Fluorphores are widely used as probes in biology as an aid to visualize cellular activities. However, many of the fluorophores currently available to biologist often are metabolized rapidly, have difficulty passing through cellular membranes, are excreted from cells at a rapid rate, or have other complications. This is especially true for fluorescent probes used to detect calcium ions. Fluorinated aminopyronin fluorophores possess many characteristics that could lead to promising new calcium sensors, given that they are linked to Ca<sup>2+</sup> chelating moieties such as 1,2-bis(o-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA). For example, aminopyronins rapidly diffuse through cellular membranes and covalently link to the side chains of lysine and arginine residues on proteins within the cell. In the synthesis presented, we have generated a fluorinated aminopyronin molecule with olephinic attachment points to which BAPTA or other molecules of interest could be tethered through palladium coupling or olephin metathesis. This aminopyronin was generated in 5 linear steps from commercially available material in an overall yield of approximately 50%. We are currently examining methods of appending BATPA to the synthesized aminopyrinin.

Synthesis of a highly fluorescent aminopyronin calcium sensor

249th National Meeting (2015)

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