Platinum diolefin complexes - synthesis, structures, and cytotoxicity

Anna Luning, Michael Neugebauer, Verena Lingen, Alexander Krest, Kathrin Stirnat, Glen Berenger Deacon, Penny R Drago, Ingo Ott, Julia Schur, Ingo Pantenburg, Gerd Meyer, Axel Klein

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Abstract

The synthesis, spectroscopy, structures and chemical reactivity of platinum(II) diolefin complexes cis-[( ? )PtCl2], cis-[( ? )PtCl(R)] and cis-[( ? )Pt(R)2] [ ? = chelate diolefin ligand: 1,5-cyclooctadiene (COD), 1,5-dimethylocta-1,5-diene (Me2COD), norbornadiene (NBD), 1,5-hexadiene (HEX), 3-allyloxypropene (All2O, diallyl ether), diallylamine (All2NH); R = Me, Bn, C6F5, C6F4H-4 (or -5), or C=C(4-Me)Ph] have been explored. The relative exchange rates of the cis-[( ? )-PtCl2] complexes towards the diimine ligand diisopropyl-1,4-diazabutadiene (iPr-DAB) increased along the series COD <Me2COD <NBD <HEX <All2O by a factor of 4. The presumably dimeric complex [(All2NH)PtCl2]2 undergoes a unique rearrangement process in dimethyl sulfoxide (DMSO) solution to yield the dimeric piperazine complex [PtCl(dmso)-(C6H10N)]2, which has been characterised by single-crystal XRD. For selected platinum complexes, cytotoxic effects in HT-29 colon carcinoma and MCF-7 breast cancer cell lines were evaluated. For comparison, the dicationic complexes [(COD)Pt(Bn)(L)][PF6]2 with the very labile coligands N-methyl-4,4 -bipyridinium (MQ+) and N-methyl-1,4-pyrazinium (Mpz+) were added to the study. Although the hexadiene complexes [(HEX)Pt(C6F4H-4)2] and [(HEX)Pt(C6F4H-5)2] show strong cytotoxicity, the introduction of labile diolefin ligands or the labile cationic MQ+ or Mpz+ coligands does not generally lead to markedly increased cytotoxicity.
Original languageEnglish
Pages (from-to)226 - 239
Number of pages14
JournalEuropean Journal of Inorganic Chemistry
Volume2015
Issue number2
DOIs
Publication statusPublished - 2015

Cite this

Luning, A., Neugebauer, M., Lingen, V., Krest, A., Stirnat, K., Deacon, G. B., Drago, P. R., Ott, I., Schur, J., Pantenburg, I., Meyer, G., & Klein, A. (2015). Platinum diolefin complexes - synthesis, structures, and cytotoxicity. European Journal of Inorganic Chemistry, 2015(2), 226 - 239. https://doi.org/10.1002/ejic.201402954