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

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 09期

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.

引用

页码：2465 / 2469

页数：5

共 23 条

[1] CATIONIC ANTHRAQUINONE DERIVATIVES AS CATALYTIC DNA PHOTONUCLEASES - MECHANISMS FOR DNA-DAMAGE AND QUINONE RECYCLING [J].

ARMITAGE, B ;

YU, CJ ;

DEVADOSS, C ;

SCHUSTER, GB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :9847-9859

[2] SELECTIVE ELECTROCHEMICAL RECOGNITION OF THE DIHYDROGEN PHOSPHATE ANION IN THE PRESENCE OF HYDROGEN SULFATE AND CHLORIDE-IONS BY NEW NEUTRAL FERROCENE ANION RECEPTORS [J].

BEER, PD ;

CHEN, Z ;

GOULDEN, AJ ;

GRAYDON, A ;

STOKES, SE ;

WEAR, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (24) :1834-1836

[3] CHARGED GUEST RECOGNITION BY REDOX RESPONSIVE LIGAND SYSTEMS [J].

BEER, PD .

ADVANCED MATERIALS, 1994, 6 (7-8) :607-609

[4]

BLANKESPOOR RL, 1984, J ORG CHEM, V49, P4441, DOI 10.1021/jo00197a021

[5] UNUSUAL 1-2 LIGAND-METAL COMPLEX-FORMATION BETWEEN AN ANTHRAQUINONE CRYPTAND AND LI+ [J].

CHEN, ZH ;

SCHALL, OF ;

ALCALA, M ;

LI, Y ;

GOKEL, GW ;

ECHEGOYEN, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :444-451

[6] REDOX-ACTIVE CROWN ETHERS - ELECTROCHEMICAL AND ELECTRON-PARAMAGNETIC RESONANCE STUDIES ON ALKALI-METAL COMPLEXES OF QUINONE CROWN ETHERS [J].

DELGADO, M ;

WOLF, RE ;

HARTMAN, JR ;

MCCAFFERTY, G ;

YAGBASAN, R ;

RAWLE, SC ;

WATKIN, DJ ;

COOPER, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8983-8991

[7] CONTROL OF THE REDOX ACTIVITY OF ANTHRAQUINONE THROUGH AN APPENDED NICKEL(II)-CYCLAM SIDE-CHAIN - A 2-SITE 3-ELECTRON REDOX SYSTEM [J].

DESANTIS, G ;

FABBRIZZI, L ;

MANGANO, C ;

POGGI, A ;

SEGHI, B .

INORGANICA CHIMICA ACTA, 1990, 177 (01) :47-49

[8]

DRYHURST G, 1982, BIOL ELECTROCHEMISTR, pCH1

[9] EFFICIENT SYNTHESIS OF ALKOXYANTHRAQUINONES FROM FLUOROANTHRAQUINONES AND THEIR PRELIMINARY ELECTROCHEMISTRY [J].

ECHEGOYEN, L ;

HAFEZ, Y ;

LAWSON, RC ;

DEMENDOZA, J ;

TORRES, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2009-2012

[10] CYCLIC VOLTAMMETRY STUDIES ON THE COMPLEXATION OF METAL-CATIONS BY CRYPTANDS CONTAINING THE FERROCENE UNIT [J].

HALL, CD ;

SHARPE, NW ;

DANKS, IP ;

SANG, YP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) :419-421

← 1 2 3 →