Search Results (149)

In this study, a series of novel β-phenylalanine derivatives were synthesised and evaluated for their anticancer activity. The 3-(4-methylbenzene-1-sulfonamido)-3-phenylpropanoic acid (2) was prepared using β-phenylalanine as a core scaffold. The β-amino acid derivative 2 was converted to the corresponding hydrazide 4, which enabled the development of structurally diverse heterocyclic derivatives including pyrrole 5, pyrazole 6, thiadiazole 8, oxadiazole 11, triazoles 9 and 12 with Schiff base analogues 13 and series1,2,4-triazolo [3,4-b][1,3,4]thiadiazines 14. These modifications were designed to enhance chemical stability, solubility, and biological activity. All compounds were initially screened for cytotoxicity against the A549 human lung adenocarcinoma cell line, identifying N-[3-(3,5-dimethyl-1H-pyrazol-1-yl)-3-oxo-1-phenylpropyl]-4-methylbenzenesulfonamide (5) and (E)-N-{2-[4-[(4-chlorobenzylidene)amino]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]-1-phenylethyl}-4-methylbenzenesulfonamide (13b) as the most active. The two lead candidates were further evaluated in H69 and H69AR small cell lung cancer lines to assess activity in drug-sensitive and multidrug-resistant models. Schiff base 13b containing a 4-chlorophenyl moiety, retained potent antiproliferative activity in both H69 and H69AR cells, comparable to cisplatin, while compound 5 lost efficacy in the resistant phenotype. These findings suggest Schiff base derivative 13b may overcome drug resistance mechanisms, a limitation commonly encountered with standard chemotherapeutics such as doxorubicin. These results demonstrate the potential role of β-phenylalanine derivatives, azole-containing sulphonamides, as promising scaffolds for the development of novel anticancer agents, particularly in the context of lung cancer and drug-resistant tumours. Full article

The efficient recovery of rhenium (Re), a critical metal in high-tech industries, is essential to address its growing demand and reduce reliance on primary mining. In this study, we developed novel anion-exchange resins for the selective adsorption and recovery of Re(VII) ions from acidic solutions, simulating industrial by-products. The resins were synthesized from a vinylbenzyl chloride-co-divinylbenzene copolymer modified with aliphatic, heterocyclic, and aromatic weakly basic amines, selected from among bis(3-aminopropyl)amine (BAPA), 1-(2-pyrimidinyl)piperazine (PIP), thiosemicarbazide (TSC), 2-amino-3-hydroxypyridine (AHP), 1-(2-hydroxyethyl)piperazine (HEP), 4-amino-2,6-dihydroxypyrimidine (AHPI), and 2-thiazolamine (TA). The adsorption of Re on BAPA, PIP, and HEP resins obeyed the Langmuir model, and the resins exhibited high adsorption capacities, with maximum values reaching 435.4 mg Re g⁻¹ at pH 6. Furthermore, strong selectivity for ReO₄⁻ ions over competing species, including Mo, Cu, and V, was noted in solutions simulating the leachates of the by-products of Cu-Mo ores. Additionally, complete elution of Re was possible. The developed resins turned out to be highly suitable for the continuous-flow-mode adsorption of ReO₄⁻, revealing outstanding adsorption capacities before reaching column breakthrough. In this context, the novel anion-exchange resins developed offer a reference for further Re recovery strategies. Full article

