Russian Journal of Bioorganic Chemistry最新文献

Objective: A pair of fluorogenic dyes with three electron-donating groups, based on arylideneimidazolones, is presented. Methods: The formation of imines of the corresponding aldehydes with the subsequent [3 + 2] cycloaddition was used for the synthesis of arylidene-imidazolones. The optical properties of the new compounds were studied. The fluorescence microscopy was used for imaging lipid droplets of the living cells, labeled by the dyes. Results and Discussion: We discovered that a pair of the proposed substances is characterized by a significant bathochromic shift of the absorption and emission maxima, as well as by a noticeable variation of the position of the emission maximum depending on the properties of the environment. We demonstrated that (Z)-5-(3,5-bis(dimethylamino)-4-(ethylamino)benzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one can stain lipid droplets in HeLa Kyoto and Huh 7.5 cell lines. Conclusions: We designed a new selective fluorogenic dye based on arylidene-imidazolones and showed that it can be applicable for lipid droplets labeling in living cells.

The chemical reactivity profiles and structures of pyridine derivatives, as well as several techniques for their synthesis, are discussed. Several heterocycles, which are pharmacologically active natural molecules and agrochemicals, are synthesized using these substances as precursors. This review is based on a literature search that included several synthesis techniques and applications of pyridine derivatives. Important chemical compounds with a wide range of uses include pyridine and its derivatives. We have outlined the uses of several pyridine derivatives, both medicinal and non-medicinal, in this review. Numerous biological activities of pyridine derivatives have been documented, and several of the compounds are used in therapeutic settings. Additionally, pyridine derivatives are becoming increasingly significant for contemporary medical applications.

Objective: This study aims to identify and characterize secondary metabolites from the leaves of Jasminum sambac and Jasminum grandiflorum, focusing on their bioactive compounds and antioxidant potential. Methods: Ethanolic extracts of Jasminum sambac and Jasminum grandiflorum were used to isolate secondary metabolites ((JG-3–JG-5), (JS-3–JS-5)). These compounds were characterized using IR, NMR, and mass spectrometry. Density functional theory (DFT) was applied to analyze their antioxidant potential through electronic properties (HOMO–LUMO gaps and molecular electrostatic potential). Results and Discussion: Six compounds ((JG-3–JG-5), (JS-3–JS-5)) were successfully isolated and characterized. The DFT analysis revealed potential antioxidant properties based on HOMO–LUMO gaps and MEP maps. The study enhances the knowledge of the secondary metabolites of Jasminum sambac and Jasminum grandiflorum. Computational analysis supports the antioxidant activity of the isolated compounds, suggesting their therapeutic potential and use as quality control markers. Conclusions: Six bioactive compounds were identified and characterized, providing insights into their antioxidant potential and offering opportunities for further pharmacological investigation.

Objective: Pyrimidine base derivatives having a wide spectrum of pharmacological activity along with low toxicity are used as active ingredients of many drugs. Specifically, a large number of uracil series compounds have antitumor, anti-inflammatory, antiviral, and immunomodulatory effects, which makes relevant the synthesis of new biologically active derivatives of the pyrimidine series. It is known that the mechanism of hepatotoxicity of chemical compounds is largely associated with the activation of lipid peroxidation, therefore, the objects of the study were uracil derivatives containing a proton-donating group in position C5, which significantly increases the antioxidant properties of the compound. Methods: For the synthesis of uracil derivatives, modification of 5-hydroxy- and 5-amino-6-methyluracils, containing pre-protected C5 functional groups, with various alkyl substituents introduced at N¹,N³ positions was carried out. The method of preliminary etching of cells with the hepatotoxicant carbon tetrachloride and their treatment with the tested compounds was selected for the study of the hepatoprotective activity. Results and Discussion: The introduction of various alkyl substituents at the N¹,N³ positions of 5-hydroxy- and 5-amino-6-methyluracils was shown to increase the solubility of these compounds; the hepatoprotective activity of the synthesized compounds was revealed. Conclusions: New di- and monoalkyl derivatives of 5-hydroxy- and 5-amino-6-methyluracils were obtained, and their hepatoprotective activity was tested in vitro. According to the test results, five of the 20 new compounds synthesized promote cell survival when pretreated with carbon tetrachloride.

Objective: There has never been a compilation of (E)-2-(4-((4-((1-(2,4-dichlorophenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)methyl)-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamide derivatives produced before. For the synthesis of (VIIa–VIIh), (E)-1-(2,4-dichlorophenyl)-4-(3-methoxy-4-(prop-2-yn-1-yloxy)benzylidene)-3-methyl-1H-pyrazol-5(4H)-one (V) was utilized. Methods: The compounds were synthesized using the Click chemistry process. We used the tube-dilution approach to test for antimicrobial and antifungal activity. Results and Discussion: Mass spectrometry, ¹H, ¹³C NMR, and IR spectroscopy were used to validate the eight newly produced compounds. The antibacterial and antifungal properties of the new compounds were tested. While seven compounds ((VIIa–VIIc), (VIIe–VIIh)) demonstrated antimicrobial activity against a range of bacterial strains, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes, the activity was comparable to that of the drug ampicillin, whereas (VIIh) exhibited good antifungal activity compared to its standard drug Griseofulvin against Candida albicans. Conclusions: We conclude that the newly synthesized 1,2,3-triazoles showed good antibacterial activity and can be used as precursors for drug molecules in the future.

