Merocyanine dyes are especially well suited for live cell imaging applications because they are bright, they can be tuned to emit at longer wavelengths that are less toxic to cells, and they can exhibit significant changes in fluorescence intensity or excitation/emission maxima in response to changes in solvation environment.  Several structural analogues of a parent merocyanine dye were prepared and screened for membrane permeability and uniform cellular distribution.  The incorporation of two acetoxymethyl ester groups on the donor portion of the dye was found to be optimal.  A conjugatable version of this dye was prepared through a convergent synthetic strategy involving late stage deprotection of a photolabile protecting group to allow integration of a free carboxylic acid.  The dye is currently being applied in both in vivo protein labeling and live cell biosensor applications.

Membrane permeant and conjugatable merocyanine dyes for live cell imaging applications

244th National Meeting (2012)

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