Efficient guest inclusion by β-cyclodextrin attached to the ends of DNA oligomers upon hybridization to various DNA conjugates.
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.
Kuzuya
Akinori
A
Research Center for Advanced Science and Technology, The University of Tokyo, Tokyo, Japan.
Ohnishi
Toshiyuki
T
Wasano
Tsugutoshi
T
Nagaoka
Suguru
S
Sumaoka
Jun
J
Ihara
Toshihiro
T
Jyo
Akinori
A
Komiyama
Makoto
M
D000085:Acetates / Q000737:chemistry; D000218:Adamantane / Q000031:analogs & derivatives / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D005453:Fluorescence; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
C507636:1-adamantaneacetic acid; D000085:Acetates; D047392:beta-Cyclodextrins; D004247:DNA; C031215:betadex; D000218:Adamantane