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1.
Biol Pharm Bull ; 47(1): 318-327, 2024 Jan 27.
Artículo en Inglés | MEDLINE | ID: mdl-38148018

RESUMEN

Some bacteria, such as Fusobacterium nucleatum, act as dimethyl trisulfide (DMTS) producers in the host in vivo. DMTS acts as a sulfane sulfur donor and chemically modifies the sulfhydryl groups. This study explored the post-translational modifications of human serum albumin using DMTS. Quantitative assessments were conducted on mixed disulfides of mercaptoalbumin with mercaptomethane (Alb-SS-CH3) and albumin hydropersulfide (Alb-SSH) as post-translationally modified species. The hydropersulfide group was alkylated with iodoacetamide, resulting in the formation of an albumin-mercaptoacetamide mixed disulfide. The mixed disulfides were subsequently reduced with tris(2-carboxyethyl)phosphine, and the liberated mercaptomethane and mercaptoacetamide were fluorescently labeled with 4-fluoro-7-sulfamoylbenzofurazan (ABD-F). Quantification was performed using HPLC with fluorescence detection. Using this methodology, we examined the formation of Alb-SS-CH3 and Alb-SSH via the reaction between 4% human serum albumin and DMTS at 10-100 µM concentrations. Approximately two molecules of Alb-SS-CH3 and one molecule of Alb-SSH were generated from one DMTS molecule. Moreover, hydrogen sulfide was identified as an intermediate, suggesting its generation and subsequent reaction with intraprotein disulfide bonds, leading to the production of Alb-SSH. These results suggest the production of DMTS in humans in vivo should be involved in the elevation of Alb-SS-CH3 and Alb-SSH contents in plasma samples.


Asunto(s)
Albúmina Sérica Humana , Sulfuros , Humanos , Disulfuros/metabolismo , Procesamiento Proteico-Postraduccional
2.
Int J Mol Sci ; 25(14)2024 Jul 13.
Artículo en Inglés | MEDLINE | ID: mdl-39062944

RESUMEN

Polysulfides are endogenously produced in mammals and generally associated with protective functions. Our aim was to investigate the effect of dimethyl trisulfide (DMTS) in a mouse model of acute stress. DMTS activates transient receptor potential ankyrin 1 (TRPA1) channels and leads to neuropeptide release, potentially that of substance P (SP). We hypothesize that DMTS might inhibit the degrading enzymes of endocannabinoids, so this system was also investigated as another possible pathway for mediating the effects of DMTS. Trpa1 gene wild-type (WT) and knockout (KO) mice were used to confirm the role of the TRPA1 ion channel in mediating the effects of DMTS. C57BL/6J, NK1 gene KO, and Tac1 gene KO mice were used to evaluate the effect of DMTS on the release and expression of SP. Some C57BL/6J animals were treated with AM251, an inhibitor of the cannabinoid CB1 receptor, to elucidate the role of the endocannabinoid system in these processes. Open field test (OFT) and forced swim test (FST) were performed in each mouse strain. A tail suspension test (TST) was performed in Trpa1 WT and KO animals. C-FOS immunohistochemistry was carried out on Trpa1 WT and KO animals. The DMTS treatment increased the number of highly active periods and decreased immobility time in the FST in WT animals, but had no effect on the Trpa1 KO mice. The DMTS administration induced neuronal activation in the Trpa1 WT mice in the stress-related brain areas, such as the locus coeruleus, dorsal raphe nucleus, lateral septum, paraventricular nucleus of the thalamus, and paraventricular nucleus of the hypothalamus. DMTS may have a potential role in the regulation of stress-related processes, and the TRPA1 ion channel may also be involved in mediating the effects of DMTS. DMTS can be an ideal candidate for further study as a potential remedy for stress-related disorders.


Asunto(s)
Modelos Animales de Enfermedad , Ratones Endogámicos C57BL , Ratones Noqueados , Sulfuros , Canal Catiónico TRPA1 , Animales , Canal Catiónico TRPA1/metabolismo , Canal Catiónico TRPA1/genética , Ratones , Sulfuros/farmacología , Masculino , Sustancia P/metabolismo , Estrés Psicológico/metabolismo , Estrés Fisiológico/efectos de los fármacos , Proteínas Proto-Oncogénicas c-fos/metabolismo
3.
J Environ Sci (China) ; 127: 824-832, 2023 May.
Artículo en Inglés | MEDLINE | ID: mdl-36522110

