NDLI: On the Stability of $Pt^{IV}$ Pro-Drugs with Haloacetato Ligands in the Axial Positions

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On the Stability of $Pt^{IV}$ Pro-Drugs with Haloacetato Ligands in the Axial Positions

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On the Stability of $Pt^{IV}$ Pro-Drugs with Haloacetato Ligands in the Axial Positions

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Gibson, Dan Yavin, Eylon Wexselblatt, Ezequiel Salameh, Sawsan Raveendran, Raji Friedman-ezra, Aviva
Description	Author Affiliation: Wexselblatt E ( Institute for Drug Research, School of Pharmacy, The Hebrew University, Jerusalem, 91120 (Israel).)
Abstract	The design of $Pt^{IV}$ pro-drugs as anticancer agents is predicated on the assumption that they will not undergo substitution reactions before entering the cancer cell. Attempts to improve the cytotoxic properties of $Pt^{IV}$ pro-drugs included the use of haloacetato axial ligands. Herein, we demonstrate that $Pt^{IV}$ complexes with trifluoroacetato (TFA) or dichloroacetato (DCA) ligands can be unstable under biologically relevant conditions and readily undergo hydrolysis, which results in the loss of the axial TFA or DCA ligands. The half-lives for $Pt^{IV}$ complexes with two TFA or DCA ligands at pH 7 and 37 °C range from 6 to 800 min, which is short relative to the duration of cytotoxicity experiments that last 24–96 h. However, complexes with two monochloroacetato (MCA) or acetato axial ligands are stable under biologically relevant conditions. The loss of the axial ligands depends primarily on the electron-withdrawing strength of the axial ligands, but also upon the nature of the equatorial ligands. We were unable to find obvious correlations between the structures of the $Pt^{IV}$ complexes and the rates of decay of the parent compounds. The X-ray crystal structures of the bis-DCA and bis-MCA $Pt^{IV}$ derivatives of oxaliplatin did not reveal any significant structural differences that could explain the observed differences in stability.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	7
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-02-09
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Platinum Chemistry Prodrugs Hydrolysis Ligands Magnetic Resonance Spectroscopy Molecular Structure Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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