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Topic: Isothiocyanate


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  Thornalley Lab - Chemoprevention of Cancer by Dietary Isothiocyanates   (Site not responding. Last check: 2007-10-18)
Isothiocyanates and cysteine conjugates had increased potency against HL60 cells in serum-free medium - the GC values were 0.8-0.9 µM; the potency of the compounds decreased with increased serum content of the medium but that of the cysteine conjugates decreased more markedly.
Growth inhibition and toxicity was characterized by a rapid interaction of the isothiocyanate with the cells in the first hour of culture – or exposure to isothiocyanate liberated from the cysteine conjugate in the initial 3 h of culture, inhibition of macromolecule synthesis and commitment to apoptosis which developed in the initial 24 h.
S-(N-phenethylthiocarbamoyl)glutathione spontaneously fragmented to GSH and phenethyl isothiocyanate: GSH oxidized to GSSG and glutathionyl-protein disulphides, and phenethyl isothiocyanate hydrolyzed to phenylethylamine.
www.essex.ac.uk /bs/staff/thornalley/homepage/research_interests/isothiocyanates   (1827 words)

  
 Patent 6,737,441
In one embodiment of the current invention, the isothiocyanate for use in the current invention is sulforaphane, or a derivative thereof.
Sulforaphane (4-methylsulfinylbutyl isothiocyanate or (-)-1-isothiocyanato-4(R)-(methylsulfinyl) butane) and sulforaphene (4-methylsulfinylbutenyl isothiocyanate) and their cognate glucosinolates (glucoraphanin and glucoraphenin, respectively), are known to be produced by plants, such as hoary cress, radish and other plants (Mislow et al., J. Am.
In another embodiment, the known modulators for use in the assay of the current invention are isothiocyanate, sulforaphane, sulforaphene, erysolin, erucin, iberin, alyssin, berteroin, iberverin, cheirolin, 5-methylsulfinylpentyl isothiocyanate, 6-hexylsulfinyl isothiocyanate, 7-methylsulfinylheptyl isothiocyanate, 8-methylsulfinyloctyl isothiocyanate, 9-methylsulfinylnonyl isothiocyanate, 10-methylsulfinyldecyl isothiocyanate, phenylethyl isothiocyanate, 4-(.alpha.-L-rhamnopyranosyloxy)benzyl isothiocyanate, 3-(.alpha.-L-rhamnopyranosyloxy)benzyl isothiocyanate, 2-(.alpha.-L-rhamnopyranosyloxy)benzyl isothiocyanate, 4-(4'-O-acetyl-.alpha.-L-rhamnopyranosyloxy)benzyl isothiocyanate or a derivative thereof.
www.pharmcast.com /Patents100/Yr2004/May2004/051804/6737441_Heliobacter051804.htm   (4509 words)

  
 Disposition and Pharmacokinetics of Phenethyl Isothiocyanate and 6-Phenylhexyl Isothiocyanate in F344 Rats -- Conaway ...
Disposition and Pharmacokinetics of Phenethyl Isothiocyanate and 6-Phenylhexyl Isothiocyanate in F344 Rats -- Conaway et al.
Disposition and Pharmacokinetics of Phenethyl Isothiocyanate and 6-Phenylhexyl Isothiocyanate in F344 Rats
Guo Z, Smith TJ, Wang E, Eklind KI, Chung F-L and Yang CS (1993) Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: Metabolism and modulation of xenobiotic metabolizing enzymes in rats and mice.
dmd.aspetjournals.org /cgi/content/full/27/1/13   (4743 words)

  
 BoDD (Botanical Dermatology Database) - CRUCIFERAE
These isothiocyanates, otherwise known as mustard oils, are derived from compounds known as glucosinolates by the action of myrosinase, an enzyme.
Cole (1976) observed that allyl isothiocyanate together with a small quantity of 2-phenylethyl isothiocyanate was released from the glucosinolates of this plant on autolysis.
Allyl isothiocyanate is released from the plant material on autolysis of its glucosinolates (Cole 1976).
bodd.cf.ac.uk /BotDermFolder/BotDermC/CRUC.html   (5558 words)

