cometadata/datacite-titles-descriptions-related-identifiers huggingface dataset:
DOI: 10.6084/m9.figshare.14304251.v1
title: Inhibition of Acetylcholinesterase by Coumarin-Linked Amino Acids Synthetized via Triazole Associated with Molecule Partition Coefficient

description: A previous study for the identification of acetylcholinesterase (AChE) inhibitors demonstrated that the hybrid between tyrosol, the 1,2,3-triazole nucleus, and the coumarin group, namely 7-({1-[2-(4-hydroxyphenyl)ethyl]-1H-1,2,3-triazol-4-yl}methoxy)-4-methyl-2H-chromen-2-one (10), has a high enzyme inhibitory activity. Here, we synthesized analogues of 10 via triazole with pharmacophoric groups represented by tyrosine, phenylalanine, tryptophan, and glycine in addition to evaluating the impact of coumarin-linked amino acids on AChE inhibition. We obtained eight triazoles, six of which are undescribed. In general, the presence of carboxylic acid decreased the inhibitory activity, while aromatic amino acids increased enzymatic inhibition compared to glycine. The derivative containing tyrosine, structurally most similar to 10, presented the lowest inhibition percentage, indicating that phenolic hydroxyl is not the preponderant factor for inhibition. Molecular docking was not enough to explain in vitro experiments. On the other hand, MlogP (logP calculated by the Moriguchi method) was related positively to enzymatic inhibition. To increase the hydrophobicity of the molecules, we tested the esterified triazole derivatives comparatively with the enzyme. The compound ethyl 2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)acetate (6) presented an increment of inhibitory activity of 46.97 ± 1.75% at 100 μmol L-1. We also associated the best activity with the lowest van der Waals volume and molar mass values.
DOI: 10.6084/m9.figshare.14304246.v1
title: Synthesis of 1,2,3-Triazole Benzophenone Derivatives and Evaluation of in vitro Sun Protection, Antioxidant Properties, and Antiproliferative Activity on HT-144 Melanoma Cells

description: Benzophenones display several biological activities, including antioxidant, anticancer, and photoprotective. Furthermore, antioxidants can minimize both ultraviolet absorption and tumor development. In the present investigation, a series of twenty-six 1,2,3-triazole-benzophenone derivatives were synthesized and had their antioxidant, anticancer, and photoprotective effects evaluated. For the compounds synthesis, 4,4’-dihydroxybenzophenone (1a) and 2,4-dihydroxybenzophenone (1b) were propargylated, affording the alkynes bis(4-(prop-2-yn-1-yloxy))benzophenone (2a) and (2-hydroxy-4-(prop-2-yn-1-yloxy))benzophenone (2b), respectively. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction between the compounds 2a/2b and several benzyl azides gave the 1,2,3-triazole-benzophenone derivatives with yields ranging from 35 to 95%. The 1,2,3-triazole-benzophenone derivatives at the concentration of 0.2 μg mL-1 (a no-cytotoxic concentration) exhibited a solar protection factor (SPF) comparable to positive control benzophonen-3 (BP-3). Concerning their antioxidant and cytotoxic effects, the derivatives from 1b showed high in vitro antioxidant effects as well as cytotoxicity against A549 (lung carcinoma), MCF-7 (breast carcinoma), and HT-144 (metastatic melanoma) cell lines, without significant cytotoxicity to a non-cancerous cell line. Derivatives 19, 20, and 24 induced cell death and cell cycle arrest at G1/S in HT-144 melanoma cells.
DOI: 10.6084/m9.figshare.14304244.v1
title: Metal Distribution in the Environmental Compartments of Manguaba Lagoon (Alagoas State, Brazil)

