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PubMed1986

Protein pico-sequencing with 4-([5-(dimethylamino)-1-naphthylsulfonyl]amino) phenyl isothiocyanate.

A novel manual liquid phase protein sequencing method using the fluorescent reagent, 4-([5-(dimethylamino)-1-naphthylsulfonyl] amino) phenyl isothiocyanate proposed by Jin et al. (FEBS Lett. 198, 150, 1986) has been established. This method allowed sequence determination using 100 pmol and 1 nmol of insulin B chain (oxidised) for 9 and 19 cycles respectively with thin-layer chromatographic identification of the fluorescent thiohydantoin amino-acid derivatives. The method compares favorably in sensitivity with other conventional manual protein sequencing methods.

Amino Acid Sequence↗

PubMed1996

Lack of inhibitory effect of benzyl isothiocyanate on 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP)-induced mammary carcinogenesis in rats.

Modifying effects of benzyl isothiocyanate (BITC), a glucosinolate compound, were investigated on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced mammary carcinogenesis in female SD rats. One hundred twenty five female rats were divided into 4 groups. Starting at 6 weeks of age, rats were fed high fat diet containing 23.5% corn oil (Groups 1 and 4) or the experimental diet (high fat diet with 400 ppm BITC) (Groups 2 and 3). At 7 weeks of age, Groups 1 and 2 were given PhIP (100 mg/kg body weight, 8 times for 16 days) by intragastric tube. One week after the final PhIP treatment, the experimental diet for Groups 2 and 3 switched to high fat diet. At the termination (31 weeks after the start of experiment), mammary adenocarcinomas were recognized in Group 1 (PhIP alone) and Group 2 (PhIP + BITC). The incidence of neoplasms was 74.2% in Group 1, and 62.5% in Group 2. The multiplicity of them was 1.71 +/- 1.70 in Group 1, and 1.91 +/- 2.94 in Group 2. Mean sizes of tumors were 9.9 +/- 7.1 mm in Group 1, and 10.8 +/- 6.8 mm in Group 2. But no significant differences for tumors were available between the two groups. These results imply that the glucosinolate compound does not have clear inhibitory effects on PhIP-induced mammary carcinogenesis in rats.

Animals↗

PubMed2005

Degradation of methyl isothiocyanate and chloropicrin in forest nursery soils.

Recent studies have observed enhanced degradation of methyl isothiocyanate (MITC) from repeated fumigation in agricultural soils. Little is known about fumigant degradation in forest and nursery soils. This study was conducted to determine degradation rates of MITC and chloropicrin (CP) in two forest soils and the impacts of nursery management on degradation of MITC and CP. The half-life values of MITC and CP were evaluated in the laboratory under isothermal conditions (22 +/- 2 degrees C). Three rates representing 0.5x, 1x, and 2x field application rates for each fumigant were used in laboratory incubations. Effect of microbial degradation was determined by conducting incubations with both fresh and sterilized soils. Soil moisture effects were also studied. There was no difference in MITC or CP degradation between fumigated and nonfumigated forest nursery soils. Soil sterilization and high soil moisture content (15% by wt.) reduced MITC and CP degradation. The degradation rates of MITC and CP varied with factors such as nursery history, fumigant application rates, and freshness of tested soils.

Biodegradation, Environmental↗

PubMedDate not supplied

Effect of combined application of methyl isothiocyanate and chloropicrin on their transformation.

Combining several soil fumigants to increase the broad spectrum of pest control is a common fumigation practice in current production agriculture. In this study, we investigated the effect of combined application of chloropicrin and methyl isothiocyanate (MITC) on their transformations and persistence in the environment. In aqueous solution, no direct reaction between MITC and chloropicrin occurred and relatively slow rates of hydrolysis of these compounds were observed in aquatic environments free of suspended solids. The transformation of chloropicrin, however, was accelerated in aqueous solution with MITC because of a reduction reaction with bisulfide (HS(-)), which is a by-product of MITC hydrolysis. In soil, when fumigants were applied simultaneously, the degradation of MITC was suppressed under the bi-fumigant application due to the inhibition of soil microbial activity and a possible abiotic competition with chloropicrin for a limited number of reaction sites on the surface of soil particles. However, the degradation rate of chloropicrin was significantly enhanced in the bi-fumigant soil system, which was primarily attributed to the reaction of chloropicrin and HS(-). Two sequential application approaches were developed to investigate the feasibility of the combined application of metam sodium (parent compound of MITC) and chloropicrin in soil and assess their potential effects on environmental fate. For both application sequences, the degradation of chloropicrin was accelerated and that of MITC, as a major breakdown product of metam sodium, was inhibited in soil.