This study integrated non-targeted metabolomics and transcriptomics to investigate dynamic changes in Antheraea pernyi pupae across five developmental stages. Metabolomic analysis identified 1246 metabolites, primarily organic acids, lipids, heterocyclic compounds, and oxygen-containing organics. Principal component analysis revealed stage-specific metabolic profiles: amino acid derivatives (pyruvate, proline, lysine) declined, while pyrimidines (cytidine, uridine, β-alanine) and monosaccharides (glucose, mannose) increased. 18β-glycyrrhetinic and ursolic acids accumulated significantly in the middle and late stages. Transcriptomic analysis identified 7230 differentially expressed genes (DEGs), with 366, 1705, and 5159 significantly differentially expressed genes in the T1, T3, and T5 comparison groups, respectively. KEGG enrichment highlighted ABC transporters, amino acid/pyrimidine metabolism, and tyrosine pathways as developmentally critical, with aminoacyl-tRNA biosynthesis upregulated in later phases. Integrated multi-omics analysis revealed coordinated shifts in metabolites and genes across developmental phases, reflecting dynamic nutrient remodeling during pupal maturation. This study systematically delineates the molecular transitions driving pupal development in Antheraea pernyi pupae, uncovering conserved pathway interactions and mechanistic insights into nutrient metabolism. These findings provide a scientific foundation for leveraging pupal resources in functional food innovation and bioactive compound discovery for pharmaceutical applications. Full article

In recent years, amino-gem-bisphosphonic acids and their esters have been considered a family of compounds of great chemical and pharmacological interest due to their important biological properties and their value as key synthons in the synthesis of more complex molecules with biological interest. This explains why several research groups are interested in developing new methods for the preparation of these compounds. Therefore, we would like to report here a summary of the synthetic strategies published in the last fifteen years for the synthesis of acyclic and heterocyclic α-, β- and γ-amino-gem-bisphosphonates, as well as their application in the preparation of selected compounds of chemical and pharmacological interest. This information can be of general knowledge to researchers working in this area, as it provides the starting point for new methods and applications of these compounds. Full article

The tea tree root system is an important tissue for nutrient uptake, accumulation, and transport, and pH is an important environmental factor regulating the growth of tea tree (Camellia sinensis). However, the physiological and molecular mechanisms of how the tea tree root system responds to pH are unclear. In this study, Tieguanyin tea tree was used as the research object, and treated with different pH values to determine the morphological indexes of the tea plant root system and systematically study the physiological and molecular mechanisms of the effect of pH on the growth of the tea plant root system using transcriptomics in combination with metabolomics. The results showed that total root length, root surface area, root volume, total root tips, root fork number, and root crossing number of root crosses of the tea plant root system increased significantly (p < 0.05) with increasing pH. Transcriptome analysis showed that a total of 2654 characteristic genes were obtained in response to pH regulation in the root system of the tea plant, which were mainly enriched in six metabolic pathways. Metabolomics analysis showed that the metabolites with the highest contribution in differentiating tea plant responses to different pH regulations were mainly heterocyclic compounds, amino acids and derivatives, alkaloids, and flavonoids. Interaction network analysis showed that pH positively regulated the metabolic intensity of the MAPK signaling pathway (plant, plant hormone signal transduction, and RNA degradation pathway), positively regulated the content of the heterocyclic compound, amino acids and derivatives, and alkaloids, and positively regulated tea plant root growth. However, it negatively regulated ribosome, protein processing in the endoplasmic reticulum, and phenylpropanoid biosynthesis pathway intensity, and negatively regulated the flavonoid content. This study reveals the physiological and molecular mechanisms of the tea plant root system in response to pH changes and provides an important theoretical basis for the cultivation and management of tea plants in acidified tea plantations. Full article

Kujingcha (KJC) is a widely consumed substitute tea due to its unique flavor quality and health benefits. However, the biochemical basis for the formation of KJC’s unique flavor quality and health benefits remain unclear. In this study, using Camellia sinensis green tea and its processed fresh leaves as a control, we systematically analyzed the non-volatile and volatile components in KJC and its processed fresh leaves. The results indicate that high levels of flavonoids and water-soluble sugars, and low levels of amino acids and water-soluble proteins, are important biochemical foundations for the formation of taste quality in KJC. High aldehyde, alkene and heterocyclics contents contribute significantly to the aroma of KJC, among which heterocyclics are the key components for the formation of KJC’s rich pan-fried bean-like aroma. Flavonoids such as neohesperidin, hyperoside, rutin, astilbin and morin are important components for the formation of KJC’s health benefits. Full article

