Search Results (73)

Four novel crystalline architectures based on benzo[c]cinnolininium trifluoromethanesulonate salts, [C₁₂H₉N₂]⁺[CF₃SO₃]⁻, have been isolated as single-crystals, and their structures have been determined by X-ray diffraction analysis. The formation of the new salts results from reactions involving the dimeric hydroxo di-n-butylstannane trifluoromethanesulfonato complex [n-Bu₂Sn(OH)(H₂O)(CF₃SO₃)]₂ (1) and benzo[c]cinnoline (C₁₂H₈N₂, BCC). Organic salts I, II, III, and IV were crystallized through slow evaporation at room temperature from a mixture of toluene/dichloromethane. The cystallographic structures of I, II, and IV exhibit the presence of monoprotonated benzo[c]cinnolinium cations in interactions with a free benzo[c]cinnoline molecule through N–H···N hydrogen bonding, while for salt III, the monoprotonated cation directly interacts with the CF₃SO₃⁻ anion via an N–H···O interaction. For all four salts, aromatic π-π interactions involving rings of various components (free benzo[c]cinnoline molecule, benzo[c]cinnolinium cation, toluene molecule), combined with weak C–H···O and C–H···F interactions implying the trifluoromethanesulfonate anion, promote the solid-state self-assembly of supramolecular stacks. In parallel to the formation of benzo[c]cinnolinium based-salts, organotin(IV) 1 was converted into a distannoxane compound, ²_∞{[n-Bu₂(μ-OH)SnOSn(μ-η²-O₃SCF₃)n-Bu₂]₂[n-Bu₂(η¹-O₃SCF₃)SnOSn(μ-OH)n-Bu₂]₂} (3), which was also isolated as a single crystal and whose crystallographic structure was previously established by us. Full article

Alzheimer’s disease (AD) is a progressive neurodegenerative disorder characterized by synaptic dysfunction and neuronal loss due to the accumulation of amyloid-β peptides and tau proteins. In the pursuit of novel neuroprotective strategies, organotin(IV) compounds have garnered attention due to their unique chemical and biological properties. This study evaluates the inhibitory potential of two triphenyltin(IV) derivatives—(3-propan-1-ol)triphenyltin(IV) (Ph₃SnL₁) and (4-butan-1-ol)triphenyltin(IV) (Ph₃SnL₂)—in both free form and immobilized into mesoporous silica SBA-15~Cl, targeting acetylcholinesterase (AChE), a key enzyme involved in AD pathophysiology. The SBA-15~Cl|Ph₃SnL₂ nanostructures exhibited the most potent inhibitory activity against AChE (IC₅₀ = 0.58 μM), significantly outperforming the standard drug galantamine. Molecular docking, molecular dynamics simulations, and MM/GBSA and MM/PBSA analyses confirmed the stability and selectivity of interactions with AChE, primarily driven by hydrophobic interactions. Compound transport was also simulated using a multi-scale 3D mouse brain model to evaluate brain tissue distribution and blood–brain barrier permeability. The results highlight the strong potential of SBA-15-loaded organotin(IV) compounds as biocompatible neuroprotective agents for novel treatments of neurodegenerative diseases. Full article

In this work, we present the green synthesis of complex A–E derived from β-hidroxymethylidene indanones by ultrasound, which allowed for the obtaining of compounds in a shorter time and with good yields. These organotin complexes were then doped with cobalt porphine and incorporated into a poly(3,4-ethylenedioxythiophene):poly(4-styrenesulfonate) matrix to manufacture composite semiconductor films. The semiconductor films were characterized through atomic force microscopy, examining their topography, Knoop hardness (around 17 HK), and tensile strength, which varied from 5 × 10⁻⁴ to 7 × 10⁻² Pa. The optical behavior was evaluated, revealing that the changes in these characteristics are related to the type of organotin complex present in the composite film: the transmittance ranged from 77% to 86%, while the reflectance varied from 13% to 17%. The band gap, calculated using the Kubelka–Munk function F(KM), was approximately 3.7 ± 0.19 eV for all the semiconductor films. Finally, we assessed the electrical behavior of the composite films through current–voltage (I–V) measurements under different lighting conditions. The I–V curves demonstrated that they share a saturation current density of 3.46 mA/mm². However, they differ in their conduction rates within the ohmic regimen. These composite films’ optical and electrical properties suggest their potential use in developing electronic devices like organic diodes. Full article

