A ZINC(II)-CYCLEN COMPLEX ATTACHED TO AN ANTHRAQUINONE MOIETY THAT ACTS AS A REDOX-ACTIVE NUCLEOBASE RECEPTOR IN AQUEOUS-SOLUTION

被引:37
作者
TUCKER, JHR [1 ]
SHIONOYA, M [1 ]
KOIKE, T [1 ]
KIMURA, E [1 ]
机构
[1] HIROSHIMA UNIV, SCH MED, DEPT MED CHEM, MINAMI KU, HIROSHIMA 734, JAPAN
关键词
D O I
10.1246/bcsj.68.2465
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Recently, we demonstrated that a zinc(II) macrocyclic tetraamine complex, Zn-II-cyclen (cyclen=1,4,7,10-tetraazacyclododecane), could bind to thymidine (dT) and uridine (U) selectively among the DNA/RNA bases in aqueous solution at physiological pH. This paper describes the design and synthesis of the zinc(II) complex of an anthraquinone-pendant cyclen. The interaction of this complex with a variety of nucleosides has been studied by potentiometric pH titration, H-1 NMR, and a polarographic technique. The effect of the anthraquinone functionality in this complex is an enhanced 1:1 association with N(3)-deprotonated dT (log K=6.6+/-0.1 against 5.6 for Zn-II-cyclen system at 25 degrees C with I=0.10 (NaNO3)) and its congeners, implying an additional anthraquinone-thymine aromatic stacking pi-pi interaction. This complex, moreover, can electrochemically recognize thymidine and other related organic substrates in aqueous solution, and is therefore a new prototype for electrochemical oligonucleotide recognition.
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页码:2465 / 2469
页数:5
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