New functionalized mercaptoundecahydrododecaborate derivatives for potential application in boron neutron capture therapy: synthesis, characterization and dynamic visualization in cells

European Journal of Medicinal Chemistry
Afaf R GenadyMohamed E El-Zaria

Abstract

A series of mercaptoundecahydrododecaborate (B12H11SH(2-), BSH) bearing mono- and dicarboxyalkyl derivatives was prepared, characterized, and their reactivity towards amidation and esterification in DMF was evaluated. Symmetrical alkylation of BSH was achieved by treatment with primary haloalkyl carboxylic acids in aqueous acetonitrile to produce S,S-bis(carboxyalkyl)sulfonium-undecahydro-closo-dodecaborate tetramethylammonium salts. Unsymmetrically substituted sulfonium salts were obtained through a similar treatment of cyanoethylthioether-undecahydro-closo-dodecaborate tetramethylammonium salt with haloalkyl carboxylic acid. Selective removal of the remaining cyanoethyl group upon treatment with tetramethylammonium hydroxide yielded S-carboxyalkyl-thioether-undecahydro-closo-dodecaborate ditetramethylammonium salts. N,N'-dicyclohexylcarbodiimide (DCC) activated amidation of S,S-bis(carboxyalkyl)sulfonium-undecahydro-closo-dodecaborate or S-carboxyalkyl-thioether-undecahydro-closo-dodecaborate tetramethylammonium salts with propargylamine provided the opportunity to install terminal acetylene groups for further conjugation. These compounds acted as powerful building blocks for the synthesis of a broad range of 1,4-disubstitute...Continue Reading

Citations

Jul 13, 2016·Pharmaceutical Research·Micah John LudererAbdel Kareem Azab
Jul 28, 2016·Journal of Cancer Research and Therapeutics·Hamid Reza MirzaeiHamed Mirzaei
Aug 28, 2015·Organic & Biomolecular Chemistry·Charles Beromeo BheeterMatthias Beller
Feb 20, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fayaz AliYinghuai Zhu

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