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1.
Environ Res ; 246: 118162, 2024 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-38218517

RESUMO

This study investigated the application of adsorption with activated carbons (ACs) and photodegradation to reduce the concentration of triclosan (TCS) in aqueous solutions. Concerning adsorption, ACs (Darco, Norit, and F400) were characterised and batch experiments were performed to elucidate the effect of pH on equilibrium. The results showed that at pH = 7, the maximum adsorption capacity of TCS onto the ACs was 18.5 mg g-1 for Darco, 16.0 mg g-1 for Norit, and 15.5 mg g-1 for F400. The diffusional kinetic model allowed an adequate interpretation of the experimental data. The effective diffusivity varied and increased with the amount of TCS adsorbed, from 1.06 to 1.68 × 10-8 cm2 s-1. In the case of photodegradation, it was possible to ensure that the triclosan molecule was sensitive to UV light of 254 nm because the removal was over 80 % using UV light. The removal of TCS increased in the presence of sulfate radicals. It was possible to identify 2,4-dichlorophenol as one of the photolytic degradation products of triclosan, which does not represent an environmental hazard at low concentrations of triclosan in water. These results confirm that the use of AC Darco, Norit, and F400 and that photodegradation processes with UV light and persulfate radicals are effective in removing TCS from water, reaching concentration levels that do not constitute a risk to human health or environmental hazard. Both methods effectively eliminate pollutants with relatively easy techniques to implement.


Assuntos
Triclosan , Poluentes Químicos da Água , Humanos , Triclosan/química , Carvão Vegetal/química , Adsorção , Fotólise , Água , Poluentes Químicos da Água/análise
2.
Colloids Surf B Biointerfaces ; 231: 113542, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37717312

RESUMO

The presence of bacterial biofilms has presented a significant challenge to human health. This study presents the development of biofilm microenvironment-responsive polymeric micelles as a novel approach to address the challenges posed by bacterial biofilms. These micelles are composed of two key components: a zwitterionic component, inspired by protein isoelectric points, containing balanced quantities of primary amines and carboxylic groups that undergo a positive charge transformation in acidic microenvironments, and a hydrophobic triclosan conjugate capable of releasing triclosan in the presence of bacterial lipases. Through the synergistic combination of pH-responsiveness and lipase-responsiveness, we have significantly improved drug penetration into biofilms and enhanced its efficacy in killing bacteria. With their remarkable drug-loading capacity and the ability to specifically target and eliminate bacteria within biofilms, these zwitterionic polymeric micelles hold great promise as an effective alternative for treating biofilm-associated infections. Their unique properties enable efficient drug delivery and heightened effectiveness against biofilm-related infections.


Assuntos
Anti-Infecciosos , Triclosan , Humanos , Micelas , Triclosan/farmacologia , Triclosan/química , Antibacterianos/farmacologia , Antibacterianos/química , Portadores de Fármacos/química , Concentração de Íons de Hidrogênio , Anti-Infecciosos/farmacologia , Biofilmes , Polímeros/farmacologia , Polímeros/química
3.
Chemosphere ; 337: 139377, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37402425

RESUMO

In this study, the selective adsorption of aromatic compounds on mesoporous MIL-53(Al) was investigated, and followed the order: Biphenyl (Biph) > Triclosan (TCS) > Bisphenol A (BPA) > Pyrogallol (Pyro) > Catechol (Cate) > Phenol (Phen), and exhibited high selectivity toward TCS in binary compounds. In addition to hydrophobicity and hydrogen bonding, π-π interaction/stacking predominated, and more evidently with double benzene rings. TCS-containing halogens could increase π interaction on the benzene rings via forming Cl-π stacking with MIL-53(Al). Moreover, site energy distribution confirmed that complementary adsorption mainly occurred in the Phen/TCS system, as evidenced by ΔQpri (the decreased solid-phase TCS concentration of the primary adsorbate) < Qsec (the solid-phase concentrations of the competitor (Phen)). In contrast, competitive sorption occurred in the BPA/TCS and Biph/TCS systems within 30 min due to ΔQpri = Qsec, followed by substitution adsorption in the BPA/TCS system, but not for the Biph/TCS system, likely attributed to the magnitude of energy gaps (Eg) and bond energy of TCS (1.80 eV, 362 kJ/mol) fallen between BPA (1.74 eV, 332 kJ/mol) and Biph (1.99 eV, 518 kJ/mol) according to the density-functional theory of Gaussian models. Biph with a more stable electronic homeostasis than TCS lead to the occurrence of substitution adsorption in the TCS/BPA system, but not in the TCS/Biph system. This study provides insight into the mechanisms of different aromatic compounds on MIL-53(Al).


