Diphenhydramine is an antihistamine used to relieve symptoms of allergy, hay fever, and the common cold. Jan 01, 2000 in the present study, the inhibitory effect of diphenyl diselenide and diphenyl ditelluride after in vitro, acute a single dose, or chronic exposure 14 doses was examined in mice 24 hours after the last administration. Diphenyl diselenide cas no 16663 material safety data sheet sdsmsds section 1. Indiumi iodide promoted cleavage of diphenyl diselenide. In vitro, diphenyl diselenide, and diphenyl ditelluride inhibited aminolevulinate dehydratase ala. However, the use of dpds in pharmacology is limited due to in vivo prooxidative effects. In light of these foundations, this study revealed the biochemical mechanism of diphenyl diselenide on escherichia coli, a possible involvement on sulphydrylcontaining protein in invitro and invivo. Reduction of diphenyl diselenide and analogs by mammalian thioredoxin reductase is independent of their gluthathione peroxidaselike activity. Pdf diphenyl diselenide, a simple glutathione peroxidase. Indiumi iodide promoted cleavage of diphenyl diselenide and. After 48 or 96 h of a single dose of diphenyl ditelluride, there was a significant increase in the number of micronuclei in mice when compared with control and diphenyl diselenide group fig.
Sodium selenite na 2 seo 3 is the selenium form used in the composition of dietary supplements, and diphenyl diselenide phse 2 is an important intermediate in organic synthesis, which increases the risk of human exposure to this chemical in the workplace. In a first step, reaction of chloride 3 was tested with various free and. Its potential as a neutral carrier to develop silverselective membrane electrode has been investigated. Organometallics are useful reagents, catalysts, and precursor materials with applications in thin film deposition, industrial chemistry, pharmaceuticals, led manufacturing, and others. Diphenyl diselenide was able to increase npsh levels in erythrocytes of rabbits 42 and in different tissues of mice.
The ironiii coordination with one selenium atom from the diselenide activates the other selenium toward nucleophilic attack by the alkyne to give the seleniranium ion xxi. This protocol has been utilized for the synthesis of a variety of aryl selenides in excellent yields from the readily available aryl halides and diaryl diselenides. Diphenyl diselenide and ascorbic acid changes deposition of. This study investigates the efficacy of diphenyl diselenide phse 2 in attenuating methylmercury mehginduced toxicity in rats. Diphenyl article about diphenyl by the free dictionary. Identification of the substancemixture and of the companyundertaking 1. Dpds possesses antioxidant activity, confirmed in several in vitro and in vivo systems. Diphenyl diselenide modulates oxldlinduced cytotoxicity in macrophage by improving the redox signaling.
Organoselenium compounds have been pointed out as therapeutic agents. The combination of diorganic diselenide and nchlorosuccinimide promotes the allylic oxidation of alkenes to allyl chlorides via a process which does not involve free radicals scheme 5 e 121 and combination of a diselenide with tbutyl hydroperoxide efficiently oxidizes alcohols to carbonyl compounds. Molecules free fulltext the 125te chemical shift of. Ebselen and diphenyl diselenide phse 2 are two organoselenium compounds that are recognized as promising pharmacological agents presenting antioxidant, antiinflammatory, neuroprotective, and other beneficial properties. Organometallics are useful reagent, catalyst, and precursor materials with applications in thin film deposition, industrial chemistry, pharmaceuticals, led manufacturing, and others. Since the latter is also a promising candidate as an antioxidant drug and mimic of the ubiquitous enzyme glutathione peroxidase gpx, the use of organotellurides in medicinal. Pdf interaction profile of diphenyl diselenide with. These results indicate that this polymerization proceeds.