Due to the promising characteristics of aminoguanidine Schiff bases, ongoing research focuses on synthesizing and characterizing different compounds of this class to establish structure–property relationships. However, the pronounced alkalinity of the aminoguanidine residue makes isolating its Schiff bases in neutral form challenging. In the reaction of salicylidene-aminoguanidine ([HL]NO₃) with a strong base (NaOH), the partially neutralized product of the formula [HL]NO₃∙L·H₂O was obtained in the form of single crystals. This compound could be considered a cocrystal in which protonated and neutral forms of the Schiff base coexist. Furthermore, the coordinating properties of [HL]NO₃ towards zinc and organotin were investigated, and instead of the expected crystals of complex compounds, a novel polymorph of the ligand was obtained. Additionally, the reaction of [HL]NO₃, NH₄VO₃ and salicylaldehyde was carried out to achieve the condensation of the free NH₂-group in the aminoguanidinium fragment, targeting a vanadium(V) complex with tetradentate ligand. However, a purely organic compound containing three salicylaldehyde residues and two imine groups, i.e., C₂₁H₁₈N₂O₃, was isolated. All the obtained compounds were characterized by elemental and spectroscopic analysis, conductometry and SC-XRD analysis. The data were compared to those of similar structures, and the results provide further insight into the properties of these compounds and their future investigation for potential usage. Full article

Objectives: New tributyltin(IV) complexes containing the carboxylate ligands 3-(4-methyl-2-oxoquinolin-1(2H)-yl)propanoic acid (HL1) and 2-(4-methyl-2-oxoquinolin-1(2H)-yl)acetic acid (HL2) have been synthesized. Methods: Their structures have been determined by elemental microanalysis, FT-IR and multinuclear NMR (¹H, ¹³C and ¹¹⁹Sn) spectroscopy and X-ray diffraction study. A solution state NMR analysis reveals a four-coordinated tributyltin(IV) complex in non-polar solvents, while an X-Ray crystallographic analysis confirms a five-coordinated trigonal-bipyramidal geometry around the tin atom due to the formation of 1D chains. A theoretical structural analysis was performed by optimization employing B3LYP-D3BJ functional and 6-311++G(d,p)/def2-TZVP(Sn) basis sets for H, C, N, O/Sn, respectively. The interactions between tin(IV) and surrounding atoms were examined by QTAIM approach. The in vitro antiproliferative activity of the synthesized compounds was evaluated by MTT and CV assays versus MCF-7 (human breast adenocarcinoma), HCT116 (human colorectal carcinoma), A375 (human melanoma), 4T1 (mouse breast carcinoma), CT26 (mouse colon carcinoma) and B16 (mouse melanoma) tumor cell lines. Results: Both synthesized compounds (nBu₃SnL1 and nBu₃SnL2) exerted powerful micromolar IC₅₀ cytotoxicity values and demonstrated high selectivity toward malignant cells. Both experimental drugs affected cell adhesion and induced anchorage independent apoptosis, a favorable type of cell death with an essential role in cancer dissemination prevention. The BSA-binding affinity of the obtained organotin compounds was followed by spectrofluorometric titration and molecular docking simulations. Conclusions: The tributyltin(IV) compounds selectively induce anoikis-like cell death in A375 cells, also highlighting the importance of the organic moiety on the tin(IV) ion in the mechanism of action. Full article