The Maillard reaction is a complex chemical reaction that occurs between nucleophilic groups, such as thiolates or amino groups primarily from amino acids, peptides, proteins, and carbonyl groups, particularly from reducing sugars. The pH value of the medium is a key parameter controlling the kinetics of the Maillard reaction, as it influences the concentration of nucleophilic groups. Other specific conditions of reaction medium such as temperature, reaction time (or residence time in a process), and water activity also significantly influence the Maillard reaction. Understanding the impact of these parameters is essential for optimizing the Maillard reaction to enhance sensory attributes, nutritional qualities, and product stability during the storage and distribution of the final products. The Maillard reaction is responsible for the formation of desirable sensory qualities such as flavor, aroma, color, and texture in cooked and thermally processed foods, in addition to the improvement of nutritional value and shelf life of foods. In contrast, there are limitations in its industrial applications, as it can also generate harmful compounds such as acrylamide, N(6)-carboxymethyllysine, furans, and heterocyclic amines, as well as undesired changes in the nutritional value of the food. This review provides an overview of the Maillard reaction’s mechanism, influencing parameters, pros and cons, as well as some food industrial applications. Full article

Heterocycle cores are widely used in medicinal chemistry for developing bioactive compounds. In this scenario, using cheap and accessible starting material to build these heterocycles is desirable to obtain new drug candidates for cost-efficient processes. One easily accessible source of starting material are amino acids. Usually, these compounds are employed in peptide synthesis, but their use for building heterocycle frameworks presents another appealing opportunity. Therefore, this review highlights the application of histidine and tryptophan, two heteroaromatic amino acids, in fused heterocyclic scaffold synthesis and their use in bioactive compounds. Full article

The alarming increase in antimicrobial resistance has intensified the search for novel therapeutic agents capable of combating resistant microbial strains. Copper complexes have emerged as promising antimicrobial agents due to their intrinsic redox activity, ability to disrupt microbial membranes, and interactions with vital biomolecules such as DNA and proteins. This review critically evaluates the antimicrobial potential of copper complexes reported between 2018 and 2025, emphasizing their structural diversity, mechanisms of action, and biological performance against a wide range of bacterial and fungal pathogens. Key findings reveal that Schiff base copper complexes, amino acid derivatives, heterocyclic ligands, and mixed-ligand systems exhibit potent antimicrobial activities, often surpassing standard antibiotics. Mechanistically, copper complexes induce reactive oxygen species (ROS) generation, inhibit enzyme function, cause DNA cleavage, and compromise cell membrane integrity. Furthermore, structure–activity relationship (SAR) analyses indicate that ligand type, coordination geometry, and lipophilicity significantly influence antimicrobial efficacy. Overall, the reviewed studies support the development of copper-based compounds as viable candidates for antimicrobial drug development. This review also identifies current challenges and gaps in knowledge, such as limited in vivo studies and toxicity assessments, which must be addressed to advance these compounds toward clinical application. Full article

The transforming growth factor-β (TGF-β) signaling pathway is involved in various cellular functions, including immunological response, extracellular matrix formation, differentiation, growth and development, and cell cycle regulation. The TGF β receptor type 1 (TGF-βR1) has emerged as a key component of this pathway, exhibiting significant overexpression in diverse malignancies, including hepatocellular carcinoma, gastric cancer, breast cancer, and colon cancer. Multiple therapeutic targets have been identified for the TGF-β signaling pathway, encompassing antibodies, ligand traps, vaccines, antisense oligonucleotides, and small-molecule TGF-βR1 kinase inhibitors. This review delineates the structural and functional characteristics of the small-molecule TGF-βR1 kinase inhibitors. The inhibitors discussed herein are categorized based on shared pharmacophoric features, notably a five-membered heterocyclic ring linked to three distinct features (R1, R2, and R3). These features interact with amino acids within the selectivity pocket, hinge region, or solvent-exposed area, respectively. These insights contribute to a clearer understanding of the structural requirements for selective TGF-βR1 inhibition. The presented findings in this review article offer a valuable foundation for future drug discovery efforts targeting the TGF-β signaling pathway. Full article

