Perylene- and Naphthalene-Based Linkers for Duplex and Triplex Stabilization

Bevers, Susan; O'Dea, and Timothy P.; McLaughlin, Larry W.

doi:10.1021/ja981962x

Cited by 47 publications

(52 citation statements)

References 15 publications

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“…[38] NDI fluorescence emissions show maxima between 300-800 nm, including in the spectral region where the interference from the autofluorescence of living cells may be bypassed; this makes them attractive candidates as building blocks for optical imaging probes. [38][39][40][41][42][43][44][45] NDI derivatives have been recently explored as DNA intercalators by virtue of their aromatic stacking with purines and pyrimidines [43,46,47] and as fluorescent tags for hypoxia-targeting probes such as nitroimidazoles. [48][49][50] Due to their aromatic stacking ability, fluorescence and electrochemical properties, NDIs are of interest as building blocks for biomimetic supramolecular and functional materials.…”

Section: Introductionmentioning

confidence: 99%

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Pantoş

Kuganathan

et al. 2011

Adv Funct Materials

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A new synthetic route to functionalized single walled carbon nanotubes (SWNTs) via supramolecular interactions using a specifically designed naphthalenediimide (NDI) nanoreceptor is demonstrated. The tendency of the NDI to spontaneously form composites with carbon nanomaterials leads to fluorescent amino acid tagged SWNTs, which are dispersible in widely accessible organic solvents (CHCl 3 , DMSO) as well as in biocompatible cell medium (EMEM, Eagle's modified essential medium). The X-ray crystal structure of the first iodine-tagged and amino acid-functionalized NDI molecule, designed especially to facilitate the high resolution transmission electron microscopy (HR TEM) imaging whilst retaining its ability to self-assemble into a nanodimensional receptor in weakly polar solvents, is also described. A new hybrid material, NDI@SWNT, was prepared and characterized as dispersed in organic solvents and aqueous media and in the solid state by HR TEM, tapping mode atomic force microscopy (TM AFM), scanning electron microscopy (SEM), circular dichroism, Raman and fluorescence spectroscopies (steady-state single and two-photon techniques). We have been interested in the design and spectroscopic investigation of new nanomaterials with light emitting properties.[67] The NDI nanotubular receptor recently developed [55] should have the ability to bind via donor-acceptor interactions to carbon nanomaterials, in an analogous manner to that found in the exciting new hybrids containing perylenes in SWNTselectron acceptor composites for photovoltaic applications, reported by the groups of Hirsch [12][13][14] and Guldi.[14]We report our investigations at the formation of a new nanohybrid, denoted NDI@SWNT, in solution and on a preparative scale. We report here for the first time, the recognition and coating of the aromatic surface of ultra-purified SWNTs (provided by Thomas Swan Ltd, Elicarb SWNTs, and further steampuriffied to ensure they are free of catalytic impurities or carbonaceous materials from the nanotube synthesis, Supplementary Information) by a new iodine-and amino acid-derivatized NDI. Investigations into the properties of the new material synthesized (in bulk and in dispersions in CHCl 3 , EtOH, DMSO and serum free aqueous cell culture media such as EMEM) have been carried out by Raman, circular dichroism, FT IR, UV-vis-NIR and fluorescence spectroscopies and imaged at the nanoscale by HR TEM, SEM, EDS and TM AFM. The cellular translocation of the resulting NDI@SWNT complex was investigated by a combination of fluorescence microscopy techniques including fluorescence lifetime imaging and cytotoxicity assays (MTT) in cancerous and non-cancerous cell lines. Here we have used such techniques to probe the integrity of a new nanocomposite denoted NDI@SWNT in vitro. Such an approach could aid the future understanding of the mechanism of action of supramolecular materials at the cellular level and improve the synthetic design of nanohybrids for biomedical imaging and therapeutic applications. Results and Discussions Synthe...

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Section: Introductionmentioning

confidence: 99%

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Pantoş

Kuganathan

et al. 2011

Adv Funct Materials

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“…[6][7][8] Furthermore, PDI has also been used for the functionalization of DNA. [9][10][11][12][13][14][15][16][17][18] However, even though the PDI monomer shows a high quantum yield and photostability, the quenching of PDI by nucleobases, due to electron transfer from nucleobases, has severely limited its application as a fluorophore. [10,17,19] Thus, we introduced "insulator base pairs" between PDI and nucleobases in order to enhance the fluorescence of PDI.…”

mentioning

confidence: 99%

Insulator Base Pairs for Lighting‐up Perylenediimide in a DNA Duplex

Kashida

Sekiguchi

Asanuma

2010

Chemistry A European J

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Quenched: Perylenediimide (PDI) is highly quenched by nucleobases, which greatly restricts its application as a fluorescent probe. Here, we propose "insulator base pairs" tethering cyclohexane ring through D-threoninol. When "insulator base pairs" were inserted between PDI and nucleobases, the quantum yield of PDI drastically increased several thousand-fold. The "insulator base pairs" reported here also have the potential to increase the quantum yields of other fluorophores.

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“…[73] Studien mit einem Enzym, der Helikase Sgs1, die bevorzugt G-Quadruplex-DNA entwindet, aber in geringerem Maße auch Duplex-DNA, belegten eindrucksvoll die Selektivität der Bindung von PBI 27 an DNA. [81] Watson-Crick-Basenpaarung zum einen Strang und Hoogsteen-Basenpaarung [68] zum anderen Strang tragen zur Stabilisierung bei. Im gleichen Maße wie die Tendenz zur Aggregation von 27 vom Sauren zum Basischen zunimmt -die Protonierung im Sauren wirkt der Aggregation entgegen (siehe Abschnitt 3) -so nimmt auch die Bindungs-Selektivität zu.…”

Section: Methodsunclassified

Molekülverbände von Perylenbisimid‐Farbstoffen in Wasser

2012

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Perylenbisimide zählen zu den bedeutendsten funktionellen Farbstoffen mit vielfältigen Anwendungsmöglichkeiten. Aufgrund ihrer chemischen Robustheit, Photostabilität und herausragenden optischen und elektronischen Eigenschaften wurden sie als Pigmentfarbstoffe, Fluoreszenzsonden sowie n‐Halbleiter in der organischen Elektronik und Photovoltaik eingesetzt. Das ausgedehnte quadrupolare π‐System dieser Farbstoffklasse ermöglichte außerdem die Herstellung zahlreicher supramolekularer Architekturen mit faszinierenden photophysikalischen Eigenschaften. Jedoch blieb der supramolekulare Ansatz zur Bildung von Perylenbisimid‐Molekülverbänden größtenteils organischen Medien vorbehalten. Erfreulicherweise gab es in den letzten Jahren beachtliche Bemühungen zur Entwicklung von wasserlöslichen Perylenbisimiden und deren Anwendungen in wässrigen Medien. Dieser Aufsatz gibt einen aktuellen Überblick über die Selbstorganisation von Perylenbisimiden durch π‐π‐Wechselwirkung im wässrigen Medium. Synthetische Strategien zur Herstellung von wasserlöslichen Perylenbisimiden und der Einfluss des Wassers auf die π‐π‐Stapelung von Perylenbisimiden, sowie daraus resultierende Anwendungen werden eingehend diskutiert.

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Perylene- and Naphthalene-Based Linkers for Duplex and Triplex Stabilization

Cited by 47 publications

References 15 publications

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Insulator Base Pairs for Lighting‐up Perylenediimide in a DNA Duplex

Molekülverbände von Perylenbisimid‐Farbstoffen in Wasser

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