Search Results (793)

Tetrabromobisphenol A (TBBPA), a widely utilised brominated flame retardant, demonstrates toxicological effects in aquatic organisms. Tea polyphenols (TPs), natural compounds found in tea leaves, exhibit both antioxidant and anti-inflammatory activities. The kidney is one of the major metabolic organs in common carp and serves as a target organ for toxic substances. This study evaluated the therapeutic potential of TPs in mitigating TBBPA-induced nephrotoxicity in common carp. Common carp were exposed to 0.5 mg/L TBBPA in water and/or fed a diet supplemented with 1 g/kg TPs for 14 days. In vitro, primary renal cells were treated with 60 μM TBBPA and/or 2.5 μg/L TPs for 24 h. Methods included histopathology, TUNEL assay for apoptosis, ROS detection, and molecular analyses. Antioxidant enzymes (SOD, CAT) and inflammatory cytokines (IL-1β, IL-6, TNF-α) were quantified using ELISA kits. Results showed that TBBPA induced oxidative stress, and activated the ROS-PI3K/AKT-NF-κB pathway, thereby resulting in inflammatory responses. TBBPA upregulated apoptosis-related genes (Caspase-3, Bax, and Bcl-2) and induced apoptosis. TBBPA upregulated the expression of RIPK3/MLKL, thereby exacerbating necroptosis. TPs intervention significantly mitigated these effects by reducing ROS, suppressing NF-κB activation, and restoring antioxidant enzyme activities (SOD, CAT). Moreover, TPs attenuated apoptosis and necrosis in the carp kidney, thereby enhancing the survival ability and immunity of common carp. Full article

Aqueous redox flow batteries (ARFBs) have attracted significant attention in the field of electrochemical energy storage due to their high intrinsic safety, low cost, and flexible system configuration. However, the advancement of this technology is still hindered by several critical challenges, including capacity decay, structural optimization, and the design and application of key materials as well as their performance within battery systems. Addressing these issues requires systematic theoretical foundations and scientific guidance. Numerical modeling has emerged as a powerful tool for investigating the complex physical and electrochemical processes within flow batteries across multiple spatial and temporal scales. It also enables predictive performance analysis and cost-effective optimization at both the component and system levels, thus accelerating research and development. This review provides a comprehensive overview of recent progress in the modeling of ARFBs. Taking the all-vanadium redox flow battery as a representative example, we summarize the key multiphysics phenomena involved and introduce corresponding multi-scale modeling strategies. Furthermore, specific modeling considerations are discussed for phase-change ARFBs, such as zinc-based ones involving solid–liquid phase transition, and hydrogen–bromine systems characterized by gas–liquid two-phase flow, highlighting their distinctive features compared to vanadium systems. Finally, this paper explores the major challenges and potential opportunities in the modeling of representative ARFB systems, aiming to provide theoretical guidance and technical support for the continued development and practical application of ARFB technology. Full article

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant widely used in consumer products. TBBPA is often detected in soil, water, organisms, and even in human blood and breast milk. Hence, it is accessible to developing fetuses and nursing offspring after maternal exposure. The reported evidence for the endocrine disruption of TBBPA in the brain has raised concerns regarding its effects on neurodevelopmental and behavioral functions. This study investigated the effects of TBBPA exposure on neurodevelopment. A cell-based developmental neurotoxicity assay was performed to determine whether TBBPA is a developmental neurotoxicant. The assay revealed TBBPA to be a developmental neurotoxicant. C57BL/6N maternal mice were administered TBBPA at 0, 0.24, and 2.4 mg/kg during pregnancy and lactation, and their offspring underwent behavioral testing. The behavioral experiments revealed sex-specific effects. In females, only a deterioration of the motor ability was observed. In contrast, deteriorations in motor function, memory, and social interaction were noted in males. Furthermore, we validated changes in the expression of genes associated with behavioral abnormalities, confirming that perinatal exposure to TBBPA, at the administered doses, can affect neurodevelopment and behavior in offspring. These findings highlight the need for more in-depth and multifaceted research on the toxicity of TBBPA. Full article

