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1.
Chem Pharm Bull (Tokyo) ; 72(3): 294-297, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38462461

RESUMO

Aiming to synthesize a cyclic hexaamide, 4-bromo-3-(isobutylamino)benzoic acid was subjected to self-condensation reactions in the presence of either dichlorotriphenylphosphorane in 1,1,2,2-tetrachloroethane or tetrachlorosilane in pyridine. However, instead of the targeted cyclic hexaamide, the cyclic triamide and the cyclic tetraamide were obtained. The cyclic hexaamide was successfully synthesized via the self-condensation of the dimer, which was synthesized in five steps from 4-bromo-3-(isobutylamino)benzoic acid. A thorough screening of the self-condensation conditions was performed to improve the yield of the target macrocycle. In addition, the linear hexamer was synthesized by stepwise deprotection and condensation, and its cyclization afforded the cyclic hexaamide in good yield.


Assuntos
Ácido Benzoico , Ciclização
2.
Environ Sci Pollut Res Int ; 31(10): 15597-15610, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38300497

RESUMO

Low-molecular-weight aromatic acids (LWMAAs), a ubiquitous organic substance in natural systems, are important in controlling the environmental fate of potentially toxic metals. However, little is known about the effects of LWMAAs on the interactions between biochars and potentially toxic metals. Herein, the influences of three aromatic acids, including benzoic acid (BA), p-hydroxy benzoic acid (PHBA), and syringic acid (SA), on the adsorption of Cd2+ onto biochars generated at three different pyrolysis temperatures under acidic and neutral conditions were examined. Generally, the adsorption ability of biochars for Cd2+ improved with the increase of pyrolysis temperature, which was ascribed to the increased inorganic element contents (e.g., P, S, and Si) and aromaticity, increasing the complexation between mineral anions and metal ions, and the enhanced cation-π interaction. Interestingly, aromatic acids considerably inhibited the adsorption of Cd2+ onto biochars, which was mainly ascribed to multi-mechanisms, including competition of LWMAA molecules and metal ions for adsorption sites, the pore blocking effect, the weakened interaction between mineral anions and Cd2+ induced by the adsorbed aromatic acids, and the formation of water-soluble metal-aromatic acid complexes. Furthermore, the inhibitory effects of LWMAAs on Cd2+ adsorption intensively depended on the aromatic acid type and followed the order of SA > PHBA > BA. This trend was related to the differences in the physicochemical features (e.g., the octanol/water partition coefficient (log Kow) and molecular size) of diverse LMWAAs. The results of this study demonstrate that the effects of coexisting LMWAAs should not be ignored when biochars are applied in soil remediation and wastewater treatment.


Assuntos
Cádmio , Carvão Vegetal , Minerais , Cádmio/química , Adsorção , Ácido Benzoico , Água , Ânions , Íons
3.
Mikrochim Acta ; 191(3): 133, 2024 02 14.
Artigo em Inglês | MEDLINE | ID: mdl-38353782

RESUMO

Vascular endothelial growth factor (VEGF) is an indispensable element in many physiological processes, while alterations in its level in the circulating system are signs of pathology-associated diseases. Therefore, its precise and selective detection is critical for clinical applications to monitor the progression of the pathology. In this study, an optical immunoassay biosensor was developed as a model study for detecting recombinant VEGF165. The VEGF165 sample was purified from recombinant Kluyveromyces lactis GG799 yeast cells. Indirect ELISA was used during the detection, wherein iron oxide nanoparticles (FeNPs) were utilized to obtain optical signals. The FeNPs were synthesized in the presence of lactose p-amino benzoic acid (LpAB). VEGF165 antibody was conjugated to the LpAB-FeNPs through EDC/NHS chemistry to convert the iron oxide nanoparticles into VEGF165 specific probes. The specificity of the prepared system was tested in the presence of potential serum-based interferents (i.e., glucose, urea, insulin, C-reactive protein, and serum amyloid A), and validation studies were performed in a simulated serum sample. The proposed immunoassay showed a wide detection range (0.5 to 100 ng/mL) with a detection limit of 0.29 ng/mL. These results show that the developed assay could offer a sensitive, simple, specific, reliable, and high-throughput detection platform that can be used in the clinical diagnostics of VEGF.


