水溶性金（I）配合物的可逆共价和超分子功能化
Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes.
作者信息
Kemper Benedict, von Gröning Maximilian, Lewe Vanessa, Spitzer Daniel, Otremba Tobias, Stergiou Natascha, Schollmeyer Dieter, Schmitt Edgar, Ravoo Bart Jan, Besenius Pol
机构信息
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Graduate School Materials Science in Mainz, Staudingerweg 9, 55128, Mainz, Germany.
出版信息
Chemistry. 2017 May 2;23(25):6048-6055. doi: 10.1002/chem.201700588. Epub 2017 Mar 6.
The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water-soluble Au -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.
报道了使用水溶性金（I）-N-炔基取代马来酰亚胺配合物将金（I）金属两亲物与生物分子连接的方法。为此，应用了两种不同的极性配体：1）中性的、树枝状四甘醇官能化膦；2）带电荷的、磺化的N-杂环卡宾（NHC）。呋喃保护的马来酰亚胺金（I）配合物发生逆狄尔斯-阿尔德反应，随后在温和条件下与二烯官能化生物素进行环加成反应，生成一种新型金（I）金属两亲物。所得生物素炔基金（I）膦共轭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不变。生物素化金（I）配合物对T47D人乳腺癌细胞系的细胞毒性高于顺铂。
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