The synthesis of cannabigerol—a cannabinoid with significant pharmaceutical potential—is described. The synthesis involves four stages. In the first step, (E)-non-3-en-2-one reacts with dimethyl malonate to yield a cyclic enone, which is subsequently oxidized with bromine to produce the olivetol ester. This ester then undergoes an alumina-catalyzed coupling reaction with geraniol, followed by ester hydrolysis to obtain cannabigerol. By modifying the chain length of the enone in the initial step and employing allylic alcohols other than geraniol, a range of cannabigerol derivatives can be synthesized, including the natural product cannabigerovarin. Full article

The efficient synthetic routes and evaluates cytotoxic profiles of denitroaristolochic acids II–V (DAA-II–V) were demonstrated in this study. Based on retrosynthetic analysis, a modular synthetic strategy was developed through Suzuki–Miyaura coupling, Wittig reaction, and bismuth triflate-catalyzed intramolecular Friedel–Crafts cyclization to efficiently construct the phenanthrene core. Process optimization significantly improved yields: aryl bromide intermediate A reached 50.8% yield via bromination refinement, while arylboronic ester intermediate B overcame selectivity limitations. Combining Darzens condensation with Wittig reaction enhanced throughput, achieving 88.4% yield in the key cyclization. Structures were confirmed by NMR and mass spectra. CCK-8 cytotoxicity assays in human renal proximal tubular epithelial cells revealed distinct toxicological profiles: DAA-III and DAA-IV exhibited IC₅₀ values of 371 μM and 515 μM, respectively, significantly higher than the nitro-containing prototype AA-I (270 μM), indicating that the absence of nitro group attenuates but does not eliminate toxicity, potentially via altered metabolic activation. DAA-II and DAA-V showed no detectable cytotoxicity within assay limits, suggesting reduced toxicological impact. Structure–activity analysis exhibited that the nitro group is not essential for cytotoxicity, with methoxy substituents exerting limited influence on potency. This challenges the conventional DNA adduct-dependent toxicity paradigm, implying alternative mechanisms like oxidative stress or mitochondrial dysfunction may mediate damage in denitro derivatives. These systematic findings provide new perspectives for AA analog research and a foundation for the rational use and safety assessment of Aristolochiaceae plants. Full article

Axially chiral compounds play a pivotal role in organic synthesis, materials science, and pharmaceutical development. Among the various strategies for their construction, enantioselective iodination and bromination have emerged as powerful and versatile approaches, enabling the introduction of halogen functionalities that serve as valuable synthetic handles for further transformations. This review highlights recent advances in atroposelective iodination and bromination, with a particular focus on the synthesis of axially chiral biaryl and heterobiaryl frameworks. Key catalytic systems are discussed, including transition metal complexes, small-molecule organocatalysts, and high-valent metal catalysts in combination with chiral ligands or transient directing groups. Representative case studies are presented to elucidate mechanistic pathways, stereochemical induction models, and synthetic applications. Despite notable progress, challenges remain, such as expanding substrate scope, improving atom economy, and achieving high levels of regio- and stereocontrol in complex molecular settings. This review aims to provide a comprehensive overview of these halogenation strategies and offers insights to guide future research in the atroposelective synthesis of axially chiral molecules. Full article

The pyrrolo[2,3-d]pyrimidine (7-deazapurine) scaffold is a unique heterocyclic system included in the composition of most nucleotides. In this study, series of the pyrrolo[2,3-d]pyrimidine-imines and 3-halo-substituted pyrrolo[2,3-d]pyrimidines were designed and prepared in high yields. Condensed pyrimidines are obtained via carbonyl-amine condensation and carbon-halogen bond formation. Pyrrolo[2,3-d]pyrimidine-imines containing a bromine substituent at position C-4 of the phenyl ring and azepine side-ring exhibited superior antitumor activity on the colon cancer HT-29 cell line; IC₅₀ values were 4.55 and 4.01 µM, respectively. These results revealed an interesting pattern, where condensed pyrimidinones containing an azepine ring demonstrated selective antitumor activity on the colon cancer cell line HT-29. In addition, the molecular docking results suggest that compound 8g provided a thorough understanding of its interactions with the DDR2 active site. This could pave the way for further development and optimization of DDR-targeting drugs, contributing to advancements in cancer therapeutics. This lead compound may serve as design templates for further studies. Full article

