Efficient Bioimaging with Diaminodicyanoquinodimethanes: Selective Imaging of Epidermal and Stomatal Cells and Insight into the Molecular Level Interactions

The enhanced fluorescence emission of diaminodicyanoquinodimethanes (DADQs) in rigid and aggregated states holds great promise for bioimaging applications. This is demonstrated through their efficient application in epidermal and stomatal imaging with selective staining of cell walls and nuclei. Major advantages include the small quantities (a few nmols) of the fluorophore required, choice of DADQs soluble in water and organic solvents, and quick staining of the specimen in buffer-free state and in buffer medium. The molecular level interactions that enable staining are unraveled through isothermal calorimetry, infra-red spectroscopy and microscopy with energy dispersive X-ray spectroscopy analysis. It is proposed that DADQs with ionic or H-bonding functionalities bind to the polygalacturonic acid moieties in the epidermal layer; the former can bind also to nucleic acid polyanions. Fluorescence experiments explain the emission enhancement that enables the efficient imaging. DADQs are easy to synthesize, non-cytotoxic, and thermally, chemically and photo-stable, requiring no special storage conditions; preliminary experiments point to their potential utility in imaging different classes of cells.