Assuntos
Benzeno , Triclosan , Adsorção , Fenóis/química , Fenol , Triclosan/química , Compostos Benzidrílicos
4.
Sci Total Environ ; 880: 163290, 2023 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-37030274

RESUMO

Microplastics (MP) have been recently identified as emerging water contaminants in worldwide. Owing to its physicochemical properties, MP have been considered as a vector of other micropollutants and may affect their fate and ecological toxicity in the water environment. In this study, triclosan (TCS), which is a widely-used bactericide, and three frequently found types of MP (PS-MP, PE-MP, and PP-MP) were investigated. The adsorption behavior of TCS on MP was investigated by the effect of reaction time, initial concentration of TCS, and other water chemistry factors. Elovich model and Temkin model are the most fitted well with kinetics and adsorption isotherms, respectively. The maximum TCS adsorption capacities were calculated for PS-MP (9.36 mg/g), PP-MP (8.23 mg/g), and PE-MP (6.47 mg/g). PS-MP had higher affinity to TCS owing to hydrophobic and π-π interaction. The TCS adsorption on PS-MP was inhibited by decreasing concentrations of cations, and increasing concentration of anion, pH, and NOM concentration. At pH 10, only 0.22 mg/g of adsorption capacity was obtained because of the isoelectric point (3.75) of PS-MP and pKa (7.9) of TCS. And almost no TCS adsorption occurred at NOM concentration of 11.8 mg/L. Only PS-MP had no acute toxic effect on D. magna, whereas TCS showed acute toxicity (EC50,24h of TCS = 0.36 ± 0.4 mg/L). Although survival rate increased when TCS with PS-MP due to lower the TCS concentration in solution via adsorption, PS-MP was observed in intestine and body surface of D. magna. Our findings can contribute to understanding the combined potential effects of MP fragment and TCS to aquatic biota.


Assuntos
Triclosan , Poluentes Químicos da Água , Microplásticos/química , Triclosan/toxicidade , Triclosan/química , Plásticos/química , Adsorção , Antibacterianos , Poluentes Químicos da Água/análise
5.
Int J Mol Sci ; 24(8)2023 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-37108083

RESUMO

Cost-effective therapy of neglected and tropical diseases such as malaria requires everlasting drug discovery efforts due to the rapidly emerging drug resistance of the plasmodium parasite. We have carried out computational design of new inhibitors of the enoyl-acyl carrier protein reductase (ENR) of Plasmodium falciparum (PfENR) using computer-aided combinatorial and pharmacophore-based molecular design. The Molecular Mechanics Poisson-Boltzmann Surface Area (MM-PBSA) complexation QSAR model was developed for triclosan-based inhibitors (TCL) and a significant correlation was established between the calculated relative Gibbs free energies of complex formation (∆∆Gcom) between PfENR and TCL and the observed inhibitory potencies of the enzyme (IC50exp) for a training set of 20 known TCL analogues. Validation of the predictive power of the MM-PBSA QSAR model was carried out with the generation of 3D QSAR pharmacophore (PH4). We obtained a reasonable correlation between the relative Gibbs free energy of complex formation ∆∆Gcom and IC50exp values, which explained approximately 95% of the PfENR inhibition data: pIC50exp=-0.0544×∆∆Gcom+6.9336,R2=0.95. A similar agreement was established for the PH4 pharmacophore model of the PfENR inhibition (pIC50exp=0.9754×pIC50pre+0.1596, R2=0.98). Analysis of enzyme-inhibitor binding site interactions suggested suitable building blocks to be used in a virtual combinatorial library of 33,480 TCL analogues. Structural information derived from the complexation model and the PH4 pharmacophore guided us through in silico screening of the virtual combinatorial library of TCL analogues to finally identify potential new TCL inhibitors effective at low nanomolar concentrations. Virtual screening of the library by PfENR-PH4 led to a predicted IC50pre value for the best inhibitor candidate as low as 1.9 nM. Finally, the stability of PfENR-TCLx complexes and the flexibility of the active conformation of the inhibitor for selected top-ranking TCL analogues were checked with the help of molecular dynamics. This computational study resulted in a set of proposed new potent inhibitors with predicted antimalarial effects and favourable pharmacokinetic profiles that act on a novel pharmacological target, PfENR.


