Russian Chemical Bulletin最新文献

{"title":"Complex formation of nucleic acids with 5-[4′-(2″-amino-6″-oxo-1″H-purin-8″-yl)phenyl]-10,15,20-tris(N-methylpyridin-3′-yl)porphyrin in solutions","authors":"N. Sh. Lebedeva,&nbsp;E. S. Yurina,&nbsp;S. S. Guseinov,&nbsp;K. I. Mamaeva,&nbsp;A. N. Kiselev,&nbsp;M. A. Lebedev,&nbsp;S. A. Syrbu","doi":"10.1007/s11172-025-4611-9","DOIUrl":"10.1007/s11172-025-4611-9","url":null,"abstract":"<div><p>Asymmetrically substituted porphyrin containing a guanine residue at the periphery of the porphyrin cycle was synthesized in an acetic acid medium using the C—H activation method. The quaternization of the product was carried out to prepare water-soluble porphyrin. The structure of the porphyrin was confirmed by electronic absorption spectroscopy, ¹H NMR spectroscopy, and mass spectrometry. According to the results of studying the photochemical properties and complexing ability of the synthesized porphyrin with respect to representative oligonucleotides poly[d(AT)₂] and poly[d(GC)₂] and natural calf thymus DNA, the porphyrin forms intercalation complexes with poly[d(GC)₂] and DNA and binds to poly[d(AT)₂] in the groove. The photoirradiation of the porphyrin complexes with poly[d(AT)₂] leads to the formation of associates, while the photoirradiation of the porphyrin complexes with poly[d(GC)₂] and DNA induces a partial destruction of the nucleic acid.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"1177 - 1187"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073603","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 antimycotic activity of quaternary ammonium salts based on pyridoxine","authors":"N. V. Shtyrlin,&nbsp;S. A. Lisovskaya,&nbsp;S. V. Sapozhnikov,&nbsp;A. G. Iksanova,&nbsp;A. M. Aimaletdinov,&nbsp;L. R. Valiullin,&nbsp;K. V. Balakin,&nbsp;Yu. G. Shtyrlin","doi":"10.1007/s11172-025-4604-8","DOIUrl":"10.1007/s11172-025-4604-8","url":null,"abstract":"<div><p>The <i>in vitro</i> screening of the antifungal activity in a series of quaternary ammonium salts based on pyridoxine revealed a highly active bis-ammonium compound, <i>N</i>,<i>N</i>′-{[(2,2,8-trimethyl-4<i>H</i>-[1,3]dioxino[4,5-<i>c</i>]pyridine-5,6-diyl]bis(methylene)} bis(<i>N</i>-dodecyl-<i>N</i>,<i>N</i>-dimethylammonium) dichloride (<b>KFU-04</b>), which exhibited pronounced antimycotic activity against a panel of various mycelial and yeast fungal pathogens, in particular, 3 reference strains and 15 clinical isolates, including drug-resistant ones. It was found that <b>KFU-04</b> exerts a rapid dose-dependent effect, allowing to reduce the number of CFU of the pathogen by two to three orders of magnitude within two days, with a significant effect being observed already after 8 h from the start of incubation. In contrast to fluconazole and terbinafine, which are used world-wide to treat onychomycosis (fungal nail infections), <b>KFU-04</b> under the conditions of a model experiment was found to efficiently and dose-dependently inhibit the formation of fungal biofilms of the aggressive clinical isolate <i>C. albicans</i> isolated from nail plates. Using two different types of high-resolution microscopy, confocal laser scanning and electron microscopy, it was shown that the membrane and possibly the cell wall of fungi are among the main targets of compound <b>KFU-04</b>. The described powerful and complex antimicrobial effects were not accompanied by toxicity both when applied externally and when administered systemically: <i>in vivo</i> experiments on rodents demonstrated the high safety of <b>KFU-04</b> (LD₅₀ &gt; 2000 mg kg⁻¹). In general, the obtained experimental results provided strong grounds for continuing studies of compound <b>KFU-04</b> as a potential highly efficient broad-spectrum antifungal agent for combating dangerous infections.