RESUMEN

With a large amount of domestic sewage and industrial wastewater discharged into the water bodies, sulfur-containing organic matter in wastewater produced volatile organic sulfide, such as dimethyl trisulfide (DMTS) through microorganisms, caused the potential danger of drinking water safety and human health. At present, there is still a lack of technology on the removal of DMTS. In this study, the ultraviolet/peroxymonosulfate (UV/PMS) advanced oxidation processes was used to explore the degradation of DMTS. More than 90% of DMTS (30 µg/L) was removed under the conditions of the concentration ratio of DMTS to PMS was 3:40, the temperature (T) was 25 ± 2℃, and 10 min of irradiation by a 200 W mercury lamp (365 nm). The kinetics rate constant k of DMTS reacting with hydroxyl radical (HO·) was determined to be 0.2477 min-1. Mn2+, Cu2+ and NO3- promoted the degradation of DMTS, whereas humic acid and Cl- in high concentrations inhibited the degradation process. Gas chromatography-mass spectrometry was used to analyze the degradation products and the degradation intermediates were dimethyl disulfide and methanethiol. Density functional theory was used to predict the possible degradation mechanism according to the frontier orbital theory and the bond breaking mechanism of organic compounds. The results showed that the SS, CS and CH bonds in DMTS molecular structure were prone to fracture in the presence of free radicals, resulting in the formation of alkyl radicals and sulfur-containing radicals, which randomly combined to generate a variety of degradation products.


Asunto(s)
Aguas Residuales , Contaminantes Químicos del Agua , Humanos , Contaminantes Químicos del Agua/análisis , Peróxidos/química , Sulfuros , Oxidación-Reducción , Azufre
4.
Int J Mol Sci ; 22(7)2021 Mar 25.
Artículo en Inglés | MEDLINE | ID: mdl-33806000

RESUMEN

Pharmacotherapy of neuropathic pain is still challenging. Our earlier work indicated an analgesic effect of dimethyl trisulfide (DMTS), which was mediated by somatostatin released from nociceptor nerve endings acting on SST4 receptors. Somatostatin release occurred due to TRPA1 ion channel activation. In the present study, we investigated the effect of DMTS in neuropathic pain evoked by partial ligation of the sciatic nerve in mice. Expression of the mRNA of Trpa1 in murine dorsal-root-ganglion neurons was detected by RNAscope. Involvement of TRPA1 ion channels and SST4 receptors was tested with gene-deleted animals. Macrophage activity at the site of the nerve lesion was determined by lucigenin bioluminescence. Density and activation of microglia in the spinal cord dorsal horn was verified by immunohistochemistry and image analysis. Trpa1 mRNA is expressed in peptidergic and non-peptidergic neurons in the dorsal root ganglion. DMTS ameliorated neuropathic pain in Trpa1 and Sstr4 WT mice, but not in KO ones. DMTS had no effect on macrophage activity around the damaged nerve. Microglial density in the dorsal horn was reduced by DMTS independently from TRPA1. No effect on microglial activation was detected. DMTS might offer a novel therapeutic opportunity in the complementary treatment of neuropathic pain.


Asunto(s)
Neuralgia/tratamiento farmacológico , Sulfuros/farmacología , Canal Catiónico TRPA1/metabolismo , Animales , Ganglios Espinales/metabolismo , Hiperalgesia , Masculino , Ratones , Ratones Endogámicos C57BL , Ratones Noqueados , Microglía/metabolismo , Microscopía Confocal , ARN Mensajero/metabolismo , Nervio Ciático/patología , Somatostatina/metabolismo
5.
Toxicol Ind Health ; 35(5): 387-397, 2019 May.
Artículo en Inglés | MEDLINE | ID: mdl-30991910

RESUMEN

Cytochrome P450 2E1 (CYP2E1) can be induced by diabetes mellitus, nonalcoholic liver disease, and obesity. This study assessed the protective effects of three sulfur compounds, namely phenethyl isothiocyanate (PEITC), dimethyl trisulfide (DMTS), and sodium thiosulfate (STS), on acrylonitrile (ACN)-induced acute toxicity in rats enriched with CYP2E1. PEITC and DMTS were administered intragastrically (i.g.), whereas STS was injected intraperitoneally (i.p.) at an identical dose of 0.5 mmol/kg for 3 days in acetone-pretreated rats before ACN (90 mg/kg) injection (i.p.). Acetone-treated rats that expressed high levels of CYP2E1 were more susceptible to ACN-induced acute toxicity. The sulfur compounds reduced the rate of convulsions and loss of the righting reflex in acute ACN-exposed CYP2E1-induced rats; PEITC and DMTS also increased the survival rates. PEITC inhibited hepatic CYP2E1 activity and protected hepatic and cerebral cytochrome c oxidase (CcOx) activities in acute ACN-exposed CYP2E1-enriched rats; DMTS protected hepatic CcOx activity. DMTS attenuated ACN-induced oxidative injury by reducing malondialdehyde (MDA) levels and increasing glutathione content in the brain. STS only reduced cerebral MDA levels, whereas PEITC did not exhibit any antioxidant effects. Collectively, PEITC provided superior protective effects against ACN-induced acute toxicity in rats with increased CYP2E1 activity, followed by DMTS; STS provided limited effects. PEITC and DMTS might be considered as promising chemopreventive agents against ACN-induced acute toxicity in vulnerable subpopulations with increased CYP2E1 activity.