description: The metal concentrations in water, sediments and mollusks (Tagelus plebeius) of the Manguaba Lagoon and the influence of humic substances from water and sediments in the distribution of these metals were investigated in this work. The mean metal concentrations in water were: Mg (89.0 ± 0.11), Ca (32.0 ± 0.10), Fe (0.97 ± 0.02), Mn (0.52 ± 0.01), Zn (0.33 ± 0.10) and Pb (0.22 ± 0.02) mg L-1. The Pb concentrations were above the Brazilian legislation limit. All sediment data were below maximum limit established by the National Council for the Environment (CONAMA, Brazil) of the Ministry of the Environment, and the concentration ranges for metals were: Fe (1199-60000), Mg (339-8870), Ca (461-3838), Cr (&lt; LOQ-39.5) and Pb (&lt; LOQ-12.5) mg kg-1 (LOQ: limit of quantification). None of the principal contaminants (Cr, Pb and Cd) was determined in Tagelus plebeius, being a positive fact once the population nearby Manguaba Lagoon consumes large amounts of this mollusk. According to the results, the influence of humic substances in the contaminant retention is evident as they become unavailable for absorption by mollusks of Manguaba Lagoon.
DOI: 10.6084/m9.figshare.14304243.v1
title: PhotoMetrix UVC: A New Smartphone-Based Device for Digital Image Colorimetric Analysis Using PLS Regression

description: A novel free PhotoMetrix UVC is proposed for both the operation of a universal serial bus video camera (UVC) and multivariate image analysis, allowing a full solution for point-of-use analysis. A UVC was placed in an open-source 3D-printed chamber illuminated by a white light-emitting diode (LED) with controlled intensity of light. The digital images captured were converted into red, green, and blue (RGB) histograms, and regression models were used within the app. As a proof-of-concept, four adulterants in raw milk samples were determined. The coefficient of determination (R2Cal) for all models was higher than 0.99, and no significant differences (p &lt; 0.05) between the measured and predicted values were identified. The root mean square error of calibration (RMSEC) and root mean square error of cross validation (RMSECV) were satisfactory, with values less than 0.1 and 0.7 g L-1, respectively. The recoveries ranged from 90 to 120% in spiked milk samples, and partial least square (PLS) models showed root mean square error of prediction (RMSEP) of 0.28, 0.33, 0.48 and 0.39 g L-1 for chloride, hypochlorite, hydrogen peroxide and starch, respectively. The PhotoMetrix UVC app was feasible for the colorimetric chemical analysis using a smartphone improving the applicability, mobility, and usability.
DOI: 10.6084/m9.figshare.14304241.v1
title: Organic Matter Leached from Tropical Soils by Simulated Rain, Hard (NaOH) and Soft (NaNO3) Extractions: A Realistic Study about Risk Assessment in Soils

description: Alkaline extractions from humic material are used to risk assessment in soils. However, there are questions about the type of extraction most suitable for this evaluation. Thus, this work evaluated different soil extractions in search of realistic environmental conditions (simulated rain). The parameters obtained revealed significant differences between the levels and structural characteristics of organic matter, depending on the extractant used, reinforcing the importance of developing methodologies and analytical procedures that minimize structural changes and may be more representative of the molecular structures of organic matter found in soils. The results showed that the material extracted by simulated rain is similar to the fulvic acids of the soil organic matter extracted by alkaline extraction showing the importance of this type of extraction for risk assessment studies in soils.
DOI: 10.6084/m9.figshare.14304237.v1
title: Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action

description: Benzodiazepines derivatives are nitrogen heterocyclic compounds that have various industrial, synthetic, and medicinal applications. Therefore, its potential fully justifies every effort towards the improvement of new, selective, and competent production of these heterocyclic compounds. The novelty of this study encompasses the synthesis of new hydroxylated analogs of 1,5-benzodiazepine together with the evaluation of their biological potential as antioxidants and antifungals candidates. Additionally, the reported antifungal activity against fungi of the Sporothrix schenckii complex inaugurates an unprecedented property for this class of compounds. The results of biological activities assays suggest that the novel 2,7-dimethyl-2,4-bis(4-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine possesses a high antifungal activity against all fungal strains evaluated of the Sporothrix genus and outstanding total antioxidant capacity. Besides, in silico studies have evidenced that the hydroxylated derivatives have the best aqueous solubility and cell permeability profile, which makes them superior in comparison with the commercial antifungal itraconazole, a drug commonly used in the treatment of sporotrichosis.
DOI: 10.6084/m9.figshare.14304236.v1
title: Synthesis and Biological Evaluation of Benzo[f]indole-4,9-diones N-Linked to Carbohydrate Chains as New Type of Antitumor Agents