Assuntos
Colorimetria , Fator A de Crescimento do Endotélio Vascular , Humanos , Fatores de Crescimento do Endotélio Vascular , Imunoensaio , Ácido Benzoico , Nanopartículas Magnéticas de Óxido de Ferro
4.
Biol Pharm Bull ; 47(2): 434-442, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38369342

RESUMO

Non-alcoholic steatohepatitis (NASH), which is on the rise due to the increasing obese population and changing lifestyles, causes fibrosis over time and carries the risk of progression to cirrhosis and hepatocellular carcinoma. However, there are no approved effective treatments for NASH. Recent studies suggest that increased lipid metabolism and reduced nitric oxide content are responsible for NASH; 3-amino-4-hydroxy benzoic acid (AHBA) was identified as an inhibitor for the phosphatase activity of soluble epoxy hydrolase, which in turn inhibits lipid metabolism and endothelial nitric oxide synthase activity. The aim of this study was to assess the efficacy of AHBA in a mouse model of NASH. NASH was induced in mice by streptozotocin administration and a high-fat diet loading. The efficacy of AHBA was determined by measuring liver function using serum and liver samples and conducting a morphological assessment. AHBA considerably attenuated the increase in the liver weight and alkaline phosphatase content, which occurred due to the progression of NASH. Hepatocellular steatosis, inflammatory cell infiltration, and hepatocellular ballooning of hepatocytes remained unaltered. In contrast, AHBA treatment significantly ameliorated the fibrotic alterations within liver tissue that were induced by the onset of NASH. These results demonstrate the potential of AHBA as a therapeutic pharmaceutical compound that can treat NASH.


Assuntos
Neoplasias Hepáticas , Hepatopatia Gordurosa não Alcoólica , Camundongos , Animais , Hepatopatia Gordurosa não Alcoólica/patologia , Fígado/metabolismo , Cirrose Hepática/tratamento farmacológico , Cirrose Hepática/complicações , Modelos Animais de Doenças , Dieta Hiperlipídica/efeitos adversos , Neoplasias Hepáticas/metabolismo , Ácido Benzoico/farmacologia , Ácido Benzoico/uso terapêutico , Ácido Benzoico/metabolismo , Camundongos Endogâmicos C57BL
5.
Eur J Med Chem ; 266: 116137, 2024 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-38237343

RESUMO

Present article is devoted to the purposeful search of novel anti-inflammatory agents among carboxyl-containing partially hydrogenated [1,2,4]triazolo[1,5-с]quinazolines and products of their tandem cyclization. It has been shown that target compound's could be obtained via interaction between [2-(3-R-1H-1,2,4-triazol-5-yl)phenyl]amines and oxo-containing carboxylic acids and their esters of various structure. The structures of synthesized compounds were verified by appropriate methods, the features of NMR-spectra patterns were discussed as well. The low predicted toxicity of obtained compounds has been estimated using in silico methods. In vivo study on the model of acute aseptic inflammation (carrageenan test) have been revealed that synthesized compounds expose anti-inflammatory activity in the range of 0.94-52.66%. 4-(2-(Ethoxycarbonyl)-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolin-5-yl)benzoic acid has been identified as most active compound. Additionally, the effects of some (2-R-5,6-dihydro[1,2,4]triazolo[1,5-c]quinazolin-5-yl)benzoic acids (compounds 3) on the levels of key inflammatory markers have been estimated. It has been shown that studied compounds decrease the level of neutrophils, COX-2, nitrotyrosine, IL-1b, C-reactive protein and increase level of eNOS. 4-(2-(Ethoxycarbonyl)-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolin-5-yl)benzoic acid (3.2) has been identified as compound with most expressed anti-inflammatory activity and significant effect on the levels of marker of inflammatory processes. Molecular docking study towards СОХ-1 and СОХ-2 has been conducted to substantiate possible mechanism of obtained compounds anti-inflammatory activity. It has been found that fixation of 4-(2-(ethoxycarbonyl)-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolin-5-yl)benzoic acid (3.2) molecule in active site of enzyme is outstandingly similar to the reference ligands. The essential value of carboxylic group for presence of anti-inflammatory activity has been estimated as result of SAR-analysis. It has been found that studied class of compounds is perspective for further structural modification aimed to the creation of novel anti-inflammatory agents.


