Oxidation of cis-Diamminediacetato PtII with Hydrogen Peroxide Can Give Rise to Two Isomeric PtIV Products

D. Khattib, M. Ishan, S. Karmakar, H. Kostrhunova, V. Brabec, D. Gibson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The oxidation of cis-[Pt(NH3)2(OAc)2] with H2O2 yields a mixture of two isomers: ctc-[Pt(NH3)2(OH)2(OAc)2] and ctc-[Pt(NH3)2(OH)(OAc)(OH)(OAc)]. Following modification with 4-phenylbutyric (PhB) anhydride, two isomers were separated and characterized; the symmetric ctc-[Pt(NH3)2(PhB)2(OAc)2] (1) and the nonsymmetric ctc-[Pt(NH3)2(PhB)(OAc)(PhB)(OAc)] (2). They differ in their log P values and despite having similar cellular uptake and similar DNA platination levels, the symmetric ctc-[Pt(NH3)2(OH)2(OAc)2] is more than 4-fold more potent than the nonsymmetric isomer in a panel of 4 cancer cell lines.

Original languageEnglish
Pages (from-to)9475-9480
Number of pages6
JournalChemistry - A European Journal
Volume26
Issue number43
DOIs
StatePublished - 3 Aug 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • cytotoxicity
  • diammindiacetatoplatinum(II)
  • isomerization
  • oxidation
  • Pt anticancer agents

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