description: In this work, we report the synthesis of three series of carbohydrate-based benzo[f]indole-4,9-diones and amino-1,4-naphthoquinone derivatives and evaluated their cytotoxic activity against eight human cancer cell lines. Several compounds showed a promising cytotoxic activity toward the tumor cell lines (half maximal inhibitory concentration (IC50) &lt; 10.0 μM). The importance of the substitution pattern of the quinone derivatives on the antitumor activity was also discussed. 3-Carboethoxy-2-methyl-benzo[f]indole-4,9-dione derivatives were more cytotoxic than their parent compounds and amino-1,4-naphthoquinones. Unlike clinically useful anticancer agent doxorubicin, the majority of synthesized compounds did not exhibit any lytic effects against erythrocytes or normal human leukocytes.
DOI: 10.6084/m9.figshare.14304231.v1
title: New Greener Method for the Preparation of Heteropolyacid Compounds (HPW) Modified with Metallic Tin and Application in the Lactic Acid Esterification Reaction

description: The main objective of this work was to design an innovative method to prepare heterogeneous heteropolyacid catalysts. The heteropolyacid H3PW12O40 (HPW) was modified with tin(II) by two methodologies: a conventional aqueous ion-exchange (CS) and a redox solid-state (SS). In both cases, Fourier transform infrared spectroscopy (FTIR) and X-ray diffraction (XRD) measurements evidenced that Keggin structure was preserved. All materials were active in the esterification of lactic acid with several alcohols and a mechanism was proposed. The best results were obtained for octanol and benzyl alcohol, where higher conversion values were obtained. The catalytic activity (turnover frequency, TON) showed an efficient performance for the materials prepared with 4 h of calcination (CS4h and SS4h). However, the catalyst prepared by the SS method was in accordance with the development of environmentally friendly processes.
DOI: 10.6084/m9.figshare.14304228.v1
title: Magnetic and Mesoporous Silica-Niobia Material as Modifier of Carbon Paste Electrode for p-Nitrophenol Electrochemical Determination

description: In the present work, the sol-gel synthesis method was employed as strategy to obtain a magnetic and mesoporous silica-niobia material. The planned synthesis was based on the hetero-condensation of niobium and silicon alkoxide precursors, in the presence of spherical magnetite particles. The resulting material presented interesting characteristics such as magnetism, large mesopores, in the range from 20 to 50 nm, and 68 m2 g-1 of surface area. These features allowed its use as modifier of carbon paste electrode for p-nitrophenol determination, since niobia has never been used in electrochemical sensors for the determination of nitrophenol compounds. By using differential pulse voltammetry technique, the electrode can be applied in a wide range of p-nitrophenol concentration, from 10 to 490 μmol L-1, with a limit of detection of 1.2 µmol L-1 and sensitivity up to 0.60 µA L µmol-1. The proposed electrode presented good sensitivity and selectivity and it was applied in real water samples.
DOI: 10.6084/m9.figshare.14304227.v1
title: Multivariate Optimization of Extraction Variables of PAH in Particulate Matter (PM10) in Indoor/Outdoor Air at Campos dos Goytacazes, Brazil

description: Polycyclic aromatic hydrocarbons (PAH) are products of incomplete combustion of biomass and fossil fuels, that are produced on a larger scale by anthropogenic sources. Burning sugarcane plantations can be a source of atmospheric PAH in regions where this culture predominates. Campos dos Goytacazes, Brazil, is surrounded by sugarcane crops that still use fire as a facilitating method for the harvesting process. This study aims to evaluate the presence of outdoor and indoor PAH in 10 µm particulate matter (PM10) at one university in Campos dos Goytacazes. PM10 samples were collected from January to November 2018. Samples were extracted using an ultrasonic probe and analyzed by gas chromatography coupled to mass spectrometry (GC-MS). The ideal extraction conditions (3 min; 150 W; 50 mL) were defined by 23 full factorial design. The analysis showed a significant PM10 level increase (23.19 to 34.50 µg m-3 in outdoor, and 15.15 to 31.66 µg m-3 in indoor samples) and higher total PAH concentration in the harvesting season (outdoor: 0.73 ng m-3; indoor 0.52 ng m-3) than in non-harvesting season (outdoor: 0.49 ng m-3; indoor: 0.28 ng m-3), however, average PAH values found in outdoor samples in harvesting season did not show significant difference from non-harvesting season.
DOI: 10.6084/m9.figshare.14304224.v1
title: Evaluation of the Direct Interaction between Amino Acids and Glutathione-Coated CdTe Quantum Dots and Application in Urinalysis for Histidine Determination

