Cytoprotective Effects and Intranuclear Localization of Sulfur-Containing Derivative of Buckminsterfullerene.

Background: There is a growing interest in exploring the biological characteristics of nanoparticles and exploring their potential applications. However, there is still a lack of research into the potential genotoxicity of fullerene derivatives and their impact on gene expression in human cells. In this study, we investigated the effects of a water-soluble fullerene derivative, C60[C6H4SCH2COOK]5H (F1), on human embryonic lung fibroblasts (HELF).

Buckyballs to fight pandemic: Water-soluble fullerene derivatives with pendant carboxylic groups emerge as a new family of promising SARS-CoV-2 inhibitors.

Herein, we present the first experimental study of individual water-soluble fullerene derivatives proving their ability to inhibit SARS-CoV-2 in vitro. The initial screening allowed us to identify a few new compounds that have demonstrated pronounced antiviral activity with IC values as low as 390 nM and selectivity indexes reaching 214. Time-of-addition analysis and molecular docking results suggested that the viral protease and/or the spike protein are the most probable targets inhibited by the fullerene derivatives.

Dose-Response Effect of Various Concentrations of Cl-Containing Water-Soluble Derivatives of C Fullerenes on a Selective Regulation of Gene Expression in Human Embryonic Lung Fibroblasts (HELF).

Background: The new synthesized water-soluble derivatives of C fullerenes are of a great interest to researchers since they can potentially be promising materials for drug delivery, bioimaging, biosonding, and tissue engineering. Surface functionalization of fullerene derivatives changes their chemical and physical characteristics, increasing their solubility and suitability for different biological systems applications, however, any changes in functionalized fullerenes can modulate their cytotoxicity and antioxidant properties. The toxic or protective effect of fullerene derivatives on cells is realized through the activation or inhibition of genes and proteins of key signaling pathways in cells responsible for regulation of cellular reactive oxygen species (ROS) level, proliferation, and apoptosis.

Synthesis of -symmetrical C tetra-adducts reactions of CCl with CH-acids and enol silyl ester.

Here we report the synthesis of novel fullerene derivatives with attached aliphatic residues based on the previously unknown reactions of chlorofullerene CCl with CH-acids and silyl enol ether.

Anthraquinone-Quinizarin Copolymer as a Promising Electrode Material for High-Performance Lithium and Potassium Batteries.

The growing demand for cheap, safe, recyclable, and environmentally friendly batteries highlights the importance of the development of organic electrode materials. Here, we present a novel redox-active polymer comprising a polyaniline-type conjugated backbone and quinizarin and anthraquinone units. The synthesized polymer was explored as a cathode material for batteries, and it delivered promising performance characteristics in both lithium and potassium cells.

Water-Soluble Fullerene C Derivatives Are Effective Inhibitors of Influenza Virus Replication.

The influenza virus genome features a very high mutation rate leading to the rapid selection of drug-resistant strains. Due to the emergence of drug-resistant strains, there is a need for the further development of new potent antivirals against influenza with a broad activity spectrum. Thus, the search for a novel, effective broad-spectrum antiviral agent is a top priority of medical science and healthcare systems.

Electrostatic effects on water-soluble fullerene derivatives interaction with cytochrome c and cytochrome c oxidase.

Water-soluble fullerene derivatives are good candidates for various biological applications such as anticancer or antimicrobial therapy, cytoprotection, enzyme inhibition, and many others. Their toxicity, both in tissue culture and in vivo, is a critical characteristic for the development and restriction of these applications. The effects of six water-soluble cationic and anionic polysubstituted fullerene derivatives on cytochrome c oxidase activity in rat brain mitochondria and the possibility of cytochrome c binding were studied.

A regioselective step-by-step CCl functionalization approach affords a novel family of CArTh'Th''H fullerene derivatives with promising antiviral properties.

We report a novel reaction of the recently discovered family of fullerene derivatives -CArTh' with thiophene derivatives Th''H yielding a previously unknown family of -CArTh'Th''H compounds with three different types of functional aromatic addends attached to the carbon cage. The discovered reaction paves a way to the synthesis of novel C fullerene derivatives with promising antioxidant and antiviral properties.