Hongqujiu, one of the three principal varieties of yellow wine, is a traditional fermented beverage originating from China that employs Hongqu as the fermentation agent. In this study, an untargeted metabolomics approach based on gas chromatography–mass spectrometry (GC-MS) and liquid chromatography–mass spectrometry (LC-MS) was applied to systematically analyze the volatile compounds (VOCs) and non-volatile compounds (NVCs) in Hongqujiu across different aging years for the first time. The analysis identified a total of 262 VOCs and 2564 NVCs in samples of Hongqujiu aged for six distinct years. Based on metabolic differences, the samples were categorized into two groups: the low-year group (5-year, 6-year) and the high-year group (8-year, 10-year, 15-year, 20-year). Nineteen VOCs (e.g., 4-amino-butyric acid and diethanolamine) and thirty NVCs (e.g., palmitoylethanolamide and erinacine D) were identified as key differential metabolites distinguishing the low-year group from the high-year group. The higher-year group is enriched with a variety of substances with different flavors or biological activities, such as sugar derivatives, amino acids and their complexes, organic acids and their intermediate metabolites, steroids and terpenoid compounds, lipids and their derivatives, nitrogen-containing heterocycles, and aromatic compounds. The accumulation of these substances not only shapes the unique and rich flavor characteristics of aged red rice wine (such as the caramel aroma and umami peptide flavor), but also endows red rice wine with potential health benefits due to the physiological regulatory functions of some active ingredients. This study contributes to a deeper understanding of the composition and dynamic variations in metabolites in Hongqujiu, offering a scientific foundation for identifying aged Hongqujiu and conducting further research to enhance its quality. Full article

Heterocyclic aromatic amines (HAAs), known for their mutagenic and carcinogenic potential, are formed during the heating of protein-rich food items. Detecting HAAs swiftly and accurately poses challenges due to complex food matrices and low HAA concentrations. In this study, a simple and efficient magnetic solid-phase extraction (MSPE) strategy was developed for the simultaneous isolation and enrichment of three HAAs such as 2-amino-3,4,8-trimethylimidazo [4,5-f]quinoxaline (4,8-DiMeIQx), 2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline (MeIQx), and 2-amino-3-methylimidazo [4,5-f]quinoline (IQ) in processed meats, employing the magnetic covalent organic framework Fe₃O₄@MOF-545-AMSA as an adsorbent. It was synthesized via a solvothermal method, with Fe₃O₄ as the magnetic core. Its building blocks are as follows: zirconium (Zr) as the coordination metal ion, tetrakis(4-carboxyphenyl)porphyrin and benzoic acid as organic ligands, and aminomethanesulfonic acid (AMSA). This composite captures targeted HAAs efficiently by exploiting the unique porous MOF-545-AMSA structure, specific metal–ligand coordination, and AMSA’s amino and sulfonic acid groups. The quantification of HAAs was achieved through the combination of Ultra-Performance Liquid Chromatography–Tandem Mass Spectrometry (UPLC-MS/MS) and MSPE, demonstrating satisfactory linearity (R² ≥ 0.9917), high recovery rates (83.7–111.0%), and low detection limits (0.1–1.0 μg/kg). Moreover, an automated high-throughput detection system was developed using MSPE to assess the presence of HAAs in meat products. Full article