  
 Last eval.: Allyl Isothiocyanate (Vol73)   (Site not responding. Last check: 2007-10-18)
Exposure to allyl isothiocyanate occurs as a result of its presence in foods as the chief constituent of mustard oil and as a flavouring agent.
Allyl isothiocyanate was tested for carcinogenicity in one experiment in mice and one experiment in rats by oral administration.
Major sex- and species-related differences in the tissue distribution of allyl isothiocyanate were restricted to the urinary bladder, where higher concentrations of allyl isothiocyanate-derived radiolabel were found in the bladders of male rats than in mice or female rats.
monographs.iarc.fr /htdocs/monographs/vol73/73-01.html   (268 words)

  
 Phenyl isothiocyanate derivatives and their production - Patent 4248869
The phenyl isothiocyanates (I) are useful as agricultural fungicides against various phytopathogenic fungi such as cucurbitaceae powdery mildew, cucurbitaceae downy mildew, cucurbitaceae anthracnose, rice plant blast and drooping diseases of various crops.
Fifty parts by weight of 3-methoxycarbonyl-4-methoxyphenyl isothiocyanate, 35 parts by weight of diatomaceous earth, 10 parts by weight of white carbon, 2 parts by weight of sodium alkylbenzenesulfonate and 3 parts by weight of calcium lignin sulfonate are triturated and mixed to provide wettable powder.
Three parts by weight of 3-methoxycarbonyl-4,6-dimethoxyphenyl isothiocyanate, 2 parts by weight of sodium alkylbenzenesulfonate, 45 parts by weight of clay and 50 parts by weight of bentonite are mixed, kneaded with a suitable amount of water and granulated by an extrusive granulator.
www.freepatentsonline.com /4248869.html   (2936 words)

  
 Complexes for immobilizing isothiocyanate natural precursors in cyclodextrins, preparation and use - US Patent 6716827   (Site not responding. Last check: 2007-10-18)
The precise subject of this present invention is bacteriostatic, bactericidal and/or fungicidal compositions in which the organic isothiocyanate is stabilised in the form of an inclusion complex in a cyclodextrin, permitting its solubilisation in an aqueous medium and control over its release.
According to the invention, the inclusion complexes of natural precursors of organic isothiocyanates in cyclodextrins may be used to prepare an inclusion complex of an organic isothyanate in a cyclodextrin.
Also, it is noted that the benzyl isothiocyanate formed by the action of myrosinase is always complexed in the cyclodextrin and therefore remains soluble in an aqueous solution.
www.patentstorm.us /patents/6716827.html   (2818 words)

  
 Previous eval.: Allyl Isothiocyanate (Vol36)   (Site not responding. Last check: 2007-10-18)
Allyl isothiocyanate is also prepared from the seeds of mustard plants, Brassica nigra and B.
Allyl isothiocyanate was tested for carcinogenicity by gastric intubation in mice of one strain and in rats of one strain.
Allyl isothiocyanate was not teratogenic to mice, rats, hamsters or rabbits, but resorptions were seen in mice and rats.
monographs.iarc.fr /htdocs/monographs/vol36/allylisothiocyanate.html   (236 words)

  
 NTP: Abstract for TR-234 - Allyl Isothiocyanate
The increased incidence of cytoplasmic vacuolization in the liver of dosed male mice was related to administration of allyl isothiocyanate (controls, 2/49, 4%; low-dose, 8/49, 16%; high-dose, 13/50, 26%).
Under the conditions of this bioassay, allyl isothiocyanate was carcinogenic for male F344/N rats, causing transitional-cell papillomas in the urinary bladder.
Evidence for associating allyl isothiocyanate with subcutaneous fibrosarcomas in female F344/N rats was equivocal.
ntp-server.niehs.nih.gov /ntpweb/index.cfm?objectid=070654C2-FBED-FAFA-564F802B36ACA523   (545 words)