Assuntos
Antimaláricos , Triclosan , Triclosan/farmacologia , Triclosan/química , Plasmodium falciparum , Proteína de Transporte de Acila , Enoil-(Proteína de Transporte de Acila) Redutase (NADH)/química , Farmacóforo , Simulação de Dinâmica Molecular , Antimaláricos/farmacologia , Antimaláricos/química , Relação Quantitativa Estrutura-Atividade , Simulação de Acoplamento Molecular
6.
Water Sci Technol ; 87(5): 1072-1081, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36919734

RESUMO

This study aims to elucidate interaction of organics with microplastics in a comparative manner via the use of two model compounds (i.e., triclosan (TCS) and malachite green (MG)) having different physicochemical properties, onto polyethylene (PE). TCS, is hydrophobic with low solubility, while MG is hydrophilic with high aqueous solubility. Kinetic studies indicate faster sorption (teq = 24 h) and equilibrium studies show much higher capacity (qe = 6,921 µg/g) for TCS, when compared to those of MG (teq = 5 d, qe = 221 µg/g). While pseudo-kinetic model fits sorption of both organics to PE, equilibrium isotherms as well as the results on effect of particle size and pH indicate dissimilar sorption mechanisms. Considering pHPZC = 2, observation of favourable sorption of TCS in acidic regions and sorption being unaffected by particle size was explained by TCS sorption to be dominated by hydrophobic interactions in amorph regions of PE. Higher removal of MG was observed at lower surface charge of PE, and a clear favourable impact of surface area on MG sorptive capacity pointed to the presence of non-specific van der Waals type interactions on the surface of PE. Mechanistic evaluations presented here contribute to our understanding of interaction of MPs with organics in aquatic ecosystems.


Assuntos
Triclosan , Poluentes Químicos da Água , Polietileno/química , Microplásticos/química , Plásticos , Triclosan/química , Cinética , Ecossistema , Adsorção , Poluentes Químicos da Água/química
7.
Water Res ; 233: 119736, 2023 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-36801581

RESUMO

Recently, increased production and consumption of disinfectants such as triclosan (TCS) and triclocarban (TCC) have led to massive pollution of the environment, which draws global concern over the potential risk to aquatic organisms. However, the olfactory toxicity of disinfectants in fish remains elusive to date. In the present study, the impact of TCS and TCC on the olfactory capacity of goldfish was assessed by neurophysiological and behavioral approaches. As shown by the reduced distribution shifts toward amino acid stimuli and hampered electro-olfactogram responses, our results demonstrated that TCS/TCC treatment would cause deterioration of the olfactory ability of goldfish. Our further analysis found that TCS/TCC exposure suppressed the expression of olfactory G protein-coupled receptors in the olfactory epithelium, restricted the transformation of odorant stimulation into electrical responses by disturbing the cAMP signaling pathway and ion transportation, and induced apoptosis and inflammation in the olfactory bulb. In conclusion, our results demonstrated that an environmentally realistic level of TCS/TCC would weaken the olfactory capacity of goldfish by constraining odorant recognition efficiency, disrupting olfactory signal generation and transduction, and disturbing olfactory information processing.


Assuntos
Carbanilidas , Desinfetantes , Triclosan , Animais , Triclosan/toxicidade , Triclosan/química , Carpa Dourada , Odorantes , Carbanilidas/química , Transdução de Sinais
8.
Environ Technol ; 44(8): 1099-1113, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34649467

RESUMO

The contamination of the aquatic environment with emerging micro-pollutants is a serious global concern. The aim of this investigation was to synthesize novel functionalized material (BNAPTES) precursor to natural bentonite in a single pot facile synthetic route. The material was utilized for efficient and selective removal of tetracycline (TC) and triclosan (TCS) in aqueous wastes. The grafting of silane was confirmed with the FT-IR (Fourier Transform Infra-Red) analysis and the EDX (Energy Dispersive X-ray) analysis showed the incorporation of amino group with the bentonite. The structural changes of clay due to silane grafting were studied with the help of XRD (X-ray Diffraction) and BET (Brunner-Emmett-Teller) surface area analyses. Batch adsorption studies showed that functionalized clay significantly increased the selectivity and adsorption capacity of bentonite for TC and TCS. The Langmuir monolayer adsorption capacity was found to be 15.36 and 17.15 mg/g for TC and TCS, respectively. The rapid uptake of TC and TCS by functionalized material followed pseudo-second-rate kinetics. Further, a total of 78% of TC and 73% of TCS were removed within 5 min of contact and the adsorption equilibrium was achieved within 120  min. The influence of background electrolytes and co-existing ions indicated that TC and TCS were selective towards BNAPTES. The loading capacities of the column packed with BNAPTES were found to be 56.00 and 44.42 mg/g for TC and TCS, respectively. Further, BNAPTES was found efficient even in real water treatment since the attenuation of TC and TCS was not affected significantly in the real water matrix.


