Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Tansil, N.C. et al.

Direct detection of DNA with an electrocatalytic threading intercalator.

Herein we report the synthesis, intercalating properties, and analytical applications of an imidazole-substituted naphthalene diimide, N,N'-bis(3-propylimidazole)-1,4,5,8-naphthalene diimide (PIND), functionalized with electrocatalytic redox moieties. PIND was prepared in a single-step reaction from the corresponding dianhydride. Attachment of the redox moieties to PIND relied upon ligand exchange with one of the liable chloride ligands of an Os(bpy)(2)Cl(2) (bpy = 2,2'-bipyridine) complex. The Os(bpy)(2)Cl(2) complex was grafted onto PIND through coordinative bonds with the two imidazole groups at its termini, forming a PIND-[Os(bpy)(2)Cl](+) compound (PIND-Os). Gel electrophoretic studies revealed that PIND-Os binds more strongly to double-stranded DNA (ds-DNA) than its parent compound 1,4,5,8-naphthalene diimide. The naphthalene diimide group binds to ds-DNA in a "classical" threading intercalation mode, while the two Os(bpy)(2)Cl(+) pendants interact with DNA via electrostatic interaction, reinforcing the intercalation by "locking up" the naphthalene diimide group in place. An electrochemical biosensor was fabricated using the redox-active and catalytic PIND-Os intercalator. An increase in sensitivity of 2500-fold over direct voltammetry was obtained in electrocatalytic amperometry, making this an interesting system for amperometric DNA sensing. Under optimized experimental conditions, the biosensor allowed the detection of a 50-mer target DNA in the range of 1.0-300 pM with a detection limit of 600 fM (1.5 amol, 23 fg).[1]

References

Direct detection of DNA with an electrocatalytic threading intercalator. Tansil, N.C., Xie, H., Xie, F., Gao, Z. Anal. Chem. (2005) [Pubmed]

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