Search Results (170)

The reaction between glycine-type aminonaphthol derivatives substituted with 2- or 1-naphthol and indole or 7-azaindole has been tested. Starting from 2-naphthol as a precursor, the reaction led to the formation of ring-closed products, while in the case of a 1-naphthol-type precursor, the desired biaryl ester was isolated. The synthesis of a bifunctional precursor starting from 5-chloro-8-hydroxyquinoline, morpholine, and ethyl glyoxylate via modified Mannich reaction is reported. The formed Mannich base 10 was subjected to give bioconjugates with indole and 7-azaindole. The effect of the aldehyde component and the amine part of the Mannich base on the synthetic pathway was also investigated. In favor of having a preliminary overview of the structure-activity relationships, the derivatives have been tested on cancer and normal cell lines. In the case of bioconjugate 16, as the most powerful scaffold in the series bearing indole and a 5-chloro-8-hydroxyquinoline skeleton, a potent toxic activity against the resistant Colo320 colon adenocarcinoma cell line was observed. Furthermore, this derivative was selective towards cancer cell lines showing no toxicity on non-tumor fibroblast cells. Full article

Here, we report for the first time on the mechanisms of action of the essential oil of Ruta graveolens (REO) against the plant pathogen Colletotrichum gloeosporioides. In particular, the presence of REO drastically affected the morphology of hyphae by inducing changes in the cytoplasmic membrane, such as depolarization and changes in the fatty acid profile where straight-chain fatty acids (SCFAs) increased by up to 92.1%. In addition, REO induced changes in fungal metabolism and triggered apoptosis-like responses to cell death, such as DNA fragmentation and the accumulation of reactive oxygen species (ROS). The production of essential enzymes involved in fungal metabolism, such as acid phosphatase, β-galactosidase, β-glucosidase, and N-acetyl-β-glucosaminidase, was significantly reduced in the presence of REO. In addition, C. gloeosporioides activated naphthol-As-BI phosphohydrolase as a mechanism of response to REO stress. The data obtained here have shown that the essential oil of Ruta graveolens has a strong antifungal effect on C. gloeosporioides. Therefore, it has the potential to be used as a surface disinfectant and as a viable replacement for fungicides commonly used to treat anthracnose in the postharvest testing phase. Full article

A one-pot [3+3] aldol-S_NAr-dehydration annulation sequence was utilized to fuse hindered phenols onto aromatic substrates. The transformation joins doubly activated 1,3-disubstituted acetone derivatives (dinucleophiles) with C5-activated 2-fluorobenzaldehyde S_NAr acceptors (dielectrophiles) in the presence of K₂CO₃ in DMF at 65–70 °C to form polysubstituted 2-naphthols and 7-hydroxyquinolines. The reaction is regioselective in adding the most stable anionic center to the aldehyde followed by S_NAr closure of the less stabilized anion to the electron-deficient aromatic ring. Twenty-seven examples are reported, and a probable mechanism is presented. In two cases where S_NAr activation on the acceptor ring was lower (a C5 trifluoromethyl group on the aromatic ring or a 2-fluoropyridine), diethyl 1,3-acetonedicarboxylate initiated an interesting Grob-type fragmentation to give cinnamate esters as the products. Full article

Phenolic environmental endocrine-disrupting chemicals (PEDCs) are persistent EDCs that are widely found in food packaging materials and environmental media and seriously threaten human health and ecological security. Human estrogen-related receptor γ (hERRγ) has been proposed as a mediator for the low-dose effects of many environmental PEDCs; however, the atomic-level descriptions of dynamical structural features and interactions of hERRγ and PEDCs are still unclarified. Herein, how three PEDCs, 4-(1-methylpropyl)phenol (4-sec-butylphenol), 5,6,7,8-tetrahydro-2-naphthol (tetrahydro-2-napthol), and 2,2-bis(4-hydroxy-3,5-dimethoxyphenyl)propane (BP(2,2)(Me)), interact with hERRγ to produce its estrogenic disruption effects was studied. Molecular docking and multiple molecular dynamics (MD) simulations were first conducted to distinguish the detailed interaction pattern of hERRγ with PEDCs. These binding structures revealed that residues around Leu271, Leu309, Leu345, and Phe435 are important when binding with PEDCs. Furthermore, the binding energies of PEDCs with hERRγ were also characterized using the molecular mechanics/Poisson Boltzmann surface area (MM-PBSA) and solvated interaction energy (SIE) methods, and the results showed that the interactions of CH-π, π-π, and hydrogen bonds are the major contributors for hERRγ binding to these three PEDCs. What is striking is that the methoxide groups of BP(2,2)(Me), as hydrophobic groups, can help to reduce the binding energy of PEDCs binding with hERRγ. These results provide important guidance for further understanding the influence of PEDCs on human health problems. Full article