Assuntos
Triclosan , Poluentes Químicos da Água , Bentonita/química , Termodinâmica , Argila , Espectroscopia de Infravermelho com Transformada de Fourier , Descontaminação , Silanos , Antibacterianos , Tetraciclina , Triclosan/química , Adsorção , Cinética , Poluentes Químicos da Água/análise
9.
Environ Technol ; 44(10): 1518-1529, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-34781849

RESUMO

Biotreatment of triclosan is mainly performed in conventional activated sludge systems, which, however, are not capable of completely removing this antibacterial agent. As a consequence, triclosan ends up in surface and groundwater, constituting an environmental threat, due to its toxicity to aquatic life. However, little is known regarding the diversity and mechanism of action of microbiota capable of degrading triclosan. In this work, an immobilized cell bioreactor was setup to treat triclosan-rich wastewater. Bioreactor operation resulted in high triclosan removal efficiency, even greater than 99.5%. Nitrogen assimilation was mainly occurred in immobilized biomass, although nitrification was inhibited. Based on Illumina sequencing, Bradyrhizobiaceae, followed by Ferruginibacter, Thermomonas, Lysobacter and Gordonia, were the dominant genera in the bioreactor, representing 38.40 ± 0.62% of the total reads. However, a broad number of taxa (15 genera), mainly members of Xanthomonadaceae, Bradyrhizobiaceae and Chitinophagaceae, showed relative abundances between 1% and 3%. Liquid Chromatography coupled to Quadrupole Time-Of-Flight Mass Spectrometry (LC-QTOF-MS) resulted in the identification of catabolic routes of triclosan in the immobilized cell bioreactor. Seven intermediates of triclosan were detected, with 2,4-dichlorophenol, 4-chlorocatechol and 2-chlorohydroquinone being the key breakdown products of triclosan. Thus, the immobilized cell bioreactor accommodated a diverse bacterial community capable of degrading triclosan.


Assuntos
Triclosan , Triclosan/química , Águas Residuárias , Células Imobilizadas/química , Esgotos/microbiologia , Reatores Biológicos
10.
Sci Total Environ ; 842: 156832, 2022 Oct 10.
Artigo em Inglês | MEDLINE | ID: mdl-35760165

RESUMO

Microplastics (MPs) pollution has been becoming serious and widespread in the global environment. Although MPs have been identified as vectors for contaminants, adsorption and desorption behaviors of chemicals with non-biodegradable and biodegradable MPs during the aging process is limited. In this work, the adsorption behaviors of triclosan (TCS) by non-biodegradable polyethylene (PE) and polypropylene (PP), and biodegradable polylactic acid (PLA) were investigated. The differences in morphology, chemical structures, crystallization, and hydrophilicity were investigated after the ultraviolet aging process and compared with the virgin MPs. The results show that the water contact angles of the aged MPs were slightly reduced compared with the virgin MPs. The aged MPs exhibited a stronger adsorption capacity for TCS because of the physical and chemical changes in MPs. The virgin biodegradable PLA had a larger adsorption capacity than the non-biodegradable PE and PP. The adsorption capacity presented the opposite trend after aging. The main adsorption mechanism of MPs relied on hydrophobicity interaction, hydrogen bonding, and electrostatic interaction. The work provides new insights into TCS as hazardous environmental contaminants, which will enhance the vector potential of non-biodegradable and biodegradable MPs.


Assuntos
Triclosan , Poluentes Químicos da Água , Adsorção , Microplásticos , Plásticos/química , Poliésteres , Polietileno , Polipropilenos , Triclosan/química , Poluentes Químicos da Água/análise
11.
J Control Release ; 347: 379-388, 2022 07.
Artigo em Inglês | MEDLINE | ID: mdl-35550914

RESUMO

Wound biofilm infections caused by multidrug-resistant (MDR) bacteria constitute a major threat to public health; acquired resistance combined with resistance associated with the biofilm phenotype makes combatting these infections challenging. Biodegradable polymeric nanoemulsions that encapsulate two hydrophobic antimicrobial agents (eugenol and triclosan) (TE-BNEs) as a strategy to combat chronic wound infections are reported here. The cationic nanoemulsions efficiently penetrate and accumulate in biofilms, synergistically eradicating MDR bacterial biofilms, including persister cells. Notably, the nanoemulsion platform displays excellent biocompatibility and delays emergence of resistance to triclosan. The TE-BNEs are active in an in vivo murine model of mature MDR wound biofilm infections, with 99% bacterial elimination. The efficacy of this system coupled with prevention of emergence of bacterial resistance highlight the potential of this combination platform to treat MDR wound biofilm infections.


