Heteroaromatic oligoamides with dDNA affinity

被引:19
作者
Gallmeier, HC [1 ]
König, B [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany
关键词
DNA binding; heterocycles; molecular recognition; oligoamides;
D O I
10.1002/ejoc.200300096
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heteroaromatic oligoamides are selective ligands for sequence-specific dDNA binding, many artificial oligoamides modeled on naturally occurring compounds and their dDNA binding motifs having been prepared over the last ten years. The large number of reported individual compounds does not allow each structure to be covered within the scope of this review, so we concentrate on examples of the most successful linear and tethered oligoamide structures, such as hairpin, H- pin, or cyclic structures, and the ensemble of heteroaromatic amino acids used as their building blocks. This provides an overview of which chemical structures are currently in use for sequence-specific dDNA recognition by artificial ligands and what they can achieve. (C) Wiley-VCH Verlag GmbH Co.
引用
收藏
页码:3473 / 3483
页数:11
相关论文
共 175 条
[1]   SYNTHESIS OF NOVEL CROSS-LINKED BIS-LEXITROPSINS [J].
ALSAID, NH ;
LOWN, JW .
TETRAHEDRON LETTERS, 1994, 35 (41) :7577-7580
[2]   A CONVENIENT SYNTHESIS OF CROSS-LINKED HOMODIMERIC BIS-LEXITROPSINS [J].
ALSAID, NH ;
LOWN, JW .
SYNTHETIC COMMUNICATIONS, 1995, 25 (07) :1059-1070
[3]   Towards a minimal motif for artificial transcriptional activators [J].
Ansari, AZ ;
Mapp, AK ;
Nguyen, DH ;
Dervan, PB ;
Ptashne, M .
CHEMISTRY & BIOLOGY, 2001, 8 (06) :583-592
[4]   STRUCTURE + SYNTHESIS OF DISTAMYCIN A [J].
ARCAMONE, F ;
NICOLELL.V ;
PENCO, S ;
OREZZI, P ;
PIRELLI, A .
NATURE, 1964, 203 (494) :1064-+
[5]   SYNTHESIS, DNA-BINDING PROPERTIES, AND ANTITUMOR-ACTIVITY OF NOVEL DISTAMYCIN DERIVATIVES [J].
ARCAMONE, FM ;
ANIMATI, F ;
BARBIERI, B ;
CONFIGLIACCHI, E ;
DALESSIO, R ;
GERONI, C ;
GIULIANI, FC ;
LAZZARI, E ;
MENOZZI, M ;
MONGELLI, N ;
PENCO, S ;
VERINI, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) :774-778
[6]   BINDING-PROPERTIES AND DNA SEQUENCE-SPECIFIC RECOGNITION OF 2 BITHIAZOLE-LINKED NETROPSIN HYBRID MOLECULES [J].
BAILLY, C ;
COLSON, P ;
HOUSSIER, C ;
HOUSSIN, R ;
MRANI, D ;
GOSSELIN, G ;
IMBACH, JL ;
WARING, MJ ;
LOWN, JW ;
HENICHART, JP .
BIOCHEMISTRY, 1992, 31 (35) :8349-8362
[7]   Sequence-specific DNA minor groove binders. Design and synthesis of netropsin and distamycin analogues [J].
Bailly, C ;
Chaires, JB .
BIOCONJUGATE CHEMISTRY, 1998, 9 (05) :513-538
[8]   Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids [J].
Baird, EE ;
Dervan, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) :6141-6146
[9]   Novel benzoyl nitrogen mustard derivatives of pyrazole analogues of distamycin A: Synthesis and antileukemic activity [J].
Baraldi, PG ;
Cozzi, P ;
Geroni, C ;
Mongelli, N ;
Romagnoli, R ;
Spalluto, G .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) :251-262
[10]   Design, synthesis, DNA binding, and biological evaluation of water-soluble hybrid molecules containing two pyrazole analogues of the alkylating cyclopropylpyrroloindole (CPI) subunit of the antitumor agent CC-1065 and polypyrrole minor groove binders [J].
Baraldi, PG ;
Balboni, G ;
Pavani, MG ;
Spalluto, G ;
Tabrizi, MA ;
De Clercq, E ;
Balzarini, J ;
Bando, T ;
Sugiyama, H ;
Romagnoli, R .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (16) :2536-2543