Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes.
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.
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Benedict
B
Kemper
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Maximilian
M
von Gröning
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.
Vanessa
V
Lewe
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Daniel
D
Spitzer
Organic Chemistry Institute, Westfälische Wilhelms-University Münster, Corrensstrasse 40, 48149, Münster, Germany.
Tobias
T
Otremba
Institute of Immunology, University Medical Center, Johannes Gutenberg-University Mainz, Langenbeckstrasse 1, Geb. 708, 55101, Mainz, Germany.
Natascha
N
Stergiou
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Dieter
D
Schollmeyer
Institute of Immunology, University Medical Center, Johannes Gutenberg-University Mainz, Langenbeckstrasse 1, Geb. 708, 55101, Mainz, Germany.
Edgar
E
Schmitt
Organic Chemistry Institute, Westfälische Wilhelms-University Münster, Corrensstrasse 40, 48149, Münster, Germany.
Bart Jan
BJ
Ravoo
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.
Pol
http://orcid.org/0000-0001-7478-4459
P
Besenius
Diels-Alder ligation; click chemistry; gold; metalloamphiphiles; self-assembly