Assuntos
Anti-Infecciosos , Triclosan , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Biofilmes , Farmacorresistência Bacteriana Múltipla , Camundongos , Testes de Sensibilidade Microbiana , Triclosan/química , Triclosan/farmacologia
12.
Environ Res ; 212(Pt D): 113548, 2022 09.
Artigo em Inglês | MEDLINE | ID: mdl-35613630

RESUMO

The sorption behavior of single contaminant on microplastics (MPs) has been extensively studied; however, little is known about that in the more actual scenario containing multiple contaminants. In this study, the interaction between triclosan (TCS) and its primary metabolite, methyl triclosan (MTCS) on polyethylene (PE), polystyrene (PS), and soil was investigated. Results indicate that the more hydrophobic MTCS had much higher sorption capacity and affinity than TCS. Competitive sorption between them occurred in most cases and appeared to be concentration-dependent (in the range of 0.1-5 mg TCS/L and 0.01-≤0.05 mg MTCS/L of primary solutes, respectively): more pronounced at low concentrations of primary solute, while progressively weaker with the increase of concentrations. Among the sorbents, MTCS exhibited strong antagonistic effect on TCS sorption for MPs, especially PS, while significant suppression of MTCS sorption by TCS took place for soil and PS rather than PE. Additionally, it is interesting to observe that the presence of TCS substantially facilitated the sorption of MTCS exclusively at high concentrations on both PS and soil, presumably attributed to the solute-multilayer formation. Furthermore, the magnitude of the two effects varied with solution pH: TCS sorption at alkaline pH was the most suppressed by MTCS because the less hydrophobic dissociated TCS tended to be displaced, and the highest cooperative sorption of MTCS with TCS occurred at acidic pH because neutral TCS preferentially adsorbed on sorbent surface could provide additional sorption sites for MTCS. Both competitive and cooperative effects between multiple contaminants may affect their fate and transport, thereby these findings are helpful for assessing the environmental risk of MPs and TCS in soil.


Assuntos
Triclosan , Poluentes Químicos da Água , Adsorção , Microplásticos , Plásticos , Polietileno , Poliestirenos , Solo , Triclosan/análogos & derivados , Triclosan/química , Poluentes Químicos da Água/química
13.
Environ Sci Technol ; 56(21): 14923-14936, 2022 11 01.
Artigo em Inglês | MEDLINE | ID: mdl-35594374

RESUMO

Sewage treatment plants (STPs) accumulate both antibiotic and nonantibiotic antimicrobial compounds that can select for antibiotic resistant bacteria. Herein, we aimed to identify the predominant antibacterial compounds impacting E. coli from Ontario sewage sludge consisting of thousands of unknown compounds. Among the 10 extracted sludge samples, 6 extracts exerted significant growth inhibition effects in E. coli. A total of 103 compounds were tentatively detected across the 10 sludge samples by suspect screening, among which the bacterial enoyl-ACP reductase (FabI) inhibitor triclocarban was detected at the highest abundance. A hypomorphic FabI knockdown E. coli strain was highly susceptible to the sludge extracts, confirming FabI inhibitors as the primary antibacterial compounds in the sludge. Protein affinity pulldown identified triclosan as the major ligand binding to a His-tagged FabI protein from the sludge, despite the higher abundance of triclocarban in the same samples. Effect-directed analysis was used to determine the contributions of triclosan to the observed antibacterial potencies. Antibacterial effects were only detected in F17 and F18 across 20 fractions, which was consistent with the elution of triclosan and triclocarban in the same two fractions. Further, potency mass balance analysis confirmed that triclosan explained the majority (58-113%) of inhibition effects from sludge extracts. This study highlighted triclosan as the predominant antibacterial compound in sewage sludge impacting E. coli despite the co-occurrence of numerous other antibiotics and nonantibiotics.


