Synthesis of new ω-amino- and ω-azidoalkyl carboranes

Stogniy, Marina Yu.; Sivaev, Igor B.; Godovikov, Ivan A.; Starikova, Z. A.; Bregadze, V. I.; Qi, Shicheng

doi:10.1039/c3nj00677h

Cited by 17 publications

(6 citation statements)

References 41 publications

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“…Wang et al [106] reported the gold nanoclusters with carborane amino derivatives for the targeted delivery of the carborane compound to the tumors and precise bioimaging of cancer cells. They prepared carborane derivative (NH 2 NH 3 ) + [7-NH 2 (CH 2 ) 3 S-7,8-C 2 B 9 H 11 ]according to the literature [107], and stored it at -18 • C. Gold nanoclusters (GNCs) were freshly prepared and dispersed in PBS (pH 7.2). Fluorescent GNCs were produced using glutathione (GSH), according to the reported method in the literature [108].…”

Section: Gold Nanocluster/nanoparticles With Borane For Bnctmentioning

confidence: 99%

Boron Chemistry for Medical Applications

2020

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Boron compounds now have many applications in a number of fields, including Medicinal Chemistry. Although the uses of boron compounds in pharmacological science have been recognized several decades ago, surprisingly few are found in pharmaceutical drugs. The boron-containing compounds epitomize a new class for medicinal chemists to use in their drug designs. Carboranes are a class of organometallic compounds containing carbon (C), boron (B), and hydrogen (H) and are the most widely studied boron compounds in medicinal chemistry. Additionally, other boron-based compounds are of great interest, such as dodecaborate anions, metallacarboranes and metallaboranes. The boron neutron capture therapy (BNCT) has been utilized for cancer treatment from last decade, where chemotherapy and radiation have their own shortcomings. However, the improvement in the already existing (BPA and/or BSH) localized delivery agents or new tumor-targeted compounds are required before realizing the full clinical potential of BNCT. The work outlined in this short review addresses the advancements in boron containing compounds. Here, we have focused on the possible clinical implications of the new and improved boron-based biologically active compounds for BNCT that are reported to have in vivo and/or in vitro efficacy.

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Section: Gold Nanocluster/nanoparticles With Borane For Bnctmentioning

confidence: 99%

Boron Chemistry for Medical Applications

2020

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“…Therefore, the preliminary introduction of the strongly acidic mercapto group followed by its alkylation was recently proposed to avoid this problem. In such a way, a variety of functional derivatives of closo ‐carborane 1‐R(CH 2 ) n S‐1,2‐C 2 B 10 H 11 as well as their nido ‐analogs [7‐R(CH 2 ) n S‐7,8‐C 2 B 9 H 11 ] – were synthesized …”

Section: Introductionmentioning

confidence: 99%

Synthesis of 10‐Methylsulfide and 10‐Alkylmethylsulfonium nido‐Carborane Derivatives: B–H···π Interactions between the B–H–B Hydrogen Atom and Alkyne Group in 10‐RC≡CCH₂S(Me)‐7,8‐C₂B₉H₁₁

et al. 2017

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“…In this study, GSH was added as the reducing agent and stabilizer in the synthesis of GNCs. It is already known that GNCs stabilized by glutathione have unique optical properties and excellent biocompatibility; especially, GNCs in vivo can be readily excreted out with liquid urine, which is a kind of metabolizable supersmall nanoparticle. − Therefore, here we adopt GSH as the reducing agent and stabilizer for the synthesis of fluorescent GNCs, which is characterized by fluorescence spectroscopy and transmission electron microscopy (TEM), as shown in Figure . Our observations demonstrate that the as-prepared GNCs have good monodispersity (with particle size of ∼1.8 nm).…”

Section: Resultsmentioning

confidence: 99%

“…Reagents. The carborane derivative (NH 2 NH 3 ) + [7-NH 2 (CH 2 ) 3 S-7,8-C 2 B 9 H 11 ] − was synthesized as described in the literature, 44 stored at −18 °C and freshly prepared in aqueous solution immediately before use. Gold nanoclusters (GNCs) were freshly synthesized and dispersed in PBS (pH 7.2).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Carborane Derivative Conjugated with Gold Nanoclusters for Targeted Cancer Cell Imaging

Wang

Chen

et al. 2017

Biomacromolecules

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Polyhedral borane derivatives have been utilized in the treatment of boron neuron capture therapy (BNCT) for brain glioma, and much attention has been paid to search excellent biocompatible boron-rich composites for effective cancer BNCT therapy. In this study, we have exploited the self-assembly of the gold nanoclusters with carborane amino derivatives (GNCs-CB) for the precise bioimaging of cancer cells and targeted delivery of this carborane compound to the tumors. Our observations demonstrate that the GNCs-CB can readily realize accurate tumor imaging and long-term accumulation in tumor sites by EPR effect and nanometer size effect, and thus efficiently implement tumor-targeting delivery of the carborane derivative and facilitate the real-time fluorescent visualization monitoring of the carborane targeted delivery process. This makes it possible to realize the accurate location of the tumor by the carborane derivative and reduce the damage to normal tissues in the process of boron neutron capture therapy through imaging guided treatment.

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Synthesis of new ω-amino- and ω-azidoalkyl carboranes

Cited by 17 publications

References 41 publications

Boron Chemistry for Medical Applications

Boron Chemistry for Medical Applications

Synthesis of 10‐Methylsulfide and 10‐Alkylmethylsulfonium nido‐Carborane Derivatives: B–H···π Interactions between the B–H–B Hydrogen Atom and Alkyne Group in 10‐RC≡CCH₂S(Me)‐7,8‐C₂B₉H₁₁

Carborane Derivative Conjugated with Gold Nanoclusters for Targeted Cancer Cell Imaging

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Synthesis of new ω-amino- and ω-azidoalkyl carboranes

Cited by 17 publications

References 41 publications

Boron Chemistry for Medical Applications

Boron Chemistry for Medical Applications

Synthesis of 10‐Methylsulfide and 10‐Alkylmethylsulfonium nido‐Carborane Derivatives: B–H···π Interactions between the B–H–B Hydrogen Atom and Alkyne Group in 10‐RC≡CCH2S(Me)‐7,8‐C2B9H11

Carborane Derivative Conjugated with Gold Nanoclusters for Targeted Cancer Cell Imaging

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Synthesis of 10‐Methylsulfide and 10‐Alkylmethylsulfonium nido‐Carborane Derivatives: B–H···π Interactions between the B–H–B Hydrogen Atom and Alkyne Group in 10‐RC≡CCH₂S(Me)‐7,8‐C₂B₉H₁₁