Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates

Meschaninova, Mariya I.; Новопашина, Д. С.; Semikolenova, O. A.; Silnikov, Vladimir N.; Venyaminova, Alya G.

doi:10.3390/molecules24234266

Cited by 27 publications

(30 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis of 3'-alkyne derivatives of oligonucleotides was performed using modified polymer support 3'-alkyne-Modifier Serinol CPG for solid-phase phosphoramidite synthesis. For 5'-alkyne derivatives, we employed the previously described by us method [10] based on the activation of a 5'-hydroxy group of protected support-bound oligonucleotide by N,N'-disuccinimidyl carbonate (DSC) followed by the interaction with propargylamine. The series of alkyne-modified oligomers included 3'-, 5'-and dual 3',5'-modified oligodeoxyribonucleotides, oligoribonucleotides, oligo(2'-O-methylribonucleotides), and oligoribonucleotides with all pyrimidine nucleotides replaced by their 2'-fluoro analogs.…”

Section: Synthesis Of 5'-and/or 3'-alkyne-modified Oligonucleotidesmentioning

confidence: 99%

“…Oligonucleotides bearing a 3'-alkyne group were synthesized using modified polymer support 3'-alkyne-Modifier Serinol CPG (Glen Research, USA). Oligonucleotides with 5'-alkyne modification were obtained in analogy with [10] (see Supplementary for more details). After synthesis, cleavage from support and deprotection of the oligonucleotides were carried out with 300 μL of 40% aq.…”

Section: Synthesis Of Oligonucleotidesmentioning

confidence: 99%

“…The most common methods of incorporating boron clusters to the oligonucleotides rely on modifications of ribose 2'-position or heterocyclic bases, using pre-synthetic or post-synthetic techniques [1,8,9]. So far, only one study has been published on the terminal oligonucleotide modifications by the boron clusters [10]. Along with that, most of the works on oligonucleotides bearing boron clusters deal with non-modified DNA oligonucleotides [4][5][6], with one exception for siRNA [3].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Terminal Mono- and Bis-Conjugates of Oligonucleotides with Closo-Dodecaborate: Synthesis and Physico-Chemical Properties

Новопашина

Vorobyeva

Lomzov

et al. 2020

Preprint

Self Cite

View full text Add to dashboard Cite

Oligonucleotide conjugates with boron clusters have found applications in different fields of molecular biology, biotechnology, and biomedicine as potential agents for boron neutron capture therapy, siRNA components, and antisense agents. Particularly, closo-dodecaborate anion represents a high-boron containing residue with remarkable chemical stability and low toxicity, suitable for the engineering of different constructs for biomedicine and molecular biology. In the present work, we synthesized novel oligonucleotide conjugates of closo-dodecaborate attached to the 5'-, 3'-, or both terminal positions of DNA, RNA, 2'-O-Me RNA, and 2'-F-Py RNA oligomers. For their synthesis, we employed click reaction with the azido derivative of closo-dodecaborate. The key physicochemical characteristics of the conjugates have been investigated using high-performance liquid chromatography, gel electrophoresis, UV thermal melting, and circular dichroism spectroscopy. Incorporation of closo-dodecaborate residues at the 3'-end of all oligomers stabilized their complementary complexes, while analogous 5'-modification decreased duplex stability. Two boron clusters attached to the opposite ends of the oligomer only slightly influence the stability of complementary complexes of RNA oligonucleotide and its 2'-O-methyl and 2'-fluoro analogs. On the contrary, the same modification of DNA oligonucleotides significantly destabilized DNA/DNA duplex but gave a strong stabilization of the duplex with RNA target. According to CD spectroscopy results, two terminal closo-dodecaborate residues cause a prominent structural rearrangement of complementary complexes with a substantial shift from B-form to the A-form of the double helix. The revealed changes of key characteristics of oligonucleotides caused by incorporation of terminal boron clusters, such as the increase of hydrophobicity, change of duplex stability, and prominent structural changes for DNA conjugates, should be taken into account for the development of antisense oligonucleotides, siRNAs, or aptamers bearing boron clusters. These features may also be used for engineering of developing NA constructs with pre-defined properties.

show abstract

Section: Synthesis Of 5'-and/or 3'-alkyne-modified Oligonucleotidesmentioning

confidence: 99%

Section: Synthesis Of Oligonucleotidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Terminal Mono- and Bis-Conjugates of Oligonucleotides with Closo-Dodecaborate: Synthesis and Physico-Chemical Properties