Assuntos
Triclosan , Triclosan/farmacologia , Triclosan/química , Enoil-(Proteína de Transporte de Acila) Redutase (NADH)/química , Enoil-(Proteína de Transporte de Acila) Redutase (NADH)/metabolismo , Esgotos , Antibacterianos/farmacologia , Escherichia coli , Ontário , Bactérias/metabolismo
14.
Nat Commun ; 13(1): 136, 2022 01 10.
Artigo em Inglês | MEDLINE | ID: mdl-35013263

RESUMO

Emerging research supports that triclosan (TCS), an antimicrobial agent found in thousands of consumer products, exacerbates colitis and colitis-associated colorectal tumorigenesis in animal models. While the intestinal toxicities of TCS require the presence of gut microbiota, the molecular mechanisms involved have not been defined. Here we show that intestinal commensal microbes mediate metabolic activation of TCS in the colon and drive its gut toxicology. Using a range of in vitro, ex vivo, and in vivo approaches, we identify specific microbial ß-glucuronidase (GUS) enzymes involved and pinpoint molecular motifs required to metabolically activate TCS in the gut. Finally, we show that targeted inhibition of bacterial GUS enzymes abolishes the colitis-promoting effects of TCS, supporting an essential role of specific microbial proteins in TCS toxicity. Together, our results define a mechanism by which intestinal microbes contribute to the metabolic activation and gut toxicity of TCS, and highlight the importance of considering the contributions of the gut microbiota in evaluating the toxic potential of environmental chemicals.


Assuntos
Proteínas de Bactérias/antagonistas & inibidores , Carcinógenos/antagonistas & inibidores , Colite/prevenção & controle , Neoplasias Colorretais/prevenção & controle , Glucuronidase/antagonistas & inibidores , Inibidores de Glicosídeo Hidrolases/farmacologia , Triclosan/antagonistas & inibidores , Animais , Anti-Infecciosos Locais/química , Anti-Infecciosos Locais/metabolismo , Anti-Infecciosos Locais/toxicidade , Anticarcinógenos/química , Anticarcinógenos/farmacologia , Proteínas de Bactérias/química , Proteínas de Bactérias/genética , Proteínas de Bactérias/metabolismo , Sítios de Ligação , Biotransformação , Carcinogênese/efeitos dos fármacos , Carcinogênese/metabolismo , Carcinógenos/química , Carcinógenos/metabolismo , Carcinógenos/toxicidade , Colite/induzido quimicamente , Colite/enzimologia , Colite/microbiologia , Colo/efeitos dos fármacos , Colo/microbiologia , Colo/patologia , Neoplasias Colorretais/induzido quimicamente , Neoplasias Colorretais/enzimologia , Neoplasias Colorretais/microbiologia , Microbioma Gastrointestinal/efeitos dos fármacos , Expressão Gênica , Glucuronidase/química , Glucuronidase/genética , Glucuronidase/metabolismo , Inibidores de Glicosídeo Hidrolases/química , Humanos , Camundongos , Camundongos Endogâmicos C57BL , Modelos Moleculares , Ligação Proteica , Conformação Proteica em alfa-Hélice , Conformação Proteica em Folha beta , Domínios e Motivos de Interação entre Proteínas , Proteínas Recombinantes/química , Proteínas Recombinantes/genética , Proteínas Recombinantes/metabolismo , Triclosan/química , Triclosan/metabolismo , Triclosan/toxicidade
15.
Protein Sci ; 31(3): 568-579, 2022 03.
Artigo em Inglês | MEDLINE | ID: mdl-34882866

RESUMO

The enzyme enoyl-ACP reductase (also called FabI in bacteria) is an essential member of the fatty acid synthase II pathway in plants and bacteria. This enzyme is the target of the antibacterial drug triclosan and has been the subject of extensive studies for the past 20 years. Despite the large number of reports describing the biochemistry of this enzyme, there have been no studies that provided direct observation of the protein and its various ligands. Here we describe the use of native MS to characterize the protein-ligand interactions of FabI with its coenzymes NAD+ and NADH and with the inhibitor triclosan. Measurements of the gas-phase affinities of the enzyme for these ligands yielded values that are in close agreement with solution-phase affinity measurements. Additionally, FabI is a homotetramer and we were able to measure the affinity of each subunit for each coenzyme, which revealed that both coenzymes exhibit a positive homotropic allosteric effect. An allosteric effect was also observed in association with the inhibitor triclosan. These observations provide new insights into this well-studied enzyme and suggest that there may still be gaps in the existing mechanistic models that explain FabI inhibition.


