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1.
J Agric Food Chem ; 70(14): 4165-4181, 2022 Apr 13.
Artículo en Inglés | MEDLINE | ID: mdl-35357820

RESUMEN

Widely consumed thermally processed corn-based foods can have a great contribution to acrylamide dietary intake, thus bearing a high public health risk and requiring attention and application of strategies for its reduction. This paper reviews the literature on the acrylamide content of corn-based food products present in the market around the world. The potential of corn for acrylamide formation due to its content of free asparagine and reducing sugars is described. Human exposure to acrylamide from corn-based foods is also discussed. The content of acrylamide in corn/tortilla chips, popcorn, and corn flakes, as widely consumed products all over the world, is reported in the literature to be between 5 and 6360 µg/kg, between

Asunto(s)
Acrilamida , Zea mays , Acrilamida/análisis , Comida Rápida , Contaminación de Alimentos/análisis , Manipulación de Alimentos , Humanos
2.
Molecules ; 27(3)2022 Feb 04.
Artículo en Inglés | MEDLINE | ID: mdl-35164325

RESUMEN

Using two ways of functionalizing amiridine-acylation with chloroacetic acid chloride and reaction with thiophosgene-we have synthesized new homobivalent bis-amiridines joined by two different spacers-bis-N-acyl-alkylene (3) and bis-N-thiourea-alkylene (5) -as potential multifunctional agents for the treatment of Alzheimer's disease (AD). All compounds exhibited high inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with selectivity for BChE. These new agents displayed negligible carboxylesterase inhibition, suggesting a probable lack of untoward drug-drug interactions arising from hydrolytic biotransformation. Compounds 3 with bis-N-acyl-alkylene spacers were more potent inhibitors of both cholinesterases compared to compounds 5 and the parent amiridine. The lead compounds 3a-c exhibited an IC50(AChE) = 2.9-1.4 µM, IC50(BChE) = 0.13-0.067 µM, and 14-18% propidium displacement at 20 µM. Kinetic studies of compounds 3a and 5d indicated mixed-type reversible inhibition. Molecular docking revealed favorable poses in both catalytic and peripheral AChE sites. Propidium displacement from the peripheral site by the hybrids suggests their potential to hinder AChE-assisted Aß42 aggregation. Conjugates 3 had no effect on Aß42 self-aggregation, whereas compounds 5c-e (m = 4, 5, 6) showed mild (13-17%) inhibition. The greatest difference between conjugates 3 and 5 was their antioxidant activity. Bis-amiridines 3 with N-acylalkylene spacers were nearly inactive in ABTS and FRAP tests, whereas compounds 5 with thiourea in the spacers demonstrated high antioxidant activity, especially in the ABTS test (TEAC = 1.2-2.1), in agreement with their significantly lower HOMO-LUMO gap values. Calculated ADMET parameters for all conjugates predicted favorable blood-brain barrier permeability and intestinal absorption, as well as a low propensity for cardiac toxicity. Thus, it was possible to obtain amiridine derivatives whose potencies against AChE and BChE equaled (5) or exceeded (3) that of the parent compound, amiridine. Overall, based on their expanded and balanced pharmacological profiles, conjugates 5c-e appear promising for future optimization and development as multitarget anti-AD agents.


Asunto(s)
Enfermedad de Alzheimer/tratamiento farmacológico , Aminoquinolinas/química , Antioxidantes/farmacología , Butirilcolinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Fármacos Neuroprotectores/farmacología , Acetilcolinesterasa , Antioxidantes/química , Inhibidores de la Colinesterasa/química , Proteínas Ligadas a GPI/antagonistas & inhibidores , Humanos , Cinética , Modelos Moleculares , Simulación del Acoplamiento Molecular , Estructura Molecular , Fármacos Neuroprotectores/química , Relación Estructura-Actividad
3.
ACS Appl Mater Interfaces ; 13(41): 48555-48568, 2021 Oct 20.
Artículo en Inglés | MEDLINE | ID: mdl-34617725