Chemical Warfare Agents↗

PubMed2006

Modeling methyl isothiocyanate soil flux and emission ratio from a field following a chemigation of metam-sodium.

Metam-sodium had become the most heavily used soil fumigant in recent years as the deadline approached for methyl bromide to phase out in January 2005. After application, metam-sodium decomposes rapidly to methyl isothiocyanate (MITC), a highly toxic compound capable of killing a wide spectrum of soil-borne pests. Inhalation risk of MITC ranked high among airborne agricultural pesticides in California. Information about off-gassing intensity and percentage of emission is essential for exposure risk assessment and mitigation measures, but is limited, especially for new application methods such as drip chemigation. Air concentrations of MITC were monitored around a field treated with metam-sodium through surface drip irrigation system. The field was tarped with plastic films before the chemigation. The air concentrations at receptor locations were simulated for the period of air monitoring with the Industrial Source Complex (ISC3) Dispersion Model, and soil flux density of MITC at various periods after chemigation was estimated through a back-calculation procedure. The estimated soil flux density of MITC showed a diurnal pattern, with the daytime flux stronger than nighttime. However, the average air concentration at nighttime was higher than that at daytime. Soil flux density peaked at 4.30 microg m-2 s-1 in the first 12-h period after chemigation, then declined with time. The MITC emission percentage in the first 60-h was 2.65% of applied mass, of which 57% occurred in the first 24-h after chemigation. The study indicated that the tarped bed drip application method of metam-sodium had a relatively good control of MITC emission from soil.

Isothiocyanates↗

PubMed2002

Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans.

Isothiocyanates (ITCs) are a group of naturally occurring compounds that occur as thioglucoside conjugates, termed glucosinolates, in plants and cruciferous vegetables such as watercress, Brussels sprouts, broccoli, cabbage, kai choi, kale, horseradish, radish and turnip. ITCs inhibit the development of tumors in many of the experimental models investigated, and are being investigated as possible chemopreventive agents for specific human cancers. The goal of this review is to provide a mechanistic understanding for the biological activities of ITCs and to relate the metabolism of ITCs to their action as chemopreventive agents. In vivo animal studies have been conducted to address issues of tissue disposition, pharmacokinetics, and metabolism of ITCs. Methods for analysis of ITCs and their metabolites in urine and plasma have been developed. The metabolism of several naturally occurring ITCs as constituents of foodstuffs or as drugs has also been investigated in human studies. Finally, based on recent epidemiological studies, the role of dietary consumption of vegetables containing ITCs in prevention of human cancers and human cancer susceptibility is discussed.

Animals↗

PubMed2004

Isothiocyanates in the chemoprevention of bladder cancer.

Development of effective preventive strategies for bladder cancer is of critical importance. Bladder cancer is among the most common human malignancies and typically recurs after treatment. Many plant-derived isothiocyanates (ITCs) have shown cancer-preventive activity in a variety of rodent organs. They are known to inhibit carcinogen-activating enzymes, and to induce carcinogen-detoxifying enzymes, apoptosis, cell cycle arrest, and differentiation of cancer cells. More importantly, orally ingested ITCs are efficiently absorbed, rapidly and almost exclusively excreted and concentrated in the urine as N-acetylcysteine conjugates (NAC-ITC). NAC-ITCs also possess anticarcinogenic activity, perhaps due largely to their facile dissociation to free ITCs. Storage of urine in the bladder makes the bladder epithelium, which lines the inner surface of the bladder and gives rise to the majority of bladder cancers, the most exposed tissue to ITCs/NAC-ITCs upon their ingestion. Storage of urine in the bladder also will increase the release of ITCs from NAC-ITCs. Consequently, the amount of ITCs needed orally to achieve cancer prevention in the bladder may be much lower than that required for other organs. As a result, potential systemic adverse effects of ITCs may be minimized when using ITCs for chemoprevention of bladder carcinogenesis. Taken together, ITCs may be especially useful for the prevention of bladder cancer.