Asunto(s)
Acrilonitrilo/toxicidad , Isotiocianatos/farmacología , Reflejo de Enderezamiento/efectos de los fármacos , Convulsiones/prevención & control , Sulfuros/farmacología , Tiosulfatos/farmacología , Animales , Citocromo P-450 CYP2E1/administración & dosificación , Sistema Enzimático del Citocromo P-450/análisis , Estimación de Kaplan-Meier , Masculino , Mortalidad , Distribución Aleatoria , Ratas , Convulsiones/inducido químicamente , Compuestos de Azufre/farmacología
6.
Toxicol Mech Methods ; 29(6): 438-444, 2019 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-30822191

RESUMEN

Formulation optimization and antidotal combination therapy are the two important tools to enhance the antidotal protection of the cyanide (CN) antidote dimethyl trisulfide (DMTS). The focus of this study is to demonstrate how the formulation with polysorbate 80 (Poly80), an excipient used in pharmaceutical technology, and the combinations with other CN antidotes having different mechanisms of action enhance the antidotal efficacy of the unformulated (neat) DMTS. The LD50 for CN was determined by the statistical Dixon up-and-down method on mice. Antidotal efficacy was expressed as antidotal potency ratio (APR). CN was injected subcutaneously one minute prior to the antidotes' injection intramuscularly. The APR values of 1.17 (dose: 25 mg/kg bodyweight) and 1.45 (dose: 50 mg/kg bodyweight) of the neat DMTS were significantly enhanced by the Poly80 formulation at both investigated doses to 2.03 and 2.33, respectively. The combination partners for the Poly80 formulated DMTS (DMTS-Poly80; 25 and 50 mg/kg bodyweight) were 4-nitrocobinamide (4NCbi) (20 mg/kg bodyweight) and aquohydroxocobinamide (AHCbi; 50, 100, and 250 mg/kg bodyweight). When DMTS-Poly80 (25 and 50 mg/kg bodyweight; APR = 2.03 and 2.33, respectively) was combined with 4NCbi (20 mg/kg bodyweight; APR = 1.35), significant increase in the APR values were noted at both DMTS doses (APR = 2.38 and 3.12, respectively). AHCbi enhanced the APR of DMTS-Poly80 (100 mg/kg bodyweight; APR = 3.29) significantly only at the dose of 250 mg/kg bodyweight (APR = 5.86). These studies provided evidence for the importance of the formulation with Poly80 and the combinations with cobinamide derivatives with different mechanisms of action for DMTS as a CN antidote candidate.


Asunto(s)
Antídotos/uso terapéutico , Cobamidas/uso terapéutico , Cianuro de Potasio/envenenamiento , Sulfuros/uso terapéutico , Animales , Antídotos/administración & dosificación , Antídotos/química , Cobamidas/administración & dosificación , Cobamidas/química , Relación Dosis-Respuesta a Droga , Composición de Medicamentos , Quimioterapia Combinada , Excipientes , Dosificación Letal Mediana , Masculino , Ratones Endogámicos , Polisorbatos , Sulfuros/administración & dosificación , Sulfuros/química
7.
World J Microbiol Biotechnol ; 36(1): 4, 2019 Dec 12.
Artículo en Inglés | MEDLINE | ID: mdl-31832786

RESUMEN

Colletotrichum gloeosporioides, one of the main agents of mango anthracnose, causes latent infections in unripe mango, and leads to huge economic losses during storage and transport. Dimethyl trisulfide (DMTS), one of the main volatile compounds produced by some microorganisms or plants, has shown antifungal activity against some phytopathogens in previous studies, but its effects on C. gloeosporioides and mechanisms of action have not been well characterized. In fumigation trials of conidia and mycelia of C. gloeosporioides for 2, 4, 6, 8, or 10 h, at a concentration of 100 µL/L of air space in vitro, DMTS caused serious damage to the integrity of plasma membranes, which significantly reduced the survival rate of spores, and resulted in abnormal hyphal morphology. Moreover, DMTS caused deterioration of subcellular structures of conidia and mycelia, such as cell walls, plasma membranes, Golgi bodies, and mitochondria, and contributed to leakage of protoplasm, thus promoting vacuole formation. In addition, to better understand the molecular mechanisms of the antifungal activity, the global gene expression profiles of isolate C. gloeosporioides TD3 treated in vitro with DMTS at a concentration of 100 µL/L of air for 0 h (Control), 1 h, or 3 h were investigated by RNA sequencing (RNA-seq), and over 62 Gb clean reads were generated from nine samples. Similar expressional patterns for nine differentially expressed genes (DEGs) in both RNA-seq and qRT-PCR assays showed the reliability of the RNA-seq data. In comparison to the non-treated control groups, we found DMTS suppressed expression of ß-1, 3-D-glucan, chitin, sterol biosynthesis-related genes, and membrane protein-related genes. These genes related to the formation of fungal cell walls and plasma membranes might be associated with the toxicity of DMTS against C. gloeosporioides. This is the first study demonstrating antifungal activity of DMTS against C. gloeosporioides on mango by direct damage of conidia and hyphae, thus providing a novel tool for postharvest control of mango anthracnose.


