Nano and dendritic structured carboranes and metallacarboranes: From materials to cancer therapy

Hosmane, Narayan S.; Zhu, Yongwei; Maguire, John A.; Kaim, Wolfgang; Takagaki, Masao

doi:10.1016/j.jorganchem.2008.11.059

Cited by 32 publications

(18 citation statements)

References 48 publications

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“…Boron neutron capture therapy (BNCT) uses a low-energy neutron beam directed at a tumour to bring about its selective destruction through interaction with administered boronated agents [1][2][3]. A localised nuclear fission reaction takes place within 10 B-containing tumour cells, which are consequentially destroyed by the produced αparticles (1.47 MeV) and recoiling 7 Li nuclei (0.84 MeV) [4,5]; the therapeutically useful amount for BNCT is ca. 20-30 µg 10 B/g tumour [6].…”

Section: Introductionmentioning

confidence: 99%

Liposome formulations of o-carborane for the boron neutron capture therapy of cancer

Olusanya

Calabrese

Fatouros

et al. 2019

Biophysical Chemistry

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Based on the promise of liposomes as convenient vehicles for the transport of boronated agents for the boron neutron capture therapy (BCNT) of cancer, this paper reports a method for the formulation and characterisation of stable o-carborane-loaded liposomes (ca. 80 -100 nm) of dipalmitoyl-phosphatidylcholine (DPPC) or 1,2distearol-sn-glycerol-3-phosphocholine (DSPC). Preliminary pharmaceutical characterisation experiments have demonstrated the integrity of both DPPC and DSPC liposomal membranes in serum and in PBS and also indicate that these o-carborane-loaded liposomes are candidate carrier vehicles for further evaluation with a view to exploitation in BNCT.

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Section: Introductionmentioning

confidence: 99%

Liposome formulations of o-carborane for the boron neutron capture therapy of cancer

Olusanya

Calabrese

Fatouros

et al. 2019

Biophysical Chemistry

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“…Carborane-containing macromolecules exhibit several properties of interest, including chemical and thermal stability, 1 aggregation induced emission 2 (AIE), radiation shielding coatings 3 that enable their use in medical applications, and boron neutron capture therapy 4,5 (BNCT). Consequently, carboranes have been incorporated into a variety of macromolecular structures, including polymers 2 and dendrimers [6][7][8][9][10][11] in order to instill water-solubility and enhance their properties and utility. These approaches primarily rely upon covalent bonding; however, biomolecular systems exploit a range of weaker, noncovalent inter-and intra-molecular forces, including van der Waals, hydrogen bonding, π-π stacking, electrostatic, and coordination to achieve macro-molecular structure.…”

Section: Introductionmentioning

confidence: 99%

Self-assembly of a family of suprametallomacrocycles: revisiting an o-carborane bisterpyridyl building block

et al. 2014

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The self-assembly of the o-carborane-based, bisterpyridyl monomer, 1,2-bis[4'-(4-ethynylphenyl)-2,2':6',2''-terpyridine]-o-carborane, utilizing either Zn(II) or Fe(II) in a precise metal : ligand ratio (1 : 1), generated a family of metallomacrocycles that were studied via ESI-TWIM-MS, (1)H NMR, and 2D NMR (COSY, NOESY). Under kinetic control, via formation of Fe(II) complexes, the main cyclic product was triangular, as is typical of 60°-based bisligands. Under thermodynamic control using more labile transition metal complexes, e.g. Zn(II), the ratio of cyclic species was found to be concentration and temperature dependent, and under an adequate entropic driving force, the cyclic dimer was formed. This system was probed via variable temperature NMR to reveal dynamic equilibrium between the entropically favored dimer and enthalpically favored trimer.

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“…[5] These properties have made them suitable for potential application in the fields of catalysis, [6] material science such as heat-stable polymer or hybrid materials, [7] and especially in medicine. [8] Due to the versatility of o-carboranes to be chemically modified, [1c, 9] they have been an ideal group for the preparation of stable, agile, and suitable building blocks that can be subsequently attached to a molecule, such as star-shaped systems; [10] dendrons and dendrimers; [11,12] or porphyrins. [13] In addition, it is also possible to achieve the partial degradation of the closo clusters to obtain the corresponding nido-carborane derivatives, thereby transforming neutral molecules into anionic systems.…”

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confidence: 99%

Synthesis and Characterization of New Fluorescent Styrene‐Containing Carborane Derivatives: The Singular Quenching Role of a Phenyl Substituent

Ferrer‐Ugalde

Juárez-Pérez

Teixidor

et al. 2011

Chemistry A European J

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A set of neutral and anionic carborane derivatives in which the styrenyl fragment is introduced as a fluorophore group has been successfully synthesized and characterized. The reaction of the monolithium salts of 1-Ph-1,2-C(2)B(10)H(11), 1-Me-1,2-C(2)B(10)H(11) and 1,2-C(2)B(10)H(12) with one equivalent of 4-vinylbenzyl chloride leads to the formation of compounds 1-3, whereas the reaction of the dilithium salt of 1,2-C(2)B(10)H(12) with two equivalents of 4-vinylbenzyl chloride gives disubstituted compound 4. The closo clusters were degraded using the classical method, KOH in EtOH, to afford the corresponding nido species, which were isolated as tetramethylammonium salts. The crystal structure of the four closo compounds 1-4 were analyzed by X-ray diffraction. All compounds, except 1, display emission properties, with quantum yields dependent on the nature of the cluster (closo or nido) and the substituent on the second C(cluster) atom. In general, closo compounds 2-4 exhibit high fluorescence emission, whereas the presence of a nido cluster produces a decrease of the emission intensity. The presence of a phenyl group bonded to the C(cluster) results in an excellent electron-acceptor unit that produces a quenching of the fluorescence. DFT calculations have confirmed the charge-separation state in 1 to explain the quenching of the fluorescence and the key role of the carboranyl fragment in this luminescent process.

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Nano and dendritic structured carboranes and metallacarboranes: From materials to cancer therapy

Cited by 32 publications

References 48 publications

Liposome formulations of o-carborane for the boron neutron capture therapy of cancer

Liposome formulations of o-carborane for the boron neutron capture therapy of cancer

Self-assembly of a family of suprametallomacrocycles: revisiting an o-carborane bisterpyridyl building block

Synthesis and Characterization of New Fluorescent Styrene‐Containing Carborane Derivatives: The Singular Quenching Role of a Phenyl Substituent

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