Hypoglycemic and hypolipidemic effect of pentaamino acid fullerene C derivative in rats with metabolic disorder.

Pentaamino acid fullerene C derivative is a promising nanomaterial, which exhibited antihyperglycemic activity in high-fat diet and streptozotocin-induced diabetic rats. This study investigates the effect of pentaaminoacid C derivative (PFD) in rats with metabolic disorders. Rats were assigned to 3 groups (of 10 rats each) as follows: Group 1 (normal control), group 2 included the protamine-sulfate-treated rats (the untreated group of animals with the model metabolic disorder); group 3 (Protamine sulfate + PFD) included the protamine-sulfate-treated model rats that received an intraperitoneal injection of PFD.

The Phosphonate Derivative of C Fullerene Induces Differentiation towards the Myogenic Lineage in Human Adipose-Derived Mesenchymal Stem Cells.

Inductors of myogenic stem cell differentiation attract attention, as they can be used to treat myodystrophies and post-traumatic injuries. Functionalization of fullerenes makes it possible to obtain water-soluble derivatives with targeted biochemical activity. This study examined the effects of the phosphonate C fullerene derivatives on the expression of myogenic transcription factors and myogenic differentiation of human mesenchymal stem cells (MSCs).

Water-Promoted Reaction of CArCl Compounds with Thiophenes Delivers a Family of Multifunctional Fullerene Derivatives with Selective Antiviral Properties.

Here we report a reaction of the fullerene derivatives CArCl, which enables the substitution of Cl with thiophene residues and the formation of the novel family of -symmetrical C fullerene derivatives with six functional addends CArTh. The discovered reaction provided a straightforward approach to the synthesis of previously inaccessible multifunctional water-soluble fullerene derivatives, including the compounds with antiviral activity against human immunodeficiency and influenza viruses.

Identification of potential descriptors of water-soluble fullerene derivatives responsible for antitumor effects on lung cancer cells via QSAR analysis.

Water-soluble fullerene derivatives are actively investigated as potential drugs for cancer treatment due to their favorable membranotropic properties. Herein, cytotoxic effects of twenty fullerene derivatives with different solubilizing addends were evaluated in three different types of non-small-cell lung carcinoma (NSCLC). The potential structural descriptors of the solubilizing addends related to the inhibitory activities on each type of lung cancer cell were investigated by the quantitative structure-activity relationship (QSAR) approach.

Thiophene-based water-soluble fullerene derivatives as highly potent antiherpetic pharmaceuticals.

Here we report the Friedel-Crafts arylation of chlorofullerenes C60Cl6 and C70Cl8 with thiophene-based methyl esters. While C60Cl6 formed expected Cs-C60R5Cl products, C70Cl8 demonstrated a tendency for both substitution of chlorine atoms and addition of an extra thiophene unit, thus forming Cs-C70R8 and C1-C70R9H compounds. The synthesized water-soluble C60 and C70 fullerene derivatives with thiophene-based addends demonstrated high activity against a broad range of viruses, including human immunodeficiency virus, influenza virus, cytomegalovirus, and herpes simplex virus.

Water-soluble fullerene-based nanostructures with promising antiviral and myogenic activity.

Here we report a straightforward method for the synthesis of a water-soluble C60 fullerene derivative decorated with five residues of phosphonic acid. Self-assembly of the synthesized compound in aqueous solution leads to the formation of nanostructures with unprecedented myogenic and antiviral activity.

Effects of Functionalized Fullerenes on ROS Homeostasis Determine Their Cytoprotective or Cytotoxic Properties.

Background: Functionalized fullerenes (FF) can be considered regulators of intracellular reactive oxygen species (ROS) homeostasis; their direct oxidative damage-as well as regulation of oxidant enzymes and signaling pathways-should be considered.

Methods: Uptake of two water-soluble functionalized C fullerenes with different types of aromatic addends (ethylphenylmalonate and thienylacetate) in human fetal lung fibroblasts, intracellular ROS visualization, superoxide scavenging potential, NOX4 expression, NRF2 expression, oxidative DNA damage, repair genes, cell proliferation and cell cycle were studied.