Environmental contamination with xenobiotics affects organisms and the symbiotic relations between them. A convenient object to study relationships between parasites and their hosts is the host–parasite system “Tenebrio molitor Linnaeus, 1758 (Coleoptera, Tenebrionidae)—Gregarina polymorpha (Hammerschmidt, 1838) Stein, 1848 (Eugregarinorida, Gregarinidae)”. For this experiment, we took 390 T. molitor larvae and 24 organic compounds. Groups of mealworms, 15 in each, were subjected to those compounds for 10 days. Then, we recorded the vitality of both the larvae of T. molitor and G. polymorpha. To assess how G. polymorpha had affected the hosts’ wellbeing, we looked for changes in the larvae’s body mass and compared them to the number of gregarines in their intestines. The vitality of the larvae was inhibited by cyclopentanol and 2-naphthol. The intensity of gregarine invasion was reduced by diphenyl ether, benzyl alcohol, catechol, and 3-aminobenzoic acid. No effect on the number of gregarines was produced by 3,4,5-trihydroxybenzoic acid, cyclohexanemethanol, phenol, benzalkonium chloride, maleic anhydride, cyclohexanol, resorcin, benzoic acid, 2-methylfuran, terpinen-4-ol, 1-phenylethylamine, dibutyl phthalate, 3-furancarboxylic acid, 5-methyl furfural, 6-aminohexanoic acid, succinic anhydride, o-xylene, and benzaldehyde. In the infected T. molitor individuals, the mean number of G. polymorpha equaled 45 specimens per host. The groups of smaller mealworms had fewer gregarines. Positive correlation was seen between growth rates of T. molitor larvae and the intensity of invasion by gregarines. Full article

Nanomaterials have attracted specific consideration due to their specific characteristics and uses in several promising fields. In the present study, Chondrilla juncea was employed as a biological extract to facilitate the reduction of copper and silver ions within garlic peel powders. The resulting garlic-CuO and garlic-AgO nanocomposites were characterized using several analytical methods including FTIR, TGA/DTG, SEM, TEM, and XRD analyses. The garlic peel exhibited a rough surface. The nanoparticles were evenly dispersed across its surface. The incorporation of CuO and AgO nanoparticles affected the crystal structure of garlic peel. The establishment of CuO and AgO nanoparticles was evidenced by the highest residual mass values observed for the prepared nanocomposites. The thermogravimetric analysis showed that the prepared nanocomposites had lower thermal stability compared with garlic peel powders. The prepared nanocomposites were used for catalytic degradation of naphthol blue black B and calmagite. The decolorization process depended on the quantity of H₂O₂, initial concentration of azo dyes, duration of contact, and temperature of the bath. The calculated activation energy (Ea) values for the garlic-CuO nanocomposites were found to be 18.44 kJ mol⁻¹ and 23.28 kJ mol⁻¹ for calmagite and naphthol solutions, respectively. However, those calculated for garlic-AgO nanocomposites were found to be 50.01 kJ mol⁻¹ and 12.44 kJ mol⁻¹ for calmagite and naphthol, respectively. Full article

