Kemper Benedict, von Gröning Maximilian, Lewe Vanessa, Spitzer Daniel, Otremba Tobias, Stergiou Natascha, Schollmeyer Dieter, Schmitt Edgar, Ravoo Bart Jan, Besenius Pol
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.
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。
