N-heterocyclic carbene gold(i) and silver(i) complexes bearing functional groups for bio-conjugation. Issue 4 (9th December 2014)

• Record Type: Journal Article
• Authors: Garner, Mary E.; Niu, Weijia; Chen, Xigao; Ghiviriga, Ion; Abboud, Khalil A.; Tan, Weihong; Veige, Adam S.
• Is Part Of: Dalton transactions. Volume 44:Issue 4(2015)
• Page Start: 1914
• Page End: 1923
• Publication Date: 2014-12-09
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c4dt02850c
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : This work describes several synthetic approaches to append organic functional groups, suitable for biomolecule conjugation, to gold and silver N-heterocyclic carbene (NHC) complexes. Abstract : This work describes several synthetic approaches to append organic functional groups to gold and silver N-heterocyclic carbene (NHC) complexes suitable for applications in biomolecule conjugation. Carboxylate appended NHC ligands (3) lead to unstable Au I complexes that convert into bis-NHC species (4). A benzyl protected carboxylate NHC–Au I complex2 was synthesized but deprotection to produce the carboxylic acid functionality could not be achieved. A small library of new alkyne functionalized NHC proligands were synthesized and used for subsequent silver and gold metalation reactions. The alkyne appended NHC gold complex13 readily reacts with benzyl azide in a copper catalyzed azide–alkyne cycloaddition reaction to form the triazole appended NHC gold complex14 . Cell cytotoxicity studies were performed on DLD-1 (colorectal adenocarcinoma), Hep-G2 (hepatocellular carcinoma), MCF-7 (breast adenocarcinoma), CCRF-CEM (human T-Cell leukemia), and HEK (human embryonic kidney). Complete spectroscopic characterization of the ligands and complexes was achieved using 1 H and 13 C NMR, gHMBC, ESI-MS, and combustion analysis.