With the global ban on tributyltin (TBT), the pollution of triphenyltin (TPhT) is an emerging issue in some aquatic ecosystems. In this study, we investigated the concentrations of typical butyltin and phenyltin compounds in the surface water and sediments in the lower Yangtze River, analyzed their occurrence and sources, and assessed their ecological risks. The findings indicate that butyltin and phenyltin compounds are widespread. The total concentration of organotin compounds in surface water was as high as 42.41 ng Sn/L, with an average of 25.71 ng Sn/L, and the total concentration of organotins in sediments reached up to 111.5 ng Sn/g dw, averaging 61.1 ng Sn/g dw. Since the implementation of the AFS Convention, the concentration of organotins in surface water has been significantly reduced. However, the ecological risk of TBT is still high, and the risk of TPhT is also noteworthy. The findings also suggest that the primary source of butyltins in the lower Yangtze River is historical input residues. In contrast, the main source of PhTs is the recent input of agricultural runoff. Therefore, organotin contamination in the lower Yangtze River has changed, but its governance still presents challenges. Full article

Triphenyltin (TPT) is a commonly encountered organotin compound known for its endocrine-disrupting properties; it frequently interacts with antibiotics in aquatic environments. In this study, common carp (Cyprinus carpio) (17.43 ± 4.34 g, 11.84 ± 0.88 cm) were chosen as the experimental organisms. According to the environmental concentration in the heavily polluted area, the control group and the experimental groups were exposed for 21 days to the following treatments: 1 μg/L TPT, 1 mg/L NOR, and a combination of 1 μg/L TPT plus 1 mg/L NOR. The investigation examined the individual and combined toxicities of TPT and norfloxacin (NOR) on the gill, liver, and gut tissues of common carp in highly polluted areas. The findings revealed tissue-specific variations in 1L-1β enzyme activity; specifically, 1L-1β enzyme activity exhibited a significant reduction in liver tissue under both NOR exposure and combined exposure, indicating that high concentrations of NOR had the most pronounced impact on the immune system of liver tissue. Furthermore, the gene expression levels of IL-1β, Lysozyme-C, NKA, and CPT1 in the liver, intestinal, and gill tissues showed differences after exposure. In addition, TPT exerted the most significant effect on intestinal tissue, followed by the liver and gill tissues. Interestingly, when TPT and NOR were exposed together, the toxic effects on all tissues were reduced, suggesting the existence of antagonistic effects. Full article

A motivating class of compounds with interest in the research field of biological active metallopharmaceuticals for cancer treatment is based on organometallic complexes of Sn(IV), exhibiting advantages such as improved cellular uptake and body excretion, lower toxicity, and fewer side effects compared to platinum-based drugs. In this study, the mononuclear organotin coordination complex [(CH₃)₂SnCl₂(mebta)₂] was synthesized and characterized using vibrational spectroscopy (IR, Raman), ¹H NMR, ¹³C{¹H} NMR, and X-ray crystallography. Its antiproliferative properties were thoroughly assessed across an aggressive triple-negative human breast cancer cell line. Notably, comparative studies with precursor materials verified that the observed biological activity is intrinsic to the complex itself. This study highlights the compound’s ability to induce cell fate by disrupting essential cellular functions, such as proliferation. By exploring the antiproliferative effects of organotin(IV) derivatives, we introduce a novel class of Sn complexes with 1-methylbenzotriazole (mebta), demonstrating significant potential as promising antitumor agents in the field of organotin compounds. Full article

The general synthesis of boron-containing cyclic compounds (boracycles) necessitates toxic organotin precursors or highly reactive boron halides. Here, we report the synthesis of seven- and five-membered boracycles utilizing arylboronic acid pinacol esters (ArBpins) as stable boron sources. Grignard reagents generated from 2,2′-dibromodibenzyl or 2,2′-dibromobiphenyl reacted with ArBpins, where Ar = 9-anthryl (Anth), 2,4,6-trimethylphenyl (Mes), or 2,4,6-triisopropylphenyl (Tip), to give 10,11-dihydro-5H-dibenzo[b,f]borepins or dibenzoborole derivatives. This Bpin-based method was successfully applied to a one-shot double boracycle formation, providing a dihydrodibenzoborepin–anthracene–dihydrodibenzoborepin triad molecule in a good yield. The dihydrodibenzoborepin bearing the Anth group was directly converted to the unsaturated borepin by NBS/AIBN. All products were characterized by NMR, HRMS, and in some cases, single-crystal X-ray diffraction analysis. Additionally, the photophysical properties of the products are also reported. Full article