Assuntos
Anti-Inflamatórios , Quinazolinas , Anti-Inflamatórios/farmacologia , Ácido Benzoico , Simulação de Acoplamento Molecular , Quinazolinas/farmacologia , Quinazolinas/química , Relação Estrutura-Atividade , Triazóis/química , Triazóis/farmacologia
6.
Chem Res Toxicol ; 37(2): 227-233, 2024 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-38241642

RESUMO

Electronic nicotine delivery systems (ENDS) are battery-powered devices introduced to the market as safer alternatives to combustible cigarettes. Upon heating the electronic liquid (e-liquid), aerosols are released, including several toxicants, such as volatile organic compounds (VOCs). Benzene has been given great attention as a major component of the VOCs group as it increases cancer risk upon inhalation. In this study, several basic e-liquids were tested for benzene emissions. The Aerosol Lab Vaping Instrument was used to generate aerosols from ENDS composed of different e-liquid combinations: vegetable glycerin (VG), propylene glycol (PG), nicotine (nic), and benzoic acid (BA). The tested mixtures included PG, PG + nic + BA, VG, VG + nic + BA, 30/70 PG/VG, and 30/70 PG/VG + nic + BA. A carboxen polydimethylsiloxane fiber for a solid-phase microextraction was placed in a gas cell to trap benzene emitted from a Sub-Ohm Minibox C device. Benzene was adsorbed on the fiber during the puffing process and for an extra 15 min until it reached equilibrium, and then it was determined using gas chromatography-mass spectrometry. Benzene was quantified in VG but not in PG or the 30/70 PG/VG mixtures. However, benzene concentration increased in all tested mixtures upon the addition of nicotine benzoate salt. Interestingly, benzene was emitted at the highest concentration when BA was added to PG. However, lower concentrations were found in the 30/70 PG/VG and VG mixtures with BA. Both VG and BA are sources of benzene. Enhanced emissions, however, are mostly noticeable when BA is mixed with PG and not VG.


Assuntos
Sistemas Eletrônicos de Liberação de Nicotina , Nicotina , Nicotina/análise , Benzeno/análise , Propilenoglicol/química , Glicerol/química , Aerossóis , Verduras , Ácido Benzoico
7.
Anal Chem ; 96(5): 2135-2141, 2024 02 06.
Artigo em Inglês | MEDLINE | ID: mdl-38252409

RESUMO

A facile route for exponential magnification of transconductance (gm) in an organic photoelectrochemical transistor (OPECT) is still lacking. Herein, photoresponsive hydrogen-bonded organic frameworks (PR-HOFs) have been shown to be efficient for gm magnification in a typical poly(ethylene dioxythiophene):poly(styrenesulfonate) OPECT. Specifically, 450 nm light stimulation of 1,3,6,8-tetrakis (p-benzoic acid) pyrene (H4TBAPy)-based HOF could efficiently modulate the device characteristics, leading to the considerable gm magnification over 78 times from 0.114 to 8.96 mS at zero Vg. In linkage with a DNA nanomachine-assisted steric hindrance amplification strategy, the system was then interfaced with the microRNA-triggered structural DNA evolution toward the sensitive detection of a model target microRNA down to 0.1 fM. This study first reveals HOFs-enabled efficient gm magnification in organic electronics and its application for sensitive biomolecular detection.


Assuntos
Ácido Benzoico , MicroRNAs , Hidrogênio , Polietileno , DNA
8.
Biophys Chem ; 306: 107172, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38183957

RESUMO

Benzoic acid (BA) is a microbe-inhibiting flavoring agent used extensively as an additive in foods, pharmaceuticals, and hygiene and cosmetic products. The level of BA in foodstuffs prescribed by world bodies and governmental agencies is assumed to be safe so as to prevent adverse health effects. The safety level of BA is however controversial, and whether different conditions of its use would be generally regarded as safe (GRAS) has been rarely determined. In the quest of how food additives affect the structure and conformation of proteins, this study evaluates the interaction of BA with an intrinsically disordered protein (IDP) at pH 4.2 that matches the pH conditions applicable for the commercial use of benzoate preservatives, and examines its structural transformation by NMR, fluorescence, and high-resolution microscopy. The interaction with BA transforms the protein to a denatured aggregated mesophase that undergoes reconfiguration to yield rigid amyloid fibrils. Significantly, fibrils are observed even with 0.1 mM BA while the recommended level of its use as a preservative is in the 0.4-8 mM range. The discussion refrains from safety comments with no projection of the BA level that could be GRAS.