Results & Conclusion: The intracellular effects of ethylphenylmalonate C derivative (FF1) can be explained in terms of upregulated NOX4 activity.

Memory devices based on novel alkyl viologen halobismuthate(iii) complexes.

Four novel halobismuthate(iii) complexes with alkyl viologen cations: (R2Viol)2[Bi2X10] (R = n-butyl, n-pentyl, X = Cl, Br) have been synthesized. Both chloride complexes revealed photochromic behavior and were successfully utilized for the fabrication of OFET-based memory devices with high switching coefficients and good write-read-erase cycling stability.

Fullerene Derivatives as Lung Cancer Cell Inhibitors: Investigation of Potential Descriptors Using QSAR Approaches.

Background: Nanotechnology-based strategies in the treatment of cancer have potential advantages because of the favorable delivery of nanoparticles into tumors through porous vasculature.

Materials And Methods: In the current study, we synthesized a series of water-soluble fullerene derivatives and observed their anti-tumor effects on human lung carcinoma A549 cell lines. The quantitative structure-activity relationship (QSAR) modeling was employed to investigate the relationship between anticancer effects and descriptors relevant to peculiarities of molecular structures of fullerene derivatives.

Direct arylation of CCl and CCl with carboxylic acids: a synthetic avenue to water-soluble fullerene derivatives with promising antiviral activity.

We report unprecedented Friedel-Crafts arylation of chlorofullerenes C60Cl6 and C70Cl8 with unprotected carboxylic acids as an efficient single-step synthesis of the inherently stable water-soluble fullerene derivatives. Using this method, a series of previously unaccessible compounds was obtained without chromatographic purification in almost quantitative yields. Promising anti-HIV activity comparable to characteristics of commercial drugs was demonstrated for some of these compounds.

Anti-amyloid activities of three different types of water-soluble fullerene derivatives.

Anti-amyloid activity, aggregation behaviour, cytotoxicity and acute toxicity were investigated for three water-soluble fullerene derivatives with different types of solubilizing addends. All investigated compounds showed a strong anti-amyloid effect in vitrocaused by interaction of the water-soluble fullerene derivatives with the Ab(1-42)-peptide and followed by destruction of the amyloid fibrils. Notably, all of the studied fullerene derivatives showed very low cytotoxicity and low acute toxicity in mice (most promising compound 3 was more than four times less toxic than aspirin).

Diversion of the Arbuzov reaction: alkylation of C-Cl instead of phosphonic ester formation on the fullerene cage.

We report an "inversed" Arbuzov reaction of the fullerene derivatives CArCl with trialkyl phosphites P(OR) producing alkylated fullerene derivatives CArR (R = Me, Et, iPr, nBu) with almost quantitative yields. This reaction provides a convenient synthetic route for the preparation of a large variety of functionalized fullerene derivatives with tailored properties, e.g.

Antioxidant Properties of Fullerene Derivatives Depend on Their Chemical Structure: A Study of Two Fullerene Derivatives on HELFs.

Oxidative stress is a major issue in a wide number of pathologies (neurodegenerative, cardiovascular, immune diseases, and cancer). Because of this, the search for new antioxidants is an important issue. One of the potential antioxidants that has been enthusiastically discussed in the past twenty years is fullerene and its derivatives.

Self-diffusion of water-soluble fullerene derivatives in mouse erythrocytes.

Self-diffusion of water-soluble fullerene derivative (WSFD) C[S(CH)SONa]H in mouse red blood cells (RBC) was characterized by H pulsed field gradient NMR technique. It was found that a fraction of fullerene molecules (~13% of the fullerene derivative added in aqueous RBC suspension) shows a self-diffusion coefficient of (5.5 ± 0.

Synthesis of different types of alkoxy fullerene derivatives from chlorofullerene CCl.

We report novel synthetic routes for facile preparation of highly functionalized fullerene derivatives C(OR)X (X = H, Cl, Br), C(OR)O and C(OR) from chlorofullerene CCl. The first water-soluble fullerene compound bearing residues of 3-oxypropanoic acid demonstrated a potent anti-HIV activity.