Assuntos
Triclosan , Coenzimas , Enoil-(Proteína de Transporte de Acila) Redutase (NADH)/química , Ácido Graxo Sintase Tipo II , Ligantes , Triclosan/química , Triclosan/metabolismo , Triclosan/farmacologia
16.
Anal Bioanal Chem ; 413(25): 6355-6364, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34378070

RESUMO

In this work, the applicability of direct analysis in real time coupled to accurate mass spectrometry (DART-MS) to the quantitative determination of triclosan (TCS) in samples with increasing complexity, from personal care products to extracts from sewage, is investigated. In the first term, DART-MS spectra of TCS as free phenol and as derivatized species are characterized; thereafter, the effects of several instrumental variables in the detectability of TCS (i.e., temperature, solvent, and compound holder) are discussed. Under final selected conditions, TCS was determined from its [M-H]- ions, without need of derivatization, attaining an instrumental limit of quantification of 5 ng mL-1, with a linear response range up to 1000 ng mL-1. Complex matrices, such as solid-phase extracts obtained from environmental water samples, moderately inhibited the ionization efficiency of TCS, with signal attenuation percentages in the range of 6 to 57%, depending on the sample type and on the concentration factor provided by the SPE procedure. The accuracy of results obtained by DART-MS was evaluated using liquid chromatography (LC) with MS detection; in both cases, a time-of-flight (TOF) MS instrument was employed for the selective determination of the [M-H]- ions of TCS (m/z values 286.9439 and 288.9410) using a mass window of 20 ppm. DART-MS did not only provide enough sensitivity to detect the presence of TCS in environmental samples (raw and treated wastewater as well as freeze-dried sludge), but also measured concentrations matched those determined by LC-ESI-TOF-MS, with only slightly higher standard deviations. During analysis of personal care products, containing much higher concentrations of TCS in a less complex matrix, both techniques were equivalent in terms of accuracy and precision. Graphical abstract.


Assuntos
Misturas Complexas/química , Espectrometria de Massas/métodos , Triclosan/química , Poluentes Químicos da Água/química , Águas Residuárias/química
17.
Molecules ; 26(9)2021 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-34068616

RESUMO

In the late 1930s and early 1940s, it was discovered that the substitution on aromatic rings of hydrogen atoms with chlorine yielded a novel chemistry of antimicrobials. However, within a few years, many of these compounds and formulations showed adverse effects, including human toxicity, ecotoxicity, and unwanted environmental persistence and bioaccumulation, quickly leading to regulatory bans and phase-outs. Among these, the triclocarban, a polychlorinated aromatic antimicrobial agent, was employed as a major ingredient of toys, clothing, food packaging materials, food industry floors, medical supplies, and especially of personal care products, such as soaps, toothpaste, and shampoo. Triclocarban has been widely used for over 50 years, but only recently some concerns were raised about its endocrine disruptive properties. In September 2016, the U.S. Food and Drug Administration banned its use in over-the-counter hand and body washes because of its toxicity. The withdrawal of triclocarban has prompted the efforts to search for new antimicrobial compounds and several analogues of triclocarban have also been studied. In this review, an examination of different facets of triclocarban and its analogues will be analyzed.


Assuntos
Carbanilidas/farmacologia , Animais , Antibacterianos/farmacologia , Biotransformação/efeitos dos fármacos , Carbanilidas/química , Carbanilidas/toxicidade , Ecotoxicologia , Humanos , Triclosan/química , Triclosan/toxicidade
18.
Carbohydr Polym ; 267: 118225, 2021 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-34119178

RESUMO

Due to their large active surface, high loading efficiency, and tunable dissolution profiles, nanofibrous mats are often cited as promising drug carriers or antimicrobial membranes. Hyaluronic acid has outstanding biocompatibility, but it is hydrophilic. Nanofibrous structures made from hyaluronan dissolve immediately, making them unsuitable for controlled drug release and longer applications. We aimed to prepare a hyaluronan-based antimicrobial nanofibrous material, which would retain its integrity in aqueous environments. Self-supporting nanofibrous mats containing octenidine dihydrochloride or triclosan were produced by electrospinning from hydrophobized hyaluronan modified with a symmetric lauric acid anhydride. The nanofibrous mats required no cross-linking to be stable in PBS for 7 days. The encapsulation efficiency of antiseptics was nearly 100%. Minimal release of octenidine was observed, while up to 30% of triclosan was gradually released in 72 h. The nanofibrous materials exhibited antimicrobial activity, the fibroblast viability was directly dependent on the antiseptic content and its release.