Asunto(s)
Antifúngicos/farmacología , Colletotrichum/efectos de los fármacos , Mangifera/microbiología , Sulfuros/farmacología , Quitina/metabolismo , Colletotrichum/aislamiento & purificación , Contaminación de Alimentos , Microbiología de Alimentos , Regulación Fúngica de la Expresión Génica , Hifa/efectos de los fármacos , Proteínas de la Membrana/metabolismo , Viabilidad Microbiana , Microscopía Electrónica de Transmisión , Micelio/efectos de los fármacos , Enfermedades de las Plantas/microbiología , ARN de Hongos/genética , ARN de Hongos/aislamiento & purificación , Reproducibilidad de los Resultados , Alineación de Secuencia , Análisis de Secuencia de ARN , Esporas Fúngicas/efectos de los fármacos , Esporas Fúngicas/aislamiento & purificación , Esteroles/metabolismo , beta-Glucanos/metabolismo
8.
Hemoglobin ; 42(5-6): 315-319, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-30747047

RESUMEN

Dimethyl trisulfide (DMTS) is a natural organic trisulfide that has been patented as a promising antidotal candidate against cyanide (CN). The primary mode of action of DMTS is as a sulfur donor that enables the conversion of CN to thiocyanate. Recently, it was discovered that DMTS is capable of oxidizing hemoglobin (Hb) to methemoglobin (MetHb) in vitro. The goal of these experiments was to measure the extent of DMTS-induced MetHb formation in vivo. In these experiments, intramuscular (IM) injections of formulated DMTS were administered to mice. Following the IM injection, blood was drawn and analyzed for MetHb using a rapid spectrophotometric method. Methemoglobin levels peaked in a dose-dependent manner between 20 and 30 min., and then began dropping. The highest MetHb levels measured for the 50, 100, 200 and 250 mg/kg doses of DMTS were respectively 3.28, 6.12, 9.69, and 10.76% MetHb. These experiments provide the first experimental evidence that IM administered DMTS generates MetHb in vivo and provide additional evidence for the presence of a secondary therapeutic pathway for DMTS - CN scavenging by DMTS-generated MetHb.


Asunto(s)
Cianuros/antagonistas & inhibidores , Metahemoglobina/efectos de los fármacos , Sulfuros/farmacología , Animales , Antídotos , Hemoglobinas/química , Metahemoglobina/química , Ratones , Sulfuros/química , Sulfuros/uso terapéutico , Tiocianatos/química
9.
Nitric Oxide ; 65: 10-21, 2017 05 01.
Artículo en Inglés | MEDLINE | ID: mdl-28137611

RESUMEN

TRPA1 receptors are calcium-permeable ligand-gated channels expressed in primary sensory neurons and involved in inflammation and pain. Activation of these neurons might have analgesic effect. Suggested mechanism of analgesic effect mediated by TRPA1 activation is the release of somatostatin (SOM) and its action on sst4 receptors. In the present study analgesic effect of TRPA1 activation on primary sensory neurons by organic trisulfide compound dimethyl trisulfide (DMTS) presumably leading to SOM release was investigated. Opening of TRPA1 by DMTS in CHO cells was examined by patch-clamp and fluorescent Ca2+ detection. Ca2+ influx upon DMTS administration in trigeminal ganglion (TRG) neurons of TRPA1 receptor wild-type (WT) and knockout (KO) mice was detected by ratiometric Ca2+ imaging. SOM release from sensory nerves of murine skin was assessed by radioimmunoassay. Analgesic effect of DMTS in mild heat injury-induced mechanical hyperalgesia was examined by dynamic plantar aesthesiometry. Regulatory role of DMTS on deep body temperature (Tb) was measured by thermocouple thermometry with respirometry and by telemetric thermometry. DMTS produced TRPA1-mediated currents and elevated [Ca2+]i in CHO cells. Similar data were obtained in TRG neurons. DMTS released SOM from murine sensory neurons TRPA1-dependently. DMTS exerted analgesic effect mediated by TRPA1 and sst4 receptors. DMTS-evoked hypothermia and hypokinesis were attenuated in freely-moving TRPA1 KO animals. Our study has presented original evidence regarding analgesic action of DMTS which might be due to TRPA1-mediated SOM release from sensory neurons and activation of sst4 receptors. DMTS could be a novel analgesic drug candidate.


