Russian Journal of Bioorganic Chemistry最新文献

{"title":"Pathogenic Bacteria of the Enterobacteriaceae Family: Mechanisms of Adaptation to the Host Organism, Modern Trends in Overcoming Antibiotic Resistance, Taking Into Account the Role of G-Quadruplexes in the Bacterial Genome","authors":"Iu. V. Iakushkina,&nbsp;L. A. Nikiforova,&nbsp;I. A. Ivanov,&nbsp;T. S. Oretskaya,&nbsp;E. A. Kubareva,&nbsp;M. V. Monakhova","doi":"10.1134/S1068162026603939","DOIUrl":"10.1134/S1068162026603939","url":null,"abstract":"<p>Gram-negative bacteria of the ESKAPE group belonging to the <i>Enterobacteriaceae</i> family are in the top of the WHO list of priority pathogens that pose the greatest threat to human health. This is due not only to the fact that these bacteria have developed resistance to a single antibiotic or a single class of antibiotics, but also to the emergence of multiple drug resistance, which leads to the higher morbidity and mortality rates, as well as an increased burden on the healthcare system. Enterobacteria from the ESKAPE group (<i>Klebsiella pneumoniae</i>, <i>Enterobacter</i> spp.) demonstrate high ecological plasticity, actively exchange with genes of virulence and antimicrobial resistance, and also participate in the development of chronic inflammatory and oncological diseases of the intestine. This review summarizes modern data on the key factors of enterobacterial pathogenicity and the causes of antibiotic resistance. As a comparison, data on well-studied pathogenic <i>Escherichia coli</i> lines, which also belong to the <i>Enterobacteriaceae</i> family, are presented. Special attention is paid to G-quadruplexes (G4s)—non-canonical secondary structures of nucleic acids that can form in regulatory regions of genes and modulate the virulence factors expression and genes responsible for stress adaptation. The data on the occurrence of G4 motifs in the genomes of enterobacteria are reviewed. The results on the effect of G4 binding with low molecular weight ligands on the vital activity of a bacterial cell, including the efflux systems suppression and the antibiotic sensitivity restoration, are discussed. Promising directions for further research have been identified, including the validation of G4 targets in clinical strains and the development of selective modulators for G4-mediated regulation.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132422","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Strategies for Increasing the Bioavailability of Anti-Tuberculosis Nucleoside Analogues","authors":"V. A. Sokhraneva,&nbsp;Iu. S. Zhivotova,&nbsp;E. S. Matyugina,&nbsp;I. L. Karpenko,&nbsp;V. I. Popenko,&nbsp;S. N. Andreevskaya,&nbsp;T. G. Smirnova,&nbsp;A. E. Enina,&nbsp;E. G. Goncharova,&nbsp;E. S. Gromova,&nbsp;S. N. Kochetkov,&nbsp;A. L. Khandazhinskaya","doi":"10.1134/S1068162026600546","DOIUrl":"10.1134/S1068162026600546","url":null,"abstract":"<p><b>Objective:</b> The widespread rise of drug-resistant tuberculosis poses a serious public health problem because standard therapy is ineffective, which stimulates the development of new anti-tuberculosis drugs. Carbocyclic uridine analogs with 5-tetradecenyl and 5-dodecyloxymethyl substituents have demonstrated significant activity against <i>Mycobacterium tuberculosis</i> strains, including MDR ones, <i>in vitro</i>. The hydrophobicity of these compounds limits solubility and cellular penetration. In this study, strategies for improving bioavailability, such as liposomal encapsulation, encapsulation in nanoparticles, and the synthesis of water-soluble prodrugs, were applied to uridine analogs <b>I</b> and <b>II</b> to overcome these limitations. <b>Methods:</b> The manuscript describes the production of PLGA-based polymer particles using a single emulsification method. Lecithin-based liposomes were synthesized using ultrasonication. To obtain the PEG forms of compounds <b>I</b> and <b>II</b>, the 4'-hydroxyl group of the analogs was activated with carbonyldiimidazole (CDI) and reacted with tetraethylene glycol. The resulting systems were characterized by IR spectroscopy (to confirm the absence of chemical interactions), UV spectroscopy, DLS, TEM (spherical shape, dimensions 100–200 nm), and physicochemical analysis. <b>Results and Discussion:</b> Different strategies were applied to improve the bioavailability of hydrophobic uridine analogs <b>I</b> and <b>II</b> by creating polymeric nanoparticles, soy lecithin liposomes, and water-soluble prodrugs. Using modern physicochemical methods, effective incorporation of the active substance into nanoparticles and liposomes was demonstrated. The