γ-amino butyric acid (GABA) is an inhibitory neurotransmitter whose deficiency has been associated with various neurological disorders. However, its low liposolubility limits its use as a supplement. Thus, multiple investigations have focused on searching for lipophilic GABA analogs that can modulate the activity of the GABA_B receptor, which could be associated with the etiology of some central nervous system disorders. The GABA analogs available on the market are Vigabatrin, Gabapentin as well as Pregabalin and Baclofen. In this work, we report on the synthesis of GABA analogs, taking the scaffold of GABA, Pregabalin, and Baclofen as a starting point. The analogs include structural features that could favor the affinity of the molecules for the GABA_B receptor, such as heterocyclic rings in the γ-position and alkyl or p-Cl-phenyl substituents (in analogy to Pregabalin and Baclofen, respectively). These analogs were synthesized by a sequence of reactions involving an N-alkylation, a 1,4-conjugated addition of dialkyl and diarylcuprates and a basic hydrolysis. Furthermore, a computational molecular docking over the GABA_B receptor was performed to evaluate the interaction of each compound in the Baclofen binding site. With this information, we evaluated our compounds as GABA_B agonists through a QSAR analysis. Finally, by means of molecular similarity analysis, and in silico ADME prediction, we support our three best compounds (8a–b, 8d) as potential GABA_B receptor agonists. Full article

Background/Objectives: Acridine, an aromatic heterocyclic compound, serves as a basis for the synthesis of potent bioactive derivatives, displaying a broad spectrum of biological activity, such as antibacterial, antitumor, and antiparasitic activity. With the ability to undergo various types of electrophilic substitutions, introducing different side chains could lead to compounds being active towards various and potentially multiple biotargets. Toxoplasma gondii, a ubiquitous protozoan parasite with worldwide distribution, poses a major health threat, particularly in immunocompromised patients and fetuses. Current treatment options for toxoplasmosis are scarce, with notable limitations, especially regarding side myelotoxicity and inactivity towards T. gondii cysts, causing a need for novel drug candidates. The aim of this study was to evaluate selected N-(9-acrydinil) amino acid derivatives as potential anti-T. gondii agents. Methods: Synthesis of new derivatives was performed using a two-step method, with the initial mixing of 9-chloroacridine with methanol and sodium alkoxide solution and subsequent adding of appropriate amino acids. Cytotoxicity of the tested compounds was evaluated on the Vero cell line using a MTT assay, while their anti-T. gondii activity was investigated using T. gondii RH strain tachyzoites. Results: CC₅₀ values of the derivatives ranged from 41.72 to 154.10 µM. Anti-T. gondii activity, displayed as a reduction in the number of viable tachyzoites compared to the untreated control, ranged from 0 to 33.3%. One of the derivatives displayed activity comparable to the standard treatment option while retaining acceptable cytotoxicity. Esterification, presence of aromatic substituents and the length of the amino acid side chain were identified as key factors that affect both toxicity and activity of these derivatives. Conclusions: Promising results obtained throughout this study provide guidelines for further structural modifications of N-(9-acrydinil) amino acid derivatives in order to synthesize drug candidates competitive to standard treatment options for toxoplasmosis. Full article

The present study investigated the dynamics changes in physicochemical properties and non-volatile metabolites during Bulang pickled tea fermentation. A combination of artificial sensory evaluation, chemical-physical analysis, ultra performance liquid chromatography coupled with quadrupole/time-of-flight mass spectrometry (UPLC-QTOF-MS), and multivariate statistical analysis were employed to examine the differences among four fermentation stages of Bulang pickled tea. The bitterness, astringency, sweetness after taste, sourness and fermentation taste tended to increase with fermentation. The highest lactic acid bacteria, aerobic bacteria, total titratable acidity, total soluble sugar, total polyphenols, and total flavonoids were recorded at the second month of fermentation, while fungi, total free amino acids, total antioxidant capacity and hydroxyl free radical scavenging capacity increased with fermentation. Mantel test demonstrated significant associations between lactic acid bacteria /fungal communities and taste characteristics. UPLC-QTOF-MS analysis led to the identification of 35 differential non-volatile metabolites, predominantly comprising heterocyclic compounds, organic acids with their derivatives, and flavonoids. Nine non-volatile metabolites are related to antioxidant activity, and morin, malvidin and 7-methylxanthine exhibit relatively strong antioxidant activity. This study provides comprehensive insights into the non-volatile metabolites and antioxidant function of Bulang pickled tea. Full article