Asunto(s)
Analgésicos/uso terapéutico , Sulfuros/uso terapéutico , Canal Catiónico TRPA1/agonistas , Acetanilidas/farmacología , Analgésicos/farmacología , Animales , Temperatura Corporal/efectos de los fármacos , Células CHO , Calcio/metabolismo , Células Cultivadas , Cricetulus , Femenino , Humanos , Hiperalgesia/tratamiento farmacológico , Ratones , Ratones Noqueados , Actividad Motora/efectos de los fármacos , Purinas/farmacología , Receptores de Somatostatina/metabolismo , Células Receptoras Sensoriales/efectos de los fármacos , Células Receptoras Sensoriales/metabolismo , Somatostatina/metabolismo , Sulfuros/farmacología , Canal Catiónico TRPA1/antagonistas & inhibidores , Canal Catiónico TRPA1/genética
10.
J Chem Ecol ; 42(1): 40-50, 2016 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-26637207

RESUMEN

We investigated foraging decisions by adult females of the common green bottle fly, Lucilia sericata, in accordance with their physiological state. When we gave female flies a choice between visually occluded, fresh canine feces (feeding site) and a CO2-euthanized rat (carrion oviposition site), 3-d-old "protein-starved" females responded equally well to feces and carrion, whereas protein-fed gravid females with mature oocytes responded only to carrion, indicating resource preferences based on a fly's physiological state. Dimethyl trisulfide (DMTS) is known to attract gravid L. sericata females to carrion. Therefore, we analyzed headspace from canine feces by gas chromatographic-electroantennographic detection (GC-EAD) and GC/mass spectrometry. In bioassays, of the 17 fecal odorants that elicited GC-EAD responses from fly antennae, a blend of indole and one or more of the alcohols phenol, m-/p-cresol and 1-octen-3-ol proved as attractive to flies as canine feces. Unlike young females, gravid females need to locate carrion for oviposition and distinguish between fresh and aging carrion, the latter possibly detrimental to offspring. Gravid female L. sericata accomplish this task, in part, by responding to trace amounts of DMTS emanating from fresh carrion and by discriminating against carrion as soon it begins to produce appreciable amounts of indole, which is also the second-most abundant semiochemical in fresh canine feces, and apparently serves as an indicator of food rather than oviposition resources. Our results emphasize the importance of studying foraging choices by flies in accordance with their physiological stage.


Asunto(s)
Dípteros/fisiología , Heces/química , Olfato , Animales , Conducta Animal/efectos de los fármacos , Dióxido de Carbono/farmacología , Dípteros/efectos de los fármacos , Perros , Femenino , Cromatografía de Gases y Espectrometría de Masas , Indoles/farmacología , Odorantes/análisis , Feromonas/análisis , Ratas , Sulfuros/farmacología , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/química
11.
J Chem Ecol ; 42(8): 756-767, 2016 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-27369281

RESUMEN

In the necrophagous burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae), cadaver preference appears to depend on cadaver size and on the maturity of the beetle. We previously showed that newly emerged females with immature ovaries prefer later stages of decomposition of large cadavers. Our present aim is the determination of specific chemical compounds involved in the discrimination of cadaveric odor bouquets and the recognition of specific stages of decomposition. We used headspace samples of maggot-infested piglet cadavers at various decomposition stages and performed gas chromatography coupled with electroantennography (GC-EAD) to record 45 EAD-active compounds. Using GC coupled with mass spectrometry, we identified 13 of the EAD-active compounds. The headspace of the fresh decomposition stage was characterized mainly by high relative amounts of trimethylpyrazine. High relative amounts of dimethyl trisulfide were characteristic of bloated, post-bloating, and advanced decay stages. The advanced decay and dry remains stages were dominated by high relative amounts of phenol. Statistically, this compound had the highest impact on discrimination between the fresh decomposition stage, which is important for mature burying beetles for reproduction, and the advanced decay stage, which is nutritionally more attractive for newly emerged beetles. Phenol might, therefore, function as a key substance for newly emerged female burying beetles, so that they can locate suitable cadavers for feeding to maturation.


Asunto(s)
Escarabajos/efectos de los fármacos , Escarabajos/fisiología , Percepción Olfatoria/efectos de los fármacos , Porcinos , Compuestos Orgánicos Volátiles/farmacología , Animales , Bioensayo , Cadáver , Fenómenos Electrofisiológicos/efectos de los fármacos , Femenino , Cromatografía de Gases y Espectrometría de Masas , Masculino , Compuestos Orgánicos Volátiles/análisis
12.
Toxicol Ind Health ; 32(12): 2009-2016, 2016 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-26939832