creation of prodrugs of carbocyclic analogs of uridine <b>I</b> and <b>II</b> based on tetraethylene glycol improved the solubility of the original compounds in aqueous media by more than 100 times. <b>Conclusions:</b> The development of drug delivery systems is a current challenge, but the issues with sterilization of polymer nanoparticles and liposomes make it difficult to demonstrate their therapeutic efficacy <i>in vitro</i>. The synthesis of tetraethylene glycol-based prodrugs of nucleoside analogs <b>I</b> and <b>II</b> improved the water solubility of the starting compounds. The resulting PEG forms did not demonstrate activity <i>in vitro</i>, probably due to their prolonged release, and further research is needed to better understand their therapeutic potential.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132438","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis and Cytotoxic Activity of Azepane Derivatives Based on 2-Oxo-Allobetulin and Methyl 2-Oxo-Oleanoate","authors":"L. M. Zakirova,&nbsp;E. V. Tretyakova,&nbsp;O. B. Kazakova","doi":"10.1134/S1068162025605166","DOIUrl":"10.1134/S1068162025605166","url":null,"abstract":"<p><b>Objective:</b> Triterpene lactams and azepanes were synthesized using 2-oxo-allobetulin oxime and methyl 2-oxo-oleanoate oxime. <b>Methods:</b> The cytotoxic activity of the synthesized compounds was studied <i>in vitro</i> on 60 tumor cell lines from nine different types of human cancer. <b>Results and Discussion:</b> C2-Azepano-allobetulin was shown to be active against leukemia, non-small cell lung cancer, and colon cancer cell lines, while C2-azepano-erythrodiol exhibited high activity (GI₅₀ 1.16–16.80 μM) against all studied cell lines, with the compound’s activity exceeding that of the reference drug, 5-fluorouracil, against 14 cell lines. <b>Conclusions:</b> The high cytotoxic activity of the synthesized compounds demonstrates their potential as new antitumor agent candidates and justifies further study of their selectivity, as well as of their pharmacokinetic and toxicological profiles, to expand the possibilities for developing pharmacologically relevant agents based on 2-oxo-triterpenoids.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132344","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Crystal Structure of the Monomeric Green Fluorescent Protein mTurquoise2-1710 at 1.45 Å Resolution","authors":"N. V. Pletneva,&nbsp;D. A. Gorbachev,&nbsp;I. V. Artemyev,&nbsp;S. F. Arkhipova,&nbsp;V. Z. Pletnev","doi":"10.1134/S1068162026602715","DOIUrl":"10.1134/S1068162026602715","url":null,"abstract":"&lt;p&gt;&lt;b&gt;Objective:&lt;/b&gt; Green fluorescent proteins with a tyrosine-based chromophore typically lose their fluorescence under acidic conditions, which limits their utility for imaging biological processes occurring in acidic cellular compartments. The monomeric green fluorescent protein mTurquoise2-1710 (λ&lt;sub&gt;ex&lt;/sub&gt;/λ&lt;sub&gt;em&lt;/sub&gt; 482 nm/519 nm), which carries a tryptophan-based chromophore, exhibits high pH stability and represents a promising alternative for such applications. The aim of this work was to determine the spatial structure of mTurquoise2-1710 at high resolution and to elucidate the molecular basis of its enhanced quantum yield and brightness relative to the parent variant mTurquoise2-T203Y. &lt;b&gt;Methods&lt;/b&gt;&lt;b&gt;&lt;i&gt;:&lt;/i&gt;&lt;/b&gt; The mTurquoise2-1710 variant was obtained from mTurquoise2-T203Y by three rounds of random mutagenesis. The recombinant protein was expressed in &lt;i&gt;Escherichia coli&lt;/i&gt; and purified by metal-affinity and size-exclusion chromatography. Crystals were grown by the hanging-drop vapor diffusion method. X-ray diffraction data were collected at 100 K at a synchrotron source, and the three-dimensional structure was solved by molecular replacement and refined to 1.45 Å resolution. We compared the structure of mTurquoise2-1710 with that of the blue fluorescent precursor, mTurquoise2, to identify structural features responsible for differences in their photophysical properties. &lt;b&gt;Results and Discussion&lt;/b&gt;&lt;b&gt;&lt;i&gt;:&lt;/i&gt;&lt;/b&gt; The structure of mTurquoise2-1710 adopts the canonical β-barrel fold characteristic of GFP-like proteins, with a coplanar chromophore formed from the Ser-Trp-Gly tripeptide. Comparison with mTurquoise2 revealed two key structural rearrangements associated with the substitutions Y145S and F146S: reorientation of the β-segment containing residues 145–146 and rotation of the chromophore about an axis perpendicular to its