Synthesis of Boron Cluster Lipids:  closo-Dodecaborate as an Alternative Hydrophilic Function of Boronated Liposomes for Neutron Capture Therapy

• Published in: Organic letters Vol. 9; no. 2; pp. 323 - 326
• Main Authors: Lee, Jong-Dae, Ueno, Manabu, Miyajima, Yusuke, Nakamura, Hiroyuki
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.01.2007; Amer Chemical Soc
• Subjects: Animals; Boron Compounds - chemical synthesis; Boron Compounds - chemistry; Boron Compounds - toxicity; Boron Neutron Capture Therapy - methods; Chemistry; Chemistry, Organic; Hydrophobic and Hydrophilic Interactions; Lipids - chemical synthesis; Lipids - chemistry; Lipids - toxicity; Liposomes - chemistry; Mice; Particle Size; Physical Sciences; Science & Technology; Sensitivity and Specificity; Time Factors; ANTIBODIES; DTPA COMPLEX; UNILAMELLAR LIPOSOMES; BIOLOGICAL EVALUATION; EPIDERMAL GROWTH-FACTOR; CANCER; DERIVATIVES; CARRIER; BRAIN-TUMORS; DELIVERY
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol062840+

We succeeded in the synthesis of the double-tailed boron cluster lipids 4a−c and 5a−c, which have a B12H11S moiety as a hydrophilic function, by S-alkylation of B12H11SH (BSH) with bromoacetyl and chloroacetocarbamate derivatives of diacylglycerols for a liposomal boron delivery system on neutron capture therapy. Calcein encapsulation experiments revealed that the liposomes, prepared from the boron cluster lipid 4b, DMPC, PEG-DSPE, and cholesterol, are stable at 37 °C in FBS solution for 24 h.