Новопашина

Vorobyeva

Lomzov

et al. 2020

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…Meschaninova et al [45] stated a novel synthesis of oligonucleotide conjugates through solid-phase synthesis based on the interaction of free 5-hydroxyl oligonucleotides and amino-containing ligands such as closo-dodecaborate, oestrone, cholesterol and alphatocopherol. Initially, functionalization of 5-hydroxyl oligonucleotides catalysed by N,N-disuccinimidyl carbonate followed by interaction with an amino group-containing ligand which led to the formation of a wide range of oligonucleotide conjugates such as closo-dodecaborate, lipophilic residues, aliphatic diamines, pyrene, short peptide and propargylamine.…”

Section: Synthesis Of Organic Compoundsmentioning

confidence: 99%

An overview of recent progress in modern synthetic approach—combinatorial synthesis

Gopi¹,

Krupamai²,

Sri³

et al. 2020

Beni-Suef Univ J Basic Appl Sci

View full text Add to dashboard Cite

Background In recent times, a powerful tool of combinatorial synthesis has been used for the preparation of large chemical entities through a small set up of reactions between different building blocks using solid-phase and solution-phase techniques. This method reduced the time and cost of the drug discovery process substantially. Main text Thousands of compounds are synthesised in a few reactions through combinatorial synthesis instead of getting a few compounds in the traditional method. This method also helps to identify chemical lead of the compounds and optimise them through the biological screening using a high-throughput method. There is no review concerning the recent research finding of combinatorial synthesis. Hence, an attempt had been made on the latest research findings (2002–2020) of newly synthesised compounds using combinatorial synthesis and their biological activities. Conclusion To the best of our knowledge, the current review has completely analysed the importance of combinatorial synthesis and furnished an overview of solid-phase and solution-phase techniques as well as helped mankind by improving higher productivity at low cost, lead identification and optimization and preventing environmental pollution. Graphical abstract

show abstract

“…DSC is widely used to produce modified polymer surfaces and to introduce PEG to the definite sites of proteins or nucleic acids. The advantages of DSC are a longer lifespan, wide range of suitable solvents and higher reactivity towards the activated hydroxyl groups [ 27 ]. Several studies have shown that DSC-mediated amination techniques provide higher coupling yields [ 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

The Covalent Tethering of Poly(ethylene glycol) to Nylon 6 Surface via N,N′-Disuccinimidyl Carbonate Conjugation: A New Approach in the Fight against Pathogenic Bacteria

2020

View full text Add to dashboard Cite

Different forms of unmodified and modified Poly(ethylene glycols) (PEGs) are widely used as antifouling and antibacterial agents for biomedical industries and Nylon 6 is one of the polymers used for biomedical textiles. Our recent study focused on an efficient approach to PEG immobilization on a reduced Nylon 6 surface via N,N′–disuccinimidyl carbonate (DSC) conjugation. The conversion of amide functional groups to secondary amines on the Nylon 6 polymer surface was achieved by the reducing agent borane-tetrahydrofuran (BH3–THF) complex, before binding the PEG. Various techniques, including water contact angle and free surface energy measurements, atomic force microscopy, scanning electron microscopy, X-ray photoelectron spectroscopy, and Fourier-transform infrared spectroscopy, were used to confirm the desired surface immobilization. Our findings indicated that PEG may be efficiently tethered to the Nylon 6 surface via DSC, having an enormous future potential for antifouling biomedical materials. The bacterial adhesion performances against S. aureus and P. aeruginosa were examined. In vitro cytocompatibility was successfully tested on pure, reduced, and PEG immobilized samples.

show abstract

Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates

Cited by 27 publications

References 46 publications

Terminal Mono- and Bis-Conjugates of Oligonucleotides with Closo-Dodecaborate: Synthesis and Physico-Chemical Properties

Terminal Mono- and Bis-Conjugates of Oligonucleotides with Closo-Dodecaborate: Synthesis and Physico-Chemical Properties

An overview of recent progress in modern synthetic approach—combinatorial synthesis

The Covalent Tethering of Poly(ethylene glycol) to Nylon 6 Surface via N,N′-Disuccinimidyl Carbonate Conjugation: A New Approach in the Fight against Pathogenic Bacteria

Contact Info

Product

Resources

About