RESUMEN

In the present studies, the in vitro and in vivo efficacies of a novel cyanide countermeasure, dimethyl trisulfide (DMTS), were evaluated. DMTS is a sulfur-based molecule found in garlic, onion, broccoli, and similar plants. DMTS was studied for effectiveness as a sulfur donor-type cyanide countermeasure. The sulfur donor reactivity of DMTS was determined by measuring the rate of the formation of the cyanide metabolite thiocyanate. In experiments carried out in vitro in the presence of the sulfurtransferase rhodanese (Rh) and at the experimental pH of 7.4, DMTS was observed to convert cyanide to thiocyanate with greater than 40 times higher efficacy than does thiosulfate, the sulfur donor component of the US Food and Drug Administration-approved cyanide countermeasure Nithiodote® In the absence of Rh, DMTS was observed to be almost 80 times more efficient than sodium thiosulfate in vitro The fact that DMTS converts cyanide to thiocyanate more efficiently than does thiosulfate both with and without Rh makes it a promising sulfur donor-type cyanide antidote (scavenger) with reduced enzyme dependence in vitro The therapeutic cyanide antidotal efficacies for DMTS versus sodium thiosulfate were measured following intramuscular administration in a mouse model and expressed as antidotal potency ratios (APR = LD50 of cyanide with antidote/LD50 of cyanide without antidote). A dose of 100 mg/kg sodium thiosulfate given intramuscularly showed only slight therapeutic protection (APR = 1.1), whereas the antidotal protection from DMTS given intramuscularly at the same dose was substantial (APR = 3.3). Based on these data, DMTS will be studied further as a promising next-generation countermeasure for cyanide intoxication.


Asunto(s)
Antídotos/farmacología , Cianuros/toxicidad , Sulfuros/farmacología , Animales , Antídotos/química , Brassica/química , Cianuros/química , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Ajo/química , Concentración de Iones de Hidrógeno , Inyecciones Intramusculares , Dosificación Letal Mediana , Masculino , Ratones , Cebollas/química , Tiocianatos/metabolismo , Tiosulfato Azufretransferasa/metabolismo , Tiosulfatos/farmacología
13.
Angew Chem Int Ed Engl ; 55(34): 10027-31, 2016 08 16.
Artículo en Inglés | MEDLINE | ID: mdl-27411083

RESUMEN

An organotrisulfide (RSSSR, R is an organic group) has three sulfur atoms which could be involved in multi-electron reduction reactions; therefore it is a promising electrode material for batteries. Herein, we use dimethyl trisulfide (DMTS) as a model compound to study its redox reactions in rechargeable lithium batteries. With the aid of XRD, XPS, and GC-MS analysis, we confirm DMTS could undergo almost a 4 e(-) reduction process in a complete discharge to 1.0 V. The discharge products are primarily LiSCH3 and Li2 S. The lithium cell with DMTS catholyte delivers an initial specific capacity of 720 mAh g(-1) DMTS and retains 82 % of the capacity over 50 cycles at C/10 rate. When the electrolyte/DMTS ratio is 3:1 mL g(-1) , the reversible specific energy for the cell including electrolyte can be 229 Wh kg(-1) . This study shows organotrisulfide is a promising high-capacity cathode material for high-energy rechargeable lithium batteries.

14.
J Med Entomol ; 52(4): 527-31, 2015 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-26335458

RESUMEN

The sheep blowfly, Lucilia sericata Meigen (Diptera: Calliphoridae), causes sheep myiasis in various parts of the world. Female flies are attracted to sheep following various olfactory cues emanating from the sheep's body, and oviposit on suitable substrates on sheep ultimately causing myiasis. Earlier workers attempted to reduce fly population in the field, with some success, using traps baited with various attractants. This research was conducted to determine if L. sericata would respond to a recently developed synthetic attractant that has attracted gravid screwworms, Cochliomyia hominivorax Coquerel, and stimulated them to oviposit. Results of the laboratory bioassays demonstrated that gravid females L. sericata were attracted to substrates treated with the synthetic screwworm attractant composed of five compounds--dimethyl disulfide, dimethyl trisulfide, phenol, p-cresol, and indole. Tests with various combinations of these compounds suggest that the sulfur compounds and indole are the most important compounds to elicit attraction and stimulate oviposition, while phenol and p-cresol may have minor roles. Semiochemical baits based on these compounds may be useful in the field to trap gravid L. sericata.


Asunto(s)
Dípteros/efectos de los fármacos , Control de Insectos/métodos , Miasis , Feromonas/farmacología , Animales , Quimiotaxis , Dípteros/fisiología , Femenino , Indoles/farmacología , Miasis/parasitología , Miasis/prevención & control , Oviposición/efectos de los fármacos , Oviposición/fisiología , Ovinos , Compuestos de Azufre/farmacología
15.
J Biosci Bioeng ; 137(4): 268-273, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38310037

