Design of Functional Diversity in Oligonucleotides via Zwitter-Ionic Derivatives of Deprotected Oligonucleotides

Zarytova, Valentina P.; Иванова, Е. М.; Ven’yaminova, A. G.

doi:10.1080/07328319808005207

Cited by 19 publications

(6 citation statements)

References 3 publications

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“…Terminal phosphates serve as reactive groups for the postsynthetic functionalization of oligonucleotides , and have been used extensively in parallel TFOs. − …”

Section: Moieties Inserted At the 5′- Or 3′-end Of The Sequencementioning

confidence: 99%

Molecular Engineering of Guanine-Rich Sequences: Z-DNA, DNA Triplexes, and G-Quadruplexes

2013

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“…Terminal phosphates serve as reactive groups for the postsynthetic functionalization of oligonucleotides , and have been used extensively in parallel TFOs. − …”

Section: Moieties Inserted At the 5′- Or 3′-end Of The Sequencementioning

confidence: 99%

Molecular Engineering of Guanine-Rich Sequences: Z-DNA, DNA Triplexes, and G-Quadruplexes

2013

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“…The 5′-pyrene model oligodeoxyribonucleotide conjugates Pyr22, PyrHEG22, Pyr17, and PyrHEG17 (Table S-3 in the SI) were synthesized similarly to those in ref by coupling 1-pyrenylmethylamine with the 5′-terminal phosphate group of the oligonucleotide that was selectively activated using triphenylphosphine and 2,2′-dipyridyl disulfide in the presence of 4-( N , N ′-dimethylamino)pyridine as the nucleophilic catalyst. , The pyrene residues were conjugated with the oligonucleotides via a phosphamide bond. The hexakis(ethylene glycol) linker provided the conformational mobility in the pyrene residue, thus facilitating its interaction with SWCNTs.…”

Section: Resultsmentioning

confidence: 99%

Novel Multifunctional Hybrids of Single-Walled Carbon Nanotubes with Nucleic Acids: Synthesis and Interactions with Living Cells

Apartsin

Новопашина

Ryabchikova

et al. 2014

ACS Appl. Mater. Interfaces

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Novel hybrids of fluorescein-labeled poly(ethylene glycol)-modified single-walled carbon nanotubes (SWCNTs) with nucleic acids were prepared. 5'-Pyrene conjugates of oligodeoxyribonucleotides were used to construct the noncovalent hybrids, with the pyrene residues acting as anchor groups, immobilizing an oligonucleotide on the SWCNT surface. The hybrid formation characteristics were studied using ζ-potential measurements and adsorption isotherm plots. Transmission electron microscopy (TEM) of the samples stained with contrast agents proved that the pyrene conjugates of oligonucleotides were adsorbed onto the surfaces of the functionalized SWCNTs. On the basis of the MTT assay, the functionalized SWCNTs and their hybrids with oligonucleotides exhibited low toxicity toward HeLa, KB-3-1, and KB-8-5 cells. A TEM study of ultrathin sections of cells treated with SWCNTs revealed that the nanotubes directly interacted with the cellular surface.

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“…The terminal phosphate of oligo(2′-O-methylribonucleotides) has been chosen as a position of labeling as such coupling does not prevent conjugates from forming stable duplexes with DNA targets. We have selected a convenient postsynthetic method of terminal phosphate activation by oxidation-reduction pair triphenylphosphine-dipyridyldisulfide in the presence of nucleophilic catalyst N,N-dimethylaminopyridine followed by the reaction with ligand bearing nucleophilic group [ 31 ].…”

Section: Resultsmentioning

confidence: 99%

Multipyrene Tandem Probes for Point Mutations Detection in DNA

Kholodar

Новопашина

Meschaninova

et al. 2013

Journal of Nucleic Acids

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Here we report design, synthesis and characterization of highly sensitive, specific and stable in biological systems fluorescent probes for point mutation detection in DNA. The tandems of 3′- and 5′-mono- and bis-pyrene conjugated oligo(2′-O-methylribonucleotides), protected by 3′-“inverted” thymidine, were constructed and their potential as new instruments for genetic diagnostics was studied. Novel probes have been shown to exhibit an ability to form stable duplexes with DNA target due to the stabilizing effect of multiple pyrene units at the junction. The relationship between fluorescent properties of developed probes, the number of pyrene residues at the tandem junction, and the location of point mutation has been studied. On the basis of the data obtained, we have chosen the probes possessing the highest fluorescence intensity along with the best mismatch discrimination and deletion and insertion detection ability. Application of developed probes for detection of polymorphism C677T in MTHFR gene has been demonstrated on model systems.

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Design of Functional Diversity in Oligonucleotides via Zwitter-Ionic Derivatives of Deprotected Oligonucleotides

Cited by 19 publications

References 3 publications

Molecular Engineering of Guanine-Rich Sequences: Z-DNA, DNA Triplexes, and G-Quadruplexes

Molecular Engineering of Guanine-Rich Sequences: Z-DNA, DNA Triplexes, and G-Quadruplexes

Novel Multifunctional Hybrids of Single-Walled Carbon Nanotubes with Nucleic Acids: Synthesis and Interactions with Living Cells

Multipyrene Tandem Probes for Point Mutations Detection in DNA

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