Pdf diphenyl diselenide derivatives inhibit microbial. The pharmacology of synthetic organoselenium compounds indicates that they can be used as antioxidants, enzyme inhibitors, neuroprotectors, antitumor and antiinfectious agents, and immunomodulators. Diphenyl selenide undergoes oxidation to form selenoxides on treating with nbromosuccinimide followed by alkaline hydrolysis. Pdf pharmacology and toxicology of diphenyl diselenide in. Yalda rangraz, firouzeh nemati and ali elhampour, diphenyl diselenide immobilized on magnetic nanoparticles. Diphenyl diselenide dd is a synthetic compound of selenium which has been shown to have hepatic protective effects costa et al. Diphenyl diselenide is used as a source of the phse unit in organic synthesis. Adult rats were treated with mehg 5 mgkgday, intragastrically i. Copper oxide nanoparticlecatalyzed coupling of diaryl. Hazardous in case of eye contact irritant, of ingestion, of. Diselenide bonds as an alternative to outperform the. Research unity of valorization of natural resources bioactive molecules, physicochemical and biological. Diphenyl diselenide is used in the methoxyselenenylation of alkenes, dihydroxylation of double bonds, hydrothiolation of terminal alkynes. Among all the tested species, diphenyl diselenide based materials appear to be the most promising ones due to the decrease on the reaction barriers, instead of weaker diselenide bonds, as thought up to now.
Otrityl oximes of 5 and 6iodoaldehydes undergo radical cyclization to produce oximes when treated in refluxing tetrahydrofuran thf with bu3snh, 1,1azobiscyclohexanecarbonitrile, ipr2net, and diphenyl diselenide phseseph. These compounds can exert their pharmacological effects by mimicking the native glutathione peroxidase enzyme gpxlike. Pharmacology and toxicology of diphenyl diselenide in several. Diphenyl diselenide is a simple synthetic organoselenium compound, which exhibits numerous interesting effects when used in pharmacological doses. Carbocyclization by radical closure onto otrityl oximes. This orangecoloured solid is the oxidized derivative of benzeneselenol. A series of 16 new diselenide acylselenourea conjugates have been designed following the fragmentbased drug strategy. Indium i iodidemediated cleavage of diphenyl diselenide. Diphenyl diselenide itself is also a source of a weakly electrophilic phse group in reactions with relatively powerful nucleophiles like grignard reagents, lithium reagents and ester enolates but not ketone enolates or weaker nucleophiles. Diphenyl definition of diphenyl by medical dictionary. Biochemical mechanism of diphenyl diselenide on escherichia. The treatment of nallylacetylhydrazides 120 with diphenyl diselenide at.
Recently, we demonstrated that diphenyl diselenide inhibits human low density lipoprotein oxidation in vitro and this phenomenon was related to its thiol. Determination of decabrominated diphenyl ether in soils by soxhlet extraction and high performance liquid chromatography. Free radical scavenging in vitro and biological activity of diphenyl. Pdf antisecretory and antiulcer effects of diphenyl. Body weight gain and motor deficits were evaluated prior to treatment, on treatment days 11 and 21. Diphenyl diselenide decreases serum levels of total. Buy diphenyl diselenide cas 16663, a biochemical for proteomics research, from santa cruz. Diphenyl diselenide manufacturers, producers, cas no 1666. Diphenyl diselenide a janusfaced molecule article pdf available in journal of the brazilian chemical society 2111. Reaction of bis2chlorocarbonylphenyl diselenide with. Differential genotoxicity of diphenyl diselenide phse2 and. Effects of diphenyl diselenide on methylmercury toxicity. At room temperature, the initially formed 1,3,4oxadiazines 122 are converted completely to. Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection.
The results of the present study demonstrated that. Diphenyl diselenide is the chemical compound with the formula c6h52se2, abbreviated ph2se2 this orangecoloured solid is the oxidized derivative of benzeneselenol. The reactions of vinylidencyclopropanes 1 with diphenyl diselenide 2 in the presence of aibn produced the corresponding products 4 or 5 in moderate to good yields under mild conditions. Additionally, by uploading or otherwise transmitting material to any area of the web site you are granting the company a irrevocable, royalty free, worldwide right to publish, reproduce, use, adapt, edit andor modify such material in any way, in any and all media now known or hereafter discovered, worldwide, including on the internet and world. A new, efficient and ligandfree crosscoupling reaction of aryl halides and diaryl diselenides using a catalytic amount of nanocrystalline cuo as a recyclable catalyst with koh as the base in dmso at 110 c is reported. Diphenyl diselenide selenium atherosclerosis macrophage glutathione peroxidase ldl oxidation in. Molecules free fulltext reduction of diphenyl diselenide. Involvement of the glutathionedependent antioxidant system. Compound in vitro cytotoxic potential was evaluated against six human cancer cell lines and two nonmalignant derived cell lines with the aim of determining their potency and selectivity. Its standard enthalpies of combustion, formation and the mean bonddissociation energy have been calculated. Files are available under licenses specified on their description page. Diphenyl diselenide and diphenyl ditelluride differentially.
