Mechanistic pathway for controlled extraction of guest molecule bound to herring sperm DNA using α-cyclodextrin

trans-2-[4-(Dimethylamino)styryl]benzothiazole (DMASBT) is known to have dual emitting states where the locally excited (LE) state is responsible for fluorescence in less polar environment and in polar milieu fluorescence is from the twisted intramolecular charge transfer (TICT) state. This compound also undergoes minor groove binding to herring sperm DNA (hsDNA) evidenced by the absorption spectra before and after the binding process and an effect on DMASBT fluorescence by an anionic quencher. The binding occurs efficiently in a 1:1 manner, i.e. one guest molecule binds to one site on the hsDNA. Instead of following the DNA twist, the aromatic part seems to project outward. Thus, the bound molecule can be successfully extracted out from the DNA in a controlled way by the hydrophobic cavity of α-cyclodextrin (α-CD). The extraction starts even with a low concentration of α-CD and increases as the concentration is increased. Absorption, steady-state and time resolved fluorescence spectroscopic methods have been employed to explore the mechanistic pathway of binding of DMASBT to hsDNA. The mechanistic approach toward controlled extraction of the guest molecules from hsDNA by α-CD is reported and is expected to serve a significant purpose in treatment of drug overdose.

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► trans-2-[4-(Dimethylamino)styryl]benzothiazole (DMASBT) has dual emitting states.
► Locally excited (LE) state fluoresces in less polar solvents and twisted intramolecular charge transfer (TICT) state emits in polar milieu.
► DMASBT undergoes minor groove binding to herring sperm DNA.
► The bound molecule can be successfully extracted out from the DNA in a controlled way by the hydrophobic cavity of α-cyclodextrin.
► Mechanistic approach toward controlled extraction of the guest molecules from hsDNA by α-cyclodextrin is reported.