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

Mariya I. Meschaninova, Darya S. Novopashina, Olga A. Semikolenova, Vladimir N. Silnikov, Alya G. Venyaminova

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A novel and convenient approach for the solid-phase 5'-functionalization of oligonucleotides is proposed in this article. The approach is based on the activation of free 5'-hydroxyl of polymer support-bound protected oligonucleotides by N,N'-disuccinimidyl carbonate followed by interaction with amino-containing ligands. Novel amino-containing derivatives of closo-dodecaborate, estrone, cholesterol, and α-tocopherol were specially prepared. A wide range of oligonucleotide conjugates bearing closo-dodecaborate, short peptide, pyrene, lipophilic residues (cholesterol, α-tocopherol, folate, estrone), aliphatic diamines, and propargylamine were synthesized and characterized to demonstrate the versatility of the approach. The developed method is suitable for the conjugate synthesis of oligonucleotides of different types (ribo-, deoxyribo-, 2'-O-methylribo-, and others).

Original languageEnglish
Article number4266
Number of pages14
JournalMolecules (Basel, Switzerland)
Volume24
Issue number23
DOIs
Publication statusPublished - 22 Nov 2019

Keywords

  • amino ligands
  • boron clusters
  • N,N′-disuccinimidyl carbonate (DSC)
  • oligonucleotide conjugates
  • solid-phase 5′-functionalization
  • Boron clusters
  • Oligonucleotide conjugates
  • Amino ligands
  • Solid-phase 5'-functionalization
  • N,N'-disuccinimidyl carbonate (DSC)
  • REAGENT
  • ATTACHMENT
  • solid-phase 5 '-functionalization
  • STABILITY
  • BORON CLUSTERS
  • N,N '-disuccinimidyl carbonate (DSC)
  • DELIVERY
  • N-(2-HYDROXYETHYL)PHENAZINIUM
  • DNA
  • SIRNA
  • CLICK
  • OXONIUM DERIVATIVES

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