This review focuses on the current status and perspectives of the application of polyhedral boron hydrides in medicine. The main topics discussed are boron neutron capture therapy for cancer and radionuclide diagnostics and therapy. X-ray contrast diagnostics, antitumor activity of some metal derivatives of carboranes, and drug design including carborane fragments are discussed as well.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Polyhedral Boranes for Medical Applications: Current Status and Perspectives

There is an urgent need to understand the behavior of the novel coronavirus (SARS-COV-2), which is the causative agent of COVID-19, and to develop point-of-care diagnostics. Here, a glyconanoparticle platform is used to discover that N-acetyl neuraminic acid has affinity toward the SARS-COV-2 spike glycoprotein, demonstrating its glycan-binding function. Optimization of the particle size and coating enabled detection of the spike glycoprotein in lateral flow and showed selectivity over the SARS-COV-1 spike protein. Using a virus-like particle and a pseudotyped lentivirus model, paper-based lateral flow detection was demonstrated in under 30 min, showing the potential of this system as a low-cost detection platform.

The SARS-COV-2 Spike Protein Binds Sialic Acids, and Enables Rapid Detection in a Lateral Flow Point of Care Diagnostic Device

Cyclic oxonium derivatives of polyhedral boron hydrides are a relatively new class of boron compounds. They have great potential for the modification of various types of organic and bioorganic molecules and the synthesis of compounds that could be used in different fields from the treatment of nuclear wastes to the treatment of cancer. In the present Perspective we would like to present an overview of the results of the preparation and synthetic application of these compounds.

Cyclic oxonium derivatives of polyhedral boron hydrides and their synthetic applications

Common side reactions of the glycosyl donor in chemical glycosylation.

A general approach to the synthesis of nucleoside conjugates con- taining carborane and metallocarbor- ane complexes, based on Huisgen 1,3- dipolar cycloaddition ("chemical liga- tion"), is described. Boron-cluster- donors bearing terminal azide or eth- ynyl groups were prepared in the ring- opening reaction of dioxane-boron- cluster adducts and an azide anion or suitable alkynol-derived alcoholate nu- cleophile. Analogous derivatives bear- ing terminal sulfhydryl groups were also prepared. Nucleosides with various spacers containing terminal azide or ethynyl groups, located within nucleo- bases or sugar residues, were used as boron-cluster acceptors. The proposed methodology provides a convenient way to synthesize libraries of boron- cluster-modified nucleosides for various applications.

"Chemical ligation": a versatile method for nucleoside modification with boron clusters.

Practical synthesis of 1,4-dioxane derivative of the closo -dodecaborate anion and its ring opening with acetylenic alkoxides

N,N-Diacetylsialyl chloride--a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter.

Treatment of the readily available peracetylated N-acetylneuraminic acid glycosyl chloride [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-β-D-glycero-D-galactononulopyranosonate)] with anhydrous Na 2 HPO 4 in refluxing MeCN quantitatively affords the peracetylated N-acetylneuraminic acid glycal [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2,6-anhydro-D-glycero-D-galacto-non-2-enonate], which can be isolated from the reaction mixture by simple filtration and subsequent evaporation of the solvent. No glycal formation was detected at room temperature even after prolonged treatment with Na 2 HPO 4 . The method proposed is experimentally simple and allows ready preparation of substantial amounts of the title compound, which is an important intermediate in sialic acid chemistry.

Nadezhda Yu. Kulikova

Papers

Practical synthesis of 1,4-dioxane derivative of the closo -dodecaborate anion and its ring opening with acetylenic alkoxides

N,N-Diacetylsialyl chloride--a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter.

A facile synthesis of N-acetylneuraminic acid glycal

A Facile Synthesis of N-Acetylneuraminic Acid Glycal.