Objective: In order to understand whether the lipid composition of the plasma membrane is related to the lifespan, we conducted a comparative study of the profiles of molecular species of four main classes of plasma membrane phospholipids (phosphatidylcholines (PC), phosphatidylethanolamines (PE), phosphatidylserines (PS), and phosphatidylinositols (PI)) for the long-lived mussel Crenomytilus grayanus and the long-lived sea urchin Mesocentrotus nudus and the short-lived mussel Mytilus trossulus and sea urchin Strongylocentrotus intermedius. Methods: The molecular profiles of these membrane lipids were determined using high-performance liquid chromatography in combination with high-resolution mass spectrometry. Results and Discussion: It was shown that the profile of PI molecular species is not related to the lifespan of the mussels and the sea urchins, in contrast to the profiles of PC, PE, and PS molecular species. Sea urchins M. nudus and mussel C. grayanus with longer lifespans were characterized by an increased content of PC, PE, and PS with odd-numbered alkyl/acyl chains, as well as of molecular species with arachidonic acid (20:4n-6), whose higher content can contribute to a better adaptation of the mussel C. grayanus and of the sea urchin M. nudus and, thereby, to a longer lifespan. Conclusions: The lipidomic approach to studying the gerontological problem using sea urchins and bivalves as an example has revealed a clear relationship between the profile of molecular species of the membrane lipids and the lifespan. The exact mechanisms of this relationship need to be further clarified.

Objective: A multi-component development method that does not include a catalyst has been developed for the environmentally friendly synthesis of pyranopyrazole derivatives containing a thioether bond. Methods: This method includes non-hazardous solvents and catalysts, conducts a basic workup, and achieves quantitative yields to eliminate contaminants. Furthermore, the antifungal and antibacterial characteristics of all the reported compounds were examined. Results and Discussion: Compounds (Ve) and (Vf) demonstrated superior antifungal activity compared to fluconazole against both C. albicans and S. cerevisiae at a concentration of 40 µg/mL. Conclusions: The findings provide evidence that these active chemicals could be a solid foundation for future research into developing novel antioxidant and antibacterial medications.

This review aims to evaluate the mechanisms of action of current and emerging anti-TB drugs and molecules, emphasizing hydrazone functionality. Hydrazone compounds, featuring an azomethine group (R₁–HN–N=CR₂R₃), exhibit potent anti-TB and broad-spectrum anti-infective properties. It includes the synthesis and biological testing of hydrazide-hydrazones, with a focus on their anti-TB activities reported in the literature. It highlights promising candidates for future anti-TB therapies, underscoring hydrazones’ role as a crucial pharmacophore in drug design against tuberculosis and other infectious diseases. This review summarizes pivotal findings in the development of hydrazone-based compounds, contributing to the ongoing search for effective anti-infective agents.

Objective: In the present work we set ourselves the following tasks: to perform a comparative XRD study of samples of the powder lignocellulose isolated from hardwood pulp and the same samples containing embedded silver and also to perform a computer-aided construction of an atomic con-figuration that describes the structure of the silver-modified cellulose. Methods: The structure of silver-modified powder cellulose isolated from hardwood lignocellu-lose was studied by X-ray structural analysis and computer simulation. Results and Discussion: A full-profile analysis showed that the studied sample belongs to the monoclinic phase of cellulose Iβ with an antiparallel arrangement of molecules, with the unit cell lattice parameters a = 7.881 Å, b = 7.837 Å, c = 10.603 Å, γ = 95.63°, and volume V = 652 ų. The sizes of the coherent scattering regions (CSRs) of the sample were calculated by the Scherrer equation and used to analyze the supramo-lecular structure. An increase in the CSR in the [100] direction and a decrease in the CSR in the [001] direction compared to the respective parameters of powder lignocellulose were observed. The cross-sectional area of the fibril of the modified sample in the ab plane (980 Ų) was found to be ~8% larger than that of powder cellulose. The crystallinity index (CI) calculated by the Ruland method estimated at 79% which was 7% higher than that of powder cellulose. Conclusions: The final cluster formula of the silver-modified powder cellulose was determined as C₆O₅H_10.12Ag_0.08.

Objective: The main goal of this study was to investigate the thermochemical conversion of wheat straw dioxane lignin in a sub/supercritical dimethyl carbonate medium. The object of our study was the dioxane lignin isolated from wheat straw. The conversion of wheat straw dioxane lignin in a sub/supercritical dimethyl carbonate medium was studied. Methods: The experiment was performed in an autoclave in a temperature range from 200°C to 350°C. The low-molecular-weight products were extracted from the liquid fraction using hexane; GC-MS was used to study their composition. The solid products were analyzed by IR spectroscopy. Results and Discussion: The low-molecular-weight products consist of esters, aldehydes, ketones, and alkyl aromatic compounds. Thirty-four compounds were identified by GC-MS, including 12 C₆–C₃ compounds, i.e., those whose structures match the generally recognized phenylpropane unit of lignin. The low-molecular-weight products fraction is predominantly comprised of methyl esters of aromatic and fatty acids. More than 95% of the identified low-molecular-weight products are veratric-type compounds. New data on the conversion undergone by the wheat straw dioxane lignin in a sub/supercritical dimethyl carbonate medium were obtained. It was shown that high solubility of dioxane lignin under subcritical conditions may be due to cleavage of intermolecular interaction, including hydrogen bonds between the dioxane lignin macromolecules, as a result of thermal exposure and methylation reactions. Fragmentation of the dioxane lignin macromolecules under supercritical conditions involves the processes of radical cleavage of the alkyl aryl ether bonds, as well as the dealkylation, dehydration, methylation, transesterification, and demetoxylation reactions. Conclusions: New data on the conversion of wheat straw dioxane lignin in a sub/supercritical dimethyl carbonate medium were obtained.