Synthesis of boron-containing cholesterol derivatives for incorporation into unilamellar liposomes and evaluation as potential agents for BNCT

Polyhedral Boranes for Medical Applications: Current Status and Perspectives

“…The initial compounds synthesized were esters of carborane carboxylic acid with various fatty acid alcohols. [84] Later, some other derivatives of cholesterol were synthesized, [85,86] and LDLs were proposed as tumor delivery agents for carborane-containing porphyrins. [87] While LDLs are natural lipoproteins with a proclivity for those tumor cells in which the receptors for these vesicles are overexpressed, liposomes can be considered as related synthetic vesicles.…”

“…Cholesterol is another major component of the mammalian cell membrane and most liposomal formulations. Therefore, the development of carborane- [85,86] and closo-dodecaborate- [104] containing derivatives of cholesterol is potentially an effective ap-proach for delivery of boron to cancer cells via both liposomes and LDL. More recently, a novel strategy for the design and synthesis of carboranyl cholesterol mimics has been proposed.…”

Pharmacokinetic and in vitro cytotoxic evaluation of cholesterol-rich nanoemulsion of cholesteryl-succinyl-5-fluorouracil

“…Targeted-drug delivery to cancer cells is known to enhance the chemotherapeutic efficacy of anticancer medicines [1,2]. One of the targeted-drug delivery approaches is based on the fact that cancer cells required high demand of cholesterol for targeted-drug delivery [3][4][5].…”

Chemistry of α‐Aminoboronic Acids and their Derivatives

“…The bioinorganic chemistry of boron-containing compounds is therefore an area of growing interest, and has recently expanded to include purine nucleosides, psuedocryptands (which mimic the naturally occurring antibiotics boromycin and aplasmomycin), steroids, calixarenes, carbohydrates, fatty acids, porphyrins, and amino acids [11][12][13][14][15][16][17]. Boronic acids [RB(OH) 2 ] and boronate esters [RB(OR 1 ) 2 ] have been found to facilitate the transport of various ribonucleosides in and out of liposomes -an important attribute in the area of drug design [18][19][20]. Simple aminoboron compounds have also found some utility in boron neutron capture therapy [21,22] and other forms of cancer therapy [1][2][3].…”

“…The pinane amidoboronic esters (18,19 and 20a,b) could be synthesized by using similar chemistry (Scheme 4.4) [42]. Enzyme inhibition studies have shown that the D-amino acid analogs (20a,b) were active inhibitors of Bacillus cereus b-lactamase, with K i ¼ 44 and 49 mM at pH 7, respectively [43].…”