Cobaltabisdicarbollide‐based Synthetic Vesicles

Teixidor, Clara Viñas; Teixidor, Francesc; Harwood, Adrian J.

doi:10.1002/9781119275602.ch2.2

Cited by 7 publications

(2 citation statements)

References 30 publications

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“…At a dose of 20 mg/kg, 1 @FMX localized in tissues ranging from 0 to 65 μg of B per gram of tissue, suggesting that encapsulation of dodecaborate-based compounds in a polymer matrix can potentially have favorable effects on the biodistribution results. More broadly, this work suggests the potential importance of noncovalent interaction between boron clusters and polymers stemming from nonelectrostatic interactions and points to new avenues for creating hybrid boron-cluster-based nanomaterials without covalent attachment. − …”

Section: Discussionmentioning

confidence: 90%

Ex Vivo and In Vivo Evaluation of Dodecaborate-Based Clusters Encapsulated in Ferumoxytol Nanoparticles

et al. 2021

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Host-guest interactions represent a growing research area with recent work demonstrating an 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 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, or 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 guest molecules.

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Section: Discussionmentioning

confidence: 90%

Ex Vivo and In Vivo Evaluation of Dodecaborate-Based Clusters Encapsulated in Ferumoxytol Nanoparticles

et al. 2021

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“…The bis(icosahedral) cobalta bis(dicarbollide)(1-) ion, discovered by M. F. Hawthorne in 1965 [ 1 , 2 , 3 , 4 , 5 ], contains two η 5 coordinated dicarbollide ligands that sandwich a central Co(III) atom [ 4 , 5 , 6 ]. Due to its unique properties, such as aromaticity [ 7 ], space-filling properties, high thermal and chemical stability, low toxicity, hydrophobic interactions due to the hydridic character of B-H bonds [ 4 , 8 , 9 , 10 ], the formation of dihydrogen bonds [ 9 , 11 ], and easy penetration across phospholipid bilayers [ 12 , 13 , 14 , 15 ] and cell membranes [ 15 , 16 , 17 , 18 , 19 , 20 ], this ion has been applied in different areas of contemporary materials research [ 4 , 21 ] and medicinal chemistry [ 4 , 22 , 23 , 24 ]. The scope of potential applications in drug design includes enzyme inhibitors such as HIV-protease [ 25 , 26 , 27 ], carbonic anhydrase IX [ 16 , 28 , 29 ], anticancer compounds [ 16 , 29 , 30 ], antibiotics and antimycotics [ 31 , 32 , 33 , 34 , 35 ] and components for modulating the hydrophobic interactions of biomolecules [...…”

Section: Introductionmentioning

confidence: 99%

Electrochemistry of Cobalta Bis(dicarbollide) Ions Substituted at Carbon Atoms with Hydrophilic Alkylhydroxy and Carboxy Groups

et al. 2022

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In this study we explore the effect on the electrochemical signals in aqueous buffers of the presence of hydrophilic alkylhydroxy and carboxy groups on the carbon atoms of cobalta bis(dicarbollide) ions. The oxygen-containing exo-skeletal substituents of cobalta bis(dicarbollide) ions belong to the perspective building blocks that are considered for bioconjugation. Carbon substitution provides wider versatility and applicability in terms of the flexibility of possible chemical pathways. However, until recently, the electrochemistry of compounds substituted only on boron atoms could be studied, due to the unavailability of carbon-substituted congeners. In the present study, electrochemistry in aqueous phosphate buffers is considered along with the dependence of electrochemical response on pH and concentration. The compounds used show electrochemical signals around −1.3 and +1.1 V of similar or slightly higher intensities than in the parent cobalta bis(dicarbollide) ion. The signals at positive electrochemical potential correspond to irreversible oxidation of the boron cage (the C2B9 building block) and at negative potential correspond to the reversible redox process of (CoIII/CoII) at the central atom. Although the first signal is typically sharp and its potential can be altered by a number of substituents, the second signal is complex and is composed of three overlapping peaks. This signal shows sigmoidal character at higher concentrations and may be used as a diagnostic tool for aggregation in solution. Surprisingly enough, the observed effects of the site of substitution (boron or carbon) and between individual groups on the electrochemical response were insignificant. Therefore, the substitutions would preserve promising properties of the parent cage for redox labelling, but would not allow for the further tuning of signal position in the electrochemical window.

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The Rise of Boron-Containing Compounds: Advancements in Synthesis, Medicinal Chemistry, and Emerging Pharmacology

Grams,

Santos,

Scorei

et al. 2024

Chem. Rev.

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Boron-containing compounds (BCC) have emerged as important pharmacophores. To date, five BCC drugs (including boronic acids and boroles) have been approved by the FDA for the treatment of cancer, infections, and atopic dermatitis, while some natural BCC are included in dietary supplements. Boron's Lewis acidity facilitates a mechanism of action via formation of reversible covalent bonds within the active site of target proteins. Boron has also been employed in the development of fluorophores, such as BODIPY for imaging, and in carboranes that are potential neutron capture therapy agents as well as novel agents in diagnostics and therapy. The utility of natural and synthetic BCC has become multifaceted, and the breadth of their applications continues to expand. This review covers the many uses and targets of boron in medicinal chemistry.

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Cobaltabisdicarbollide‐based Synthetic Vesicles

Cited by 7 publications

References 30 publications

Ex Vivo and In Vivo Evaluation of Dodecaborate-Based Clusters Encapsulated in Ferumoxytol Nanoparticles

Ex Vivo and In Vivo Evaluation of Dodecaborate-Based Clusters Encapsulated in Ferumoxytol Nanoparticles

Electrochemistry of Cobalta Bis(dicarbollide) Ions Substituted at Carbon Atoms with Hydrophilic Alkylhydroxy and Carboxy Groups

The Rise of Boron-Containing Compounds: Advancements in Synthesis, Medicinal Chemistry, and Emerging Pharmacology

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