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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
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Novel cis-[(NHC)1(NHC)2(L)Cl]platinum(ii) complexes - synthesis, structures, and anticancer activities
Tobias Rehm1, Matthias Rothemund, Julienne K Muenzner
1Organic Chemistry Laboratory, University Bayreuth, Universitaetsstrasse 30, 95440 Bayreuth, Germany. Rainer.Schobert@uni-bayreuth.de.
Dalton Transactions (Cambridge, England : 2003)
|September 8, 2016
Summary
Novel platinum(II) complexes with two cis-oriented N-heterocyclic carbene (NHC) ligands were synthesized. These complexes exhibit potent cytotoxicity against human cancer cell lines, with some showing specific activity and DNA interaction.
Area of Science:
- Organometallic Chemistry
- Medicinal Chemistry
- Materials Science
Background:
- Platinum(II) complexes are crucial in cancer therapy.
- N-heterocyclic carbene (NHC) ligands offer tunable electronic and steric properties.
- Developing novel platinum-based anticancer agents with improved efficacy and specificity is an ongoing challenge.
Purpose of the Study:
- To synthesize novel platinum(II) complexes featuring two distinct, cis-oriented N-heterocyclic carbene (NHC) ligands.
- To evaluate the cytotoxic activity of these new complexes against a panel of human cancer cell lines.
- To investigate the interaction of these complexes with plasmid DNA.
Main Methods:
- Synthesis of cis-[PtII(NHC)2Cl2] and mixed cis-[PtII(NHC)1(NHC)2Cl2] complexes.
- Structural characterization using NMR spectroscopy (1H, 13C, 195Pt) and X-ray diffraction.
- Cytotoxicity assays (IC50 values) against seven human cancer cell lines.
- Electrophoretic mobility shift assays (EMSA) to assess DNA interaction.
Main Results:
- Ten new platinum(II) complexes with benzylated and alkylated imidazol-2-ylidene ligands were successfully synthesized and characterized.
- Both neutral and cationic complexes demonstrated significant cytotoxicity, with IC50 values in the micromolar and nanomolar ranges, respectively.
- Complex 5h, mimicking Combretastatin A-4, showed specific cytotoxicity against sensitive cancer cell lines.
- Cis-biscarbene complexes induced unwinding or aggregation of plasmid DNA, unlike trans-biscarbene complexes.
Conclusions:
- The developed synthetic strategy allows for the facile preparation of diverse cis-bis(NHC)platinum(II) complexes.
- These novel platinum(II)-NHC complexes represent promising candidates for anticancer drug development due to their potent and sometimes specific cytotoxic activities.
- The observed DNA interaction by cis-biscarbene complexes suggests a potential mechanism of action.
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