A series of water-soluble dinitrosyl iron complexes (DNICs) were synthesized using various N-heterocyclic carbene (NHC) ligands. DNICs are biological molecules that are linked to the storage and transport of nitric oxide (NO) in the body. Synthesis of water-soluble, biocompatible DNICs will hopefully aid in the transfer of NO to biological systems towards possible pharmaceutical applications. The N-heterocyclic carbene ligand precursors were synthesized from formaldehyde and glyoxal with glycine methyl ester, alanine, and taurine, respectively. 1H NMR and IR spectroscopies were used to confirm the formation and purity of the three NHC ligand precursors. The ligand precursors were deprotonated with sodium tert-butoxide and reacted with the starting iron complex [Fe(CO)2(NO)2] in order to synthesize the {Fe(NO)2}10 mono-NHC DNICs, [(L)(CO)Fe(NO)2], where L = glycine methyl ester, alanine, or taurine NHC. The resulting complexes were identified via 1H NMR and IR spectroscopies, and subjected to water-solubility tests. Future work will be conducted to determine the reactivity of these complexes in aqueous media in order to gain a better understanding of the mechanism by which these complexes store and transfer nitric oxide.

Synthesis and characterization of water-soluble dinitrosyl iron complexes with amino acid derived N-heterocyclic carbene ligands

251st National Meeting (2016)

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