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"1106 - 1119"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073607","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":"Effect of structural and solvation factors on aggregation, pH stability, lipophilicity, and antimicrobial activity of mono- and diiodo-substituted boron(iii) dipyrromethene luminophores","authors":"G. B. Guseva,&nbsp;D. R. Baidamshina,&nbsp;U. D. Paramonova,&nbsp;E. Y. Trizna,&nbsp;A. R. Kayumov,&nbsp;S. A. Lisovskaya,&nbsp;I. R. Gilfanov,&nbsp;L. E. Nikitina,&nbsp;E. V. Antina","doi":"10.1007/s11172-025-4590-x","DOIUrl":"10.1007/s11172-025-4590-x","url":null,"abstract":"<div><p>A comparative analysis was carried out to examine the effect of solvent nature and the specific features of molecular structure on aggregation behavior, pH stability, hydrophobicity, and antimicrobial activity of 2-iodo-tetramethyl-ethyl-BODIPY (where BODIPY is boron(<span>iii</span>) dipyrromethene) (<b>1</b>), 2,6-diiodo-tetramethyl-BODIPY (<b>2</b>), and 2,6-diiodo-tetramethyl-BODIPY containing an ester residue of butanoic acid (<b>3</b>) in the <i>meso</i>-spacer as potential photosensitizers for antimicrobial photodynamic therapy. All the studied compounds demonstrated a sufficiently high stability in both acidic and alkaline media. The introduction of iodine atoms into the pyrrole rings and the substitution of the hydrogen atom at the <i>meso</i>-position of the BODIPY core with an ester residue significantly (up to ∼1.4 times) increase the hydrophobicity of the luminophores compared to the tetramethylated analogue. In this case, compound <b>1</b> exhibits bactericidal activity against <i>Staphylococcus aureus</i> under irradiation at a wavelength of 530 nm, compound <b>2</b> demonstrates an activity that is 16 times lower, and BODIPY <b>3</b> does not show any antimicrobial activity under these experimental conditions.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"956 - 964"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073643","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":"Photochemistry of cis-[Ru(bpy)2(NH3)2]2+ complex, a promising light-activated anticancer agent","authors":"A. A. Kokorenko,&nbsp;V. P. Grivin,&nbsp;I. P. Pozdnyakov,&nbsp;A. V. Mikheylis,&nbsp;Yu. A. Belikov,&nbsp;A. A. Melnikov,&nbsp;S. V. Chekalin,&nbsp;D. B. Vasilchenko,&nbsp;E. M. Glebov","doi":"10.1007/s11172-025-4588-4","DOIUrl":"10.1007/s11172-025-4588-4","url":null,"abstract":"<div><p>Complex <i>cis</i>-[Ru(bpy)₂(NH₃)₂]²⁺ (<b>1</b>) is a promising photo-activated chemotherapy (PACT) agent; however, its photophysical and photochemical properties have been poorly studied. In this work photoreactions of complex <b>1</b> in aqueous solutions were studied by means of steady-state photolysis, nanosecond laser flash photolysis, and ultrafast transient absorption spectroscopy. Excitation of <b>1</b> in the wavelength range of 254–505 nm results in substitution of two ammonia ligands by water molecules followed by partial dissociation with the formation of complexes <i>cis</i>-[Ru(bpy)₂(H₂O)₂]²⁺ (<b>2</b>) and <i>cis</i>-[Ru(bpy)₂(H₂O)(OH)]⁺ (<b>3</b>), which exist in equilibrium. The quantum yield of photo-aquation is rather low (about 1%) and decreases on going from the UV to visible spectral range. Excitation of complex <b>1</b> in the region of the intra-ligand transition (350 nm) results in the formation of vibrationally hot, triplet excited metal-to-ligand charge transfer (³MLCT) state with a characteristic time shorter than 100 fs. The vibrational cooling time was about 3 ps. The thermally equilibrated ³MLCT state decays within 120 ns in two parallel processes, <i>viz.</i>, intersystem crossing to the ground state and exchange of NH₃ ligand with a water molecule to give the complex <i>cis</i>-[Ru(bpy)₂(NH₃)(H₂O)]²⁺ (<b>4</b>). Possible reactions of complex <b>4</b> include the inverse substitution of water molecule by the ammonia ligand with the restoration of the initial structure of the complex and the exchange of the second NH₃ ligand with a water molecule with the formation of reaction products, <i>viz.</i>, complexes <b>2</b> and <b>3</b>. The photochemical properties of complex <b>1</b> are independent of the presence of dissolved oxygen in solution, which is favorable for the PACT applications.