plane. These rearrangements result in the loss of two hydrogen bonds between the chromophore and residues of its immediate environment. The reduced number of hydrogen bonds lowers the probability of non-radiative transition of the chromophore from the excited to the ground state, thereby accounting for the nearly four-fold increase in quantum yield and the corresponding enhancement in brightness. Additional substitutions identified during random mutagenesis (A37V, I128T, N164H, D173G, D234G, Y237T, K238S) are located on the protein surface or at the C-terminus and likely contribute to improved folding and chromophore maturation. &lt;b&gt;Conclusions&lt;/b&gt;&lt;b&gt;&lt;i&gt;:&lt;/i&gt;&lt;/b&gt; High-resolution X-ray crystallography established the spatial structure of the pH-stable green fluorescent protein mTurquoise2-1710 and revealed the structural determinants underlying its improved photophysical performance. The disruption of hydrogen bonds in the chromophore environment, caused by rotation and displacement of the chromophore, is the principal factor responsible for the increased quantum yield. These findings provide a str","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132343","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A Conjugate of Two Antitumor Agents: Are Two Heads Better Than One?","authors":"Iu. S. Zhivotova,&nbsp;V. A. Sokhraneva,&nbsp;I. L. Karpenko,&nbsp;S. N. Kochetkov,&nbsp;E. S. Matyugina,&nbsp;A. L. Khandazhinskaya","doi":"10.1134/S1068162026603587","DOIUrl":"10.1134/S1068162026603587","url":null,"abstract":"&lt;p&gt;&lt;b&gt;Objective:&lt;/b&gt; Cancer is one of the major global health challenges nowadays. Oncologists use various approaches to treat malignant tumors, the most common of which is chemotherapy. Despite decades of research into the development of new anticancer drugs, there are still limitations that have to be overcome such as, anticancer drugs resistance, limited solubility and bioavailability, and insufficient selectivity leading to side effects. The co-drug strategy may help resolve problems described above. Co-drugs are chemical compounds consisting of two or more active fragments (pharmacophores). Such chimeric molecules can improve the pharmacodynamic selectivity and pharmacokinetics of a drug (solubility, stability, bioavailability), reduce toxicity, and sometimes overcome the mechanisms responsible for tumor cell resistance to one of the pharmacophores. &lt;b&gt;Methods:&lt;/b&gt; The manuscript describes design and synthesis of the new co-drug compound based on nucleoside analogue floxuridine (FUDR) and nitrogen mustard (NM). Compound &lt;b&gt;III&lt;/b&gt; was obtained in two steps using bromoacetyl bromide as acylation agent. Conjugate &lt;b&gt;III&lt;/b&gt; was analyzed for cytotoxicity &lt;i&gt;in vitro&lt;/i&gt; on three cell lines (SH-SY5Y, HL-60, K-562 cell lines). &lt;b&gt;Results and Discussion:&lt;/b&gt; Nucleoside analog floxuridine (FUDR) and nitrogen mustard (NM) were chosen as a pharmacophores of co-drug based on their different mechanisms of action. We assumed that combination of these fragments into a single molecule could improve therapeutic efficacy and overcome some limitations of the parent drugs, including resistance and insufficient selectivity. The target conjugate &lt;b&gt;III&lt;/b&gt; was obtained in two steps using fragment of acetic acid as a linker for the chimeric molecule. On the first step we synthesized bromoacetic derivative of floxuridine &lt;b&gt;IV&lt;/b&gt;, which we then used in alkylation reaction with nitrogen mustard &lt;b&gt;II&lt;/b&gt; to obtain 5ʹ-&lt;i&gt;N&lt;/i&gt;-(bis(2-chloroethyl))glycyl-2ʹ-deoxy-5-fluorouridine &lt;b&gt;III&lt;/b&gt;. The chimeric compound &lt;b&gt;III&lt;/b&gt; showed a slight improvement in activity &lt;i&gt;in vitro&lt;/i&gt; on three cell lines (SH-SY5Y, HL-60, K-562 cell lines) compared to the parent floxuridine. This data confirms the ability of the co-drug &lt;b&gt;III&lt;/b&gt; to release at least one active component. However, a more reliable assessment of the advantages of the new co-drug requires &lt;i&gt;in vivo&lt;/i&gt; studies. &lt;b&gt;Conclusions:&lt;/b&gt; A new compound has been developed and obtained, which is a conjugate of floxuridine and nitrogen mustard: 5ʹ-&lt;i&gt;N&lt;/i&gt;-(bis(2-chloroethyl))glycyl-2ʹ-deoxy-5-fluorouridine &lt;b&gt;III&lt;/b&gt;. This molecule is a co-drug with pharmacophores that exhibit different mechanisms of action. &lt;i&gt;In vitro&lt;/i&gt; screening revealed a slight improvement in the cytotoxicity of &lt;b&gt;III&lt;/b&gt; compared to the parent