A simple synthetic entryway into (<i>N</i>‐heterocyclic carbene)gold‐steroidyl complexes and their anticancer activity
Thomas Scattolin, Petra Lippmann, Marek Beliš, Kristof Van Hecke, Ingo Ott, Steven P. Nolan
Abstract
A straightforward synthetic route to new N ‐heterocyclic carbene (NHC)‐gold‐steroidyl complexes is reported. The desired complexes were obtained using a weak base (such as K 2 CO 3 ) through a concerted‐metallation‐deprotonation (CMD) reaction mechanism occurring between [Au(NHC)Cl] and ethisterone as a model steroid‐based alkyne. Most complexes displayed good cytotoxicity against a panel of cancer cell lines with IC 50 values in the low micromolar range. Cellular uptake of the most active complex 2a into MCF‐7 breast cancer cells was facilitated by the coordinated ethisterone ligand.
Topics & Concepts
CarbeneChemistryDeprotonationLigand (biochemistry)CytotoxicityCombinatorial chemistryStereochemistryAlkyneCancer cell linesMedicinal chemistryCancer cellOrganic chemistryIn vitroCancerCatalysisBiochemistryReceptorInternal medicineIonMedicineN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry MethodsCatalytic Alkyne Reactions