Assuntos
Ácido Benzoico , Proteínas Intrinsicamente Desordenadas , Ácido Benzoico/farmacologia , Amiloide/química , Proteínas Amiloidogênicas , Preparações Farmacêuticas
9.
Genome Biol Evol ; 16(2)2024 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-38290535

RESUMO

We investigated the flowering plant salicylic acid methyl transferase (SAMT) enzyme lineage to understand the evolution of substrate preference change. Previous studies indicated that a single amino acid replacement to the SAMT active site (H150M) was sufficient to change ancestral enzyme substrate preference from benzoic acid to the structurally similar substrate, salicylic acid (SA). Yet, subsequent studies have shown that the H150M function-changing replacement did not likely occur during the historical episode of enzymatic divergence studied. Therefore, we reinvestigated the origin of SA methylation preference here and additionally assessed the extent to which epistasis may act to limit mutational paths. We found that the SAMT lineage of enzymes acquired preference to methylate SA from an ancestor that preferred to methylate benzoic acid as previously reported. In contrast, we found that a different amino acid replacement, Y267Q, was sufficient to change substrate preference with others providing small positive-magnitude epistatic improvements. We show that the kinetic basis for the ancestral enzymatic change in substate preference by Y267Q appears to be due to both a reduced specificity constant, kcat/KM, for benzoic acid and an improvement in KM for SA. Therefore, this lineage of enzymes appears to have had multiple mutational paths available to achieve the same evolutionary divergence. While the reasons remain unclear for why one path was taken, and the other was not, the mutational distance between ancestral and descendant codons may be a factor.


Assuntos
Metiltransferases , Ácido Salicílico , Metiltransferases/química , Metiltransferases/genética , Metiltransferases/metabolismo , Sequência de Aminoácidos , Ácido Salicílico/metabolismo , Plantas , Ácido Benzoico/metabolismo , Aminoácidos/genética , Evolução Molecular , Especificidade por Substrato
10.
Environ Res ; 242: 117805, 2024 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-38042518

RESUMO

The present study involved monitoring the distribution of two widely consumed parabens (methyl paraben (MeP) and butyl paraben (BuP)) and their transformation products in indoor dust from different categories of settlement (urban, semi-urban, rural, and tribal homes). The results revealed a prevalent occurrence of parabens in all the settlement categories. A non-normal distribution pattern for MeP and BuP levels across the sampling sites was noted. While comparing the residence time of parabens in dust samples, it was found that the half-lives of the analytes were greater in the dust from urban (MeP t1/2: 47.510 h; BuP t1/2: 22.354 h) and rural (MeP t1/2: 27.725 h and BuP t1/2: 31.500 h) areas. The presence of paraben metabolites, such as hydroxy methylparaben (OH-MeP), para hydroxy benzoic acid (p-HBA), and benzoic acid (BA) in dust samples supports their transformation within indoor spaces. The average daily intake of parabens through dust ingestion and dermal absorption by children was higher than adults. BuP was the prime contributor (>85%) to the total estradiol equivalency quotient (tEEQ) in all the settlement categories.


Assuntos
Poeira , Parabenos , Adulto , Criança , Humanos , Parabenos/análise , Ácido Benzoico , Exposição Ambiental/análise
11.
Spectrochim Acta A Mol Biomol Spectrosc ; 308: 123668, 2024 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-38029599

RESUMO

Second near-infrared (NIR-II,1000 âˆ¼ 1700 nm) therapeutic window presents an increased tissue penetration and elevated maximal permissible exposure in the application of photothermal therapy (PTT). However, the lack of NIR-II photothermal conversion agents (PCAs) limit their further development. In this work, we rationally designed and successfully developed three novel indolium-like heptamethine cyanine dyes (NFs) by installing N,N-diethylamino on the terminal ends of a conjugated polyene backbone and replacing the middle chlorine atom with o-mercapto benzoic acid and p-mercapto benzoic acid. Notably, NF2 with stronger rotating group encapsulated in organic nanoparticles (NF2 NPs) exhibited high photothermal conversion efficiency (PCE), which could come up to (61.3 %). Then we conducted serial experiments to further investigate PTT capability of NF2 NPs 4 T1 cell line and nude mice bearing 4 T1 tumor. As expected, the resulting NF2 NPs presented the excellent photothermal conversion ability and superb PTT effect both in vivo and in vitro. This study will inspire more work for future design and clinical applications of NIR-II therapeutic agents.


