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

• Published in: Chemistry : a European journal Vol. 23; no. 25; pp. 6048 - 6055
• Main Authors: Kemper, Benedict, von Gröning, Maximilian, Lewe, Vanessa, Spitzer, Daniel, Otremba, Tobias, Stergiou, Natascha, Schollmeyer, Dieter, Schmitt, Edgar, Ravoo, Bart Jan, Besenius, Pol
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 02.05.2017
• Subjects: Aqueous solutions; Biomolecules; Biotin; Breast cancer; Chemistry; click chemistry; Cycloaddition; Cytotoxicity; Diels-Alder reactions; Diels–Alder ligation; Gold; metalloamphiphiles; self-assembly; Water chemistry; gold; self-assembly; click chemistry; Diels-Alder ligation; metalloamphiphiles
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201700588

The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water‐soluble AuI‐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. Wrapped in gold: The ligation of gold(I) metalloamphiphiles with biomolecules is reported. Two different polar ligands were applied: a dendritic tetraethylene glycol‐functionalized phosphane and a sulfonated N‐heterocyclic carbene. A biotinylated alkynyl gold(I) phosphane complex was obtained by retro Diels–Alder reaction of a furan‐protected maleimide gold(I) precursor complex, followed by Diels–Alder cycloaddition with a diene functionalized biotin under mild conditions.