Efficient Guest Inclusion by β-Cyclodextrin Attached to the Ends of DNA Oligomers upon Hybridization to Various DNA Conjugates
journal contributionposted on 19.08.2009 by Akinori Kuzuya, Toshiyuki Ohnishi, Tsugutoshi Wasano, Suguru Nagaoka, Jun Sumaoka, Toshihiro Ihara, Akinori Jyo, Makoto Komiyama
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Two types of 5′-β-CyD-DNA conjugates were synthesized using two different strategies and were hybridized with cDNA conjugates bearing various possible guest compounds at the 3′ ends. One of the β-CyD conjugates was synthesized on the basis of solid-phase postmodification of DNA with a monoamino-β-CyD derivative on a synthesis column for automated DNA synthesis. The other β-CyD conjugate was synthesized by the solution-phase coupling of DNA with a monomercapto-β-CyD derivative using a heterobifunctional cross-coupling reagent. When these 5′-β-CyD-DNA conjugates were hybridized with cDNA conjugates bearing 1-adamantaneacetic acid at the 3′ ends, significant stabilization of the duplexes was observed as compared with the control duplex without β-CyD. Duplexes of 5′-β-CyD-DNA conjugates and complementary 3′-dansyl-glycine-DNA conjugates were also moderately stabilized. Thermodynamic measurements revealed that the host−guest inclusion interactions between β-CyD and 1-adamantaneacetic acid or dansyl-glycine are roughly as strong as those found in bulk solution even if they are tethered to the ends of the DNA.