Non-covalent versus covalent control of self-assembly and chirality of Nile red-modified nucleoside and DNA

Chemistry : a European Journal
Reji Varghese, Hans-Achim Wagenknecht

Abstract

A DNA-based covalent versus a non-covalent approach is demonstrated to control the optical, chirooptical and higher order structures of Nile red (Nr) aggregation. Dynamic light scattering and TEM studies revealed that in aqueous media Nr-modified 2'-deoxyuridine aggregates through the co-operative effect of various non-covalent interactions including the hydrogen bonding ability of the nucleoside and sugar moieties and the pi-stacking tendency of the highly hydrophobic dye. This results in the formation of optically active nanovesicles. A left-handed helically twisted H-type packing of the dye is observed in the bilayer of the vesicle as evidenced from the optical and chirooptical studies. On the other hand, a left-handed helically twisted J-type packing in vesicles was obtained from a non-polar solvent (toluene). Even though the primary stacking interaction of the dye aggregates transformed from H-->J while going from aqueous to non-polar media, the induced supramolecular chirality of the aggregates remained the same (left-handed). Circular dichroism studies of DNA that contained several synthetically incorporated and covalently attached Nr-modified nucleosides revealed the formation of helically stacked H-aggregates of Nr but...Continue Reading

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Citations

Mar 20, 2012·Chemical Reviews·Yin Nah Teo, Eric T Kool
Sep 28, 2012·Beilstein Journal of Organic Chemistry·Sebastian Barrois, Hans-Achim Wagenknecht
Sep 29, 2015·Accounts of Chemical Research·Philipp Ensslen, Hans-Achim Wagenknecht
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