Thin-film composite (TFC) membranes containing a metal–polyphenol network (MPN)-based selective layer were fabricated on a porous polyacrylonitrile support. The MPN layer was formed through coordination-based self-assembly between plant-based tannic acid (TA) and an Fe³⁺ ion. For the first time, we demonstrate that TFC membranes containing TA-Fe³⁺ selective layers can separate small organic solutes in aqueous media from equimolar mixtures of solutes. The effect of the assembly time on the characteristics and performance of the fabricated selective layer was investigated. An increase in the assembly time led to the formation of selective layers with smaller effective pore sizes. The tannic acid–Fe³⁺ selective layer exhibited a low rejection towards neutral solutes riboflavin and poly(ethylene glycol) while high rejections were observed for anionic dyes of orange II and naphthol green B. Permeation selectivities in the range of 2–27 were achieved between neutral and charged dyes in both single- and mixed-solute experiments, indicating the significant role of Donnan exclusion and the charge-selective nature of the membranes. The rejection efficiency improved with an increasing assembly time. Overall, this study demonstrates that the assembly time is a vital casting parameter for controlling the permeance, rejection and selectivity of thin-film composite membranes with a tannic acid–Fe³⁺ selective layer. Full article

The textile industry is one of the most important industries in the European Union. The main environmental problems of the textile industry are the high water consumption, the generated pollution, the variety of chemicals used and the high energy demand. Recently, adsorbents with a large specific surface area and low weight, such as aerogels, have attracted great interest as promising materials for removing dyes from polluted water. Cellulose aerogels are inexpensive and non-toxic. Langmuir and Freundlich isotherms were chosen as the best method to describe the performance of the adsorbent. In this study, the adsorption efficiency of Congo red, Naphthol green B, Rhodamine B and Methylene blue were determined by using an adsorbent synthesized from paper and cardboard waste. The total organic carbon concentration was chosen as an indicator of the concentration of the dyes in the solutions. The aerogel capsules had 5% cellulose content. It was found that the adsorption capacity of the aerogel in the solutions of Congo red varied from 0.028 mg/g to 14.483 mg/g; in the solutions of Naphthol green B, from 0.013 mg/g to 7.698 mg/g; in the solutions of Rhodamine B, from 0.020 mg/g to 8.768 mg/g; and in the solutions of Methylene blue, from 0.024 mg/g to 13.538 mg/g. Full article

Structural hydroxide groups in layered magnesium–aluminum double hydroxides were partially replaced by fluoride ions. Fluorinated and fluorine-free materials were used as hosts for two dyes, carminic acid and hydroxyl naphthol blue, resulting in a hybrid pigment color palette. The pigments were produced by two ways, either incorporating chromophore during the synthesis of the layered double hydroxide or in a post-synthesis step through the memory effect of the LDHs. Additionally, the pigments were protected with a magnesium hydroxide phase to prevent the color from fading over time. The pigments were stable for periods as long as 10 years. The color properties of the pigments were significantly influenced by the host of dye since the presence of fluorine directly influences the acid–base properties of the layered double hydroxides. The pigments conferred their color to white cream in the preparation of colored creams. The colored creams acquired the color of the layered pigment. Full article

In this study, TiO₂ nanospheres (TiO₂-NS) were synthesized by the solvothermal method. Firstly, the synthesized nanomaterial was characterized by X-ray diffraction (XRD), Fourier Transformed Infrared (FTIR), scanning electron microscopy (SEM) and UV-Vis Diffuse Reflectance Spectroscopy (DRS). To study the photocatalytic degradation of Tartrazine (TTZ) and Naphthol Blue Black (NBB) in a binary mixture, the influence of some key parameters such as pH, pollutant concentration and catalyst dose was taken into account under visible and UV light. The results show a 100% degradation efficiency for TTZ after 150 min of UV irradiation and 57% under visible irradiation at 180 min. The kinetic study showed a good pseudo-first-order fit to the Langmuir–Hinshelwood model. Furthermore, in order to get closer to the real conditions of textile wastewater, the influence of the presence of salt on TiO₂-NS’s photocatalytic performance was explored by employing NaCl as an inorganic ion. The optimum conditions provided by the Response Surface Methodology (RSM) were low concentrations of TTZ (2 ppm) and NBB (2.33 ppm) and negligible salt (NaCl) interference. The percentage of photodegradation was high at low pollutant and NaCl concentrations. However, this yield became very low as NaCl concentrations increased. The photocatalytic treatment leads to 31% and 53% of mineralization yield after 1 and 3 h of visible light irradiation. The synthesis of TiO₂-NS provides new insights that will help to develop an efficient photocatalysts for the remediation of contaminated water. Full article