A novel trimethyltin(IV) complex (Me₃SnL), derived from 3-(4-methyl-2-oxoquinolin-1(2H)-yl)propanoate ligand, has been synthesized and characterized by elemental microanalysis, UV/Vis spectrophotometry, FT-IR and multinuclear (¹H, ¹³C and ¹¹⁹Sn) NMR spectroscopies. Furthermore, the structure of the ligand precursor HL was solved using SC-XRD (single-crystal X-ray diffraction). The prediction of UV/Vis and NMR spectra by quantum-chemical methods was performed and compared to experimental findings. The protein binding affinity of Me₃SnL towards BSA was determined by spectrofluorometric titration and subsequent molecular docking simulations. Me₃SnL has been evaluated for its in vitro anticancer activity against three human cell lines, MCF-7 (breast adenocarcinoma), A375 (melanoma) and HCT116 (colorectal carcinoma), and three mouse tumor cell lines, 4T1 (breast carcinoma), B16 (melanoma) and CT26 (colon carcinoma), using MTT and CV assays. The strong inhibition of A375 cell proliferation, ROS/RNS upregulation and robust lipid peroxidation lead to autophagic cell death upon treatment with Me₃SnL. Full article

Marinas are semi-enclosed environments characterised by reduced hydrodynamic energy, high sedimentation rates, and reduced oxygen levels. The ongoing development of activities and infrastructure construction are leading to deterioration in the quality of coastal aquatic environments, creating environmental risks. Trace metal elements (TMEs) and organotins are significant contaminants, prompting this study to evaluate the added value of spatiotemporal monitoring compared to one-time sediment assessments. Two Mediterranean harbours, Port Camargue (PC) and Port Carnon (C), differing in morphology and size, were monitored for a year with regular water sampling, focusing on TMEs and organotins. Sediment contamination, notably in the technical zone, revealed concentrations of Cu (309 and 1210 mg kg⁻¹ for C and PC, respectively), Zn (242 and 425 mg kg⁻¹ for C and PC, respectively), and tributyltin (TBT) (198 and 4678 µg (Sn) kg⁻¹ for C and PC, respectively) surpassing the effect range medium (ERM), while other marina stations generally stayed below this threshold. Spatiotemporal water monitoring highlighted concentrations above environmental quality standards (EQS) at all stations of the larger marina. This exceedance was systematic for Cu and Zn in all samples, ranging respectively between 2.54 and 37.56 µg (Sn) L⁻¹ and 0.63 and 33.48 µg (Sn) L⁻¹. A notable temporal dynamic for TBT and Cu was also observed. Conversely, the open marina, connected to the open sea, rarely exhibited concentrations above EQS in water, despite sediment concentrations occasionally exceeding ERM values. This underscores that risk assessment in these ecosystems cannot rely solely on sediment characterisation. Full article

In this study, determination of the inorganic and organic forms of tin in waters of different salinities is considered. The possibility of the separation of speciations of tin using liquid–liquid extraction (LLE); precipitation with fluorides, iodides, ammonia, and iron (III) chloride; and sorption of organotin compounds (OTCs) was studied. The LLE and analyte precipitation methods proved to be ineffective. Inorganic and organic forms of tin were separated by the sorption of OTCs using silica gel sorbent Diapak C18. Under optimized conditions, a technique for the separate determination of the forms of tin in natural waters was developed. The technique combines hydride generation and microwave mineralization of solutions followed by ICP spectrometry. The inorganic forms of tin were determined after their solid-phase separation from organotin compounds. The lower limits of analyte quantification were 0.03 μg/L (ICP-MS) and 0.05 μg/L (ICP-OES), which provide separate determinations of inorganic and organic forms of tin in waters with different salinities. The content of OTCs in water was determined by subtracting the inorganic concentration from the total concentration of tin. The technique will allow a comprehensive assessment of the toxicological impact of tin speciations on the aquatic ecosystem. Full article

