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Updated: Dec 5, 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
Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum(II) complexes
Vladyslav V Bakhonsky1, Aleksander A Pashenko2, Jonathan Becker3
1Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany and Center for Materials Research (LaMa), Justus Liebig University, Heinrich-Buff-Ring 16, 35392 Giessen, Germany. prs@uni-giessen.de and Department of Organic Chemistry, Igor Sikorsky Kiev Polytechnic Institute, Pobedy Ave. 37, 03056 Kiev, Ukraine. aaf@xtf.kpi.ua.
Abstract:
Platinum-based antineoplastic agents play a major role in the treatment of numerous types of cancer. A new bulky, lipophilic, and chiral ligand based on 1,2-diaminodiamantane in both of its enantiomeric forms was employed for the preparation of new platinum(ii) complexes with chloride and oxalate ligands. The dichloride complexes have a higher solubility and were evaluated as anti-proliferation agents for human ovarian cancer cell lines A2780 and cisplatin-resistant A2780cis. Its R,R-enantiomer showed increased efficacy compared to cisplatin for both cancer cell lines. A chromatographic approach was used to estimate the solvent partition coefficient of the dichloride complex. The binding of diamondoid-based platinum complexes to nucleotides was tested for both enantiomers with guanosine monophosphate (GMP) and deoxyguanosine monophosphate (dGMP) and occurs at a similar or faster rate for both isomers compared to cisplatin despite greatly increased steric demand. These findings highlight the potential in 1,2-diaminodiamantane as a viable pharmacophore.
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