A convenient ‘click chemistry’ approach to perylene diimide–oligonucleotide conjugates

Устинов, Алексей Владимирович; Dubnyakova, V. V.; Korshun, Vladimir A.

doi:10.1016/j.tet.2007.11.048

Cited by 42 publications

(40 citation statements)

References 49 publications

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“…1,2 To our knowledge, the hairpin conjugates provide the only example of the formation of a discrete PDI-PDI dimer which is not assembled by covalent bonding, hydrogen bonding, or multiple PDI-PDI interactions. 4,10,16,17 As such, they are free to adopt a dimer geometry without geometric constraints imposed by either covalent or noncovalent assembly. We report here the results of our collaborative investigation of the structure and spectroscopic properties of the hairpin-forming PDI conjugates 1 and the structure of the related hairpin 2 (Chart 1).…”

Section: Introductionmentioning

confidence: 99%

Hydrophobic Dimerization and Thermal Dissociation of Perylenediimide-Linked DNA Hairpins

et al. 2009

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The structure and properties of hairpin-forming bis(oligonucleotide) conjugates possessing perylenediimide (PDI) chromophores as hairpin linkers have been investigated using a combination of spectroscopic and computational methods. These conjugates exist predominantly as monomer hairpins at room temperature in the absence of added salt and as head-to-head hairpin dimers in the presence of >50 mM NaCl. The hairpin dimer structure is consistent with the results of small-angle X-ray scattering in aqueous solution and molecular dynamics simulation. The structure of the nonconjugated PDI dimer in water is investigated using potential of mean force calculations. The salt dependence is attributed to increased cation condensation in the hairpin dimer vs monomer. Upon heating at low salt concentrations, the hairpin dimer undergoes sequential dissociation to form the monomer hairpin followed by conversion to a random coil structure; whereas at high salt concentrations both dissociation processes occur over the same temperature range. The monomer and dimer hairpins have distinct spectroscopic properties both in the ground state and excited singlet state. The UV and CD spectra provide evidence for electronic interaction between PDI and the adjacent base pair. Low fluorescence quantum yields are observed for both the monomer and dimer. The transient absorption spectrum of the dimer undergoes time-dependent spectral changes attributed to a change in the PDI-PDI torsional angle from ca. 20 degrees in the Franck-Condon singlet state to ca. 0 degrees in the relaxed singlet state, a process which occurs within ca. 40 ps.

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Section: Introductionmentioning

confidence: 99%

Hydrophobic Dimerization and Thermal Dissociation of Perylenediimide-Linked DNA Hairpins

et al. 2009

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“…Due to their simplicity and selectivity, Cu(I)-catalyzed azide-alkyne cycloadditions (CuAACs) have been extensively studied in biological and materials sciences [5][6][7]. Hence, CuAACs have been shown to be an almost universal tool for modifying polymers, dendrimers, rotaxanes, inorganic surfaces, colloidal nanoparticles, and even biological entities such as cells, viruses, or proteins [8][9][10][11][12][13]. During the last decade, controlled living radical polymerization (CLRP) techniques such as atom transfer radical polymerization (ATRP), nitroxide-mediated radical polymerization (NMRP), and reversible addition-fragmentation transfer (RAFT) polymerization have been shown to be efficient techniques for the preparation of functional polymers [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of end-functional polymers on silica nanoparticles via a combination of atom transfer radical polymerization and click chemistry

Ruan

Chen

Xiang

et al. 2009

Reactive and Functional Polymers

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“…For example, conjugation to very hydrophobic dye structures can be achieved, [29] and the synthesis of highly modified DNA strands is possible, opening up a wide array of potential applications.…”

Section: Analytical Applications Of Modified Dnamentioning

confidence: 99%

Postsynthetic DNA Modification through the Copper‐Catalyzed Azide–Alkyne Cycloaddition Reaction

et al. 2008

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The attachment of labels onto DNA is of utmost importance in many areas of biomedical research and is valuable in the construction of DNA-based functional nanomaterials. The copper(I)-catalyzed Huisgen cycloaddition of azides and alkynes (CuAAC) has recently been added to the repertoire of DNA labeling methods, thus allowing the virtually unlimited functionalization of both small synthetic oligonucleotides and large gene fragments with unprecedented efficiency. The CuAAC reaction yields the labeled polynucleotides in very high purity after a simple precipitation step. The reviewed technology is currently changing the way in which functionalized DNA strands are generated cost-efficiently in high quality for their application in molecular diagnostics systems and nanotechnological research.

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A convenient ‘click chemistry’ approach to perylene diimide–oligonucleotide conjugates

Cited by 42 publications

References 49 publications

Hydrophobic Dimerization and Thermal Dissociation of Perylenediimide-Linked DNA Hairpins

Hydrophobic Dimerization and Thermal Dissociation of Perylenediimide-Linked DNA Hairpins

Synthesis and characterization of end-functional polymers on silica nanoparticles via a combination of atom transfer radical polymerization and click chemistry

Postsynthetic DNA Modification through the Copper‐Catalyzed Azide–Alkyne Cycloaddition Reaction

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