Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes

被引：15

作者：

Kemper, Benedict ^{[1
]}

von Groening, Maximilian ^{[1
]}

Lewe, Vanessa ^{[1
,2
]}

Spitzer, Daniel ^{[1
]}

Otremba, Tobias ^{[3
]}

Stergiou, Natascha ^{[4
]}

Schollmeyer, Dieter ^{[1
]}

Schmitt, Edgar ^{[4
]}

Ravoo, Bart Jan ^{[3
]}

Besenius, Pol ^{[1
,2
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

[2] Grad Sch Mat Sci Mainz, Staudingerweg 9, D-55128 Mainz, Germany

[3] Westfal Wilhelms Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany

[4] Johannes Gutenberg Univ Mainz, Inst Immunol, Univ Med Ctr, Langenbeckstr 1,Geb 708, D-55101 Mainz, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 25期

关键词：

click chemistry; Diels-Alder ligation; gold; metalloamphiphiles; self-assembly; DIELS-ALDER CYCLOADDITION; AVIDIN-BIOTIN TECHNOLOGY; N-HETEROCYCLIC CARBENES; ARTIFICIAL METALLOENZYMES; CLICK CHEMISTRY; ENANTIOSELECTIVE CATALYSIS; BIOORTHOGONAL CHEMISTRY; PROTEIN MODIFICATION; STAUDINGER LIGATION; LUMINESCENT GOLD(I);

D O I：

10.1002/chem.201700588

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：6048 / 6055

页数：8

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