Supramolecular chemistry of anionic boron clusters and its applications in biology

Cebula, Jakub; Fink, Krzysztof; Boratyński, Janusz; Goszczyński, Tomasz M.

doi:10.1016/j.ccr.2022.214940

Cited by 23 publications

(14 citation statements)

References 113 publications

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“…5–9 On the other hand, the diametrically opposed effects that the two groups of anions can exert on biological systems have been recognized since long by the Hofmeister series, which conventionally classifies the character of ions as being salting-out (kosmotropic) or salting-in (chaotropic) in nature. 10 Recently, the supramolecular chemistry of long-known synthetic cluster anions of the borate- 11,12 and polyoxometalate-type 13 has moved into the focus, driven by the observation that their affinity with hydrophobic binding sites does exceed, 14 against expectation, those of hydrophobic guest molecules. 15–17 These large anions were recognized to expand the traditional Hofmeister series as so-called superchaotropic anions, 14,18–34 and their peculiar supramolecular chemistry has revived the interest in large anion binding in water.…”

Section: Introductionmentioning

confidence: 99%

Large anion binding in water

Assaf,

Nau

2023

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

Large anion binding in water

Assaf,

Nau

2023

Org. Biomol. Chem.

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“…Boron-containing compounds have application potential in pharmaceutical chemistry, − with boron neutron capture therapy being the most prominent example . Recently, a new cell-biological as well as medicinal-chemical application line has been documented for icosahedral dodecaborates B 12 X 12 2– (X = H, Cl, Br, and I; Figure a), because their superchaotropic ionic character − enables their use as broadband membrane carriers, that is, they enable cellular uptake of a wide range of otherwise impermeable hydrophilic molecules, including amino acids, neurotransmitters, peptides, and drugs. , This, combined with their chemical inertness, ,− high water solubility, ,, and high biocompatibility, ,,,,, defines a new research area in chaotropic inorganic cluster chemistry. Accordingly, it is of interest to investigate how variations in the boron cluster structure and topology affect their chaotropic character and, thus, their potential membrane carrier activity.…”

Section: Introductionmentioning

confidence: 99%

Metallacarborane Cluster Anions of the Cobalt Bisdicarbollide-Type as Chaotropic Carriers for Transmembrane and Intracellular Delivery of Cationic Peptides

et al. 2023

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Cobalt bisdicarbollides (COSANs) are inorganic boron-based anions that have been previously reported to permeate by themselves through lipid bilayer membranes, a propensity that is related to their superchaotropic character. We now introduce their use as selective and efficient molecular carriers of otherwise impermeable hydrophilic oligopeptides through both artificial and cellular membranes, without causing membrane lysis or poration at low micromolar carrier concentrations. COSANs transport not only arginine-rich but also lysine-rich peptides, whereas low-molecular-weight analytes such as amino acids as well as neutral and anionic cargos (phalloidin and BSA) are not transported. In addition to the unsubstituted isomers (known as ortho- and meta-COSAN), four derivatives bearing organic substituents or halogen atoms have been evaluated, and all six of them surpass established carriers such as pyrenebutyrate in terms of activity. U-tube experiments and black lipid membrane conductance measurements establish that the transport across model membranes is mediated by a molecular carrier mechanism. Transport experiments in living cells showed that a fluorescent peptide cargo, FITC-Arg8, is delivered into the cytosol.

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“…The design of supramolecular receptors is a way to develop selective sensor devices that respond to specific analytes [ 1 , 2 , 3 , 4 ]. The deposition of a supramolecular receptor on a suitable electrode surface offers the possibility of preparing a selective electrode–solution interface [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Voltammetric Detection of Vanillylmandelic Acid and Homovanillic Acid Using Urea-Derivative-Modified Graphite Electrode

Shishkanova

Králík

Synytsya

2023

Sensors

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Vanillylmandelic acid (VMA) and homovanillic acid (HVA) are diagnostic markers of neuroblastoma. The purpose of this study was to understand the reason for the discrimination of structural analogues (VMA and HVA) onto a graphite electrode coated with an electrochemically oxidized urea derivative. Density functional theory calculations (DFT), FTIR spectroscopic measurements, and electrochemical impedance spectroscopic measurements were used in this work. Density functional theory calculations (DFT) were used to identify the most suitable binding sites of the urea derivative and to describe possible differences in its interaction with the studied analytes. The FTIR measurement indicated the enhancement and disappearance of NH vibrations on graphite and platinum surfaces, respectively, that could be connected to a different orientation and thus provide accessibility of the urea moiety for the discrimination of carboxylates. Additionally, the higher the basicity of the anion, the stronger the hydrogen-bonding interaction with –NH-groups of the urea moiety: VMA (pKb = 10.6, KAds = (5.18 ± 1.95) × 105) and HVA (pKb = 9.6, KAds = (4.78 ± 1.58) × 104). The differential pulse voltammetric method was applied to detect VMA and HVA as individual species and interferents. As individual analytes, both HVA and VMA can be detected at a concentration of 1.99 × 10−5 M (RSD ≤ 0.28, recovery 110–115%).

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Supramolecular chemistry of anionic boron clusters and its applications in biology

Cited by 23 publications

References 113 publications

Large anion binding in water

Large anion binding in water

Metallacarborane Cluster Anions of the Cobalt Bisdicarbollide-Type as Chaotropic Carriers for Transmembrane and Intracellular Delivery of Cationic Peptides

Voltammetric Detection of Vanillylmandelic Acid and Homovanillic Acid Using Urea-Derivative-Modified Graphite Electrode

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