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Abstract:
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Development of organic molecules that exhibit selective
interactions with different biomolecules has immense significance
in biochemical and medicinal applications. In this context, our main
objective has been to design a few novel functionaIized molecules
that can selectively bind and recognize nucleotides and DNA in the aqueous medium through non-covalent interactions. Our strategy
was to design novel cycIophane receptor systems based on the
anthracene chromophore linked through different bridging moieties
and spacer groups. It was proposed that such systems would have a
rigid structure with well defined cavity, wherein the aromatic
chromophore can undergo pi-stacking interactions with the guest
molecules. The viologen and imidazolium moieties have been
chosen as bridging units, since such groups, can in principle, could
enhance the solubility of these derivatives in the aqueous medium
as well as stabilize the inclusion complexes through electrostatic
interactions.We synthesized a series of water soluble novel functionalized
cyclophanes and have investigated their interactions with
nucleotides, DNA and oligonucIeotides through photophysical.
chiroptical, electrochemical and NMR techniques. Results indicate
that these systems have favorable photophysical properties and
exhibit selective interactions with ATP, GTP and DNA involving
electrostatic. hydrophobic and pi-stacking interactions inside the
cavity and hence can have potential use as probes in biology. |