RESUMEN

Planar-type perovskite solar cells (p-PSCs) based on SnO2 have garnered further attention due to their simple and low-temperature fabrication. Improving the critical properties of the electron transport layer (ETL) is an effective way to enhance the performance of p-PSC devices. Here, a brand-new method is developed to relieve the contact recombination caused by the rough fluorine-doped tin oxide (FTO) surface and further boosts the electrical concentration of the ETL. A SnO2-ethylene diamine tetraacetic acid (EDTA) acylamide compound (SEAC) with hydrogen bond-induced adjustable cluster size is reported for the first time. The rational choice of the SEAC cluster size is the key for obtaining the smooth interfacial morphology of the ETL on the rugged FTO substrate. In addition, the energy band gap decreases with the increasing cluster size, and consequently, results in improved electrical conductivity of the SEAC. The upshifted Fermi energy level leads to higher electron concentration, which is an important physical quantity of the ETL. The PSC devices based on the optimized SEAC achieve an improved power conversion efficiency of 21.29% with negligible J-V hysteresis due to significantly enhanced electron transport and reduced contact charge recombination at the ETL/perovskite interface. In general, this paper comes up with a unique strategy to improve the quality of the SnO2-based ETL.

4.
Eur J Med Chem ; 209: 112898, 2021 Jan 01.
Artículo en Inglés | MEDLINE | ID: mdl-33069433

RESUMEN

N-(5-Chlorobenzo[d]oxazol-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamideox-amide has been identified as a potent inhibitor of Mtb H37Rv, with a minimum inhibitory concentration (MIC) of 0.42 µM. In this study, a series of substituted 2-acylamide-1,3-zole analogues were designed and synthesized, and their anti-Mtb activities were analyzed. In total, 17 compounds were found to be potent anti-Mtb agents, especially against the MDR- and XDR-MTB strains, with MIC values < 10 µM. These analogues can inhibit both drug-sensitive and drug-resistant Mtb. Four representative compounds were selected for further profiling, and the results indicate that compound 18 is acceptably safe and has favorable pharmacokinetic (PK) properties. In addition, this compound displays potent activity against Gram-positive bacteria, with MIC values in the range of 1.48-11.86 µM. The data obtained herein suggest that promising anti-Mtb candidates may be developed via structural modification, and that further research is needed to explore other compounds.


Asunto(s)
Antituberculosos/química , Antituberculosos/farmacología , Mycobacterium tuberculosis/efectos de los fármacos , Oxazoles/química , Oxazoles/farmacología , Animales , Antituberculosos/síntesis química , Antituberculosos/farmacocinética , Diseño de Fármacos , Femenino , Células HEK293 , Halogenación , Humanos , Masculino , Ratones , Oxazoles/síntesis química , Oxazoles/farmacocinética , Ratas Sprague-Dawley , Tiadiazoles/síntesis química , Tiadiazoles/química , Tiadiazoles/farmacocinética , Tiadiazoles/farmacología , Tuberculosis Resistente a Múltiples Medicamentos/tratamiento farmacológico , Tuberculosis Resistente a Múltiples Medicamentos/microbiología
5.
Artículo en Chino | WPRIM (Pacífico Occidental) | ID: wpr-906278

