Synthesis of 5,12-dioxocyclam nickel (II) complexes having quinoxaline substituents at the 6 and 13 positions as potential DNA bis-intercalating and cleaving agents

被引:49
作者
Hegedus, LS [1 ]
Greenberg, MM
Wendling, JJ
Bullock, JP
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
关键词
D O I
10.1021/jo020708r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several dioxocyclams containing quinoxaline moieties, as well as their nickel(II) complexes were synthesized and studied for their ability to bind and oxidatively cleave DNA. Although no evidence for binding by intercalation was found, the ability of the Ni(II) complexes to cleave DNA in the presence of Oxone was strongly dependent on both the nature and the spatial orientation of the quinoxaline moieties, suggesting at least transient association of these complexes with DNA.
引用
收藏
页码:4179 / 4188
页数:10
相关论文
共 39 条
[1]   CONFORMATIONAL HETEROGENEITY OF QUINOXALINE PEPTIDES IN SOLUTION [J].
ALFREDSON, TV ;
MAKI, AH ;
WARING, MJ .
BIOPOLYMERS, 1991, 31 (14) :1689-1708
[2]   Cooperativity in the binding of echinomycin to DNA fragments containing closely spaced CpG sites [J].
Bailly, C ;
Hamy, F ;
Waring, MJ .
BIOCHEMISTRY, 1996, 35 (04) :1150-1161
[3]   SYNTHESIS OF AZAPENAMS, DIAZEPINONES, AND DIOXOCYCLAMS VIA THE PHOTOLYTIC REACTION OF CHROMIUM ALKOXYCARBENE COMPLEXES WITH IMIDAZOLINES [J].
BETSCHART, C ;
HEGEDUS, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5010-5017
[4]   Development of a solution-phase synthesis of minor groove binding bis-intercalators based on triostin A suitable for combinatorial synthesis [J].
Boger, DL ;
Lee, JK .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5996-6000
[5]   DNA binding properties of key sandramycin analogues: Systematic examination of the intercalation chromophore [J].
Boger, DL ;
Saionz, KW .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) :315-321
[6]   (-)-Sandramycin: Total synthesis and characterization of DNA binding properties [J].
Boger, DL ;
Chen, JH ;
Saionz, KW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) :1629-1644
[7]   Synthesis of key sandramycin analogs: systematic examination of the intercalation chromophore [J].
Boger, DL ;
Chen, JH ;
Saionz, KW ;
Jin, Q .
BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (01) :85-102
[8]   Total syntheses of thiocoraline and BE-22179 and assessment of their DNA binding and biological properties [J].
Boger, DL ;
Ichikawa, S ;
Tse, WC ;
Hedrick, MP ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :561-568
[9]   Oxidative nucleobase modifications leading to strand scission [J].
Burrows, CJ ;
Muller, JG .
CHEMICAL REVIEWS, 1998, 98 (03) :1109-1151
[10]   RECOGNITION OF GUANINE STRUCTURE IN NUCLEIC-ACIDS BY NICKEL-COMPLEXES [J].
BURROWS, CJ ;
ROKITA, SE .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (10) :295-301