Animals↗

PubMed1989

Increased gut permeability to fluorescein isothiocyanate-dextran after total parenteral nutrition in the rat.

Sepsis with subsequent multiple organ failure is the commonest complication seen in the surgical intensive care unit today. A gut mucosal barrier dysfunction is assuming an increasingly important role as one possible explanation for the initiation of the septic process. It is known that the gut bacteria and endotoxins can, in the presence of a seemingly intact epithelium, translocate to extraintestinal sites, but the exact mechanism behind this process is not understood. In the present study we have approached this problem by testing the gut permeability to two macromolecules, bovine serum albumin (BSA) and fluorescein isothiocyanate (FITC)-dextran, after 7 days of enteral or parenteral nutrition in the rat. The plasma values of FITC-dextran after 4 h of marker feeding showed a significant increase in gut permeability after parenteral but not after enteral nutrition as compared with the controls. The plasma values of BSA, however, did not show any significant change in any of the groups. Thus, parenteral nutrition, with the changes occurring in the gut mucosa, may be one of the etiologic co-factors behind a gut mucosal barrier dysfunction, eventually leading to absorption of noxious agents into the systemic circulation with subsequent multiple organ failure.

Animals↗

PubMed1988

Studies on the metabolism and excretion of benzyl isothiocyanate in man.

1. Both after ingestion of benzyl isothiocyanate (BITC), a compound with antibacterial properties, and after consumption of garden cress known to contain BITC, the metabolite N-acetyl-S-(N-benzylthiocarbamoyl)-L-cysteine was identified in the urine of volunteers by comparative chromatography. 2. The chemical structure of the metabolite was confirmed by elemental analysis and by comparison of the i.r. and 1H-n.m.r. spectra with those of the synthetic product. 3. On average 53.7% of the dose of BITC was excreted as this metabolite by the renal route. 4. The metabolite was excreted rapidly, appearing with maximum concentrations some 2-6 h after dosing and being essentially complete 10-12 h after administration.

Adult↗

PubMed1990

Effect of phenethyl isothiocyanate on microsomal N-nitrosodimethylamine metabolism and other monooxygenase activities.

1. Phenethyl isothiocyanate (PEITC), a dietary compound derived from cruciferous vegetables, has previously been shown to decrease N-nitrosodimethylamine (NDMA)-induced methylation of hepatic DNA, apparently by inhibition of microsomal activation of the procarcinogen. 2. Using hepatic microsomes from acetone-treated rats, PEITC exhibited competitive inhibition of NDMA demethylase activity with an apparent Ki of 1 microM. In studies using a two-stage incubation protocol, the inhibition by PEITC was time- and metabolism-dependent. 3. Using control rat liver microsomes, PEITC selectively inhibited P450 IIE1-mediated NDMA-demethylase activity as compared to the demethylation of benzphetamine and ethylmorphine. 4. Pretreatment of rats with a single oral dose of PEITC (1 mmol/kg body wt) 24 h before killing caused a marked decrease in hepatic NDMA demethylase activity, but an 11-fold increase in 7-pentoxyresorufin O-dealkylase activity. These trends agreed with immunoblot analysis which indicated that PEITC was a suppressor of P450 IIE1 but an inducer of P450 IIB1. 5. The selective inhibition of P450 IIE1 activity and suppression of its level in microsomes indicates a role for PEITC as a chemopreventive agent against toxic or carcinogenic metabolites of this isozyme.

Animals↗

PubMedDate not supplied

Quantitative assessment of human sperm acrosome reaction by using fluorescein isothiocyanate conjugated concanavalin A--comparison between highly purified acrosome reacted with non-acrosome reacted sperm.