This paper considers the features of determining the total tin content in waters with different salinity. Direct ICP-spectrometric analysis of sea waters with a salinity of more than 6‰ significantly reduced the analytical signal of tin by 70% (ICP-MS) and 30% (ICP-OES). The matrix effect of macrocomponents was eliminated by generating hydrides using 0.50 M sodium borohydride and 0.10 M hydrochloric acid. The effect of transition metals on the formation of tin hydrides was eliminated by applying L-cysteine at a concentration of 0.75 g/L. The total analyte concentrations, considering the content of organotin compounds, were determined after microwave digestion of sample with oxidizing mixtures based on nitric acid. The generation of hydrides with the ICP-spectrometric determination of tin leveled the influence of the sea water matrix and reduced its detection limit from 0.50 up to 0.05 µg/L for all digestion schemes. The developed analysis scheme made it possible to determine the total content of inorganic and organic forms of tin in sea waters. The total content of tin was determined in the waters of the Azov and Black seas at the levels of 0.17 and 0.24 µg/L, respectively. Full article

Organotin (IV) dithiocarbamate has recently received attention as a therapeutic agent among organotin (IV) compounds. The individual properties of the organotin (IV) and dithiocarbamate moieties in the hybrid complex form a synergy of action that stimulates increased biological activity. Organotin (IV) components have been shown to play a crucial role in cytotoxicity. The biological effects of organotin compounds are believed to be influenced by the number of Sn-C bonds and the number and nature of alkyl or aryl substituents within the organotin structure. Ligands target and react with molecules while preventing unwanted changes in the biomolecules. Organotin (IV) dithiocarbamate compounds have also been shown to have a broad range of cellular, biochemical, and molecular effects, with their toxicity largely determined by their structure. Continuing the investigation of the cytotoxicity of organotin (IV) dithiocarbamates, this mini-review delves into the appropriate method for synthesis and discusses the elemental and spectroscopic analyses and potential cytotoxic effects of these compounds from articles published since 2010. Full article

Black spot disease or Alternaria black spot (ABS) of pecan (Carya illinoinensis) in South Africa is caused by Alternaria alternata. This fungal pathogen impedes the development of pecan trees and leads to low yield in pecan nut production. The present study investigated the in vitro effect of six fungicides against the mycelial growth of A. alternata isolates from ABS symptoms. Fungicides tested include Tilt (propiconazole), Ortiva (azoxystrobin), AgTin (fentin hydroxide), and Bellis (boscalid + pyraclostrobin). All fungicides were applied in 3 concentrations (0.2, 1, and 5 μg mL⁻¹). Tilt and Bumper 250 EC containing propiconazole active ingredient (demethylation Inhibitors) were the most effective and inhibited all mycelial growth from up to 6 days post-incubation. The other active ingredients (succinate dehydrogenase inhibitors, organotin compounds, and quinone outside inhibitors) showed 75–85% mycelial growth inhibition. The effective concentration to inhibit mycelial growth by 50% (EC₅₀) was estimated for each isolate and fungicide. The overall mean EC₅₀ values for each fungicide on the six isolates were 1.90 μg mL⁻¹ (Tilt), 1.86 μg mL⁻¹ (Ortiva), 1.53 μg mL⁻¹ (AgTin), and 1.57 μg mL⁻¹ for (Bellis). This initial screening suggested that propiconazole fungicide was the most effective for future field trials test and how these fungicides could be used in controlling ABS disease. Full article