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  • Title: Minimal thioflavin T modifications improve visual discrimination of guanine-quadruplex topologies and alter compound-induced topological structures.
    Author: Kataoka Y, Fujita H, Kasahara Y, Yoshihara T, Tobita S, Kuwahara M.
    Journal: Anal Chem; 2014 Dec 16; 86(24):12078-84. PubMed ID: 25417850.
    Abstract:
    We newly synthesized thioflavin T (ThT) analogs for which the methyl group at the N3 position on the benzothiazole ring was replaced with either a ((p-(dimethylamino)benzoyl)oxy)ethyl group (ThT-DB) or a hydroxyethyl group (ThT-HE). In several neutral buffers, ThT-HE bound to a parallel guanine-quadruplex (G4) DNA and selectively emitted strong fluorescence at 74- to 240-fold higher intensities than those in the presence of double-stranded DNA (dsDNA), whereas ThT resulted in only 13- to 25-fold higher intensities. Furthermore, circular dichroism (CD) analyses using ThT, ThT-DB, and ThT-HE showed that these compounds could induce topological changes in G4. In addition, the different chemical structures of the N3 substituents could alter a G4-DNA conformation. These results indicate a great potential for N3-substituted ThT analogs as G4 probes and drug leads to achieve gene expression regulation.
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