Fluoromodules are complexes of non-covalently bound fluorogenic dyes and their fluorescence activating protein partners. Previously, fluorogenic unsymmetrical cyanine dyes were used to sort a diverse protein library to obtain protein partners and create a library of fluoromodules that span the visible spectrum. The dyes were designed for easy modification for favorable spectral properties and binding specificity. Non-specific interactions with nucleic acids are minimized through the incorporation of sterically bulky or negatively charged groups, which are electrostatically repelled by the anionic phosphate backbone of DNA and RNA. However, the addition of charged groups decreases the cell permeability of dyes. In the interest of cytoplasmic imaging studies, modifications to the dyes were explored in order to allow for cell permeability and subsequent cytoplastmic fluoromodule formation. Replacement of previously used sulfonate groups with hydrolyzable acetoxymethyl esters was found to allow for cell permeability while maintaining the protein binding-affinity and specificity of the dyes.

Synthesis and characterization of selective cell permeable fluorogenic cyanine dyes

243rd National Meeting (2012)

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