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An Overview of Clinical and Biological Aspects of Current Boron Neutron Capture Therapy (BNCT) for Cancer Treatment: With Applications in Organometallics, Catalysis, Materials and Medicine(In 4 Volumes)Volume 1: Boron in Organometallic ChemistryVolume 2: Boron in CatalysisVolume 3: Boron in Materials ChemistryVolume 4: Boron in Medicine
Host-guest interactions represent a growing research area with recent work demonstrating the ability to chemically manipulate both host molecules as well as guest molecules to vary the type and strength of bonding. Much less is known about the interactions of the guest molecules and hybrid materials containing similar chemical features to typical macrocyclic hosts. This work uses in vitro and in vivo kinetic analyses to investigate the interaction of closo-dodecahydrododecaborate derivatives with ferumoxytol, an iron oxide nanoparticle with a carboxylated dextran coating. We find that several boron cluster derivatives can become encapsulated into ferumoxytol, and the lack of pH dependence in these interactions suggests that ion pairing, hydrophobic/hydrophilic interaction, and hydrogen bonding are not the driving force for encapsulation in this system. Biodistribution experiments in BALB/c mice show that this system is nontoxic at the reported dosage and demonstrate that encapsulation of dodecaborate-based clusters in ferumoxytol can alter the biodistribution of the guest molecules.
Bis(carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 (n = 0, 1) were prepared by the reactions of the corresponding carboranyl acyl chlorides with ethylenediamine. Crystal molecular structure of 1,1′-μ-(CH2NH(O)C-1,2-C2B10H11)2 was determined by single crystal X-ray diffraction. Treatment of bis(carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 with ammonium or cesium fluoride results in partial deboronation of the ortho-carborane cages to the nido-carborane ones with formation of [7,7′(8′)-μ-(CH2NH(O)C(CH2)n-7,8-C2B9H11)2]2−. The attempted reaction of [7,7′(8′)-μ-(CH2NH(O)CCH2-7,8-C2B9H11)2]2− with GdCl3 in 1,2-dimethoxy- ethane did not give the expected metallacarborane. The stability of different conformations of Gd-containing metallacarboranes has been estimated by quantum-chemical calculations using [3,3-μ-DME-3,3′-Gd(1,2-C2B9H11)2]− as a model. It was found that in the most stable conformation the CH groups of the dicarbollide ligands are in anti,anti-orientation with respect to the DME ligand, while any rotation of the dicarbollide ligand reduces the stability of the system. This makes it possible to rationalize the design of carborane ligands for the synthesis of gadolinium metallacarboranes on their base.
Two ways of synthesis of theragnostic compounds for Gd-guided boron neutron capture therapy of cancer are proposed. The first way is based on modification of DO3A ligand, which a capable to form stable complexes with gadolinium, with attachment of boron-containing moieties and additional functional groups which can be used for conjugation with various biomacromolecules. The second way is based on the introduction of additional chelating groups into a boron-containing moiety—carborane-based ligand. It is expected that this will significantly improve the stability of the gadolinium bis(dicarbollide) complexes.
A series of boron‐containing lipids were prepared by reactions of cyclic oxonium derivatives of polyhedron boranes and metallacarboranes ( closo‐ dodecaborate anion, cobalt and iron bis(dicarbollides)) with amine and carboxylic acids which are derived from cholesterol. Stable liposomal formulations, on the basis of synthesized boron‐containing lipids, HSPC and DSPE‐PEG as excipients, were prepared and then characterized by dynamic light scattering (DLS) that revealed the formation of particles to be smaller than 200 nm in diameter. The resulting liposomal formulations showed moderate to excellent loading and entrapment efficiency, thus justifying the design of the compounds to fit in the lipid bilayer and ensuring ease of in vivo use for future application. The liposome formulations based on cobalt and iron bis(dicarbollide)‐based lipids were found to be non‐toxic against both human breast normal epithelial cells MCF‐10A and human breast cancer cells MCF‐7.
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