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

  1. Benelita T. Elie1,
  2. Chaya Levine1,2,
  3. Iban Ubarretxena-Belandia3,
  4. Armando Varela-Ramírez4,
  5. Renato J. Aguilera4,
  6. Rafael Ovalle2,
  7. María Contel1

Article first published online: 30 JUN 2009

DOI: 10.1002/ejic.200900279

Issue

European Journal of Inorganic Chemistry

European Journal of Inorganic Chemistry

Volume 2009, Issue 23, pages 3421–3430, August 2009

Additional Information

How to Cite

Elie, B. T., Levine, C., Ubarretxena-Belandia, I., Varela-Ramírez, A., Aguilera, R. J., Ovalle, R. and Contel, M. (2009), Water-Soluble (Phosphane)gold(I) Complexes – Applications as Recyclable Catalysts in a Three-Component Coupling Reaction and as Antimicrobial and Anticancer Agents. Eur. J. Inorg. Chem., 2009: 3421–3430. doi: 10.1002/ejic.200900279

Author Information

  1. 1

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

  2. 2

    Department of Biology, Brooklyn College, Brooklyn, NY 11210, USA

  3. 3

    Department of Structural and Chemical Biology, Mount Sinai School of Medicine, 1425 Madison Avenue, Box 1677, New York, NY 10029, USA

  4. 4

    Department of Biological Sciences, The University of Texas at El Paso, El Paso, TX 79968, USA

  1. †

    Dedicated to Professor Emeritus Martin A. Bennett

  2. ‡

    In recognition of his outstanding contributions to organometallic and inorganic chemistry.

Publication History

  1. Issue published online: 3 AUG 2009
  2. Article first published online: 30 JUN 2009
  3. Manuscript Received: 24 MAR 2009

Funded by

  • Brooklyn College
  • Professional Staff Congress – City University of New York (PSC-CUNY). Grant Number: PSCOOC-38-78
  • National Institutes of Health (NIH) – National Institute of General Medical Sciences (NIGMS) – Support of Competitive Research (SCORE) – Minority Biomedical Research Support (MBRS). Grant Number: 3S06GM076168-02S1
  • National Science Foundation (NSF). Grant Number: MCB-0546087
  • Cell Culture and High Throughput Screening (HTS) Core Facility. Grant Number: 5G12RR008124
  • Border Biomedical Research Center (BBRC)
  • National Center for Research Resources (NCRR) of the NIH

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Keywords:

  • Gold;
  • Nanoparticles;
  • Recy­clable catalysts;
  • Antimicrobial agents;
  • Cytotoxicity;
  • Apoptosis

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. 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) (mC6H4SO3Na) 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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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