Dimeric Calixarenes: A New Family of Major-Groove Binders
Dimeric Calixarenes: A New Family of Major-Groove Binders
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DOI：
10.1002/chem.201100634
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发表时间：
2012-03-01
影响因子：
4.3
通讯作者：
Schrader, Thomas
中科院分区：
文献类型：
--
作者：
Hu, Wenbin;Blecking, Caroline;Schrader, Thomas
提出了一类新的有效的DNA结合剂。在杯[4]芳烃的上边缘具有阳离子基团和柔性烷基桥的二聚杯[4]芳烃可以由三酰基保护的杯[4]芳烃四胺以相对短的合成序列（35步）合成。这些化合物以非共价方式将自身附着到双链核酸上，具有微摩尔至纳摩尔的亲和力。胍头基与它们的延伸的氢键指比铵基团更强大，并且苄胺系列上级苯胺系列（见下文）。新的配体很容易区分RNA和各种DNA类型，并在UV/维斯，荧光，CD以及NMR光谱中产生特征变化。特别是超过100个碱基对的延伸寡核苷酸与RNA的亲和力增加（10 μ M Kd）
A new class of potent DNA binding agents is presented. Dimeric calix[4]arenes with cationic groups at their upper rims and flexible alkyl bridges can be synthesized from triply acyl-protected calix[4]arene tetramines in relatively short synthetic sequences (35 steps). The compounds attach themselves to double-stranded nucleic acids in a noncovalent fashion, with micro- to nanomolar affinities. Guanidinium headgroups with their extended hydrogen-bonding fingers are more powerful than ammonium groups, and the benzylamine series is superior to the anilinium series (see below). The new ligands easily distinguish between RNA and various DNA types, and produce characteristic changes in UV/Vis, fluorescence, CD, as well as NMR spectra. Especially extended oligonucleotides of more than 100 base pairs are bound with affinities increasing from RNA (10 mu M Kd)