  
 RedOrbit - Science - Dietary Isothiocyanates Inhibit Caco-2 Cell Proliferation and Induce G^Sub 2^/M Phase Cell Cycle ...   (Site not responding. Last check: 2007-10-18)
Benzyl isothiocyanate and phenethyl isothiocyanate, two aromatic phytochemicals present in substantial concentrations in edible vegetables of the genus Brassica, were investigated for their effects on Caco-2 cell proliferation.
Benzyl and phenethyl isothiocyanate inhibited DNA synthesis, with 50% inhibitory concentrations of 5.1 and 2.4 mol/L, respectively, and significantly increased the doubling times of Caco-2 cells from 32 h to 220 and 120 h, respectively.
These results suggest that the antiproliferative effects of benzyl and phenethyl isothiocyanates toward Caco-2 cells are due at least in part to the activation of the G^sub 2^/M DNA damage checkpoint, and that sustained G^sub 2^/M phase cell cycle arrest in response to benzyl and phenethyl isothiocyanates may be maintained through upregulation of p21.
www.rednova.com /news/display?id=106448   (4240 words)

  
 allyl isothiocyanate Exemption from Tolerance 5/96   (Site not responding. Last check: 2007-10-18)
Allyl isothiocyanate, the subject of this exemption request, is a component of Oil of Mustard.
Allyl isothiocyanate, as a component of oil of mustard, is on the Food and Drug Administration (FDA) Generally Recognized as Safe (GRAS) list (21 CFR 182.10, 182.20, 582.10 and 582.20).
The insecticide and repellent Allyl isothiocyanate is exempt from the requirement of a tolerance for residues when used as a component of food grade oil of mustard, in or on all raw agricultural commodities, when applied according to approved labeling.
pmep.cce.cornell.edu /profiles/insect-mite/abamectin-bufencarb/allyl-isothio/tol-ex-allyl-isothio.html   (1301 words)

  
 Hydrolysis of Glucosinolates to Isothiocyanates after Ingestion of Raw or Microwaved Cabbage by Human Volunteers -- ...
The inclusion of the watercress autolysate was to quantify postabsorptive
output as a proportion of allyl isothiocyanate ingested was
-cysteine, a principal metabolite of alkyl isothiocyanates in rat urine.
cebp.aacrjournals.org /cgi/content/full/13/1/125   (4329 words)

  
 The dietary isothiocyanate sulforaphane targets pathways of apoptosis, cell cycle arrest, and oxidative stress in human ...
The dietary isothiocyanate sulforaphane targets pathways of apoptosis, cell cycle arrest, and oxidative stress in human pancreatic cancer cells and inhibits tumor growth in severe combined immunodeficient mice -- Pham et al.
The dietary isothiocyanate sulforaphane targets pathways of apoptosis, cell cycle arrest, and oxidative stress in human pancreatic cancer cells and inhibits tumor growth in severe combined immunodeficient mice
Chemoprevention of colonic aberrant crypt foci in Fischer rats by sulforaphane and phenethyl isothiocyanate.
mct.aacrjournals.org /cgi/content/full/3/10/1239   (4688 words)

  
 Inhibition and Inactivation of Human Cytochrome P450 Isoforms by Phenethyl Isothiocyanate -- Nakajima et al. 29 (8): ...
Goosen TC, Mills DE and Hollenberg PF (2001) Effects of benzyl isothiocyanate on rat and human cytochrome P450: identification of metabolites formed by P450 2B1.
Morse MA, Eklind KI, Amin SG and Chung F-L (1992) Effect of frequency of isothiocyanate administration on inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced pulmonary adenoma formation in A/J mice.
Stoner GD, Morrissey DT, Heur Y-H, Daniel EM, Galati AJ and Wagner SA (1991) Inhibitory effects of phenethyl isothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in the rat esophagus.
dmd.aspetjournals.org /cgi/content/full/29/8/1110   (2366 words)