Assuntos
Nanopartículas , Neoplasias , Animais , Camundongos , Fototerapia , Camundongos Nus , Neoplasias/tratamento farmacológico , Ácido Benzoico , Linhagem Celular Tumoral
12.
Bioorg Chem ; 143: 106983, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38016396

RESUMO

RNA polymerase is an essential enzyme involved in bacterial transcription, playing a crucial role in RNA synthesis. However, it requires the association with sigma factors to initiate this process. In our previous work, we utilized a structure-based drug discovery approach to create benzoyl and benzyl benzoic acid compounds. These compounds were designed based on the amino acid residues within the key binding site of sigma factors, which are crucial for their interaction with RNA polymerase. By inhibiting bacterial transcription, these compounds exhibited notable antimicrobial activity, and we coined them as sigmacidins to highlight their resemblance to sigma factors and the benzoic acid structure. In this study, we further modified the compound scaffolds and developed a series of sulfonamidyl benzoic acid derivatives. These derivatives displayed potent antimicrobial activity, with minimum inhibitory concentrations (MICs) as low as 1 µg/mL, demonstrating their efficacy against bacteria. Furthermore, these compounds demonstrated low cytotoxicity, indicating their potential as safe antimicrobial agents. To ascertain their mechanism of action in interfering with bacterial transcription, we conducted biochemical and cellular assays. Overall, this study showcases the effectiveness of sulfonamidyl benzoic acid derivatives as antimicrobial agents by targeting protein-protein interactions involving RNA polymerase and sigma factors. Their strong antimicrobial activity and low cytotoxicity implicate their potential in combating antibiotic-resistant bacteria.


Assuntos
Antibacterianos , Anti-Infecciosos , Antibacterianos/farmacologia , Antibacterianos/química , Fator sigma/metabolismo , RNA Polimerases Dirigidas por DNA/metabolismo , Bactérias/metabolismo , Ácido Benzoico/farmacologia , Testes de Sensibilidade Microbiana
13.
Int J Biol Macromol ; 256(Pt 1): 128433, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38008141

RESUMO

With the exponentially increase of dye pollutants, the purification of dye wastewater has been an urgent ecological problem. As a novel type of porous adsorbent, metal-organic frameworks still face challenges in recyclability, agglomeration, and environmentally unfriendly synthesis. Herein, MOF-525 was in-situ growth onto the surface of the chitosan (CS) beads to fabricate MOF-525@CS aerogel. CS was utilized as substrate to uniformly disperse MOF-525, thereby significantly mitigating agglomeration and improving recyclability of MOF-525. The characterization results shown that MOF-525@CS aerogel had a high specific surface area of 103.0 m2·g-1, and MOF-525 was uniformly distributed in the 3D porous structure of CS, and the presence of benzoic acid was detected. The MOF-525@CS aerogel had a remarkable adsorption capacity of 1947 mg·g-1 for Congo red, which is greater than the sum of its parts. MOF-525@CS aerogel also inherited the rapid adsorption ability of MOF-525, removing 80 % of Congo red within 600 min. Such excellent adsorption performance can be attributed to the benzoic acid trapped by CS via CN band to enhance the π-π stacking interactions. Additionally, the utilization of benzoic acid makes the synthesis process of MOF-525@CS aerogel more environmentally friendly. The high-efficient MOF-525@CS aerogel is a competitive candidate for dye pollution adsorption.


Assuntos
Quitosana , Estruturas Metalorgânicas , Poluentes Químicos da Água , Vermelho Congo/química , Quitosana/química , Benzeno , Poluentes Químicos da Água/química , Cinética , Água , Adsorção , Ácido Benzoico
14.
Chemosphere ; 349: 140898, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38070610