In the present study, to achieve quantitative assessment of human sperm acrosome reaction by using fluorescein isothiocyanate conjugated Concanavalin A (FITC-Con A), the optimum conditions for microscopic observation were established by comparing the fluorescent images between the purified human sperm with the intact acrosome (non-acrosome reacted sperm; non-AR sperm) and those with exposed inner acrosomal membrane (acrosome reacted sperm; AR sperm). FITC-Con A stained not only the inner acrosomal membrane but also the other portions. These non-specific bindings were excluded by the competitive dissociation with alpha-D-mannose (Man) solution, the specific labeling of the inner acrosomal membrane with FITC-Con A was accomplished in the presence of 0.5 mg/mL Man. The influence of methanol fixation on the acrosome status were examined. The assessment of the acrosome reaction should evaluate whether the inner acrosomal membrane is exposed or masked by the plasma membrane, and methanol fixation is often employed in the histochemical stain. By methanol fixation, the fluorescent profiles of AR sperm were not altered before and after the treatment, bright fluorescence were found in the acrosomal regions. On the other hand, non-AR sperm gave weak fluorescence on the sperm heads before the treatment, the acrosomal regions fluoresced brightly after the treatment similar to those of AR sperm. Methanol fixation caused false positive results, it might denaturate the plasma membranes and facilitate permeability of FITC-Con A. FITC-Con A fluorescent stain and the modified triple stain (rose bengal stain) gave good positive correlation to evaluate AR sperm. This result concluded that the optimum conditions with FITC-Con A stain in the present procedure might be an useful tool for observation of human sperm acrosome reaction.

Acrosome↗

PubMed1995

Molecular weight-dependent lymphatic transfer of fluorescein isothiocyanate-labeled dextrans after intrapulmonary administration and effects of various absorption enhancers on the lymphatic transfer of drugs in rats.

We have developed a new method to evaluate the transfer of macromolecular drugs to intrapulmonary lymph nodes in rats after intrapulmonary administration. By using this method, we observed that the transfer of fluorescein isothiocyanate dextrans (FDs) to the intrapulmonary lymph nodes was markedly higher than that to iliac lymph node, a non-intrapulmonary lymph node. The transfer of FDs to the intrapulmonary lymph nodes increased with increasing their molecular weights and the threshold for a high lymph node-to-plasma level ratio (CLN/CP) was between 10 and 20 kDa. The effects of absorption enhancers on the transfer of FDs to intrapulmonary lymph nodes were also examined in rats. Absorption enhancers used in this study were EDTA, sodium glycocholate (Na-GC), mixed micelles (MM), N-lauryl-beta-D-maltopyranoside (LM), sodium caprate (Na-Cap). The transfer of FD-20, FD-40 and FD-70 to intrapulmonary lymph nodes after intrapulmonary administration increased in the presence of LM. In particular, the lymphatic transfer of FD-40 was remarkably increased in the presence of LM. Similarly, Na-GC and MM improved the transfer of FD-40 to intrapulmonary lymph nodes. These results suggest that absorption enhancers such as LM, Na-GC and MM are effective for improving the transfer of macromolecular drugs to intrapulmonary lymph nodes.

Absorption↗

PubMed2000

Bactericidal activity of isothiocyanate against pathogens on fresh produce.

The bactericidal activity of allyl and methyl isothiocyanate (AITC and MITC) was tested with a rifampicin-resistant strain of Salmonella Montevideo and streptomycin-resistant strains of Escherichia coil O157:H7 and Listeria monocytogenes Scott A. Iceberg lettuce inoculated with high (10(7) to 10(8) CFU/g) and low (10(3) to 10(4) CFU/g) concentrations of bacterial pathogens was treated with AITC and MITC in sealed containers at 4 degrees C for 4 days. AITC showed stronger bactericidal activity than MITC against E. coli O157:H7 and Salmonella Montevideo, whereas MITC showed stronger activity against L. monocytogenes than E. coli O157:H7 and Salmonella Montevideo. Up to 8-log reduction occurred with E. coli O157:H7 and Salmonella Montevideo on lettuce following treatment with vapor generated from 400 microl of AITC for 2 and 4 days, respectively. AITC was used to treat tomatoes inoculated with Salmonella Montevideo on stem scars and skin and apples inoculated with E. coli O157:H7 on stem scars. The bactericidal effect of AITC varied with bacteria species and exposure time. Salmonella Montevideo inoculated on tomato skin was more sensitive to AITC than that on stem scars. Treatment with vapor generated from 500 microl of AITC caused an 8-log reduction in bacteria on tomato skin but only a 5-log reduction on tomato stem scars. The bactericidal activity of AITC was weaker for E. coli O157:H7 on apple stem scars; only a 3-log reduction in bacteria occurred when 600 microl of AITC was used.

