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

0431809 - ÚOCHB 2015 RIV FR eng J - Journal Article
Šnajdr, I. - Janoušek, Zbyněk - Takagaki, M. - Císařová, I. - Hosmane, N. S. - Kotora, Martin
Alpha (alpha-) and beta (beta-carboranyl-C-deoxyribosides: Syntheses, structures and biological evaluation.
European Journal of Medicinal Chemistry. Roč. 83, Aug 18 (2014), s. 389-397. ISSN 0223-5234. E-ISSN 1768-3254
R&D Projects: GA MŠMT 1M0508
Grant - others:GA MŠk(CZ) LC06070; GA ČR(CZ) GA13-15915S
Program: LC
Institutional support: RVO:61388963
Keywords : alkynes * carboranes * boron neutron capture therapy * antitumor agents * drug research
Subject RIV: CC - Organic Chemistry
Impact factor: 3.447, year: 2014

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 alpha- and beta-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.
Permanent Link: http://hdl.handle.net/11104/0236423