RESUMO

Influence of the cosolvent on the sorption of organic acids on biochar has not been well understood. For this purpose, the sorption (log Km, L kg-1) of three aromatic acids (benzoic acid (BA, pKa = 4.20), 1-naphthoic acid (1-NAPA, pKa = 3.70), and 9-anthroic acid (9-ANTA, pKa = 3.65) was evaluated as a function of methanol volume fraction (fc = 0.0, 0.25, and 0.5), liquid pH (2.5 and 7.0), ionic composition (CaCl2 and KCl) and ionic strength (0.005 M, 0.5 M, and 1 M CaCl2). A giant Miscanthus-derived biochar (ZPC of 2.86) was used as the sorbent. For all solutes, the sorption coefficients (log Km) measured at pH 2.5 (i.e., pH < pKa) tended to decrease with increasing fc, as expected from the cosolvency model, while the result obtained at pH 7.0 was not fully explained by the same model. The log Km of 1-NAPA in the CaCl2 system was always greater than in the KCl system (p < 0.05) and the impact became pronounced at high pH (>pKa) with increasing fc. Increasing the Ca2+ concentration at fc = 0.0 (from 0.005 M to 1 M) enhanced the value by 0.32 log unit of Km. These phenomena indicate a significant role of dissolved Ca2+ in the liquid phase, most likely due to the formation of cation bridges between aromatic carboxylates and the biochar surface (i.e., [R-COO--Ca2+]-{Biochar-}). A decrease in the dielectric constant of the methanol mixture could fortify the formation of this bridge. Regardless of the degree of cosolvency power (σ), as the number of aromatic rings of solutes increases, Km decreases in the order BA > 1-NAPA > 9-ANTA, where fc = 0.0. In conclusion, the sorption potential of biochar can be significantly weakened by increasing pH and fc, and in the absence of a divalent cation.


Assuntos
Ácido Benzoico , Metanol , Ácido Benzoico/química , Metanol/química , Cloreto de Cálcio , Carvão Vegetal , Soluções , Adsorção
15.
Am J Physiol Lung Cell Mol Physiol ; 326(2): L175-L189, 2024 02 01.
Artigo em Inglês | MEDLINE | ID: mdl-38147795

RESUMO

Data on the relationship between electronic cigarettes (ECs) and SARS-CoV-2 infection are limited and contradictory. Our objectives were to investigate the impact of EC aerosols on SARS-CoV-2 infection of human bronchial epithelial cells and identify the causative chemical(s). Fully differentiated human bronchial epithelial tissues (hBETs) were exposed at the air-liquid interface (ALI) to aerosols produced from JUUL "Virginia Tobacco" and BLU ECs, as well as nicotine, propylene glycol (PG), vegetable glycerin (VG), and benzoic acid, and infection was then evaluated with SARS-CoV-2 pseudoparticles. Pseudoparticle infection of hBETs increased with aerosols produced from PG/VG, PG/VG plus nicotine, or BLU ECs; however, JUUL EC aerosols did not increase infection compared with controls. Increased infection in PG/VG alone was due to enhanced endocytosis, whereas increased infection in PG/VG plus nicotine or in BLU ECs was caused by nicotine-induced elevation of the aerosol's pH, which correlated with increased transmembrane protease, serine 2 (TMPRSS2) activity. Notably, benzoic acid in JUUL aerosols mitigated the enhanced infection caused by PG/VG or nicotine, offering protection that lasted for at least 48 h after exposure. In conclusion, the study demonstrates that EC aerosols can impact susceptibility to SARS-CoV-2 infection depending on their specific ingredients. PG/VG alone or PG/VG plus nicotine enhanced infection through different mechanisms, whereas benzoic acid in JUUL aerosols mitigated the increased infection caused by certain ingredients. These findings highlight the complex relationship between ECs and SARS-CoV-2 susceptibility, emphasizing the importance of considering the specific aerosol ingredients when evaluating the potential effects of ECs on infection risk.NEW & NOTEWORTHY Data on the relationship between electronic cigarettes (ECs) and SARS-CoV-2 infection are limited and contradictory. We investigated the impact of EC aerosols and their ingredients on SARS-CoV-2 infection of human bronchial epithelial cells. Our data show that specific ingredients in EC aerosols impact the susceptibility to SARS-CoV-2 infection. Propylene glycol (PG)/vegetable glycerin (VG) alone or PG/VG plus nicotine enhanced infection through different mechanisms, whereas benzoic acid in JUUL aerosols mitigated the increased infection caused by these ingredients.