RESUMEN

Objective:To investigate the chemical constituents and antioxidant activities of Violae Herba from the Violaceae. Method:The 5 kg of Violae Herba was refluxing extracted with 3 times the amount of 95% ethanol for three times, then the extracting solution was combined, filtrated, concentrated under vacuum to get the total extract. Seven corresponding fractions were eluted with petroleum ether, dichloromethane, dichloromethane-methanol (50∶1, 10∶1, 5∶1, 2∶1) and methanol by silica gel column chromatography (60-100 mesh) on the total extract. Each fraction was isolated and purified by normal phase silica gel column chromatography, octadecylsilane chemically bonded silica (ODS) column chromatography, Sephadex LH-20 column chromatography and preparative high performance liquid chromatography (HPLC), respectively. The structures of the obtained compounds were identified by spectroscopic methods of nuclear magnetic resonance (NMR), mass spectroscopy (MS) and infrared spectroscopy (IR). Meanwhile, some of these compounds isolated from Violae Herba were carried on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging experiment. Result:Fourteen compounds were isolated from the 95% ethanol extract of Violae Herba, including <italic>N</italic>-acetyl-1-ethyl ester glutamic acid (<bold>1</bold>), <italic>N</italic>-acetyl glutamic acid-1-ethyl-5-methyl ester (<bold>2</bold>), aurantiamide (<bold>3</bold>), <italic>rel</italic>-(2<italic>α</italic>,3<italic>β</italic>)-7-<italic>O</italic>-methylcedrusin (<bold>4</bold>), oleanolic acid (<bold>5</bold>), <italic>α</italic>-tocopherol-quinone (<bold>6</bold>), tectochrysin (<bold>7</bold>), isoscopoletin (<bold>8</bold>), esculetin (<bold>9</bold>), 24-ethylcholesta-4,24(28)<italic>Z</italic>-dien-3-one (<bold>10</bold>), stigmasta-4,25-dien-3-one (<bold>11</bold>), <italic>β</italic>-sitostenone (<bold>12</bold>), <italic>β</italic>-sitosterol (<bold>13</bold>), (24<italic>R</italic>)-3<italic>β</italic>-hydroxy-ethylcholest-5-en-7-one (<bold>14</bold>). Conclusion:Compound <bold>2</bold> is a new natural product, compounds <bold>1</bold>, <bold>4</bold>, <bold>6</bold>, <bold>7</bold>, <bold>10</bold>-<bold>12 </bold>are isolated from the genus <italic>Viola</italic> for the first time. Compound <bold>9</bold> has significant antioxidant activity, while compounds <bold>2</bold>, <bold>6 </bold>and<bold> 8</bold> have certain DPPH free radical scavenging activity.

6.
Acta Crystallogr C Struct Chem ; 74(Pt 2): 139-145, 2018 Feb 01.
Artículo en Inglés | MEDLINE | ID: mdl-29400327

RESUMEN

Three new manganese(II), lead(II) and cadmium(II) coordination complexes have been prepared by reaction of N-(1H-tetrazol-5-yl)cinnamamide (HNTCA) with divalent metal salts (MnCl2, PbCl2 and CdCl2) in a mixed-solvent system, affording mononuclear to trinuclear structures namely, bis(methanol-κO)bis[5-(3-phenylprop-2-enamido)-1H-1,2,3,4-tetrazol-1-ido-κ2N1,O]manganese(II), [Mn(C10H8N5O)2(CH3OH)2], (1), bis[µ-5-(3-phenylprop-2-enamido)-1H-1,2,3,4-tetrazol-1-ido]-κ3N1,O:N2;κ3N2:N1,O-bis{aqua[5-(3-phenylprop-2-enamido)-1H-1,2,3,4-tetrazol-1-ido-κ2N1,O]lead(II)}, [Pb2(C10H8N5O)4(H2O)2], (2), and hexakis[µ2-5-(3-phenylprop-2-enamido)-1H-1,2,3,4-tetrazol-1-ido-κ3N1,O:N2]tricadmium(II), [Cd3(C10H8N5O)6], (3). The structures of these three compounds reveal that the nature of the metal ions and the side groups of the organic building blocks have a significant effect on the structures of the coordination compounds formed. Intermolecular hydrogen bonds link the molecules into two-dimensional [complex (1)] and three-dimensional hydrogen-bonded networks. Complexes (2) and (3) show significant fluorescence, while complex (1) displays no fluorescence.