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"933 - 946"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073649","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":"Design of a near-infrared fluorescent sensor for detecting fluoride anion based on 10-hydroxybenzo[h]quinoline: a theoretical study","authors":"Liangyue Cheng,&nbsp;A. G. Cherednichenko","doi":"10.1007/s11172-025-4586-6","DOIUrl":"10.1007/s11172-025-4586-6","url":null,"abstract":"<div><p>The design of near-IR fluorescence sensors is of significant importance for various <i>in vivo</i> applications. In this context, a convenient platform is provided by 10-hydroxybenzo-[<i>h</i>]quinoline (HBQ), in which intramolecular excited-state proton transfer occurs. In this work, a systematic theoretical study was conducted of five HBQ derivatives, involving an analysis of the molecular geometry during proton transfer in both the ground (S₀) and excited (S₁) states. The potential of the HBQ derivatives for detecting F⁻, Cl⁻, and Br⁻ anions was assessed based on the results of comprehensive analysis of their calculated photophysical characteristics. It was demonstrated that the strategy involving simultaneous addition of electron-withdrawing and electron-donating groups to carbon atoms of the HBQ proton donor ring and proton acceptor ring, respectively, makes it possible to obtain high-performance near-IR fluorescent sensors.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"912 - 923"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073694","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":"XXIX International Chugaev Conference on Coordination Chemistry, VI Youth School-Conference “Physicochemical Methods in the Chemistry of Coordination Compounds”","authors":"","doi":"10.1007/s11172-025-4615-5","DOIUrl":"10.1007/s11172-025-4615-5","url":null,"abstract":"","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"1202 - 1202"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073591","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":"Mono-, di-, and tetraazido derivatives of (thia)calix[4]arenes with free phenolic hydroxy groups","authors":"E. G. Makarov,&nbsp;Z. E. Iskhakova,&nbsp;V. A. Burilov,&nbsp;S. E. Solovieva,&nbsp;I. S. Antipin","doi":"10.1007/s11172-025-4600-z","DOIUrl":"10.1007/s11172-025-4600-z","url":null,"abstract":"<div><p>A thiacalix[4]arene with four azido groups on the upper rim and free hydroxy groups on the lower rim was synthesized for the first time by the diazotization reaction. A procedure for the synthesis of diazido derivatives of calix[4]arenes and thiacalix[4]arenes with free phenolic hydroxy groups <i>via</i> benzoyl protection of OH groups was developed and optimized. A similar technique was used to synthesize a monoazido derivative of calix[4]arene, the parent compound for the biscalix[4]arenes with ethylene glycol and dihydroxyphenylene linkers obtained by the azide-alkyne cycloaddition reaction. It was demonstrated that these biscalix[4]arenes can bind the cationic dye rhodamine 6G, which is not observed for the starting de-<i>tert</i>-butylated calix[4]arene. It was established that the biscalix[4]arene—rhodamine 6G system can be used for the recognition of cationic surfactants and that the more lipophilic the surfactant, the more pronounced the system’s response.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"1055 - 1068"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073594","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":"Dibenzothiaphosphonium P,I-ylides: synthesis, properties, biological activity","authors":"A. S. Nenashev,&nbsp;D. A. Dospekhov,&nbsp;M. V. Zavaruev,&nbsp;I. I. Levina,&nbsp;V. A. Roznyatovsky,&nbsp;A. V. Mironov,&nbsp;V. V. Chernyshev,&nbsp;I. A. Shutkov,&nbsp;A. A. Nazarov,&nbsp;A. S. Pavlova,&nbsp;T. A. Podrugina","doi":"10.1007/s11172-025-4609-3","DOIUrl":"10.1007/s11172-025-4609-3","url":null,"abstract":"<div><p>A series of phosphonium derivatives