Metallacarboranes as tunable redox potential electrochemical indicators for screening of gene mutation

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Within the cell nucleus, in the nucleoli, ribosomal RNAs are synthesized and participate in several biological processes. To better understand nucleoli-related processes, their visualization is often required, for which specific markers are needed. Herein, we report the design of novel fluorescent organotin compounds derived from 4-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide and their cytoplasm and nucleoli staining of B16F10 cells in vitro. Tin compounds bearing an aliphatic carbon chain (-C H ) and an electron-donating group (-OH) were prepared, and the latter could be derivatized to bear the boron cluster anions [B H ] and [3,3'-Co(1,2-C B H ) ] (COSAN). All of the conjugates have been fully characterized and their luminescence properties have been assessed. In general, they show good quantum yields in solution (24-49 %), those for the COSAN derivatives being lower. Remarkably, the linking of [B H ] and COSAN to the complexes made them more soluble, without being detrimental to their luminescence properties. Living B16F10 cells were treated with all of the compounds to determine their fluorescence staining properties; the compounds bearing the aliphatic chain showed a reduced staining capacity due to the formation of aggregates. Notably, the complexes bearing different boron clusters showed different staining effects; those bearing [B H ] showed extraordinary staining of the nucleoli and cytoplasm, whereas those bearing COSAN were only detected in the cytoplasm. The remarkable fluorescence staining properties shown by these organotin compounds make them excellent candidates for fluorescence bioimaging in vitro.

Section: Bioimagingsupporting

confidence: 61%

Section: Introductionmentioning

confidence: 99%

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Muñoz‐Flores

Cabrera‐González

Viñas

et al. 2018

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“…The cellular uptake and distribution studies of Na[COSAN] in cancer cells has shown that [COSAN] − is retained in the nuclear fractions, which contain most of the cell genetic material organized as multiple long linear DNA molecules in complex structures. To date, only the studies related to DNA interaction with Na[FESAN] are reported . Here, we have exploited the interaction between Na[COSAN] and DNA molecules to form a new nanohybrid biomaterial.…”

Section: Resultsmentioning

confidence: 99%

“…To date, only the studies related to DNA interaction with Na[FESAN] are reported. [19] Here, we have exploited the interaction between Na[COSAN] andD NA molecules to form a new nanohybrid biomaterial.S pecifically,s pectrophotometric measurements (IR and Raman) have been used to prove the interaction, and meltingt emperature (Tm), UV,c yclic voltammetry,a nd CD techniques wereu sed to discern on the nature of such interaction. Later,once proventhe formationo ft he nanohybridb iomaterial,t he hydrodynamic diameter (Ø HYD )o ft he dispersed Na[COSAN] (0.1 mm) after the addition of different concentrations of CT-dsDNA, in aqueouss olution, at room temperaturef or samples in PB (0.1 m, pH 7.0) were studied.F inally, the nanohybrid biomaterial wasv isualized by optical, TEM, and CryoTEM microscopies.…”

Section: Cellular Viabilitymentioning

confidence: 99%

“…[17] However,o nly biological studies of pristine [COSAN] À as potent inhibitor of HIV protease [18] and the interaction of pristine [FESAN] À with DNA can be found in the literature. [19] Icosahedral anionic metallacarboranes [3,3'-M(1,2-C 2 B 9 H 11 ) 2 ] À , M = Co III ;F e III .D ark grey vertices correspond to boron atoms, pink vertices to carbon, and blue to the metal atoms.…”

Section: Introductionmentioning

confidence: 99%

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Metallacarboranes on the Road to Anticancer Therapies: Cellular Uptake, DNA Interaction, and Biological Evaluation of Cobaltabisdicarbollide [COSAN]⁻

Fuentes

García‐Mendiola

Sato

et al. 2018

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120

After uptake by U87 MG and A375 cancer cells, cobaltabisdicarbollide [COSAN] distributes between membrane and nucleus and presents no relevant cytotoxicity against both cell lines even for long incubation times. The cytotoxicity of Na[COSAN] was also tested towards one normal cell line, the V79 fibroblasts, in order to ascertain the noncytotoxic profile of the compound. As the cell's nucleus contains DNA, the interaction between [COSAN] and double-stranded calf thymus DNA (CT-dsDNA) has been investigated. There is a strong interaction between both molecules forming a nanohybrid CT-dsDNA-[COSAN] biomaterial, which was fully characterized. Moreover, Na[COSAN] shows characteristic redox peaks ascribed to the oxidation/reduction of Co at a formal potential of -1.444 V and it can be accumulated at a surface-immobilized DNA layer of glassy carbon electrodes. The equilibrium surface-binding constants (K /K ), which confirm that [COSAN] interacts with DNA by an intercalative or electrostatic mode, depending on the ionic strength of the solution, were estimated. In addition, high binding affinity of Na[COSAN] to proteins was observed by B{ H} NMR and confirmed in vivo. Finally, biodistribution studies of [COSAN] in normal mice were run. After administration, Na[COSAN] was distributed into many organs but mainly accumulated in the reticuloendothelial system (RES), including liver and spleen. After 1 h, the formation of aggregates by plasma protein interaction plays a role in the biodistribution profile; the aggregates accumulate mostly in the lungs. Na[COSAN], which displays low toxicity and high uptake by relevant cancer cells accumulating boron within the nucleus, could act as a suitable compound for further developments as boron neutron capture therapy (BNCT) agents.

Dual Binding Mode of Metallacarborane Produces a Robust Shield on Proteins

Fuentes

Pujols

Viñas

et al. 2019

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An inorganic sandwich molecule, Na[Co(C 2 B 9 H 11 ) 2 ], able to produce vesicles through self-assembly and known to produce strong dihydrogen-bond interactions with amine groups is capable of interacting with proteins.T his dual non-bonding ability of Na[Co(C 2 B 9 H 11 ) 2 ]i sw hat makes this molecule unique:i tc an be firmly anchored to ap rotein surface and is capable of extending over it. To prove this, the widely available bovine serum albumin( BSA), which has many pendanta mino groups in its structure, has been taken as the model protein. It has been found that around 100 molecules of Na[Co(C 2 B 9 H 11 ) 2 ]p reserve the native structure of BSA, while endorsing it with as ignificantly increased sta-bility with respectt oc hemical-and thermal-inducedd enaturation due to efficient encapsulation. The advantages of this encapsulation technique are two-fold; the first is its simplicity as it relies on the anchoring capacity of Na[Co(C 2 B 9 H 11 ) 2 ] to the surface of the protein through the amine-containing residues and the second is its self-assembling capacity allowing it to spread across the surface. The dense shield of protection offered by Na[Co(C 2 B 9 H 11 ) 2 ]h as been demonstrated by the inhibition of BSA pseudo-esterase activity,w hich indicates that the inorganic corset around BSA protects its reactive surface residues,thereby preventing their acetylation.