Background: Hydroxyl and amino compounds play a significant role in defining the flavor and quality of sauce-flavor Baijiu, yet their comprehensive analysis remains challenging due to limitations in detection sensitivity. In this study, we developed a novel bromine isotope labeling approach combined with ultra-high performance liquid chromatography–high-resolution mass spectrometry (UHPLC-HRMS) to achieve high-coverage profiling of these compounds in sauce-flavor Baijiu. Methods: The method employs 5-bromonicotinoyl chloride (BrNC) for rapid (30 s) and mild (room temperature) labeling of hydroxyl and amino functional groups, utilizing bromine’s natural isotopic pattern (Δm/z = 1.998 Da) for efficient screening. Annotation was performed hierarchically at five confidence levels by integrating retention time, accurate mass, and MS/MS spectra. Results: A total of 309 hydroxyl and amino compounds, including flavor substances (e.g., tyrosol and phenethyl alcohol) and bioactive compounds (e.g., 3-phenyllactic acid), were identified in sauce-flavor Baijiu. The method exhibited excellent analytical performance, with wide linearity (1–4 orders of magnitude), precision (RSD < 18.3%), and stability (RSD < 15% over 48 h). When applied to sauce-flavor Baijiu samples of different grades, distinct compositional patterns were observed: premium-grade products showed greater metabolite diversity and higher contents of bioactive compounds, whereas lower-grade samples exhibited elevated concentrations of acidic flavor compounds. Conclusions: These results demonstrate that the established method is efficient for the comprehensive analysis of hydroxyl and amino compounds in complex food matrices. The findings provide valuable insights for quality control and flavor modulation in sauce-flavor Baijiu production. Full article

Skin aging is mainly caused by external factors like sunlight, which triggers oxidative stress and chronic inflammation. Natural halogenated flavonoids have demonstrated anti-inflammatory properties. Inspired by the macroalgae-derived bromophenol BDDE, we investigated the anti-inflammatory potential of structure-related chalcones (1–7). Chalcones 1 and 7 showed the least cytotoxicity in keratinocyte and macrophage cells. Chalcones 1, 2, 4, and 5 exhibited the most significant anti-inflammatory effects in murine macrophages after lipopolysaccharide stimulation, with chalcone 1 having the lowest IC₅₀ value (≈0.58 μM). A SNAP assay confirmed that chalcones do not exert their effects through direct NO scavenging. Symmetrical bromine atoms and 3,4-dimethoxy groups on both aromatic rings improved the anti-inflammatory activity, indicating a relevant structure–activity relationship. Chalcones 1 and 2 were selected for study to clarify their mechanisms of action. At a concentration of 7.5 μM, chalcone 2 demonstrated a rapid and effective inhibitory action on the protein levels of inducible nitric oxide synthase (iNOS), while chalcone 1 exhibited a gradual inhibitory action. Moreover, chalcone 1 effectively activated the nuclear factor erythroid 2-related factor 2 (Nrf2) pathway with around a 3.5-fold increase at the end of 24 h at 7.5 μM, highlighting its potential as a modulator of oxidative stress responses. These findings place chalcone 1 as a promising candidate for skincare products targeting inflammation and skin aging. Full article

