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Eur J Inorg Chem. 2009 Aug 1;2009(23):3421-3430. Epub 2009 Jun 30.

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

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  • 1Department of Chemistry, Brooklyn College and The Graduate Center, The City University of New York, 2900 Bedford Avenue, Brooklyn, NY 11210, US. Fax: #1- 7189514607 Web: http://userhome.brooklyn.cuny.edu./mariacontel/

Abstract

Water-soluble compounds of the type [AuCl(PR3)] with alkyl-bis-(m-sulfonated-phenyl)-(mC6H4SO3Na)2 and dialkyl-(m-sulfonated-phenyl)-(mC6H4SO3Na) (R = nBu, Cp) phosphanes have been prepared. Dialkyl-phosphane 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 via 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 utilizing human Jurkat T-cell acute lymphoblastic leukemia cells. Compounds with dialkyl-(m-sulfonated-phenyl)-(mC6H4SO3Na) phosphanes displayed moderate to high cytotoxicity on this cell line. Death cell mechanism occurs mainly by early apoptosis. The catalytic/biological activity of the previously described compound with commercial m-trisulfonated-triphenylphosphine [AuCl(TPPTS)] (6) has been also evaluated to compare the effects of the higher basicity and lipophilicity of the alkyl- and di-alkyl-(m-sulfonated-phenyl) phosphanes on these new compounds.

KEYWORDS:

antimicrobial; apoptosis; cytotoxicity; nanoparticles; recyclable catalysts; water-soluble gold

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