Tetrahedral DNA conjugates from pentaerythritol-based polyazides

Ponomarenko, Anna I.; Brylev, Vladimir A.; Sapozhnikova, Ksenia A.; Устинов, Алексей Владимирович; Prokhorenko, Igor A.; Zatsepin, Timofei S.; Korshun, Vladimir A.

doi:10.1016/j.tet.2016.03.051

Cited by 14 publications

(10 citation statements)

References 74 publications

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“…Earlier eluting diazide 3 (4.7 g; 27%) and triazide 4 (1.43 g; 8%) were obtained as colorless viscous liquids. Their analytical data matched with ones reported earlier 21.…”

supporting

confidence: 89%

“…Reagents and solvents were from commercial suppliers and used as received, except DMF, DMSO, CH 2 Cl 2 , CHCl 3 , EtOH and methanol were used freshly distilled from CaH 2 . Azides 4, 5, 21 tetrakis(5-hydroxy-2-oxapentyl)methane 21 and 3-Pom-5-(perylen-3-ylethynyl)uracil-1-acetic acid 6 6 were prepared as described. 500 MHz 1 H and 125.7 MHz 13 C NMR spectra were recorded on Bruker AMX-400 or Bruker Avance 500 spectrometers and referenced to DMSO- d 6 (2.50 ppm for 1 H and 39.5 ppm for 13 C) or CDCl 3 (7.26 ppm for 1 H and 77.16 ppm for 13 C).…”

Section: Methodsmentioning

confidence: 99%

“…Tuning the mesyl chloride/hydroxyl ratio leads to the desired distribution of products in the reaction. Earlier, we prepared azides 4 and 5 using 1 : 3 molar ratio of 1 to mesyl chloride 21 and used them for the assembly of complex oligonucleotide conjugates. 21,22 Here we report the synthesis of azides 2 and 3 as main products.…”

Section: Synthesis Of Compoundsmentioning

confidence: 99%

“…Earlier, we prepared azides 4 and 5 using 1 : 3 molar ratio of 1 to mesyl chloride 21 and used them for the assembly of complex oligonucleotide conjugates. 21,22 Here we report the synthesis of azides 2 and 3 as main products. Mesylation with 1 : 1.2 molar ratio (1 : MsCl), and subsequent nucleophilic substitution with sodium azide affords compounds 2 and 3 in 32% and 27% yield, respectively, together with some amount of triazide 4.…”

Section: Synthesis Of Compoundsmentioning

confidence: 99%

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Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties

et al. 2019

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“…Earlier eluting diazide 3 (4.7 g; 27%) and triazide 4 (1.43 g; 8%) were obtained as colorless viscous liquids. Their analytical data matched with ones reported earlier 21.…”

supporting

confidence: 89%

Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of Compoundsmentioning

confidence: 99%

Section: Synthesis Of Compoundsmentioning

confidence: 99%

See 2 more Smart Citations

Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties

et al. 2019

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“…136 Several fluorescent dyes were introduced to the same or different oligonucleotides in branched assemblies. 137 Furthermore, many oligonucleotide strands, obtained by a DNA synthesizer, are connected to each other by click reactions to form large DNA molecules. 138 The advantage of this method is that any chemically modified nucleotides can be incorporated to a predetermined site in large DNA.…”

Section: Dna Nanoarchitectonicsmentioning

confidence: 99%

Chemistry Can Make Strict and Fuzzy Controls for Bio-Systems: DNA Nanoarchitectonics and Cell-Macromolecular Nanoarchitectonics

Komiyama

Yoshimoto

Sisido

et al. 2017

Bulletin of the Chemical Society of Japan

281

131

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In this review, we introduce two kinds of bio-related nanoarchitectonics, DNA nanoarchitectonics and cellmacromolecular nanoarchitectonics, both of which are basically controlled by chemical strategies. The former DNA-based approach would represent the precise nature of the nanoarchitectonics based on the strict or "digital" molecular recognition between nucleic bases. This part includes functionalization of single DNAs by chemical means, modification of the main-chain or side-chain bases to achieve stronger DNA binding, DNA aptamers and DNAzymes. It also includes programmable assemblies of DNAs (DNA Origami) and their applications for delivery of drugs to target sites in vivo, sensing in vivo, and selective labeling of biomaterials in cells and in animals. In contrast to the digital molecular recognition between nucleic bases, cell membrane assemblies and their interaction with macromolecules are achieved through rather generic and "analog" interactions such as hydrophobic effects and electrostatic forces. This cell-macromolecular nanoarchitectonics is discussed in the latter part of this review. This part includes bottom-up and top-down approaches for constructing highly organized cell-architectures with macromolecules, for regulating cell adhesion pattern and their functions in twodimension, for generating three-dimensional cell architectures on micro-patterned surfaces, and for building synthetic/natural macromolecular modified hybrid biointerfaces.

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“Printing” DNA Strand Patterns on Small Molecules with Control of Valency, Directionality, and Sequence

et al. 2018

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The incorporation of synthetic molecules as corner units in DNA structures has been of interest over the last two decades. In this work, we present a facile method for generating branched small molecule‐DNA hybrids with controllable valency, different sequences, and directionalities (5′–3′) using a “printing” process from a simple 3‐way junction structure. We also show that the DNA‐imprinted small molecule can be extended asymmetrically using polymerase chain reaction (PCR) and can be replicated chemically. This strategy provides opportunities to achieve new structural motifs in DNA nanotechnology and introduce new functionalities to DNA nanostructures.

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Tetrahedral DNA conjugates from pentaerythritol-based polyazides

Cited by 14 publications

References 74 publications

Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties

Ramified derivatives of 5-(perylen-3-ylethynyl)uracil-1-acetic acid and their antiviral properties

Chemistry Can Make Strict and Fuzzy Controls for Bio-Systems: DNA Nanoarchitectonics and Cell-Macromolecular Nanoarchitectonics

“Printing” DNA Strand Patterns on Small Molecules with Control of Valency, Directionality, and Sequence

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