Photopolymerization of styrene in the presence of diphenyl diselenide proceeded smoothly. The products are readily oxidized to the selenoxides which undergo ambient temperature copetype. The alkyl diselenide has been incorporated into polyurethane networks using a parasubstituted amine diphenyl alkyl diselenide. Physicochemical and biochemical profiling of diphenyl.
Genotoxicity of diphenyl diselenide in bacteria and yeast. Antisecretory and antiulcer effects of diphenyl diselenide. Moreover, the radical formation needed in this process would also be enhanced by the fact that these species are able to absorb visible light. Diphenyl diselenide an overview sciencedirect topics. Diphenyl diselenide and ascorbic acid changes deposition of selenium and ascorbic acid in liver and brain of mice. Administration to mice during cadmium intoxication has the opposite effect, reducing oxidative stress in various tissues. Diphenyl diselenide 98% phenyl diselenide sigmaaldrich. Free radical scavenging in vitro and biological activity of. A novel and retrievable heterogeneous catalyst in the oxidation of aldehydes under mild and green conditions, journal of colloid and interface science, 10.
Free radical scavenging in vitro and biological activity. Consistent with this, we have found that the addition of both absolute ethanol and diborane in thf to a reaction mixture, generated according to either eq 2 or 3, immediately dissolves the precipitate and forms a clear, colorless, and homogeneous. Application used for antiselective michael addition of thiols and their analogs to nitroolefins. Diphenyl diselenide which is reduced to sodium phenylselenolate, presenting an electron transfer agent successfully permitted to reduce several nitroarenes, bearing different substituent groups whose electronic effects promote the formation of the azoxy or azo compounds. Diphenyl diselenide protects neuronal cells against oxidative stress and mitochondrial dysfunction. Diphenyl diselenide, a simple glutathione peroxidase mimetic, inhibits human ldl oxidation in vitro. Search results for diphenyldiselenide at sigmaaldrich. The polymer yields and the number average molecular weight mn of the polymers increased with reaction time. Pdf the pharmacology of synthetic organoselenium compounds indicates that they can. Slightly hazardous in case of skin contact irritant. Free radical scavenging in vitro and biological activity of diphenyl diselenideloaded nanocapsules. Diphenyl diselenide and ascorbic acid changes deposition. In addition, studies have shown that dpdsloaded nanocapsules dpdsncs have greater bioavailability than free dpds in mice.
Diphenyl diselenide modulates oxldlinduced cytotoxicity. The present study evaluated the comparative toxicological effects of diphenyl diselenide phse2 and diphenyl ditelluride phte2 in mice after in vivo administration. In contrast, the potential therapeutic aspects of tellurides have not yet been demonstrated. Pdf diphenyl diselenide has shown interesting biological activities in various freeradicalinduced damage models and can be considered as a potential. An indiumtmscl promoted reaction of diphenyl diselenide and diorganyl disulfides with aldehydes. Diphenyl definition of diphenyl by the free dictionary. They typically are deposited in body fat stores and are rarely mobilized except through lactation. Diphenyl diselenide byers major reference works wiley. Polybrominated diphenyl ethers pbdes are widely used brominated flame retardants which prevent ignition in textiles, plastics, and electronic products. Thus, diphenyl diselenide can lead to loss of biological functions and possibly the death of an organism 16. The interest in diphenyl ditelluride ph2te2 is related to its strict analogy to diphenyl diselenide ph2se2, whose capacity to reduce organic peroxides is largely exploited in catalysis and green chemistry.
