syn-(Me,Me)Bimane: A Fluorescent Ligand for Na+
2Chemical Engineering and Biotechnology, Ariel University, Ariel, Israel
3Chemical Research Support, Weizmann Institution of Science, Rehovot, Israel
syn-Bimanes have been used in biological systems as fluorescent-labeling agents for various biomolecules (e.g., proteins, amino acids, glutathione), due to their non-toxicity, low molecular weight and strong fluorescence. We have recently shown that one of these heterobicyclic compounds, syn-(Me,Me)bimane, coordinates Pd(II) in a chelating fashion through its two carbonyl oxygens.[1] This was the first reported case of metal-bimane coordination, to the best of our knowledge.
We have since expanded our investigation to examine the coordination chemistry of syn-(Me,Me)Bimane with a biologically important alkali metal cations, Na+.
Our study reveals that syn-(Me,Me)bimane exhibits several binding modes. The strongly fluorescent syn-(Me,Me)bimane binds Na+ cation via its carbonyl oxygens, leading to changes in its fluorescence properties. Spectroscopic evidence (NMR, UV-Vis, fluorescence) demonstrates that bimane coordination is reversible in solution.
The syntheses of Na-bimane complexes, as well as their spectroscopic and crystallographic data, will be presented.
- P. J. Das, Y. Diskin-Posner, M. Firer, M. Montag, F. Grynszpan, Dalton Trans. 2016, 45, 17123-17131
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