compound, floxuridine. Using a nucleoside analog (floxuridine) and an alkylating agent (nitrogen mustard) as pharmacophores in a single chimeric molecule appears to be a promising strategy; however, ad","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132423","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis and Evaluation of Anti-Influenza Activity of Amide Derivatives of 3-Spiro-1,2,4-trioxolanolithocholic Acid","authors":"I. E. Smirnova,&nbsp;A. S. Volobueva,&nbsp;O. B. Kazakova","doi":"10.1134/S1068162025605026","DOIUrl":"10.1134/S1068162025605026","url":null,"abstract":"<p><b>Objective:</b> To develop novel steroidal 3-spiro-1,2,4-trioxolanes based on lithocholic acid amides with trifluoromethyl ketones and to evaluate their antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) <i>in vitro</i>. <b>Methods:</b> The 3-spiro-1,2,4-trioxolanes were synthesized via co-ozonolysis of <i>O</i>-methyl ketoximes of lithocholic acid amides in the presence of trifluoromethyl ketones at 0°C in a cyclohexane–dichloromethane mixture. The structures of the products were confirmed by NMR spectroscopy, and individual diastereomers were isolated using column chromatography. Antiviral activity and cytotoxicity were assessed in MDCK cell cultures, determining IC₅₀, CC₅₀, and the selectivity index (SI). <b>Results and discussion:</b> A series of six new steroidal 3-spiro-1,2,4-trioxolanes was obtained with yields of 65–70%. Compounds with cyclohexyl or benzylamide fragments and a methyl/trifluoromethyl substituent in the trioxolane ring showed moderate activity with a selectivity index (SI) of 8 and 11, respectively. The lead compound, <i>N</i>-cyclohexyl-3,3′-spiro-[5′-trifluoromethyl-5′-phenyl-1,2,4-trioxolano-3-yl]-5β-cholan-24-amide, showed an IC₅₀ of 12.5 µM and an SI of 37. Structure–activity analysis indicated that the nature of substituents in the amide side chain and trioxolane ring significantly affects the balance between antiviral activity and cytotoxicity. <b>Conclusion:</b> The obtained 3-<i>spiro</i>-1,2,4-trioxolanes based on lithocholic acid amides demonstrate a promising profile for further preclinical studies and the development of antiviral agents against the influenza A H1N1 virus.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132979","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Search for Novel Antimicrobial Agents to Overcome Bacterial Antibiotic Resistance","authors":"T. V. Ovchinnikova,&nbsp;A. M. Egorov","doi":"10.1134/S1068162026603903","DOIUrl":"10.1134/S1068162026603903","url":null,"abstract":"<p>The widespread prevalence of antibiotic resistance among infectious disease pathogens raises an urgent need for the development of new approaches to the search for effective antimicrobial agents and the treatment of bacterial infections. This review focuses on key research areas aimed at developing therapeutic approaches to overcome bacterial antibiotic resistance. It discusses the search for next-generation antibiotics and the design of β-lactamase inhibitors, involving the use of bioinformatic analysis, artificial intelligence and machine learning methods as new stages in their development. The review also briefly discusses new areas of combined antibiotic therapy, phage therapy, and immunotherapy, including the use of antimicrobial peptides and quorum sensing inhibitors.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149133113","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"PREFACE TO THE SPECIAL ISSUE OF RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY: “ANTIBIOTIC RESISTANCE AND THE SEARCH FOR NEW ANTIMICROBIAL AGENTS”","authors":"Alexey M. Egorov, Academician of the Russian Academy of Sciences (RAS), Professor, Lomonosov Moscow State University and Tatiana V. Ovchinnikova, Professor, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS, Lomonosov Moscow State University","doi":"10.1134/S1068162026051127","DOIUrl":"10.1134/S1068162026051127","url":null,"abstract":"","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132977","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Combined Liposomal Nanoparticles Based on Dihexadecyl Ester of (4-Aminobutanoyl)-L-Aspartic Acid and Its Pegylated Analogue for Drug Delivery","authors":"A. S. Abrekova,&nbsp;U. A. Budanova,&nbsp;Y. L. Sebyakin","doi":"10.1134/S1068162025605099","DOIUrl":"10.1134/S1068162025605099","url":null,"abstract":"<p>ctive: Liposomes are one of the most promising systems for the delivery of biologically active substances (BAS) to target cells, particularly for crossing the blood–brain barrier in the treatment of central