Dose-Response Relationship, Drug↗

PubMed2000

Antibacterial mechanism of allyl isothiocyanate.

Allyl isothiocyanate (AITC), a natural compound in plants belonging to the family Cruciferae, has been shown to have strong antimicrobial activity in liquid media as well as in its vapor form. To understand its antimicrobial mechanism, AITC was tested for bactericidal activities to Salmonella Montevideo, Escherichia coli O157:H7, and Listeria monocytogenes Scott A at different stages of growth and was compared with streptomycin, penicillin G, and polymyxin B, each of known antibacterial mechanisms. Bactericidal activities were determined by measuring bacterial viability and leakage of metabolites. To determine its effects on membrane permeability, beta-galactosidase activity was examined after exposure of E. coli K-12 strain 3.300 to the three antibiotics and to AITC. The two gram-negative bacteria, Salmonella Montevideo and E. coli O157:H7, were more sensitive to AITC and to polymyxin B than the gram-positive L. monocytogenes. AITC and polymyxin B were effective bactericidal agents to bacteria at all growth stages, whereas penicillin G and streptomycin did not exhibit bactericidal activity to stationary cells. High A260 and A280 values of cellular filtrate and beta-galactosidase activity were obtained after treatments of AITC and polymyxin B. These data indicated that AITC was most similar to polymyxin B with respect to its antibacterial effect on cell membranes and on leakage of cellular metabolites. Gaseous AITC caused metabolite leakages, measurable increases in 3-galactosidase activity, and reduction of viable bacteria. The effectiveness of AITC in inhibiting bacteria at all growth stages and its strong activity in vapor phase support its application in food preservation.

Cell Membrane Permeability↗

PubMed2000

Combined effects of hydrostatic pressure, temperature, and the addition of allyl isothiocyanate on inactivation of Escherichia coli.

Combined effects of hydrostatic pressure, temperature, and the addition of allyl isothiocyanate (AIT) on the inactivation of Escherichia coli, including type O157, were investigated. Inactivation to undetectable levels by hydrostatic pressure alone requires 400 to 600 MPa. E. coli growth was delayed with increasing of applied pressure and the AIT concentration added subsequently. The antibacterial effects of AIT vapor increased on JCM 1649 and IFO 3301 after pressurization. The bactericidal effects of pressurization with the addition of AIT at 4 degrees C or 40 degrees C were greater than at 20 degrees C, and all bacteria tested were effectively killed at 200 or 250 MPa with 10 to 80 microg/ml of AIT. We tried to apply the combined treatment to a food product "Asazuke" (low salt vegetables), and it was confirmed that E. coli inoculated into the product was inactivated the same as in the in vitro test. We also studied the inactivation mechanism behind pressurization with AIT from the relationship between pressure resistance and precultivation temperature, and it was suggested that destruction of membrane structure caused bacterial kill.

Animals↗

PubMed2003

Bactericidal effects of Lactobacillus reuteri and allyl isothiocyanate on Escherichia coli O157:H7 in refrigerated ground beef.

Two naturally occurring antimicrobial agents were tested in packages of refrigerated ground beef for their ability to reduce the viability of Escherichia coli O157:H7 during storage. Allyl isothiocyanate (AITC) and Lactobacillus reuteri were tested separately and together for their action against a cocktail of five strains of E. coli O157:H7 in ground beef held at 4 degrees C for 25 days. Ground beef prepared from whole, raw inside round beef roasts was inoculated with low (3 log CFU/g) or high (6 log CFU/g) levels of the E. coli O157:H7 mixture. The beef was treated with AITC (about 1,300 ppm), L. reuteri, or both, along with 250 mM of glycerol per kg of meat at two levels (3 and 6 log CFU/g) and according to a design that yielded 8 controls plus 10 different treatments. Samples were analyzed for E. coli O157:H7 survivors, numbers of total bacteria, and lactic acid bacteria on days 0 to 25 at 5-day intervals. L. reuteri at both input levels with glycerol killed E. coli O157:H7 at both inoculated levels before day 20. AITC completely eliminated E. coli O157:H7 at the low-inoculum level (3 log CFU/g) and reduced viability >4.5 log CFU/g at the high-inoculum level (6 log CFU/g) by the end of the storage period. The combination of L. reuteri and AITC did not yield an additive effect against E. coli O157:H7 viability. L. reuteri in the presence of glycerol was highly effective against E. coli O157:H7 in ground beef during refrigerated storage (4 degrees C) in modified atmosphere packages. Sensory testing is planned to evaluate effects of treatments.