Assuntos
Antibacterianos/farmacologia , Preparações de Ação Retardada/farmacologia , Portadores de Fármacos/farmacologia , Ácido Hialurônico/farmacologia , Nanofibras/química , Células 3T3 , Animais , Antibacterianos/química , Antibacterianos/toxicidade , Preparações de Ação Retardada/química , Preparações de Ação Retardada/toxicidade , Portadores de Fármacos/química , Portadores de Fármacos/toxicidade , Liberação Controlada de Fármacos , Ácido Hialurônico/química , Ácido Hialurônico/toxicidade , Interações Hidrofóbicas e Hidrofílicas , Iminas/química , Iminas/farmacologia , Iminas/toxicidade , Camundongos , Testes de Sensibilidade Microbiana , Nanofibras/toxicidade , Pseudomonas aeruginosa/efeitos dos fármacos , Piridinas/química , Piridinas/farmacologia , Piridinas/toxicidade , Staphylococcus aureus/efeitos dos fármacos , Triclosan/química , Triclosan/farmacologia , Triclosan/toxicidade
19.
Ecotoxicol Environ Saf ; 219: 112319, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-33993090

RESUMO

Herein, we synthesized a kind of magnetic covalent organic framework nanohybrids (NiFe2O4@COF), and integrated it with polydimethyl siloxane and silicone rubber curing agent for solid phase microextraction (SPME) fiber coating. The fiber coating demonstrated a porous and uniform surface with the BET specific surface of 169.7 m2 g-1. As for seven environmental analytes, the NiFe2O4@COF-based SPME fiber coating gave the higher extraction recoveries for triclosan (TCS) and methyltriclosn (MTCS) than those of fenpropathrin, bifenthrin, permethrin, fenvalerate and deltamethrin. Several operational parameters were rigorously optimized, such as extraction temperature, extraction time, thermal desorption time, solution pH and salt effect. Combined with the GC-ECD detection, the newly developed microextraction method supplied the wide linear range of 0.1-1000 µg L-1 with the correlation coefficients of > 0.9995. The limits of detection (LODs) and limits of quantitation (LOQs) reached as low as 1-7 ng L-1 and 3.3-23 ng L-1, respectively. The intra-day and inter-day precisions in six replicates (n = 6 ) were < 3.55% and < 5.06%, respectively, and the fiber-to-fiber reproducibility (n = 3) was < 7.64%. To evaluate its feasibility in real samples, the fortified recoveries for TCS and MTCS, at low (0.2 µg L-1), middle (2.0 µg L-1) and high (20.0 µg L-1) levels, varied between 81.9% and 119.1% in tap, river and barreled waters as well as male, female and children urine samples. Especially, it is worth mentioning that the NiFe2O4@COF-based SPME coating fiber can be recycled for at least 150 times with nearly unchanged extraction efficiency. Moreover, the extraction recoveries by the as-fabricated fiber coating were much higher than those by three commercial fibers (PDMS, PDMS/DVB and PDMS/DVB/CAR). Overall, the NiFe2O4@COF-based SPME is a convenient, sensitive, efficient and "green" pretreatment method, thereby possessing important application prospects in trace monitoring of TCS-like pollutants in complex liquid matrices.


Assuntos
Triclosan/química , Poluentes Químicos da Água/química , Dimetilpolisiloxanos , Humanos , Limite de Detecção , Fenômenos Magnéticos , Estruturas Metalorgânicas , Polivinil , Reprodutibilidade dos Testes , Rios , Microextração em Fase Sólida/métodos , Temperatura , Triclosan/análogos & derivados , Triclosan/urina , Água , Poluentes Químicos da Água/urina
20.
Eur J Clin Microbiol Infect Dis ; 40(7): 1517-1520, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33635424

RESUMO

This study aimed to compare the antimicrobial action of three soaps for hand hygiene (HH): 2.0% Tea Tree Oil (TTO); 0.5% triclosan; 2.0% chlorhexidine, and to explore the perception of healthcare professionals about TTO. Two-step study: a quantitative, to determine the logarithmic reduction of Escherichia coli K12 colony-forming units before and after HH of 15 volunteers and quali-quantitative, through interviews with 23 health professionals. All the three products demonstrated antimicrobial action (a log10 reduction factor of 4.18 for TTO, 4.31 for triclosan, 3.89 for chlorhexidine, and 3.17 for reference soap). Professionals remarked the pleasant aroma and non-dryness of skin when using soap containing TTO.


Assuntos
Clorexidina/farmacologia , Higiene das Mãos , Sabões/farmacologia , Óleo de Melaleuca/química , Óleo de Melaleuca/farmacologia , Triclosan/farmacologia , Adulto , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Clorexidina/química , Estudos Cross-Over , Humanos , Pessoa de Meia-Idade , Pele/efeitos dos fármacos , Sabões/química , Triclosan/química , Adulto Jovem
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