Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes
Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes
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DOI：
10.1002/chem.201700588
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发表时间：
2017-05-02
影响因子：
4.3
通讯作者：
Besenius, Pol
中科院分区：
文献类型：
--
作者：
Kemper, Benedict;von Groening, Maximilian;Besenius, Pol
报道了使用水溶性 Au-I-N-炔基取代的马来酰亚胺络合物将金 (I) 金属两亲物与生物分子连接。为此，应用了两种不同的极性配体：1）中性的树枝状四乙二醇官能化膦和2）带电的磺化N-杂环卡宾（NHC）。呋喃保护的马来酰亚胺金 (I) 络合物发生逆狄尔斯-阿尔德反应，然后在温和条件下与二烯官能化生物素进行环加成反应，生成新型金 (I) 金属两亲物。所得生物素炔基金 (I) 膦缀合物在缓冲水溶液中的强链霉亲和素-生物素结合亲和力保持完整。生物素化金 (I) 复合物对 T47D 人乳腺癌细胞系的细胞毒性高于顺铂。
The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water-soluble Au-I-N-alkynyl substituted maleimide complexes. For this purpose, two different polar ligands were applied: 1) a neutral, dendritic tetraethylene glycol-functionalized phosphane and 2) a charged, sulfonated N-heterocyclic carbene (NHC). The retro Diels-Alder reaction of a furan-protected maleimide gold(I) complex, followed by cycloaddition with a diene-functionalized biotin under mild conditions leads to a novel gold(I) metalloamphiphile. The strong streptavidin-biotin binding affinity in buffered aqueous solution of the resulting biotin alkynyl gold(I) phosphane conjugate remains intact. The cytotoxicity of the biotinylated gold(I) complex against a T47D human breast cancer cell line is higher than for cisplatin.