Cold Temperature↗

PubMed2006

Active packaging of cheese with allyl isothiocyanate, an alternative to modified atmosphere packaging.

The natural antimicrobial compound allyl isothiocyanate (AITC), found in mustard oil, is effective against cheese-related fungi both on laboratory media and cheese. Penicillium commune, Penicillium roqueforti, and Aspergillus flavus were more sensitive to AITC when it was added just after the spores had completed 100% germination and branching had started on Czapek yeast extract agar than were spores in the dormant phase. The use of 1 AITC label (Wasaouro interior labels, LD30D, 20 by 20 mm) in combination with atmospheric air in the packaging extended the shelf life of Danish Danbo cheese from 4 1/2 to 13 weeks. Two AITC labels extended the shelf life from 4 1/2 to 28 weeks. Both 1 and 2 labels in combination with modified atmosphere packaging extended the shelf life of the cheese from 18 to 28 weeks. This study showed that AITC was absorbed in the cheese, but it was not possible to detect any volatile breakdown products from AITC in the cheese. Cheese stored for up to 12 weeks with an AITC label had an unacceptable mustard flavor. The mustard flavor decreased to an acceptable level between weeks 12 and 28. Cheese stored in atmospheric air had a fresher taste without a CO2 off-flavor than did cheese stored in modified atmosphere packaging. AITC may be a good alternative to modified atmosphere packaging for cheese. The extended shelf life of cheese in the package is very desirable: the cheese can be transported longer distances, and the packaging can be used for the final maturing of the cheese. Furthermore, AITC can address problems such as pinholes and leaking seals in cheese packaging.

Cheese↗

PubMed1999

Conversion of glucosinolates to isothiocyanates in humans after ingestion of cooked watercress.

Isothiocyanates (ITCs), major constituents of cruciferous vegetables, can inhibit tumorigenesis in rodents by modulating the metabolism of carcinogens. ITCs that occur as glucosinolates are released by myrosinase-mediated hydrolysis when raw vegetables are chopped or chewed. However, because cruciferous vegetables are commonly consumed by humans after being cooked, it is important to examine whether dietary glucosinolates are converted to ITCs after cooked cruciferous vegetables in which myrosinase is deactivated have been consumed. This information is useful for evaluating the potential role of ITCs in cruciferous vegetables in the protection against human cancers. A urinary marker, based on a cyclocondensation product formed by the reaction of ITCs and their conjugates with 1,2-benzenedithiol, was used to quantify the uptake of dietary ITCs in humans. At breakfast and lunch, nine volunteers consumed a total of 350 g of cooked watercress in which the myrosinase activity was completely deactivated. On the basis of the analysis of ITCs in the cooked watercress upon adding exogenous myrosinase, the amount of glucosinolates ingested by each subject was estimated to be 475 micromol. The 24-h urine samples showed that the total urinary excretion of ITC conjugates in the subjects ranged from 5.6 to 34.8 micromol, corresponding to 1.2-7.3% of the total amount ingested. On the basis of our previous results that approximately 50% of dietary ITCs were excreted in the urine as conjugates, these values represent the minimal in vivo conversion of glucosinolates to ITCs. For purposes of comparison, we carried out a second experiment in which 150 g of uncooked watercress were consumed. The percentage of urinary ITC conjugates excreted in this study ranged from 17.2 to 77.7% of the total ingested ITCs. These results indicate that glucosinolates are converted to ITCs in humans after ingestion of cooked watercress, in which the myrosinase has been completely inactivated. The extent of conversion, however, is considerably less than that after ingesting uncooked vegetables. Furthermore, upon incubation of the cooked watercress juice with fresh human feces under anaerobic conditions, approximately 18% of glucosinolates was hydrolyzed to ITCs in 2 h. These results suggest that the microflora in the intestinal tract are a likely source for the hydrolysis of glucosinolates to ITCs in humans.

Adult↗