Nitric oxide plays a major role in human physiology not only as a signaling agent and vasodilator, but also as a treatment for cardiovascular disease and possibly cancer. As such, compounds capable of NO storage and release (such as dinitrosyl iron complexes) are of interest in the development of therapeutic agents. In addition, metal N-heterocyclic carbene complexes (M-NHC, where M = PtII, PdII, AuI, AgI, CuI) have also shown potential as anticancer agents, with cytotoxicities in some cases equal to that of cisplatin. Hence, we seek to combine the cytotoxic properties of these two types of complexes by synthesis of N-heterocyclic carbene dinitrosyl iron complexes (NHC-DNICs). Necessary criteria for a compound to be considered for testing as a drug are both solubility and stability in water. These criteria may be met by functionalizing the R groups of the NHCs with water solubilizing groups such as SO3-, OH-, amides and sugars. Following reaction of the functionalized NHC with the DNIC, the water solubility and stabilitiy is monitored by 1H NMR and by IR, in the ?(NO) region. A particularly promising NHC is derived from 1,3-bis(2,4,6-trimethyl-3-sulfonatophenyl)imidazolium chloride (sIMesH+Cl-). The bulky IMes is known to stabilize the formation of the cationic trinitrosyl iron complex (TNIC), thus providing a complex in which an additional NO may be released. Characterization of these NHC-DNICs includes X-ray crystallography, IR, NMR and EPR. In addition, the NO release ability will also be analyzed.

Synthesis and properties of water soluble N-heterocyclic carbene dinitrosyl iron complexes

247th National Meeting (2014)

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