description: The present work aimed to direct amino acid (AA) sensing by quantum dots (QD) and development of an analytical method for potential fast clinical tests. Notably, AA with a positive charge or neutral polar chains, namely L-histidine (His) and L-threonine (Thr), responded to glutathione-coated CdTe (GSH-CdTe) (ΔF ≤ 90%, variation of fluorescence intensity). However, in ammoniacal buffer (0.25 mol L-1) at pH 8.0, 2.2 nm GSH-CdTe responded only to His. Static quenching with complex association constant (Ksv) varying from 2.81 to 0.94 (10 L mol-1) as well as van der Waals forces and/or hydrogen bonding were predicted for His-QD quenching mechanism and binding type. Additionally, thermodynamic parameters as ΔH = -76.5 kJ mol-1 (enthalpy), ΔS = -227.4 J K-1 mol-1 (entropy) and ΔG from -9.8 until -6.4 kJ mol-1 (Gibbs free energy) at 20 to 35 °C were estimated by van’t Hoff equation. Under optimal conditions, the developed method presented a linear range from 0.42 to 35 mmol L-1 (with correlation coefficient (r) of 0.9970, n = 7), good precision (relative standard deviations (RSD) &lt; 2.5% for 2.5 and 20 mmol L-1; n = 6) and limit of detection 1.6 × 10-4 mol L-1 (0.025 mg mL-1). Recovery tests were performed on artificial urine and human urine samples with recoveries ranging from 78.7 to 127.6%.
DOI: 10.6084/m9.figshare.14304219.v1
title: Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone

description: The compound 1,4-pentadien-3-one,(1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone presents the molecular formula C23H18N4O4 and was prepared in an undergraduate laboratory. The hydrazone was synthesized from the condensation between dibenzalacetone and 2,4-dinitrophenylhydrazine (DNPH) and crystallized employing water/acetone liquid-liquid diffusion. The structure presents three aromatic rings connected by an unsaturated Y-shaped system. Dinitro substituted and one of the other aromatic rings are 15º out of a coplanarity, while the other phenyl group is almost orthogonal to the first (89º). The only observed classical hydrogen bonding is an intramolecular N-H···O. The supramolecular structure was analyzed employing the Hirshfeld surface and that is organized through C-H···O hydrogen bond and C-H···π, polar-π, and π-stacking. An interaction involving NO2···NO2 was also observed.
DOI: 10.6084/m9.figshare.14304216.v1
title: HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase

description: The flavonoid rutin presents several pharmacological effects, despite this, its application in the pharmaceutical industry can be significantly limited by its low bioavailability. The development of lipophilic derivatives by esterification of hydroxyl groups with fatty acid chains may be an effective strategy to change their physicochemical properties. This work aims to use high-speed countercurrent chromatography (HSCCC) to isolate rutin esters produced by esterification reactions catalyzed by the immobilized lipase from Candida antarctica (Novozyme 435®). The lipase-catalyzed synthesis of rutin esters (R3-R18:2) in 2-methyl-2-butanol exhibited conversions that ranged from 16 to 40% and highest conversion for short chain fatty acids (R4-R12). After initial partitioning tests of the reaction mixture in different solvent proportions followed by thin layer chromatography (TLC) analysis, the biphasic solvent systems consisting in HEMWat (hexane/ethyl acetate/methanol/water) in different proportions were chosen to separate rutin esters. These esters were separated for the first time to the reaction mixture via HSCCC. This technique proved to be more advantageous than the traditionally one since it allowed quick isolation and high purity (≥ 90%) of the products. It also permitted a substrate recovery for reuse in other enzymatic reactions. Furthermore, the results add valuable information, specially concerning the structures elucidation of different rutin esters not previously described.
DOI: 10.6084/m9.figshare.14304215.v1
title: Aqueous Extract of Cumaru (Dipteryx odorata) Seeds as Corrosion Inhibitor for Mild Steel in Hydrochloric Acid Solution

