucleotides with the anthraquinonyl group at the junction point.
The synthesis of 3'-3'-linked oligodeoxynucleotides (ODNs) with the anthraquinonyl group at the junction point is described. The ODNs were synthesized on a DNA synthesizer using a controlled pore glass (CPG) carrying pentaerythritol that has an intercalator at one of the four hydroxymethyl groups. Stability of the triplexes with the target duplexes was studied by thermal denaturation. The 3'-3'-linked ODNs with the anthraquinonyl group enhanced the thermal stability of the triplexes when compared with those without the intercalator and the unmodified nonamer 10. It was found that the ODNs 12 and 13 carrying the anthraquinonyl groups can form thermally stable triplexes by skipping two or three extra base pairs between two binding domains of the target duplexes. The ability of the 3'-3'-linked ODNs to inhibit cleavage of the target DNA 22 by the restriction enzyme Hind III was tested. It was found that the 3'-3'-linked ODN 16 with the anthraquinonyl group at the junction point inhibited the cleavage by the enzyme more effectively than the nonamer 14 and the 3'-3'-linked ODN 15 without the intercalator.
Ueno
Y
Y
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Mikawa
M
M
Hoshika
S
S
Matsuda
A
A
D000880:Anthraquinones / Q000737:chemistry*; D001665:Binding Sites / Q000502:physiology; D015247:Deoxyribonuclease HindIII / Q000037:antagonists & inhibitors*; D004355:Drug Stability; D007364:Intercalating Agents / Q000737:chemistry; D009691:Nucleic Acid Denaturation / Q000502:physiology; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011409:Propylene Glycols / Q000737:chemistry*
D000880:Anthraquinones; D007364:Intercalating Agents; D009838:Oligodeoxyribonucleotides; D011409:Propylene Glycols; D015247:Deoxyribonuclease HindIII; C008783:pentaerythritol