RESUMEN

Hineka is a type of off-flavor of sake and is attributed to the presence of several compounds, including a major one called dimethyl trisulfide (DMTS). The production of the main precursor of DMTS involves yeast methionine salvage pathway. The DMTS-producing potential (DMTS-pp) of sake brewed using the Km67 strain, a non-Kyokai sake yeast, is lower than that of sake brewed using Kyokai yeast; however, the detailed mechanism is unclear. We focused on S-adenosyl-methionine (SAM) and aimed to elucidate the mechanism that prevents DMTS production in sake brewed using the Km67 strain. We revealed that SAM is involved in DMTS production in sake, and that the conversion of SAM to the DMTS precursor occurs through an enzymatic reaction rather than a chemical reaction. Based on previous reports on ADO1 and MDE1 genes, sake brewing tests were performed using the Km67 Δmde1, Δado1, and Δmde1Δado1 strains. A comparison of the SAM content of pressed sake cakes and DMTS-pp of sake produced using the Km67 Δado1 strain showed an increase in both SAM content and DMTS-pp compared to those produced using the parent strain. However, the Km67 Δmde1Δado1 strain showed little increase in DMTS-pp compared to the Km67 Δmde1 strain, despite an increase in SAM content. These results suggest that SAM accumulation in yeast plays a role in the production of DMTS in sake through the methionine salvage pathway. Moreover, the low SAM-accumulation characteristic of the Km67 strain contributes to low DMTS production in sake.


Asunto(s)
Proteínas de Saccharomyces cerevisiae , Saccharomyces cerevisiae , Sulfuros , Saccharomyces cerevisiae/metabolismo , Bebidas Alcohólicas/análisis , Proteínas de Saccharomyces cerevisiae/genética , Odorantes/análisis , Fermentación , S-Adenosilmetionina/metabolismo
16.
J Med Entomol ; 60(4): 631-636, 2023 07 12.
Artículo en Inglés | MEDLINE | ID: mdl-37079723

RESUMEN

New World screwworm flies, Cochliomyia hominivorax (Coquerel), are obligate parasites of warm-blooded animals. They were eradicated from North and Central America during the mid-20th to early-21st centuries using the sterile insect technique (SIT), a method presently employed to maintain a permanent barrier between Central and South America. Lures are an important component of the screwworm eradication program, where they are used for surveillance, sample collection, and strain evaluation in the field. The first chemical lure, later named swormlure, was developed based on the attractiveness of C. hominivorax to volatile organic compounds (VOCs) produced from decomposing animal tissues. The formulation has changed little over the years and presently contains 10 chemicals, one of which is dimethyl disulfide (DMDS). Restrictions on the transport of DMDS have recently impeded its use in swormlure-4 (SL-4). However, dimethyl trisulfide (DMTS) is not as highly restricted and can be shipped via air transportation. Both chemicals are produced by microbial decomposition of animal tissues. Here, we conducted field trials using three releases of sterile C. hominivorax, each comprising approximately 93,000 flies, to test the efficacy of SL-4, containing DMDS, to swormlure-5 (SL-5) containing DMTS. Traps baited with SL-4 and SL-5 captured 575 (mean = 191.7, SD 17.9) and 665 (mean = 221.7, SD 33.2) C. hominivorax, respectively (df = 19, F = 1.294, P = 0.269). However, traps baited with SL-5 captured considerably more Cochliomyia macellaria (Fabricius), a closely related but nontarget fly.


Asunto(s)
Dípteros , Compuestos Orgánicos Volátiles , Animales , Animales Domésticos , Calliphoridae
17.
Food Chem ; 400: 133854, 2023 Jan 30.
Artículo en Inglés | MEDLINE | ID: mdl-36067694

RESUMEN

The pickle-like odor, which was caused by the excess volatile sulfur compounds (VSCs), is an undesirable odor in soy sauce flavor Baijiu (SSB). The aim of this study was to explore the suppressing effect of kafirin, the internal prolamin of the raw material of Baijiu, on the pickle-like odor of SSB. The instrumental analysis (comprehensive two-dimensional gas chromatography, ultraviolet and visible spectrophotometry), human perceptions (aroma profile, odor thresholds) and in silico analysis methods (molecular docking) were combined to detect the changes of the pickle-like odor. After the addition of kafirin, the aroma profile of the pickle-like SSB changed and approached to that of the normal SSB. The volatility and the odor thresholds of VSCs decreased 22.05%-64.28% and increased 87.29%-232.57%, respectively. In conclusion, kafirin exhibited a significant suppressing effect on the pickle-like off-odor of SSB, and this effect could be used to reduce the off-odor of SSB and SSB-derived alcoholic beverages.


Asunto(s)
Alimentos de Soja , Compuestos Orgánicos Volátiles , Cromatografía de Gases y Espectrometría de Masas/métodos , Humanos , Simulación del Acoplamiento Molecular , Odorantes/análisis , Prolaminas , Alimentos de Soja/análisis , Compuestos de Azufre/análisis , Compuestos Orgánicos Volátiles/análisis
18.
Food Chem ; 426: 136617, 2023 Nov 15.
Artículo en Inglés | MEDLINE | ID: mdl-37336098

RESUMEN

Rapeseed oil, as one of the three major vegetable oils in the world, its matrix effect makes the decoding flavor a challenge. Solid-phase microextraction (SPME), SPME-Arrow, headspace stir bar sorptive extraction (HSSE), direct thermal desorption (DTD), and solvent-assisted flavor evaporation (SAFE) were compared based on the odorants in hot-pressed rapeseed oil. Besides, methodological validation for 31 aroma standards was conducted to compare reliability and robustness of these approaches. DTD showed the largest proportion of acids, while the other techniques extracted a majority of nitriles. The highest number of odorants was detected by SAFE (31), followed by HSSE (30), SPME-Arrow (30), SPME (24), and DTD (14). SPME-Arrow showed the best performance in linearity, recovery, and reproducibility followed by SPME, HSSE, DTD, and SAFE. Results reveal the advantages and limitations of diverse methodologies and provide valuable insights for the selection of extraction methods in an oil matrix and flavor decoding.


