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Updated: May 15, 2025

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Coupling approaches for [Pt(1,10-phenanthroline)(1S,2S-diamminocyclohexane)dihydroxide]2+ using hydrazone and oxime
Ashley Jurisinec1, Jennette Sakoff2, Jayne Gilbert2
1School of Science, Western Sydney University, Locked Bag 1797, Penrith South DC, Sydney, NSW 2751, Australia. J.Aldrich-Wright@westernsydney.edu.au.
Abstract:
Established methods for conjugating biomolecules to non-conventional complexes such as [Pt(1,10-phenanthroline)(1S,2S-diamminocyclohexane)(OH)2]2+ (PtIVPhenSS) are limited in scope. To address this, we investigated amide, ester, and carbamate strategies, however we encountered significant issues with stability and thus yield. To overcome these shortcomings, we examined an imine linking strategy, using hydrazone and oxime ligation, which proved to be rapid and effective. Here we detail the synthesis of seven platinum(IV) complexes derived from PtIVPhenSS which demonstrate the suitability of an imine conjugation method as a potential linking strategy. Furthermore, we tested these complexes in broad panel of cancer cell lines, identifying that this strategy did not diminish the biological activity of the complex.
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