Preparation of a new carboranyl lactoside for the treatment of cancer by boron neutron capture therapy: synthesis and toxicity of fluoro carboranyl glycosides for in vivo 19F-NMR spectroscopy.
The synthesis of new ortho-carboranyl lactosides 8, 17, 19 and glucosides 22 and 23 for the use in boron neutron capture therapy is reported. Carboranyl lactosides 17 and 19 as well as the glucosides 22 and 23 contain a fluorine atom to allow a noninvasive determination of these compounds in tumor cells by 19F-NMR spectroscopy. In cloning efficiency tests on human bronchial carcinoma cells the carboranyl lactosides 17 and 19 displayed almost no cytotoxicity. Thus, the considerably cytotoxic carboranyl alcohol 11 is detoxified when linked to a sugar moiety such as in carboranyl glucoside 22.
Tietze
L F
LF
Institut für Organische Chemie, Georg-August-Universität Göttingen, Germany. ltietze@gwdg.de
Bothe
U
U
Schuberth
I
I
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D016754:Boron Neutron Capture Therapy; D002470:Cell Survival / Q000187:drug effects; D005461:Fluorine; D005959:Glucosidases / Q000378:metabolism / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009369:Neoplasms / Q000532:radiotherapy*; D019906:Nuclear Magnetic Resonance, Biomolecular; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D001896:Boron Compounds; D006027:Glycosides; D006845:Hydrocarbons, Fluorinated; C008245:lactosides; D005461:Fluorine; D005959:Glucosidases