7.
J Lipid Res ; 57(5): 781-90, 2016 05.
Artículo en Inglés | MEDLINE | ID: mdl-27016726

RESUMEN

Long-chain fatty acid amides are signaling lipids found in mammals and other organisms; however, details of the metabolic pathways for the N-acylglycines and primary fatty acid amides (PFAMs) have remained elusive. Heavy-labeled precursor and subtraction lipidomic experiments in mouse neuroblastoma N18TG2 cells, a model cell line for the study of fatty acid amide metabolism, establish the biosynthetic pathways for the N-acylglycines and the PFAMs. We provide evidence that the N-acylglycines are formed by a long-chain specific glycine-conjugating enzyme, glycine N-acyltransferase-like 3 (GLYATL3). siRNA knockdown of GLYATL3 in the N18TG2 cells resulted in a decrease in the levels of the N-acylglycines and the PFAMs. This is the first report of an enzyme responsible for long-chain N-acylglycine production in cellula. The production of the PFAMs in N18TG2 cells was reported to occur by the oxidative cleavage of the N-acylglycines, as catalyzed by peptidylglycine α-amidating monooxygenase (PAM). siRNA knockdown of PAM resulted in an accumulation of [(13)C18]N-oleoylglycine and decreased levels of [(13)C18]oleamide when the N18TG2 cells were grown in the presence of [(13)C18]oleic acid. The addition of [1-(13)C]palmitate to the N18TG2 cell growth media led to the production of a family of [1-(13)C]palmitoylated fatty acid amides, consistent with the biosynthetic pathways detailed herein.


Asunto(s)
Aciltransferasas/fisiología , Ácidos Grasos/biosíntesis , Amidas/metabolismo , Animales , Línea Celular Tumoral , Técnicas de Silenciamiento del Gen , Lipogénesis , Ratones
8.
Acta Crystallogr C Struct Chem ; 71(Pt 7): 636-42, 2015 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-26146405

RESUMEN

Two new acylamide metal-organic frameworks (MOFs), based on mixed N- and O-donor ligands, with 4-connected topologies have been obtained, namely poly[[µ2-N(1),N(4)-bis(pyridin-3-yl)terephthalamide]bis(µ3-4,4'-oxydibenzoato)dizinc(II)], [Zn2(C14H8O5)2(C18H14N4O2)]n, (1), and poly[[(µ2-benzene-1,4-dicarboxylato)[µ2-N(4),N(4')-bis(pyridin-3-yl)-[1,1'-biphenyl]-4,4'-dicarboxamide]dicadmium(II)] dihydrate], {[Cd(C8H4O4)(C24H18N4O2)]·2H2O}n, (2). Complex (1) is a 4-connected CdSO4 net with no interpenetration, where the Zn(II) cation is regarded as a 4-connecting node with square geometry. Complex (2) is a 4-connected dia net with threefold interpenetration, where the Cd(II) cation acts as a 4-connecting node with tetrahedral geometry. The results of thermogravimetric and luminescence analyses are described in detail.


Asunto(s)
Cadmio/química , Complejos de Coordinación/química , Cristalografía por Rayos X , Enlace de Hidrógeno , Ligandos , Luminiscencia
9.
Biosci Biotechnol Biochem ; 78(7): 1242-5, 2014.
Artículo en Inglés | MEDLINE | ID: mdl-25229865

RESUMEN

Long-chain N-vanillyl-acylamides (LCNVAs) were generated from plant oils and vanillylamine (VA) by nucleophilic amidation without any catalytic reagents. The resulting LCNVAs varied according to the fatty acid composition of the plant oil used. Therefore, the LCNVAs contained in Capsicum oleoresins were products that were spontaneously generated from the oleoresin during storage.


Asunto(s)
Amidas/química , Aceites de Plantas/química , Aceite de Soja/química , Bencilaminas/química , Capsaicina/análogos & derivados , Capsaicina/química , Aceite de Oliva , Trioleína/química
10.
Artículo en Chino | WPRIM (Pacífico Occidental) | ID: wpr-574561

RESUMEN

Objective To synthesize the novel derivatives of 11-deoxyl glycyrrhetinic acid with high anti-inflammatory activities.Methods 11-Deoxylglycyrrhetinic acid was obtained by deoxidizing glycyrrhetinic acid with Zn(Hg)/HCl,and then a series of 11-deoxylglycyrrhetinic acid 30 acylamide derivatives were synthesized by coupling with R-Ar-isoxazole-methylamine.And the synthesized compounds were confirmed by the methods of IR,(()~1H-NMR),(()~(13)C-NMR),and MS.Two models were used to evaluate the preliminary anti-inflammatory activity of the compounds.Results The structures of all the new compound were identified by the spectra of IR,(()~1H-NMR),(()~(13)C-NMR),and MS.The compound 1,3,5 and 7 were proven to have a significant anti-inflammatory activity.Conclusion Some 30-acylamide derivatives of glycyrrhetinic acid have significant anti-inflammatory activities.

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