of cyclic 10-phenyl-10<i>H</i>-dibenzo[<i>b</i>,<i>e</i>][1,4]thiaphosphinine were synthesized, which included phosphonium-iodonium ylides stabilized by electron-withdrawing substituents of various types, along with their synthetic precursors such as phosphonium salts and ylides. A series of phosphonium-substituted furans were synthesized through the involvement of the novel P,I-ylide stabilized by a benzoyl group into heterocyclization reactions with aryl alkynes. The resulting dibenzothiaphosphonium P,I-ylides and furans were shown to have antiproliferative activity <i>in vitro</i> against several human cancer cell lines.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"1153 - 1168"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073601","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 of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity","authors":"D. A. Pitushkin,&nbsp;D. V. Danilov,&nbsp;Ya. P. Kuznetsov,&nbsp;D. A. Aksenov,&nbsp;V. N. Osipov,&nbsp;G. M. Butov,&nbsp;I. A. Novakov","doi":"10.1007/s11172-025-4610-x","DOIUrl":"10.1007/s11172-025-4610-x","url":null,"abstract":"<div><p>Isothio- and isoselenocyanates of the adamantane series were synthesized in 45–88% yields and were shown to inhibit the growth of the cancer cells lines HCT-116 (colorectal carcinoma), MCF-7 (breast adenocarcinoma), PC-3 (prostate adenocarcinoma), and A549 (lung carcinoma) with half-maximal inhibitory concentrations (IC₅₀) in the range of 1.7–67 µmol L⁻¹. The following structure—activity relationship was established: the inhibitory activity of adamantyl-containing isoselenocyanates <b>2a–f</b> against the growth of the HCT-116, MCF-7, PC-3, and A549 cancer cell lines decreases with increasing length of the spacer between the adamantane moiety and the isoselenocyanate group, showing a saw-tooth decrease in the activity. The isosteric replacement of a sulfur atom by selenium leads to an increase in the inhibitory activity. Thus, 1-isoselenocyanatoadamantane <b>2c</b> proved to be three times more active against the growth of the MCF-7 cancer cell line (IC₅₀ = 8.2 µmol L⁻¹) compared to its sulfur-containing analog. This effect noticeably decreases with increasing length of the spacer between the adamantane moiety and the isoselenocyanate group. 1-Isocyanoadamantane <b>3c</b>, which does not contain a sulfur or selenium atom, inhibits the growth of the HCT-116 cancer cell line (IC₅₀ = 40 µmol L⁻¹) and is not active against the MCF-7, PC-3, and A549 cancer cell lines.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"1169 - 1176"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073602","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":"Photophysical and electrochemical properties of bis(dithiophene)-substituted benzo[1,2-d:4,3-d′]dithiazoles","authors":"A. S. Kostyuchenko,&nbsp;E. B. Uliankin,&nbsp;T. Yu. Zheleznova,&nbsp;A. L. Shatsauskas,&nbsp;V. Yu. Shuvalov,&nbsp;A. S. Fisyuk","doi":"10.1007/s11172-025-4591-9","DOIUrl":"10.1007/s11172-025-4591-9","url":null,"abstract":"<div><p>Bis(dithiophene)-substituted benzo[1,2-<i>d</i>:4,3-<i>d</i>′]dithiazoles were synthesized by a photochemical cyclization of corresponding <i>N</i>,<i>N</i>′-(benzo[<i>c</i>][1,2,5]thiadiazole-4,7-diyl)- and <i>N</i>,<i>N</i>′-(2<i>H</i>-benzo[<i>d</i>][1,2,3]triazole-4,7-diyl)dithioamides in the presence of chloranil. The mechanism of this cyclization was analyzed. The influence of the structure of the central heterocycle on the electrochemical, electronic, and photophysical properties of the synthesized compounds was studied. Quantum yields for THF solutions of the luminophpores are in the range 0.16–0.62. An increase in the electron-withdrawing effects of the central heterocycle stabilizes the radical anion and reduces the reduction potential, E_onset^red, and the width of the band gap.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"965 - 972"},"PeriodicalIF":1.7,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144073647","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}