Assuntos
COVID-19 , Sistemas Eletrônicos de Liberação de Nicotina , Vaping , Humanos , Nicotina , Glicerol , SARS-CoV-2 , Aerossóis e Gotículas Respiratórios , Propilenoglicol , Ácido Benzoico
16.
Int J Biol Macromol ; 259(Pt 1): 129096, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38159699

RESUMO

The current study created three novel chitosan derivatives named BACS, PIBACS, and MHBACS by grafting benzoic acid (BA), p-isopropyl benzoic acid (PIBA), and m-hydroxybenzoic acid (MHBA) onto chitosan (CS). The structures of the derivatives were investigated using infrared spectroscopy (FT-IR) and nuclear magnetic resonance (13C NMR). The derivatives were discovered to be 45.06 %-60.49 % substituted using elemental analysis (EA). Based on the findings of in vitro antioxidant experiments (hydroxyl radical scavenging activity, superoxide anion radical scavenging activity, and DPPH radical scavenging activity), all of the derivatives had a higher hydroxyl radical scavenging activity than the chitosan raw material. MHBACS scavenged (31.02 ± 0.90)% of hydroxyl radicals at 0.5 mg/mL, 28.69 % more than chitosan raw. The derivatives scavenged more superoxide anion radicals than the chitosan feedstock at a particular concentration. For instance, at a test dose of 0.2 mg/mL, the scavenging rate of MHBACS on superoxide anion radicals was 7.75 % greater than that of chitosan raw materials. DPPH radical scavenging activity, on the other hand, was not as competent as chitosan feedstock. The growth rate approach was used to assess the potential of the three derivatives to inhibit the development of four phytopathogenic fungi. Chitosan derivatives have better antifungal efficacy than chitosan raw materials. PIBACS, MHBACS, BACS, and Wuyiencin inhibited Phytophthora capsici by (98.03 ± 1.95)%, (81.73 ± 1.63)%, (66.38 ± 1.81)%, and (93.01 ± 2.69)%, respectively, at 1.0 mg/mL. PIBACS had a higher inhibitory impact on Phytophthora capsici than the positive control. Based on the evidence presented above, it is reasonable to conclude that the addition of benzoic acid molecules increased the antioxidant and antifungal capabilities of chitosan.


Assuntos
Antioxidantes , Quitosana , Antioxidantes/farmacologia , Antioxidantes/química , Quitosana/química , Antifúngicos/farmacologia , Antifúngicos/química , Ácido Benzoico , Espectroscopia de Infravermelho com Transformada de Fourier , Superóxidos/química , Radical Hidroxila/química
17.
Toxins (Basel) ; 15(12)2023 12 09.
Artigo em Inglês | MEDLINE | ID: mdl-38133197

RESUMO

Ascochyta blight, caused by Ascochyta fabae, poses a significant threat to faba bean and other legumes worldwide. Necrotic lesions on stems, leaves, and pods characterize the disease. Given the economic impact of this pathogen and the potential involvement of secondary metabolites in symptom development, a study was conducted to investigate the fungus's ability to produce bioactive metabolites that might contribute to its pathogenicity. For this investigation, the fungus was cultured in three substrates (Czapek-Dox, PDB, and rice). The produced metabolites were analyzed by NMR and LC-HRMS methods, resulting in the dereplication of seven metabolites, which varied with the cultural substrates. Ascochlorin, ascofuranol, and (R)-mevalonolactone were isolated from the Czapek-Dox extract; ascosalipyrone, benzoic acid, and tyrosol from the PDB extract; and ascosalitoxin and ascosalipyrone from the rice extract. The phytotoxicity of the pure metabolites was assessed at different concentrations on their primary hosts and related legumes. The fungal exudates displayed varying degrees of phytotoxicity, with the Czapek-Dox medium's exudate exhibiting the highest activity across almost all legumes tested. The species belonging to the genus Vicia spp. were the most susceptible, with faba bean being susceptible to all metabolites, at least at the highest concentration tested, as expected. In particular, ascosalitoxin and benzoic acid were the most phytotoxic in the tested condition and, as a consequence, expected to play an important role on necrosis's appearance.


