Boron-Based Drug Design

Ban, Hyun Seung; Nakamura, Hiroyuki

doi:10.1002/tcr.201402100

Cited by 135 publications

(70 citation statements)

References 100 publications

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“…The administration of this compound showed a very high boron value and significant anti-cancer effect compared with the group administered with 100 times higher concentration of BSH [24]. In this study, the survival data with combination PD-CD133/BSH with BSH were superior to those administered single BSH in glioma implanted mice [13]. PD-CD133/BSH or BSH was given either alone or in combination, followed by BNCT.…”

Section: Discussionmentioning

confidence: 90%

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Targeting glioma stem cells enhances anti-tumor effect of boron neutron capture therapy

Sun

Huang

et al. 2016

Oncotarget

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The uptake of (10)boron by tumor cells plays an important role for cell damage in boron neutron capture therapy (BNCT). CD133 is frequently expressed in the membrane of glioma stem cells (GSCs), resistant to radiotherapy and chemotherapy, and represents a potential therapeutic target. To increase (10)boron uptake in GSCs, we created a polyamido amine dendrimer, conjugated CD133 monoclonal antibodies, encapsulating mercaptoundecahydrododecaborate (BSH) in void spaces, and monitored the uptake of the bioconjugate nanoparticles by GSCs in vitro and in vivo. Fluorescence microscopy showed the specific uptake of the bioconjugate nanoparticles by CD133-positive GSCs. Treatment with the biconjugate nanoparticles resulted in a significant lethal effect after neutron radiation due to efficient and CD133-independent cellular targeting and uptake in CD133-expressing GSCs. A significantly longer survival occurred in combination with the biconjugate nanoparticles and BSH compared with BSH alone in human intracranial GBM models employing CD133-positive GSCs xenografts. Our data demonstrated that this bioconjugate nanoparticle targets human CD133-positive GSCs and is a potential boron agent in BNCT.

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Section: Discussionmentioning

confidence: 90%

“…The design of boron carriers in BNCT possesses a high potential for the increase of boron concentration in tumor cells [13]. BSH and boronophenylalanine (BPA) are the two boron-based drugs that are currently used in clinical trials of BNCT for patients with glioma [14].…”

Section: Discussionmentioning

confidence: 99%

Targeting glioma stem cells enhances anti-tumor effect of boron neutron capture therapy

Sun

Huang

et al. 2016

Oncotarget

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“…To readily construct bioactive compounds, a variety of methodologies have been developed, including effective synthesis of heterocyclic compounds (Joule & Mills, ). Drug design of boron‐containing compounds has recently attracted a great deal of attention because of these compounds unique bioactivity derived from a reversible covalent binding to the target protein using a vacant p ‐orbital (Baker et al., ; Ban & Nakamura, ; Yang, Zhu, Zhang, & Zhou, ). In fact, some boron‐containing drugs, including bortezomib and ixazomib for the treatment of multiple myeloma, tavaborole for the treatment of onychomycosis, and crisaborole for the treatment of atopic dermatitis have been marketed (Figure ; Baker et al., ; Chen, Frezza, Schmitt, Kanwar, & Dou, ; Jarnagin et al., ; Markham, ; Rentsch et al., ; Richardson et al., ).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and evaluations of spiro‐fused benzoxaborin derivatives as novel boron‐containing compounds

et al. 2019

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Drug design using boron‐containing heterocycles has attracted a great deal of attention because these compounds are believed to possess high biological activity. However, information on the synthetic methodology and pharmacokinetic profiling of boron‐containing compounds is limited. In this study, we provide a new synthetic route for preparation of spiro‐fused benzoxaborin derivatives and investigate their in vitro pharmacokinetic properties. Our efforts led to the successful construction of a chemical library of spiro‐fused benzoxaborin derivatives with appropriate physicochemical and in vitro pharmacokinetic properties for oral drugs. These results indicate that the synthesized boron‐containing compounds are therefore eligible for classification in a novel chemical library.

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“…Another important characteristic of boronic acids is their ability to form hydrogen bonds and covalent bonds with Lewis bases, providing an interesting platform for binding to the active center of enzymes; this makes the boronic moiety an interesting auxophoric group in rational drug design.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of the Anticancer and Trypanocidal Activities of Boronic Tyrphostins

et al. 2018

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Molecules containing an (cyanovinyl)arene moiety are known as tyrphostins because of their ability to inhibit proteins from the tyrosine kinase family, an interesting target for the development of anticancer and trypanocidal drugs. In the present work, (E)-(cyanovinyl)benzeneboronic acids were synthesized by Knoevenagel condensations without the use of any catalysts in water through a simple protocol that completely avoided the use of organic solvents in the synthesis and workup process. The in vitro anticancer and trypanocidal activities of the synthesized boronic acids were also evaluated, and it was discovered that the introduction of the boronic acid functionality improved the activity of the boronic tyrphostins. In silico target fishing with the use of a chemogenomic approach suggested that tyrosine-phosphorylation-regulated kinase 1a (DYRK1A) was a potential target for some of the designed compounds.

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Boron-Based Drug Design

Cited by 135 publications

References 100 publications

Targeting glioma stem cells enhances anti-tumor effect of boron neutron capture therapy

Targeting glioma stem cells enhances anti-tumor effect of boron neutron capture therapy

Design, synthesis and evaluations of spiro‐fused benzoxaborin derivatives as novel boron‐containing compounds

Synthesis and Evaluation of the Anticancer and Trypanocidal Activities of Boronic Tyrphostins

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