A recent high-throughput screening of the NatureBank marine extract library (7616 samples) identified an extract from the Australian marine sponge Agelas axifera with in vitro activity against an economically important parasitic nematode, Haemonchus contortus (barber’s pole worm). The bioassay-guided fractionation of the CH₂Cl₂/MeOH extract from A. axifera led to the purification of a new diterpene alkaloid, agelasine Z (1), together with two known compounds agelasine B (2) and oxoagelasine B (3). Brominated compounds (–)-mukanadin C (4) and 4-bromopyrrole-2-carboxylic acid (5) were also isolated from neighbouring UV-active fractions. All compounds, together with agelasine D (6) from NatureBank’s pure compound library, were tested for in vitro anthelmintic activity against exsheathed third-stage (xL3s) and fourth-stage larvae (L4s) of H. contortus and young adult Caenorhabditis elegans. Compounds 1, 2 and 6 induced an abnormal “skinny” phenotype, while compounds 2 and 6 also reduced the motility of H. contortus L4s by 50.5% and 51.8% at 100 µM, respectively. The minimal activity of agelasines against C. elegans young adults suggests a possible species-specific mechanism warranting further investigation. For the first time, the unexpected lability of agelasine H-8′ was explored using kinetic studies, revealing rapid deuterium exchange in MeOH-d₄ at room temperature. Full article

In 1906, Charles T. Currelly participated in excavations at Deir el-Bahri, Egypt, recovering votive offerings from the Temple of Hathor (Dynasty XVIII, reign of Hatshepsut, 1479–1458 BCE). These objects became part of the founding collection of the Royal Ontario Museum, where Currelly served as the first director. Among the offerings are several paintings on linen cloth. During examination of one painted textile, a border fringe with cream (suspected undyed), yellow and blue looped threads was sampled and analysed for dyes using gas chromatography–mass spectrometry. The yellow threads were found to contain a tannin-rich dyestuff, likely derived from Rhus spp., a common dye in ancient Egypt. Unexpectedly, the blue threads yielded brominated-indigoid marker compounds, indicating the use of a Murex-derived dye. While purple shellfish dye is rare due to the high cost of its complex production, blue shellfish dye is even more exceptional and has only been identified a handful of times on archaeological textiles. Calculated values of di-brominated to mono-brominated indigoid compounds suggests the dye originated from an indigotin-rich type of Hexaplex trunculus snail, a Mediterranean species. This finding represents a rare example of blue shellfish dye use in ancient Egypt and provides new insights into the dyeing technologies of Dynasty XVIII and the importance of this sky-blue colour in the worship of the goddess Hathor. Full article

In this study, we investigate the influence of the halogen elements bromine (Br) and chlorine (Cl) on iodine defect properties primarily in FAPbI₃ through first-principles calculations, aiming to understand the effect of high defect densities on the efficiency of organic–inorganic hybrid perovskite cells. The results indicate that Br and Cl interstitials minimally alter the overall band structure of FAPbI₃ but significantly modify the defect energy levels. Br and Cl interstitials, with defect states closer to the valence band and lower formation energies, effectively convert deep-level traps induced by iodine interstitials (I_i) into shallow-level traps. This conversion enhances carrier transport by reducing non-radiative recombination while preserving light absorption efficiency. Excess Br/Cl co-doping in FAPbI₃ synthesis thereby suppresses non-radiative recombination and mitigates the detrimental effects of iodide-related defects. Full article

