Electrochemical DNA Detection Using Supramolecular Interactions

Sato, Shinobu; Takenaka, Shigeori

doi:10.2116/analsci.28.643

Cited by 10 publications

(10 citation statements)

References 28 publications

(37 reference statements)

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“…Molecular recognition has also been widely used for electrochemical detection of DNA, using supramolecular interactions in which functionalized NDI forms a complex of ferrocene−β-cyclodextrin (β-CD) (181) through intercalation. In other examples, it was shown that NDI appended with Zn(II)-cyclens acts as a receptor for the thymine base in DNA (182) . , Matile and co-workers used molecular recognition to build multichromophoric, zipper donor–acceptor, layer-by-layer (LBL) assembly systems, with nonhalogenated NDIs (RO) attached along p-oligophenyl (POP) and oligophenylethynyl (OPE) scaffolds, and they further evaluated their usefulness for zipper-assembly of artificial photosystems (183, 184) . They found that in nonhalogenated NDIs the HOMO of RO is 0.2 eV higher, and the HOMO/LUMO gap is 0.1 eV smaller.…”

Section: Supramolecular Self-assemblymentioning

confidence: 99%

“…intercalation with aromatic ligand (DAN) (Figure 61 (B)), to untwist the helix-barrel to give open barrel stave ion-channels for anions in the lipid bilayer membrane. Matile and co-workers have also described a number of designs from monomeric to cyclic to rod-shaped NDI transporters (257), in which anion−π interactions take place between the anions and π-acidic aromatics. 43 To achieve this, three NDIs were lined up in a rigid-rod oligomer, which allowed the anions to move along the π-acidic NDI surfaces within the lipid bilayer membranes (196) (Figure 33 (B)).…”

Section: Ion-channelsmentioning

confidence: 99%

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Functional Naphthalene Diimides: Synthesis, Properties, and Applications

et al. 2016

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This comprehensive review surveys developments over the past decade in the field of naphthalene diimides (NDIs). It explores their application toward: supramolecular chemistry; sensors; host-guest complexes for molecular switching devices, such as catenanes and rotaxanes; ion-channels by ligand gating; gelators for sensing aromatic systems; catalysis through anion-π interactions; and NDI intercalations with DNA for medicinal applications. We have also explored new designs, synthesis, and progress in the field of core-substituted naphthalene diimides (cNDIs), and their implications in areas such as artificial photosynthesis and solar cell technology. Also presented are some interesting synthetic routes and procedures that can be used toward further development of NDI-bearing compounds for future applications. Finally, we conclude with our views on NDI chemistry for future research endeavors, and we outline what we believe are the key obstacles that need to be overcome for NDIs to see real world applications.

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Section: Supramolecular Self-assemblymentioning

confidence: 99%

Section: Ion-channelsmentioning

confidence: 99%

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

et al. 2016

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“…15 In the past, methylene blue (MB) has oen been employed in electrochemical detection methods due to its stronger affinity for exposed guanine in single-stranded DNA; 16,17 however in this work, we have used a new indicator (FND) that specically binds to double-stranded DNA (dsDNA). The FND molecule binds to dsDNA through a threading intercalation mode, 18,19 in which the ferrocene molecule is inserted between the duplex and its two peripheral substituents (Fig. 1b).…”

Section: Introductionmentioning

confidence: 99%

“…The substituents lie in the major and minor grooves in the complex with a DNA duplex and serve as an anchor to prevent the FND molecule's dissociation from the dsDNA. This complex is stabilized by van der Waals forces, non-covalent interactions and p stacking, with a slow dissociation rate and high rigidity, 18 whereas for single-stranded DNA, the FND molecule dissociates readily due to the non-stabilizing interactions between the two peripheral substituents. Thus, this intercalator shows a huge benet for electrochemical measurements to distinguish between single-stranded and dsDNA.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical sensory detection ofSus scrofamtDNA for food adulteration using hybrid ferrocenylnaphthalene diimide intercalator as a hybridization indicator

et al. 2020

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“…PNAs and triplex-forming bicyclic oligonucleotides have been described with long lifetimes and high affinities. 10,11 While threading mono- and bisintercalators continue to be of interest, 12–15 reports of longer polyintercalators, threading or not, are rare. 16–21 …”

Section: Introductionmentioning

confidence: 99%

Threading Polyintercalators with Extremely Slow Dissociation Rates and Extended DNA Binding Sites

Smith

Iverson

2013

J. Am. Chem. Soc.

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The development of small molecules that bind DNA sequence specifically has the potential to modulate gene expression in a general way. One mode of DNA binding is intercalation, or the insertion of molecules between DNA base pairs. We have developed a modular polyintercalation system in which intercalating naphthalene diimide (NDI) units are connected by flexible linkers that alternate between the minor and major grooves of DNA when bound. We recently reported a threading tetraintercalator with a dissociation half-life of 16 days, the longest reported to date, from its preferred 14 bp binding site. Herein, three new tetraintercalator derivatives were synthesized with one, two, and three additional methylene units in the central major groove-binding linker. These molecules displayed dissociation half-lives of 57, 27, and 18 days, respectively, from the 14 bp site. The optimal major groove-binding linker was used in the design of an NDI hexaintercalator that was analyzed by gel-shift assays, DNase I footprinting, and UV-visible spectroscopy. The hexaintercalator bound its entire 22 bp binding site, the longest reported specific binding site for a synthetic, non-nucleic acid based DNA binding molecule, but with a significantly faster dissociation rate compared to the tetraintercalators.

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Electrochemical DNA Detection Using Supramolecular Interactions

Cited by 10 publications

References 28 publications

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

Electrochemical sensory detection ofSus scrofamtDNA for food adulteration using hybrid ferrocenylnaphthalene diimide intercalator as a hybridization indicator

Threading Polyintercalators with Extremely Slow Dissociation Rates and Extended DNA Binding Sites

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