Plant extracts and essential oils can be alternative environmentally friendly agents to combat pathogenic microbes and malaria vectors. Myrrh is an aromatic oligum resin that is extracted from the stem of Commiphora spp. It is used in medicine as an insecticide, cytotoxic, and aromatic. The current study assessed the effect of Commiphora myrrha resin extracts on the biological potency of the third larval stage of Aedes aegypti, as well as its antioxidant and cytotoxic properties against two types of tumor cells (HepG-2 and Hela cell lines). It also used GC–MS to determine the chemical composition of the C. myrrha resin extracts. Fifty components from the extracted plant were tentatively identified using the GC–MS method, with curzerene (33.57%) typically listed as the primary ingredient, but other compounds also make up a significant portion of the mixture, including 1-Methoxy-3,4,5,7-tetramethylnaphthalene (15.50%), β-Elemene (5.80%), 2-Methoxyfuranodiene (5.42%), 2-Isopropyl-4,7-Dimethyl-1-Naphthol (4.71%), and germacrene B (4.35%). The resin extracts obtained from C. myrrha exhibited significant efficacy in DPPH antioxidant activity, as evidenced by an IC₅₀ value of 26.86 mg/L and a radical scavenging activity percentage of 75.06%. The 50% methanol extract derived from C. myrrha resins exhibited heightened potential for anticancer activity. It demonstrated substantial cytotoxicity against HepG-2 and Hela cells, with IC₅₀ values of 39.73 and 29.41 µg mL⁻¹, respectively. Notably, the extract showed non-cytotoxic activity against WI-38 normal cells, with an IC₅₀ value exceeding 100 µg mL⁻¹. Moreover, the selectivity index for HepG-2 cancer cells (2.52) was lower compared to Hela cancer cells (3.40). Additionally, MeOH resin extracts were more efficient against the different growth stages of the mosquito A. aegypti, with lower LC₅₀, LC₉₀, and LC₉₅ values of 251.83, 923.76, and 1293.35 mg/L, respectively. In comparison to untreated groups (1454 eggs/10 females), the average daily number of eggs deposited (424 eggs/L) decreases at higher doses (1000 mg/L). Finally, we advise continued study into the possible use of C. myrrha resins against additional pests that have medical and veterinary value, and novel chemicals from this extract should be isolated and purified for use in medicines. Full article

Iodine, primarily in the form of iodide (I⁻), is the bioavailable form for the thyroid in the human body. Both deficiency and excess intake of iodide can lead to serious health issues, such as thyroid disease. Selecting iodide ions among anions has been a significant challenge for decades due to interference from other anions. In this study, we designed and synthesized a new pincer-type acridine–triazole fluorescent probe (probe 1) with an acridine ring as a spacer and a triazole as a linking arm attached to two naphthol groups. This probe can selectively recognize iodide ions in a mixed solvent of THF/H₂O (v/v, 9/1), changing its color from colorless to light yellow, making it suitable for highly sensitive and selective colorimetric and fluorescent detection in water systems. We also synthesized another molecular tweezer-type acridine–triazole fluorescent probe (probe 2) that exhibits uniform detection characteristics for iodide ions in the acetonitrile system. Interestingly, compared to probe 2, probe 1 can be detected by the naked eye due to its circulation effect, providing a simple method for iodine detection. The detection limit of probe 1 is determined to be 10⁻⁸ mol·L⁻¹ by spectrometric titration and isothermal titration calorimetry measurements. The binding stoichiometry between probe 1 and iodide ions is calculated to be 1:1 by these methods, and the binding constant is 2 × 10⁵ mol·L⁻¹. Full article