Background/Objectives: Diabetes mellitus is a group of chronic metabolic disorders characterized by persistent hyperglycemia. Aldose reductase, the first enzyme in the polyol pathway, plays a key role in the onset of long-term diabetic complications. Aldose reductase inhibition has been widely established as a potential pharmacotherapeutic approach to prevent and treat diabetes mellitus-related comorbidities. Although several promising aldose reductase inhibitors have been developed over the past few decades, they have failed in clinical trials due to unacceptable pharmacokinetic properties and severe side effects. This paper describes the design, synthesis, and pharmacological evaluation of four novel 5-halogenated N-indolylsulfonyl-2-fluorophenol derivatives (3a-d) as aldose reductase inhibitors. Methods: The design of compounds was based on a previously published lead compound (IIc) developed by our research group to enhance its inhibitory capacity. Compounds 3a-d were screened for their ability to inhibit in vitro partially purified aldose reductase from rat lenses, and their binding modes were investigated through molecular docking. Results: The presence of a sulfonyl linker between indole and o-fluorophenol aromatic rings is mandatory for potent aldose reductase inhibition. The 5-substitution of the indole core with halogens resulted in a slight decrease in the inhibitory power of 3a-c compared to IIc. Among halogens, bromine was the most capable of filling the selectivity pocket through hydrophobic interactions with Thr113 and Phe115 residues. Conclusions: Although our strategy to optimize the inhibitory potency of IIc via inserting halogen atoms in the indole scaffold was not fruitful, aromatic ring halogenation can be still utilized as a promising approach for designing more potent aldose reductase inhibitors. Full article

The novel benzanthrone derivative, 2-bromo-3-aminobenzo[de]anthracene-7-one (2-Br-3-NH₂BA), was synthesized and extensively characterized to investigate its photophysical behavior in various solvents. It was prepared through selective bromination of 3-aminobenzanthrone using N-bromosuccinimide in dimethylformamide at −20 °C. Featuring a donor–π–acceptor (D–π–A) structure, 2-Br-3-NH₂BA exhibits pronounced solvatochromism due to the intramolecular charge transfer (ICT) between the amino donor and the carbonyl acceptor groups. Optical measurements conducted in eight solvents of varying polarity revealed a significant bathochromic shift in both absorption and fluorescence emission, with emission maxima red-shifting by over 110 nm from non-polar to polar environments. Corresponding reductions in the optical band gap energies, as calculated from Tauc plots, further support solvent-induced electronic state modulation. Additionally, quantum yield analysis showed higher fluorescence efficiency in non-polar solvents, while polar solvents induced twisted intramolecular charge transfer (TICT), leading to emission quenching. These findings demonstrate the sensitivity of 2-Br-3-NH₂BA to environmental polarity, making it a promising candidate for color-tunable luminescent applications in optoelectronics and sensing. However, further studies in the solid state are required to validate its applicability in device architectures such as OLEDs. Full article

Information about the trace elements content of goose carcass parts with or without skin can be important for consumers when making dietary choices. This study aimed to (1) determine the effects of popular heat processing techniques on the content of chromium (Cr), iodine (I), manganese (Mn), and bromine (Br) in goose breast muscle, and (2) estimate the extent to which 100 g of goose meat—both with and without skin—cover the Nutrient Reference Values (NRV) for Cr, I, Mn, and the Tolerable Daily Intake (TDI) for Br in adults. The heat processing techniques used in the study were water bath cooking (WBC), Oven Convection Roasting (OCR), grilling (G), and pan frying (PF). Grilled goose breast without skin had the highest Br retention (97.4%) and TDI (2.41%). Cooked goose breast (WBC) with skin exhibited the highest retention of Cr (73.8%) and I (73.6%). The highest Mn content was found in meat without skin after OCR processing and grilled meat with skin (0.170 and 0.191 mg/100 g, respectively). The iodine content in the meat decreased (from 0.020 raw to 0.003 mg/100 g after PF) with each heat treatment. The results of our study may provide helpful information for consumers when making dietary choices and using heat treatment techniques. Goose breast muscles, depending on heat treatment and the presence of skin, provide trace elements in the range of 2.21% of NRV (Nutrient Reference Value) for Br without skin to 740.7% of NRV for Cr with skin and may be a valuable component of a varied diet (apart from iodine). The Br content in the meat decreases after WBC treatment (1.29 without skin or 1.43 with skin mg/100 g). For this reason, it seems to be the most beneficial for the consumer’s health because it minimizes the risk of exceeding the TDI value. Total hazard quotients (THQ) in meat (regardless of the treatment and skin presence) for Cr, Mn, and Br contents were <1, indicating a low risk to Polish consumer health. Full article