Preparing (Metalla)carboranes for Nanomedicine

Abstract

nanomedicine, highlighting similarities, differences and gaps in physicochemical and biological characterisation methods, are provided to encourage medicinal boron chemists to fill in the gaps between chemistry laboratory and real applications in living systems by employing bioanalytical and biophysical methods for characterising and controlling the aggregation behaviour of the clusters in solution.

Borinostats: solid-phase synthesis of carborane-capped histone deacetylase inhibitors with a tailor-made selectivity profile

“…25,27 Furthermore, carboranes play a key role in the development of boron neutron capture therapy (BNCT) agents and as carriers in nanomedicinal applications. 29,30 Carboranes are a family of polyhedral clusters comprised of CH and BH vertices with the icosahedral closo-dicarbadodecaborane (C 2 B 10 H 12 ) being the most prominent and well-examined member. 27 For symmetrical reasons, the two carbon atoms can be arranged within the icosahedron separated by one (ortho-/1,2-), two (meta-/1,7-) or three (para-carborane/closo-1,12-dicarbadodecaborane) bonds (Figure 1, bottom).…”

“…34,35 While boron-containing drugs like bortezomib, crisaborole and tavaborole are established therapeutics, carborane drugs are still scarce in clinical trials. 30,36,37,38 Within this branch, a limited number of boron-containing HDACis have been investigated. 39,40 However, only one of them was carboranebased and to the best of our knowledge none of them were tested for their HDAC6 selectivity.…”

Carboranes as unique pharmacophores in antitumor medicinal chemistry

“…Nanoparticles are able to enhance permeability and retention effects as well as targeting effects, and thus can deliver 10 B atoms into tumor tissues with high concentrations. 40 , 41 , 42 , 43 , 44 , 45 Using nanomaterials to deliver 10 B-containing compounds for BNCT can potentially improve drug accumulation in tumor tissues. 46 Hydrophobic carborane fragments and the polymerized nanoparticles can be formed on a single backbone chain.…”

Free three-dimensional carborane carbanions

“…[17][18][19] The unusual steric and electronic properties of boron cluster derivatives have been utilized in coordination chemistry, catalysis, luminescent materials, metal-organic frameworks, polymers, medicine, and energy storage. [20][21][22][23][24][25][26][27][28][29][30][31][32][33] The most commonly studied icosahedral anionic [CB 11 H 12 ] − and neutral C 2 B 10 H 12 clusters contain relatively acidic C−H bonds (for example, pK a of ortho-dicarbaborane is ca. 23).…”