The two naphthol isomers were investigated in different organic solvents by taking cyclic voltammograms, and fouling took place on a platinum electrode surface, except for dimethyl sulfoxide and dimethyl formamide. Studies in allyl alcohol rarely used in electrochemical investigations pointed to the importance of the carbon–carbon double bond as electrode deactivation was remarkably faster compared with its saturated analog solvent. Similarly, the use of the other unsaturated solvent mesityl oxide in the electropolymerization of naphthols resulted in different findings compared with methyl isobutyl ketone. As dimethyl formamide was the best choice concerning the solubility of products, it was successfully tested in electrode renewal after deactivation in an aqueous solution. The increase in dimethyl formamide content led to more and more improved reproducibility of the currents of the outlined aromatic compounds. Naphthol isomers were assessed in the suppression of layer growth originating from the electrooxidation of another monomer phloroglucinol. Its simultaneous electrooxidation with naphthol monomers had a dramatic effect on layer morphology and it was found that instead of a coherent organic layer originating from the homopolymerization of phloroglucinol, the copolymerization with naphthols led to the development of more porous and rougher deposits. The suppressed electropolymerization thus increased sensitivity towards a chosen redox active compound, 4-methoxyphenol. Full article

Over the past decade, copper (Cu) has been recognized as a crucial metal in the differential expression of soluble (sMMO) and particulate (pMMO) forms of methane monooxygenase (MMO) through a mechanism referred to as the “Cu switch”. In this study, we used Methylosinus trichosporium OB3b as a model bacterium to investigate the range of Cu concentrations that trigger the expression of sMMO to pMMO and its effect on growth and methane oxidation. The Cu switch was found to be regulated within Cu concentrations from 3 to 5 µM, with a strict increase in the methane consumption rates from 3.09 to 3.85 µM occurring on the 6th day. Our findings indicate that there was a decrease in the fold changes in the expression of methanobactin (Mbn) synthesis gene (mbnA) with a higher Cu concentration, whereas the Ton-B siderophore receptor gene (mbnT) showed upregulation at all Cu concentrations. Furthermore, the upregulation of the di-heme enzyme at concentrations above 5 µM Cu may play a crucial role in the copper switch by increasing oxygen consumption; however, the role has yet not been elucidated. We developed a quantitative assay based on the naphthalene–Molisch principle to distinguish between the sMMO- and pMMO-expressing cells, which coincided with the regulation profile of the sMMO and pMMO genes. At 0 and 3 µM Cu, the naphthol concentration was higher (8.1 and 4.2 µM, respectively) and gradually decreased to 0 µM naphthol when pMMO was expressed and acted as the sole methane oxidizer at concentrations above 5 µM Cu. Using physical protein–protein interaction, we identified seven transporters, three cell wall biosynthesis or degradation proteins, Cu resistance operon proteins, and 18 hypothetical proteins that may be involved in Cu toxicity and homeostasis. These findings shed light on the key regulatory genes of the Cu switch that will have potential implications for bioremediation and biotechnology applications. Full article

Leishmaniasis remains a significant global health concern, with current treatments relying on outdated drugs associated with high toxicity, lengthy administration, elevated costs, and drug resistance. Consequently, the urgent need for safer and more effective therapeutic options in leishmaniasis treatment persists. Previous research has highlighted selenium compounds as promising candidates for innovative leishmaniasis therapy. In light of this, a library of 10 selenium-containing diverse compounds was designed and evaluated in this study. These compounds included selenium-substituted indole, coumarin, chromone, oxadiazole, imidazo[1,2-a]pyridine, Imidazo[2,1-b]thiazole, and oxazole, among others. These compounds were screened against Leishmania amazonensis promastigotes and intracellular amastigotes, and their cytotoxicity was assessed in peritoneal macrophages, NIH/3T3, and J774A.1 cells. Among the tested compounds, MRK-106 and MRK-108 displayed the highest potency against L. amazonensis promastigotes with reduced cytotoxicity. Notably, MRK-106 and MRK-108 exhibited IC₅₀ values of 3.97 µM and 4.23 µM, respectively, and most of the tested compounds showed low cytotoxicity in host cells (CC₅₀ > 200 µM). Also, compounds MRK-107 and MRK-113 showed activity against intracellular amastigotes (IC50 18.31 and 15.93 µM and SI 12.55 and 10.92, respectively). In conclusion, the identified selenium-containing compounds hold potential structures as antileishmanial drug candidates to be further explored in subsequent studies. These findings represent a significant step toward the development of safer and more effective therapies for leishmaniasis, addressing the pressing need for novel and improved treatments. Full article