  
 BoDD (Botanical Dermatology Database) - CAPPARACEAE
Typically, the plants yield methyl isothiocyanate from methyl glucosinolate (otherwise known as glucocapparin).
Methyl isothiocyanate is a known irritant and sensitiser.
Methyl isothiocyanate, a mustard oil, is released from glucocapparin when the plant material is crushed.
bodd.cf.ac.uk /BotDermFolder/BotDermC/CAPP.html   (1400 words)

  
 Sacramento River Portal and Library
Title: Microbial ecology, toxicology and chemical fate of methyl isothiocyanate in riparian soils from the upper Sacramento River.
The soil respiration EC50s for the river soils ranged from 13.2 to 51.4 mu-g/g methyl isothiocyanate, whereas that of the agricultural soil was 72.2 mu-g/g.
The half-life of methyl isothiocyanate in soils ranged from 2.7 to 6.9 days and was longer by a factor of two in the river soils.
www.watershedportal.org /viewDoc_html?did=299   (236 words)

  
 Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bioactivation in mouse by dietary phenethyl ...
Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bioactivation in mouse by dietary phenethyl isothiocyanate.
Phenethyl isothiocyanate (PEITC), which occurs as gluconasturtiin in cruciferous vegetables, is a potent inhibitor of NNK-induced carcinogenesis.
The present study investigated the enzymatic basis for the bioactivation of NNK and the mechanisms of the inhibition of this process by dietary PEITC in mice.
www.pdg.cnb.uam.es /UniPub/iHOP/gp/7717707.html   (426 words)

  
 Dietary Organic Isothiocyanates Are Cytotoxic in Human Breast Cancer MCF-7 and Mammary Epithelial MCF-12A Cell Lines -- ...
Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice.
Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines.
Effects of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats.
www.ebmonline.org /cgi/content/full/229/8/835   (3392 words)

  
 Allyl isothiocyanate Suppresses Proliferation-Prostate Ca Cells
Epidemiological studies have suggested that increased consumption of cruciferous vegetables, e.g., broccoli, cabbage etc., may be beneficial in reducing the risk for certain types of malignancies including prostate cancer.
The anti-neoplastic activity of cruciferous vegetables is believed to be due to isothiocyanate (ITC) class of chemicals that are derived from glucosinolates.
In the present study, we demonstrate that allyl isothiocyanate (AITC), a naturally occurring member of the ITC family of phytochemicals, is a potent inhibitor of the proliferation of PC-3 (androgen-independent) and LNCaP (androgen-dependent) human prostate cancer cells in culture.
www.annieappleseedproject.org /alissupprolc.html   (419 words)

  
 Effects of Benzyl Isothiocyanate on Rat and Human Cytochromes P450: Identification of Metabolites Formed by P450 2B1 -- ...
Isothiocyanates have been shown to be potent and selective inhibitors of carcinogenesis induced by a variety of chemical carcinogens
Lee M-S (1992) Oxidative conversion by rat liver microsomes of 2-naphthyl isothiocyanate to 2-naphthyl isocyanate, a genotoxicant.
Wattenberg LW (1981) Inhibition of carcinogen-induced neoplasia by sodium cyanate, tert-butyl isocyanate, and benzyl isothiocyanate administered subsequent to carcinogen exposure.
jpet.aspetjournals.org /cgi/content/full/296/1/198   (6019 words)

  
 Molecular Mechanisms of c-Jun N-terminal Kinase-mediated Apoptosis Induced by Anticarcinogenic Isothiocyanates -- Chen ...   (Site not responding. Last check: 2007-10-18)
Isothiocyanates have strong chemopreventive properties against many carcinogen-induced cancers in experimental animal models.
Isothiocyanates Induce JNK Activation in a Dose-dependent Manner-- Human leukemia Jurkat T-cells were treated with different concentrations of PITC, PMITC, PEITC, and PPITC.
Isothiocyanates are well known for their chemopreventive effects on various carcinogens (29-33).
www.jbc.org /cgi/content/full/273/3/1769   (4722 words)

