Synthesis of conjugates of polyhedral boron hydrides with nucleosides

Versatile Method for the Site‐Specific Modification of DNA with Boron Clusters: Anti‐Epidermal Growth Factor Receptor (EGFR) Antisense Oligonucleotide Case

“…[4,5] Following these early works, we have reported the application of boron clusters as redox-activel abels for electrochemical detection of diagnostic DNA [6][7][8][9] as well as the use of boron clusters to modify siRNAsd irected toward the gene-encoding BACE1 andt heir effects on siRNA silencing activity. [10] In spite of the unique and frequently advantageous properties of boron clusters as modifying units, [4] they are better known in medicinal chemistry as part of low-molecular-weight compounds, [11][12][13] including nucleosides, [14,15] than in nucleic acid chemistry.H erein, we report as imple and convenient methodf or the incorporation of variousb oron clusters into the structure of nucleic acids and show its usefulness in the synthesis of biologically active antisense oligomers.…”

“…In spite of the unique and frequently advantageous properties of boron clusters as modifying units, they are better known in medicinal chemistry as part of low‐molecular‐weight compounds, including nucleosides, than in nucleic acid chemistry. Herein, we report a simple and convenient method for the incorporation of various boron clusters into the structure of nucleic acids and show its usefulness in the synthesis of biologically active antisense oligomers.…”

Recent Advances in the Synthesis of High Boron-Loaded Nucleic Acids for BNCT

“…Conjugation of closo -dodecaborate and carboranes with different biomolecules (amino acids, peptides, nucleic acid bases, nucleosides, DNA binding molecules, carbohydrates, porphyrins), known drugs, and other tumor-targeting compounds provides a vast diversity of potential low molecular weight boron delivery agents with improved uptake and favorable pharmacokinetic characteristics ( Druzina et al, 2016 ; Barth et al, 2018 ; Ignatova et al, 2020 ; Tsurubuchi et al, 2020 and references therein). Monoclonal antibodies, liposomes, polymers, dendrimers, and different types of nanoparticles have been intensively studied as targeted high molecular weight carriers for boron clusters due to the possibility to load them with high 10 B content and to functionalize the surface of constructs with additional tumor-targeted ligands ( Wu et al, 2006 ; Calabrese et al, 2012 ; Laurentia and Rodica, 2016 ; Barth et al, 2018 ; Hu et al, 2020 and references therein).…”

“…Joining nucleic acid and boron chemistries opens wide opportunities to create new effective boron-rich agents for BNCT. This issue is illustrated, in particular, in the series of publications by V. Bregadze’s team on the synthesis and investigation of nucleic acids precursors modified by polyhedral boron clusters ( Sivaev et al, 2000 ; Semioshkin et al, 2007 ; Sivaev and Bregadze, 2009 ; Druzina et al, 2016 and others), as well as by a large cycle of publications by Lesnikowski with co-workers on developing synthetic methods for incorporation of different types of boron clusters into nucleosides and oligonucleotides (see reviews and some papers, e.g., Schinazi et al, 1994 ; Schinazi and Lesnikowski, 1998 ; Lesnikowski et al, 1999 ; Olejniczak et al, 2002 ; Lesnikowski, 2003 ; Kwiatkowska et al, 2013 ; Olejniczak et al, 2013 ; Kaniowski et al, 2017 ; Olejniczak et al, 2018 ). The progress in the development of modular and versatile synthetic approaches to the 10 B-modification of oligonucleotides and the right balance of the properties of two constituents of the construct substantially extended the field of application for oligonucleotide-boron conjugates.…”

Comparative Study of Carborane- and Phenyl-Modified Adenosine Derivatives as Ligands for the A2A and A3 Adenosine Receptors Based on a Rigid in Silico Docking and Radioligand Replacement Assay

“…Medicinal chemists are increasingly utilizing boron clusters (polyhedral boron cages) as a new generation of 3-dimensional, abiotic privileged scaffolds, modifiers and pharmacophores in bioactive molecule design [ 7 , 8 , 9 , 10 ]. Many boron cluster conjugates with biologically important low molecular weight compounds, including amino acids, lipids, carbohydrates, porphyrins, nucleic acid bases, nucleosides and DNA groove binders, have been synthesized [ 11 , 12 , 13 , 14 ]. In addition, biopolymers bearing one or more boron cages (carboranes), including carboranyl peptides and proteins, carboranyl oligophosphates, and nucleic acids (RNA and DNA oligonucleotides), have been prepared [ 13 , 15 , 16 ].…”