Handbook of Boron Science

Jonnalagadda, Subash C.; Penczuk, Bryan J.; Twomey, Kathleen M.; Fishbein, Steven H.; Suman, Pathi

doi:10.1142/q0130

Cited by 36 publications

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“…Polyhedral boron clusters have provided a platform for rich scientific exploration with applications ranging from materials science to medicine. − The icosahedral closo- [B 12 H 12 ] 2– dianion has been a focus of investigation on account of its high stability, three-dimensional delocalized bonding, resistance to harsh chemical environments, and ease of electrophilic B–H substitution . Work describing the one-electron oxidation of [B 12 H 12 ] 2– , however, displayed cluster decomposition and dimerization, revealing the oxidative instability of this species .…”

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confidence: 99%

“…(A) Structures of polyhedral closo -boron clusters as predicted by the Wade–Mingos electron-counting rules. , (B) Examples of redox-active, perfunctionalized closo -dodecaborate clusters ([B 12 (OH) 12 ] 2– , [B 12 (CH 3 ) 12 ] 2– , and [B 12 Cl 12 ] − ). (C) Established redox chemistry for alkoxy and benzyloxy-substituted B 12 clusters, ,,,,, and this work, which introduces a third, reversible redox event for the B 12 (O-3-methylbutyl) 12 ( 1 ) derivative.…”

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A Super-Oxidized Radical Cationic Icosahedral Boron Cluster

et al. 2020

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While the icosahedral closo-[B 12 H 12 ] 2cluster does not display reversible electrochemical behavior, perfunctionalization of this species via substitution of all twelve B-H vertices with alkoxy or benzyloxy (OR) substituents engenders reversible redox chemistry, providing access to clusters in the dianionic, monoanionic, and neutral forms. Here, we evaluated the electrochemical behavior of the electron-rich B 12 (O-3-methylbutyl) 12 (1) cluster and discovered that a new reversible redox event that gives rise to a fourth electronic state is accessible through one-electron oxidation of the neutral species. Chemical oxidation of 1 with [N(2,4-Br 2 C 6 H 3) 3 ] •+ afforded the isolable [1] •+ cluster, which is the first example of an open-shell cationic B 12 cluster in which the unpaired electron is proposed to be delocalized throughout the boron cluster core. The oxidation of 1 is also chemically reversible, where treatment of [1] •+ with ferrocene resulted in its reduction back to 1. The identity of [1] •+ is supported by EPR, UV-vis, multinuclear NMR (1 H, 11 B), and X-ray photoelectron spectroscopic characterization. and characterization data for all new compounds is available free of charge via the Internet at http://pubs.acs.org.

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A Super-Oxidized Radical Cationic Icosahedral Boron Cluster

et al. 2020

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“…Icosahedral carboranes are molecular clusters 1 that have triggered abundant research interest for decades as building blocks to construct versatile ligands, 2 functional materials 3 and tunable pharmacophores. 4 The development of new methodologies to incorporate organic functionalities into carboranes holds great promise at the interface between cluster chemistry and organic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums

et al. 2021

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“…When the non-radioactive boron-10 (B-10) is irradiated with low-energy thermal/epithermal neutrons, high linear energy transfer (LET) alpha particles and recoiling lithium-7 nuclei are produced. [6][7][8][9][10] The pathlengths of these high-LET particles range from 5 to 9 μm, [11][12][13] thereby killing only tumor cells containing B-10 without additional damage to surrounding normal tissues. [14,15] Currently, sodium borocaptate (BSH) and boronophenylalanine (BPA) are clinically used as the B-10 delivery agents for the treatment of tumors through BNCT.…”

Section: Introductionmentioning

confidence: 99%

Novel Carborane Compounds Based on Cyclooxygenase‐2 Inhibitors for Effective Boron Neutron Capture Therapy of Tongue Squamous Cell Carcinoma

Zhang

et al. 2020

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To date, the mortality of tongue squamous cell carcinoma (TSCC) is still high, COX‐2 is highly expressed in the head and neck cancers, and targeting COX‐2 is a potential treatment for TSCC. Herein, a series of novel carborane compounds based on COX‐2 inhibitors have been developed for the effective treatment of TSCC by boron neutron capture therapy (BNCT). Notably, the compound 1 had high COX‐2 selectivity and low cytotoxicity against CAL27 cells. Meanwhile, the compound 1 had higher selectivity and uptake of CAL27 cells compared to the positive control group sodium borocaptate (BSH). The apoptosis of CAL27 cells treated with the compound 1 during BNCT was significantly induced by breaking DNA double strands and generating excess reactive oxygen species, and the proliferation of cancer cells was inhibited by down‐regulating the expression of cytokines associated with phosphatidylinositide 3‐kinases/protein kinase B (PI3K/Akt) and mitogen‐activated protein kinases (MAPKs) signaling pathways in BNCT. Thus, the carborane compounds based on COX‐2 inhibitors have the potential to effectively treat tongue squamous cell carcinoma through BNCT.

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Handbook of Boron Science

Cited by 36 publications

References 0 publications

A Super-Oxidized Radical Cationic Icosahedral Boron Cluster

A Super-Oxidized Radical Cationic Icosahedral Boron Cluster

Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums

Novel Carborane Compounds Based on Cyclooxygenase‐2 Inhibitors for Effective Boron Neutron Capture Therapy of Tongue Squamous Cell Carcinoma

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