Asunto(s)
Odorantes , Compuestos Orgánicos Volátiles , Odorantes/análisis , Aceite de Brassica napus , Cromatografía de Gases y Espectrometría de Masas/métodos , Reproducibilidad de los Resultados , Microextracción en Fase Sólida/métodos , Solventes , Compuestos Orgánicos Volátiles/análisis
19.
Clin Toxicol (Phila) ; 60(1): 95-101, 2022 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-34142637

RESUMEN

BACKGROUND: Cyanide is a rapid acting, lethal, metabolic poison and remains a significant threat. Current FDA-approved antidotes are not amenable or efficient enough for a mass casualty incident. OBJECTIVE: The objective of this study is to evaluate short and long-term efficacy of intramuscular aqueous dimethyl trisulfide (DMTS) on survival and clinical outcomes in a swine model of cyanide exposure. METHODS: Anesthetized swine were instrumented and acclimated until breathing spontaneously. Potassium cyanide infusion was initiated and continued until 5 min after the onset of apnea. Subsequently, animals were treated with intramuscular DMTS (n = 11) or saline control (n = 10). Laboratory values and DMTS blood concentrations were assessed at various time points and physiological parameters were monitored continuously until the end of the experiment unless death occurred. A subset of animals treated with DMTS (n = 5) were survived for 7 days to evaluate muscle integrity by repeat biopsy and neurobehavioral outcomes. RESULTS: Physiological parameters and time to apnea were similar in both groups at baseline and at time of treatment. Survival in the DMTS-treated group was 90% and 30% in saline controls (p = 0.0034). DMTS-treated animals returned to breathing at 12.0 ± 10.4 min (mean ± SD) compared to 22.9 ± 7.0 min (mean ± SD) in the 3 surviving controls. Blood collected prior to euthanasia showed improved blood lactate concentrations in the DMTS treatment group; 5.47 ± 2.65 mmol/L vs. 9.39 ± 4.51 mmol/L (mean ± SD) in controls (p = 0.0310). Low concentrations of DMTS were detected in the blood, gradually increasing over time with no elimination phase observed. There was no mortality, histological evidence of muscle trauma, or observed adverse neurobehavioral outcomes, in DMTS-treated animals survived to 7 days. CONCLUSION: Intramuscular administration of aqueous DMTS improves survival following cyanide poisoning with no observed long-term effects on muscle integrity at the injection site or adverse neurobehavioral outcomes.


Asunto(s)
Antídotos , Sulfuros , Animales , Antídotos/farmacología , Antídotos/uso terapéutico , Cianuros , Humanos , Cianuro de Potasio , Porcinos
20.
Toxins (Basel) ; 14(11)2022 11 11.
Artículo en Inglés | MEDLINE | ID: mdl-36422962

RESUMEN

Aspergillus flavus and the produced aflatoxins cause great hazards to food security and human health across all countries. The control of A. flavus and aflatoxins in grains during storage is of great significance to humans. In the current study, bacteria strain YM6 isolated from sea sediment was demonstrated effective in controlling A. flavus by the production of anti-fungal volatiles. According to morphological characteristics and phylogenetic analysis, strain YM6 was identified as Pseudomonas stutzeri. YM6 can produce abundant volatile compounds which could inhibit mycelial growth and conidial germination of A. flavus. Moreover, it greatly prevented fungal infection and aflatoxin production on maize and peanuts during storage. The inhibition rate was 100%. Scanning electron microscopy further supported that the volatiles could destroy the cell structure of A. flavus and prevent conidia germination on the grain surface. Gas chromatography/mass spectrometry revealed that dimethyl trisulfide (DMTS) with a relative abundance of 13% is the most abundant fraction in the volatiles from strain YM6. The minimal inhibitory concentration of DMTS to A. flavus conidia is 200 µL/L (compound volume/airspace volume). Thus, we concluded that Pseudomonas stutzeri YM6 and the produced DMTS showed great inhibition to A. flavus, which could be considered as effective biocontrol agents in further application.


Asunto(s)
Aflatoxinas , Pseudomonas stutzeri , Humanos , Aspergillus flavus/metabolismo , Aflatoxinas/análisis , Filogenia
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