description: The corrosion inhibition of mild steel by aqueous extract of cumaru (Dipteryx odorata) seeds and its high molecular weight fraction (HMWF) was investigated in 1 mol L-1 HCl solution. The study was carried out through gravimetric essays, open circuit potential measurements, anodic and cathodic polarization curves and electrochemical impedance analyses, as well as morphological analysis of the mild steel by scanning electron microscopy. Gravimetric tests showed that the inhibition efficiency (IE) increased with immersion time and inhibitor concentration, reaching 98% of IE using 100 mg L-1 of the HMWF, after 6 h immersion time. The activation energy (Ea) increased with the addition of both inhibitors which characterizes a physical adsorption of the constituents of the aqueous extract of cumaru on the metal surface. Polarization curves indicated that both aqueous cumaru seeds extract and its HMWF act as mixed-type inhibitor. Impedance results showed a decrease in double layer capacitance (Cdl) and an increase in charge transfer resistance (Rct) evidencing a typically screening effect. The adsorption of molecules present in the aqueous extract of cumaru followed the Langmuir isotherm. The aqueous cumaru seeds extract was characterized by Fourier transform infrared spectroscopy (FTIR), 1H, 13C and 2D nuclear magnetic resonance (NMR).
DOI: 10.6084/m9.figshare.14304213.v1
title: Synthesis, Spectroscopic Characterization, DFT Calculations and Preliminary Antifungal Activity of New Piperine Derivatives

description: Four new piperine derivatives, PC1-PC4, were synthesized, and their structures were fully characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies. Quantum chemical calculations were performed using density functional theory (DFT) with the B3LYP-D3/6-31G(d,p) and 6-311+G(2d,p) basis sets. Electronic properties, such as the energy gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) and some global chemical reactivity descriptors, were evaluated to study the reactivity and stability of the compounds. 1H and 13C NMR chemical shifts were calculated by using the gauge-invariant atomic orbital (GIAO) method and compared with experimental values. In addition, the compounds were evaluated in an antifungal study against Candida, Trichophyton and Microsporum strains, and only PC4 showed 70% inhibition in ten tested strains, with a minimum inhibitory concentration (MIC) ranging from 1.23-2.46 μmol mL-1 and a minimum fungicide concentration (MFC) ranging from 9.84-19.68 μmol mL-1, and presented a fungistatic effect.
DOI: 10.6084/m9.figshare.14304212.v1
title: Identification of Synthetic Drugs on Seized Blotter Papers Using ATR-FTIR and PLS-DA: Routine Application in a Forensic Laboratory

description: Blotter papers seizures containing synthetic drugs have intensified over the last decades. These drugs were originally conceived as “legal” alternatives to traditional illicit drugs, designed to mimic their effects and circumvent control agencies. Reference methods for determining these substances on blotter papers are based on chromatographic techniques using mass spectrometry detection. However, these procedures are destructive, expensive, and time consuming. Some compounds are also thermolabile and not suitable for regular gas chromatography analyses. In this paper, two multivariate models were presented and incorporated in the routine of a forensic laboratory as a screening method. They were developed and validated using a representative dataset of 158 seizures analyzed by attenuated total reflectance-Fourier transform infrared spectroscopy (ATR-FTIR) and a partial least squares-discriminant analysis (PLS-DA) model. The first model (model A) discriminates between samples with and without different types of drugs, and the second one (model B) discriminates between samples containing NBOMe and NBOH, two N-benzyl 2,5-dimethoxy substituted phenethylamine commonly incorporated into blotter papers. The proposed method is fast, non-destructive, and requires no sample preparation. Both models showed reliable results (misidentification errors &lt; 10%), presented good results in a real forensic laboratory routine, and can be updated to include new drugs.
DOI: 10.6084/m9.figshare.14304210.v1
title: Complementary Performance of Organoselenides and Organotellurides as Antimicrobials Agents

description: Fungi and bacteria are well-known pathogens for plants, fruits, and animals, including humans. In this context, the prospection of antimicrobial agents is crucial to provide new alternatives for the treatment of microbial diseases. Hence, selenium- and tellurium-containing compounds are underexploited and herein, antimicrobial activity of several organochalcogenated compounds was evaluated against Gram-negative and Gram-positive bacteria and fungi. A direct comparison between Se- and Te-containing compounds was performed, as well as structure-activity relationship studies. Among assayed compounds, secondary Se-amines LQ16 and LQ20 and secondary Te-amine LQ28 showed excellent results against a variety of fungi, while primary Te-amine LQ10 demonstrated promising results against bacteria. These results suggest organoselenides and organotellurides may be used for the development of new antimicrobial agents.