Cobalt bis(dicarbollide) is a DNA-neutral pharmacophore

Fink, Krzysztof; Cebula, Jakub; Tošner, Zdeněk; Psurski, Mateusz; Uchman, Mariusz; Goszczyński, Tomasz M.

doi:10.1039/d3dt01836a

Cited by 3 publications

(1 citation statement)

References 66 publications

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“…Contrary to the described conclusions, our recent research concerning [COSAN] − ’s interactions with DNA describes this molecule as DNA-neutral, which was confirmed by the series of various experimental physicochemical methods including UV–vis absorption, circular and linear dichroism and NMR spectroscopy and backed up by in vitro tests . Measured absorption spectra of both DNA and [COSAN] − in the presence of the potential interaction partner’s increasing concentrations remained unchanged, thus implying no (or very weak) complex formation between DNA and [COSAN] − .…”

Section: Metallacarboranes’ Action Within Eukaryotic Cellsmentioning

confidence: 99%

Metallacarboranes in Medicinal Chemistry: Current Advances and Future Perspectives

Gos,

Cebula,

Goszczyński

2024

J. Med. Chem.

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Metallacarboranes, exemplified by cobalt bis(dicarbollide) ([COSAN]−), have excelled their historical metallocene analogue label to become promising in drug design, medical studies, and fundamental biological research. Serving as a unique platform for conjugation with biomolecules, they also constitute an auspicious building block for biologically active derivatives and a carrier for cellular transport of membrane-impermeable cargos. Modified [COSAN]− exhibits specific antimicrobial, antiviral, and anticancer actions showing promise for preclinical trials. Contributing to the ongoing development in medicinal chemistry, metallacarboranes offer desirable physicochemical properties and low acute toxicity. This article presents a critical look at metallacarboranes in the context of their application in medicinal chemistry, emphasizing [COSAN]− as a potential game-changer in drug design and biomedical sciences. As medicinal chemistry seeks innovative building blocks, metallacarboranes emerge as an important novelty with versatile solutions and promising implications.

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Section: Metallacarboranes’ Action Within Eukaryotic Cellsmentioning

confidence: 99%

Metallacarboranes in Medicinal Chemistry: Current Advances and Future Perspectives

Gos,

Cebula,

Goszczyński

2024

J. Med. Chem.

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Chemistry of Carbon-Substituted Derivatives of Cobalt Bis(dicarbollide)(1−) Ion and Recent Progress in Boron Substitution

Pazderová,

Tüzün,

Bavol

et al. 2023

Molecules

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The cobalt bis(dicarbollide)(1−) anion (1−), [(1,2-C2B9H11)2-3,3′-Co(III)](1−), plays an increasingly important role in material science and medicine due to its high chemical stability, 3D shape, aromaticity, diamagnetic character, ability to penetrate cells, and low cytotoxicity. A key factor enabling the incorporation of this ion into larger organic molecules, biomolecules, and materials, as well as its capacity for “tuning” interactions with therapeutic targets, is the availability of synthetic routes that enable easy modifications with a wide selection of functional groups. Regarding the modification of the dicarbollide cage, syntheses leading to substitutions on boron atoms are better established. These methods primarily involve ring cleavage of the ether rings in species containing an oxonium oxygen atom connected to the B(8) site. These pathways are accessible with a broad range of nucleophiles. In contrast, the chemistry on carbon vertices has remained less elaborated over the previous decades due to a lack of reliable methods that permit direct and straightforward cage modifications. In this review, we present a survey of methods based on metalation reactions on the acidic C-H vertices, followed by reactions with electrophiles, which have gained importance in only the last decade. These methods now represent the primary trends in the modifications of cage carbon atoms. We discuss the scope of currently available approaches, along with the stereochemistry of reactions, chirality of some products, available types of functional groups, and their applications in designing unconventional drugs. This content is complemented with a report of the progress in physicochemical and biological studies on the parent cobalt bis(dicarbollide) ion and also includes an overview of recent syntheses and emerging applications of boron-substituted compounds.

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Bis(Dicarbollide) Complexes of Transition Metals: How Substituents in Dicarbollide Ligands Affect the Geometry and Properties of the Complexes

Sivaev

2024

Molecules

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The interaction between different types of substituents in dicarbollide ligands and their influence on the stabilization of various rotational conformers (rotamers) of transition metal bis(dicarbollide) complexes [3,3′-M(1,2-C2B9H11)2]− are considered. It has been shown that the formation of intramolecular CH···X hydrogen bonds between dicarbollide ligands is determined by the size of the proton acceptor atom X rather than its electronegativity. Due to the stabilization of rotamers with different dipole moments, intramolecular hydrogen bonds between ligands in transition metal bis(dicarbollide) complexes can have a significant impact on the biological properties of their derivatives. In the presence of external complexing metals, weak intramolecular CH···X hydrogen bonds can be broken to form stronger X—>M donor-acceptor bonds. This process is accompanied by the mutual rotation of dicarbollide ligands and can be used in sensors and molecular switches based on transition metal bis(dicarbollide) complexes.

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Cobalt bis(dicarbollide) is a DNA-neutral pharmacophore

Abstract: Cobalt bis(dicarbollide) (COSAN) is a metallacarborane used as a versatile pharmacophore to prepare biologically active hybrid organic‒inorganic compounds or to improve the pharmacological properties of nucleosides, antisense oligonucleotides, and DNA...

Cited by 3 publications

References 66 publications

Metallacarboranes in Medicinal Chemistry: Current Advances and Future Perspectives

Metallacarboranes in Medicinal Chemistry: Current Advances and Future Perspectives

Chemistry of Carbon-Substituted Derivatives of Cobalt Bis(dicarbollide)(1−) Ion and Recent Progress in Boron Substitution

Bis(Dicarbollide) Complexes of Transition Metals: How Substituents in Dicarbollide Ligands Affect the Geometry and Properties of the Complexes

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