title: Alpha (α-) and beta (β-carboranyl-C-deoxyribosides: syntheses, structures and biological evaluation.
abstract: 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.
authors: Department of Organic Chemistry, Charles University in Prague, Hlavova 8, 153 00 Praha 2, Czech Republic.
authors: Ivan
authors: I
authors: Šnajdr
authors: Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Praha 6, Czech Republic.
authors: Zbyněk
authors: Z
authors: Janoušek
authors: Graduate School of Human & Environmental Studies, Kyoto University, Nihonmatsu, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors: Masao
authors: M
authors: Takagaki
authors: Department of Inorganic Chemistry, Charles University in Prague, Hlavova 8, 153 00 Praha 2, Czech Republic.
authors: Ivana
authors: I
authors: Císařová
authors: Department of Chemistry & Biochemistry, Northern Illinois University, DeKalb, IL 60115-2862, USA.
authors: Narayan S
authors: NS
authors: Hosmane
authors: Department of Organic Chemistry, Charles University in Prague, Hlavova 8, 153 00 Praha 2, Czech Republic; Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Praha 6, Czech Republic. Electronic address: kotora@natur.cuni.cz.
authors: Martin
authors: M
authors: Kotora
mesh_terms: D000818:Animals; D001896:Boron Compounds / Q000737:chemistry*; D016754:Boron Neutron Capture Therapy; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D007536:Isomerism; D051379:Mice; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000627:therapeutic use; D012995:Solubility; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry
chemical_list: D001896:Boron Compounds; D009705:Nucleosides; D014867:Water
keywords: Alkynes; Antitumor agents; Boron neutron capture therapy; Carboranes; Drug research