A Journal of Postdoctoral Research.
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    ISSN : 2328-9791
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6-Mercaptopurine Nucleoside Complexes of Gold(I): Synthesis and Cytotoxicity
Ayan Maity, Nihal Deligonul, Anthony J. Berdis, and Thomas G. Gray
Massachusetts Institute of Technology
MIT, Cambridge, MA 02139.
Case Western Reserve University, Cleaveland, OH 44106.
Cleveland State University, Cleveland, OH 44115, USA,

Molecular gold compounds have shown intermittent promise as human pharmaceuticals, mostly in in vitro as-says.  Rational approaches to gold prodrugs are essential for desired cytotoxicity.  This work describes non-natural nucleosides of 6-mercaptopurine.  Binding to (organophosphine)- and (N-heterocyclic carbene)gold(I) proceeds in high-yield reactions at room temperature.  Three such metallonucleosides were prepared.  They dif-fer in the phosphine or carbene ligand on gold.  New compounds are characterized by multinuclear NMR spec-troscopy, mass spectrometry, and elemental analysis.  One complex is crystallographically characterized; gold(I) is bound to the sulfur atom of the mercaptopurine moiety, and aurophilic interactions are absent.  Experiments in human cell lines showed evidence of mitochondrial swelling, programmed cell death, and inhibition of rat liver thioredoxin reductase.


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