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Influence of Equatorial and Axial Carboxylato Ligands on the Kinetic Inertness of Platinum(IV) Complexes in the Presence of Ascorbate and Cysteine and within DLD-1 Cancer Cells

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† School of Chemistry, The University of Sydney, Sydney, New South Wales, 2006, Australia
‡ Australian Synchrotron, Clayton, Victoria, 3168, Australia
§ Institute of Materials Structure Science, KEK, Tsukuba, Ibaraki 305-0801, Japan
*E-mail: [email protected]. Phone: +61-2-9351-3320. Fax: +61-2-9351-3329.
Cite this: J. Med. Chem. 2013, 56, 21, 8757–8764
Publication Date (Web):October 10, 2013
https://doi.org/10.1021/jm401218n
Copyright © 2013 American Chemical Society
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    The rapid and premature reduction of platinum(IV) complexes in vivo is a significant impediment to these complexes being successfully employed as anticancer prodrugs. This study investigates the influence of the platinum(IV) coordination sphere on the ease of reduction of the platinum center in various biological contexts. In the presence of the biological reductants, ascorbate and cysteine, platinum(IV) complexes with dicarboxylato equatorial ligands were observed to exhibit lower reduction potentials and slower reduction rates than analogous platinum(IV) complexes with dichlorido equatorial ligands. Diaminetetracarboxylatoplatinum(IV) complexes exhibited unusually long half-lives in the presence of excess reductants; however, the complexes exhibited moderate potency in vitro, indicative of rapid reduction within the intracellular environment. By use of XANES spectroscopy, trans-[Pt(OAc)2(ox)(en)] and trans-[PtCl2(OAc)2(en)] were observed to be reduced at a similar rate within DLD-1 cancer cells. This large variability in kinetic inertness of diaminetetracarboxylatoplatinum(IV) complexes in different biological contexts has significant implications for the design of platinum(IV) prodrugs.

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    Synthesis and characterization of complexes I–V, VII, and VIII; reduction monitored by 1H NMR time course experiments and pseudo-first - fitting; normalized XANES spectra of reduction in DLD-1 cells for complexes III and V; calibration of platinum solid standards. This material is available free of charge via the Internet at http://pubs.acs.org.

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