Diphenyl diselenide is a synthetic organoselenium compound that has thiol. Pdf pharmacology and toxicology of diphenyl diselenide. Differential genotoxicity of diphenyl diselenide phse2. Diphenyl diselenide and diphenyl ditelluride increase the latency for 4aminopyridineinduced chemical seizure and prevent death in mice. Reactions of vinylidenecyclopropanes with diphenyl. Pharmacology and toxicology of diphenyl diselenide in. Diphenyl diselenide, one of the more promising organoselenium compounds, was assessed in two studies by either oral or subcutaneous route with favorable resultsthe substance significantly inhibited pain behavior in the formalin, capsaicin, glutamate, bradykinin, and writhing test savegnago et al. The transformation of 4 to the corresponding methylenecyclopropanes 6 was achieved by treatment with hydrogen peroxide h2o2 in toluene, and these were further transformed to the. All structured data from the file and property namespaces is available under the creative commons cc0 license. Molecular effects of diphenyl diselenide on cholesterol and. The reaction takes place via the pathway outlined in scheme 5.
An efficient onepot procedure for the synthesis of unsymmetrical diorganyl selenides. Diphenyl diselenide in vitro and in vivo activity against the. Sigmaaldrich offers a number of diphenyl diselenide products. Diphenyl diselenide is most frequently used as a reagent for. Diphenyl diselenide diet intake improves spatial learning. Further, a linear relationship was found for a plot of mn for polystyrene versus polymer yield. Media in category diphenyl diselenide the following 7 files are in this category, out of 7 total.
The resulting materials not only exhibit faster selfhealing properties than the corresponding disulfidebased materials, but also show the ability to be processed at temperatures as low as 60 c. Full text free radical scavenging in vitro and biological. These symptoms include rash, itching, watery eyes, itchy eyesnosethroat, cough. The substance identity section is calculated from substance identification information from all echa databases. These compounds have been reported to inhibit the cerebral and hepatic aminolevulinic acid dehydratase ala. Diphenyl diselenide did not modify the number of micronuclei when compared to the control group fig.
Reaction of diphenyl diselenide with hydrogen peroxide and inhibition of deltaaminolevulinate dehydratase from rat liver and cucumber leaves. Living radical polymerization of styrene with diphenyl. This study was designed to investigate the molecular effects of diphenyl diselenide phse 2 on cholesterol metabolism in hepg2 cell line in a dosedependent. Diphenyl diselenide catalyzed reductive coupling of. Diphenyl diselenide catalyzed reductive coupling of nitroarenes to aromatic azo and azoxy compounds with sodium borohydride in alkaline ethanol volume. It is used as a source of the phse unit in organic synthesis. Ampk, cholesterol, diphenyl diselenide, glucose, hepg2 cells, l6 myoblasts, hmgr, ldlr. The substance identifiers displayed in the infocard are the best available substance name, ec number, cas number andor the molecular and structural formulas. Some of the most frequent are the reduction of oxidative stress through the elimination of free.
Pdf genotoxicity of diphenyl diselenide in bacteria and. A cooperative action between diphenyl diselenide and the ironiii chloride is essential to provide good yields of the cyclized product. Hazardous in case of eye contact irritant, of ingestion, of inhalation. It is used in the synthesis of the unsymmetrical diorganyl selenides, 1phenylselenomethylvinyl selenides, allylic phenyl selenides. Anticancer and chemopreventive activity researchgate.
Protective effects of diphenyl diselenide in a mouse model of. Diethyl diselenide is one of numerous organoselenium compounds manufactured by american elements under the trade name ae organometallics. Nadjah belattar, samir benayache and fadila benayache affiliation. It is known that gsh is part of the glutathione peroxidase system, as an electron donor that reacts directly with free. Predicted data is generated using the us environmental protection agencys episuite.
Diphenyl diselenide is one of numerous organometallic compounds sold by american elements under the trade name ae organometallics. Hazard identification potential acute health effects. D from brain, liver, and kidney with a similar potency ic50. Since diphenyl diselenide action on low molecular endogenous thiol depends on a variety of factors including species, this organoselenium compound was investigated in different species. Diphenyl diselenide protects neuronal cells against.
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