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Issue 40, 2020
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Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum(ii) complexes

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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.

Graphical abstract: Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum(ii) complexes

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Article information


Submitted
06 Jul 2020
Accepted
28 Aug 2020
First published
28 Aug 2020

Dalton Trans., 2020,49, 14009-14016
Article type
Paper

Synthesis and antiproliferative activity of hindered, chiral 1,2-diaminodiamantane platinum(II) complexes

V. V. Bakhonsky, A. A. Pashenko, J. Becker, H. Hausmann, H. J. M. De Groot, H. S. Overkleeft, A. A. Fokin and P. R. Schreiner, Dalton Trans., 2020, 49, 14009
DOI: 10.1039/D0DT02391D

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