nervous system diseases. However, classical liposomes are rapidly taken up by cells of the reticuloendothelial system, which significantly limits their circulation time in the bloodstream. This study aimed to synthesize dihexadecyl ester of (4-aminobutanoyl)-L-aspartic acid and its pegylated analogue with MeO-PEG-2000 and to evaluate the physicochemical characteristics of the liposomal dispersions based on these compounds. <b>Methods:</b> Dihexadecyl ester of (4-aminobutanoyl)-L-aspartic acid and its MeO-PEG-2000 modified analogue were synthesized using stepwise condensation with dicyclohexylcarbodiimide and 4-dimethylaminopyridine, followed by chromatographic purification and structural characterization. Liposomal nanoparticles were prepared from the obtained lipids (and their mixtures) using thin-film hydration. <b>Results and Discussion:</b> The liposomal dispersions formed systems with mean hydrodynamic diameters of about 20–23 nm, which is optimal for functionalized transport systems. The pegylated liposomes exhibited a high ζ-potential and efficiently encapsulated hydrophilic biologically active substances, maintaining their size and charge during storage, which indicates high colloidal stability. <b>Conclusions:</b> The synthesized dihexadecyl ester of (4-aminobutanoyl)-L-aspartic acid and its MeO-PEG-2000 pegylated analogue form stable liposomal nanoparticles with high ζ-potential and high encapsulation efficiency for hydrophilic BAS. Pegylation significantly improves the colloidal stability of such liposomal systems and creates a promising platform for the development of long-circulating nanocarriers intended for drug delivery across biological barriers, including the blood–brain barrier.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132976","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis, Structure, Properties, and Antimicrobial Activity of Dialkyl(hydroxy(4-methoxyphenyl)methyl)phosphonates","authors":"R. R. Davletshin,&nbsp;А. N. Sedov,&nbsp;P. А. Kuryntseva,&nbsp;А. R. Fairushina,&nbsp;Е. А. Sokolova,&nbsp;А. V. Gerasimov,&nbsp;М. P. Shulaeva,&nbsp;К. А. Ivshin,&nbsp;А. М. Khakimzyanova,&nbsp;N. V. Davletshina","doi":"10.1134/S1068162026602430","DOIUrl":"10.1134/S1068162026602430","url":null,"abstract":"<p><b>Objective:</b> A series of dialkyl (hydroxy(4-methoxyphenyl)methyl)phosphonates 1–5 with various substituents at the phosphorus atom was obtained via the Abramov reaction. <b>Methods:</b> The structure of the isolated products was confirmed by a set of physicochemical methods: NMR, FT-IR spectroscopy, and X-ray diffraction analysis. The phytotoxicity of the obtained compounds was evaluated against radish (<i>Raphanus sativus</i> L.) and common wheat (<i>Triticum aestivum</i> L.). Ecotoxicity indices against the cladoceran <i>C. affinis</i> and the protozoan <i>P. caudatum</i> were determined. The antibacterial and antimycotic activity of the synthesized α-hydroxyphosphonates was investigated. TG and DSC analyses were performed. <b>Results and Discussion:</b> The prospects of studying compound <b>1</b> as an herbicide are shown. It was found that compounds <b>2–5</b> exhibited activity against <i>P. vulgaris</i>, <i>K. pneumoniae</i>, and <i>S. typhimurium</i>. Compounds <b>4</b> and <b>5</b> inhibited <i>B. cereus</i> and <i>S. aureus</i>. Antimycotic activity correlated with the length of the alkoxyl substituent at the phosphorus atom: with increasing substituent length, activity against <i>Candida</i> fungi and the microscopic fungus <i>S. cerevisiae</i> was manifested. TG and DSC analyses showed that the first stage of decomposition of the compounds is associated with β-elimination of alkyl groups to form hydroxymethylphosphonic acids, while the second stage corresponds to the elimination of the aromatic fragment. Above 480°C, intermolecular condensation with elimination of water is observed for all compounds. <b>Conclusions:</b> A series of dialkyl(hydroxy(4-methoxyphenyl)methyl)phosphonates 1–5 were obtained via the Abramov reaction and characterized. Compounds <b>2–5</b> showed antibacterial activity, with activity depending on the alkoxyl chain length, and increasing chain length also promoted antifungal action. All compounds were less toxic than chlorhexidine, while compound 1 showed phytotoxicity against radish and wheat, indicating prospects for its study as an herbicide.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":"52 5","pages":""},"PeriodicalIF":1.7,"publicationDate":"2026-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149132978","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}