Water-Soluble (Phosphane)gold(I) Complexes - Applications as Recyclable Catalysts in a Three-Component Coupling Reaction and as Antimicrobial and Anticancer Agents

摘要

Water-soluble compounds of the type [AuCl(PR3)] with alkyl-bis(m-sulfonated-phenyl) (MC6H4SO3Na)(2) and dialkyl-(m-sulfonated-phenyl) (mC(6)H(4)SO(3)Na) (R = nBu, Cp) phospbanes have been prepared. Dialkylphosphane compounds generate water-soluble nanoparticles of 10-15 nm radius when dissolved in water. These air-stable complexes have been evaluated as catalysts in the synthesis of propargylamines by a three-component coupling reaction of aldehydes, amines, and alkynes in water. The antimicrobial activity of the new complexes against gram-positive and gram-negative bacteria and yeast has been evaluated. The new compounds display moderate to high antibacterial activity. The more lipophilic compounds are also potent against fungi. Their cytotoxic properties have been analyzed in vitro by utilizing human Jurkat T-cell acute lymphoblastic leukemia cells. Compounds with dialkyl-(m-sulfonated-phenyl) (mC(6)H(4)SO(3)Na) phosphanes displayed moderate to high cytotoxicity on this cell line. The cell death mechanism involves mainly early apoptosis. The catalytic/biological activity of the previously described compound with commercial m-trisulfonated-triphenylphosphane [AuCl(TPPTS)] (6) has also been evaluated to compare the effects of the higher basicity and lipophilicity of the alkyl- and dialkyl-(m-sulfonated-phenyl)phosphanes on these new compounds.