Alpha (α-) and beta (β-carboranyl-C-deoxyribosides: Syntheses, structures and biological evaluation

• Reactions of 1-alkynyldeoxyriboses with dodecaborane were studied.
• The neutral closo-carboranyl-C-deoxyriboses and their cesium salts were synthesized.
• X-ray structures of some the prepared compounds were determined.
• In vitro tests for boron neutron capture therapy (BNCT) were carried out.

The syntheses of the unprotected neutral closo-carboranyl-C-deoxyriboses, starting from anomeric mixture of 1-ethynyldeoxyriboses, and their corresponding open-cage nido-derivatives have been described. The structures of both the α- and β-anomers were confirmed by single-crystal X-ray diffraction. While limited water solubility of the neutral closo-anomers led to high cytotoxicity, their cesium salts (nido-species) exhibited higher water solubility leading to lower cytotoxicity. However, in vitro boron neutron capture therapy (BNCT) investigation using the murine squamous cell carcinoma (SCCVII) cell lines showed that there are no significant differences between the survival fractions of the two species.

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