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  • Title: Closing the ring to bring up the light: synthesis of a hexacyclic acridinium cyanine dye.
    Author: Mahmood T, Wu Y, Loriot D, Kuimova M, Ladame S.
    Journal: Chemistry; 2012 Sep 24; 18(39):12349-56. PubMed ID: 22907584.
    Abstract:
    The synthesis of a geometrically constrained and near-planar hexacyclic acridinium cyanine dye 9 is reported. When compared to its unlocked and non-fluorescent monomethine cyanine dye analogue 3, this photostable dye emits in the green area of the spectrum with a remarkable quantum yield close to unity in organic solvents and above 0.5 in water. A detailed steady-state and time-resolved spectroscopic study revealed that dye 9 forms emissive aggregates in water, which are responsible for a red-shifted and broadened emission band and longer emission lifetime, τ≈33 compared to 6.5-7.0 ns for the monomeric dye. Dye 9 also binds strongly to DNA (both duplex and quadruplex) in its monomeric form and is very efficiently taken up by cells, in which it accumulates primarily into the nucleus.
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