  
 Environmental Protection Agency
Warning: Methyl isothiocyanate is very toxic and highly irritating to skin, mucous membranes, and eyes.
Signs and symptoms of acute exposure to methyl isothiocyanate is an irritant to eyes, skin, lungs, and the mucous membranes of the gastrointestinal tract.
Acute exposure to methyl isothiocyanate exposure may require decontamination and life support for the victims.
yosemite.epa.gov /oswer/CeppoEHS.nsf/firstaid/556-61-6?OpenDocument   (580 words)

  
 Allyl isothiocyanate, a constituent of cruciferous vegetables, inhibits proliferation of human prostate cancer cells by ...
Allyl isothiocyanate, a constituent of cruciferous vegetables, inhibits proliferation of human prostate cancer cells by causing G2/M arrest and inducing apoptosis -- Xiao et al.
Chung,F.-L., Conaway,C.C., Rao,C.V. and Reddy,B.S. (2000) Chemoprevention of colonic aberrant crypt foci in Fischer rats by sulforaphane and phenethyl isothiocyanate.
Yang,Y.-M., Conaway,C.C., Chiao,J.W., Wang,C.-X., Amin,S., Whysner,J., Dai,W., Reinhardt,J. and Chung,F.-L. (2002) Inhibition of benzo(a)pyrene-induced lung tumorigenesis in A/J mice by dietary N-acetylcysteine conjugates of benzyl and phenethyl isothiocyanates during the postinitiation phase is associated with activation of mitogen-activated protein kinases and p53 activity and induction of apoptosis.
carcin.oxfordjournals.org /cgi/content/full/24/5/891   (4052 words)

  
 Chemoprevention of Cancer by Isothiocyanates, Modifiers of Carcinogen Metabolism -- Hecht 129 (3): 768 -- Journal of ...   (Site not responding. Last check: 2007-10-18)
Isothiocyanates are released upon chewing or maceration of certain cruciferous
Guo Z., Smith T. J., Wang E., Eklind K. I., Chung F.-L., Yang C. Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice.
Wattenberg L. Inhibition of carcinogen-induced neoplasia by sodium cyanate, tert-butyl isocyanate, and benzyl isothiocyanate administered subsequent to carcinogen exposure.
www.nutrition.org /cgi/content/full/129/3/768S   (3431 words)

  
 Vibrational spectra and structure of cyclopropyl isothiocyanate   (Site not responding. Last check: 2007-10-18)
For cyclopropyl isothiocyanate, the IR (4000-200 cm-1) spectra in all 3 phases and the Raman spectra of the liq.
Raman depolarization data and IR gas phase band contours showed that cyclopropyl isothiocyanate exists in the cis conformation.
An assignment for 24 of the 27 fundamental vibrational modes is proposed and this assignment is in excellent agreement with vibrational assignments for other monosubstituted cyclopropanes and a no. of isothiocyanate compds.
www-personal.ksu.edu /~krish/cpncs1.htm   (90 words)

  
 EPA: Federal Register: Allyl Isothiocyanate as a Component of Food Grade Oil of Mustard; Exemption From the Requirement ...
Allyl Isothiocyanate as a Component of Food Grade Oil of Mustard; Exemption From the Requirement of a Tolerance
to establish an exemption from the requirement of a tolerance for allyl isothiocyanate (a component of oil of mustard) in or on all fruits and vegetables, nuts, berries, and grains.'' There were no public comments received as a result of the publication of the notice of filing.
The Acute Oral LD for Allyl isothiocyanate, in rats, is 339 mg/kg body weight (Toxicity Category II).
www.epa.gov /fedrgstr/EPA-PEST/1996/May/Day-17/pr-708.html   (1290 words)

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