Jump to main content
Jump to site search

Issue 20, 2012
Previous Article Next Article

Harnessing chemoselective imine ligation for tethering bioactive molecules to platinum(IV) prodrugs

Author affiliations

Abstract

Platinum(II) anticancer drugs are among the most effective and often used chemotherapeutic drugs. In recent years, there has been increasing interest in exploiting inert platinum(IV) scaffolds as a prodrug strategy to mitigate the limitations of platinum(II) anticancer complexes. In this prodrug strategy, the axial ligands are released concomitantly upon intracellular reduction to the active platinum(II) congener, offering the possibility of conjugating bioactive co-drugs which may synergistically enhance cytotoxicity on cancer cells. Existing techniques of tethering bioactive molecules to the axial positions of platinum(IV) prodrugs suffer from limited scope, poor yields and low reliability. This report explores the applications of current chemoselective ligation chemistries to platinum(IV) anticancer complexes with the aim of addressing the aforementioned limitations. Here, we describe the synthesis of a platinum(IV) complex bearing an aromatic aldehyde functionality and explored the scope of imine ligation with various hydrazide and aminooxy functionalized substrates. As a proof of concept, we tethered a six sequence long peptide mimetic (AMVSEF) of the anti-inflammatory protein, ANXA1.

Graphical abstract: Harnessing chemoselective imine ligation for tethering bioactive molecules to platinum(iv) prodrugs

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 04 Feb 2012, accepted on 13 Feb 2012 and first published on 15 Feb 2012


Article type: Paper
DOI: 10.1039/C2DT30264K
Citation: Dalton Trans., 2012,41, 6104-6111
  •   Request permissions

    Harnessing chemoselective imine ligation for tethering bioactive molecules to platinum(IV) prodrugs

    D. Y. Q. Wong, J. Y. Lau and W. H. Ang, Dalton Trans., 2012, 41, 6104
    DOI: 10.1039/C2DT30264K

Search articles by author