Assuntos
Fabaceae , Toxinas Biológicas , Vicia faba , Fabaceae/microbiologia , Vicia faba/microbiologia , Verduras , Produtos Agrícolas , Ácido Benzoico , Extratos Vegetais
18.
Anal Methods ; 15(45): 6229-6238, 2023 11 23.
Artigo em Inglês | MEDLINE | ID: mdl-37943077

RESUMO

To monitor benzoic acid (BA) residues in liquid food samples, a monoclonal antibody (mAb)-based lateral flow immunoassay (LFA) was developed in this study. First, 2-aminobenzoic acid (2-AA), 3-aminobenzoic acid (3-AA), and 4-aminobenzoic acid (4-AA) were conjugated to BSA and used as immunogens. After cell fusion, mAb 6D8 from 4-AA-BSA performed best with an IC50 value of 0.21 mg L-1 using 3-AA-OVA as a heterogeneous antigen, which represented a 3.4-fold improvement compared with the homogeneous antigen 4-AA-BSA. Subsequently, eight kinds of CGNPs with sizes varying from 20.94 nm to 90.00 nm were synthesized for screening the suitable size to develop a sensitive LFA. Finally, a sensitive LFA based on colloidal gold (23.27 nm) nanoparticles was developed for screening BA with a cut-off value of 4 mg L-1, which could meet the requirement of BA detection in milk, Fanta, Sprite, Coca-Cola, and Smart samples.


Assuntos
Anticorpos Monoclonais , Nanopartículas , Ácido Benzoico , Imunoensaio , Antígenos
19.
Int J Mol Sci ; 24(19)2023 Sep 27.
Artigo em Inglês | MEDLINE | ID: mdl-37834088

RESUMO

We designed 0D, 1D, and 2D supramolecular assemblies made of diaryliodonium salts (functioning as double σ-hole donors) and carboxylates (as σ-hole acceptors). The association was based on two charge-supported halogen bonds (XB), which occurred between IIII sites of the iodonium cations and the carboxylate anions. The sequential introduction of the carboxylic groups in the aryl ring of the benzoic acid added a dimension to the 0D supramolecular organization of the benzoate, which furnished 1D-chained and 2D-layered structures when terephthalate and trimesate anions, correspondingly, were applied as XB acceptors. The structure-directing XB were studied using DFT calculations under periodic boundary conditions and were followed by the one-electron-potential analysis and the Bader atoms-in-molecules topological analysis of electron density. These theoretical methods confirmed the existence of the XB and verified the philicities of the interaction partners in the designed solid-state structures.


Assuntos
Ácidos Carboxílicos , Halogênios , Halogênios/química , Ânions , Teoria da Densidade Funcional , Ácido Benzoico
20.
Appl Microbiol Biotechnol ; 107(24): 7451-7462, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37851105

RESUMO

Benzoic acid decarboxylases offer an elegant alternative to CO2 fixation by reverse reaction-carboxylation, which is named the bio-Kolbe-Schmitt reaction, but they are unfavorable to carboxylation. Enhancing the carboxylation efficiency of reversible benzoic acid decarboxylases is restricted by the unexplained carboxylation mechanisms. The direction of reversible enzyme catalytic reactions depends on whether catalytic residues at the active center of the enzyme are protonated, which is subjected by the pH. Therefore, the forward and reverse reactions could be separated at different pH values. Reversible 2,3-dihydroxybenzoate acid decarboxylase undergoes decarboxylation at pH 5.0 and carboxylation at pH 8.6. However, it is unknown whether the interaction of enzymes with substrates and products in the forward and reverse reactions can be exploited to improve the catalytic activity of reversible enzymes in the unfavorable direction. Here, we identify a V-shaped tunnel of 2,3-dihydroxybenzoic acid decarboxylase from Aspergillus oryzae (2,3-DHBD_Ao) through which the substrate travels in the enzyme, and demonstrate that the side chain conformation of a tyrosine residue controls the entry and exit of substrate/product during reversible reactions. Together with the kinetic studies of the mutants, it is clarified that interactions between substrate/product traveling through the enzyme tunnel in 2,3-DHBD_Ao are direction-dependent. These results enrich the understanding of the interactions of substrates/products with macromolecular reversible enzymes in different reaction directions, thereby demonstrating a possible path for engineering decarboxylases with higher carboxylation efficiency. KEY POINTS: • The residue Trp23 of 2,3-DHBD_Ao served as a switch to control the entry and exit of catechol • A V-shaped tunnel of 2,3-DHBD_Ao for decarboxylation and carboxylation reactions was identified • The results provide a promising strategy for engineering decarboxylases with direction-dependent residues inside the substrate/product traveling tunnel of the enzyme.


Assuntos
Carboxiliases , Cinética , Carboxiliases/metabolismo , Catálise , Ácido Benzoico , Especificidade por Substrato
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