organoselenium compounds

Summary

Summary: Organic compounds which contain selenium as an integral part of the molecule.

Top Publications

  1. Weekley C, Aitken J, Musgrave I, Harris H. Methylselenocysteine treatment leads to diselenide formation in human cancer cells: evidence from X-ray absorption spectroscopy studies. Biochemistry. 2012;51:736-8 pubmed publisher
    ..The differences in the speciation of Se in the selenoamino acid-treated cells may provide insight into the differing anticancer activities of MeSeCys and SeMet. ..
  2. Kassam S, Goenaga Infante H, Maharaj L, Hiley C, Jüliger S, Joel S. Methylseleninic acid inhibits HDAC activity in diffuse large B-cell lymphoma cell lines. Cancer Chemother Pharmacol. 2011;68:815-21 pubmed publisher
    ..The ability of methylselenol to inhibit HDAC activity has not been previously reported, thus providing a novel mechanism of selenium action. ..
  3. Puntel R, Roos D, Seeger R, Rocha J. Mitochondrial electron transfer chain complexes inhibition by different organochalcogens. Toxicol In Vitro. 2013;27:59-70 pubmed publisher
    ..e., Ebs, (PhSe)(2) and (PhTe)(2) can oxidize critical thiol groups from mitochondrial complexes I and II. So, mitochondrial dysfunction can be considered an important factor in the toxicity of Ebs, (PhSe)(2) and (PhTe)(2). ..
  4. Avila D, Benedetto A, Au C, Manarin F, Erikson K, Soares F, et al. Organotellurium and organoselenium compounds attenuate Mn-induced toxicity in Caenorhabditis elegans by preventing oxidative stress. Free Radic Biol Med. 2012;52:1903-10 pubmed publisher
    ..Our findings establish that the organochalcogens DPTVP and ebselen act as antiaging agents in a model of Mn-induced toxicity and aging by regulating DAF-16/FOXO signaling and attenuating oxidative stress. ..
  5. de Souza Prestes A, Stefanello S, Salman S, Pazini A, Schwab R, Braga A, et al. Antioxidant activity of ?-selenoamines and their capacity to mimic different enzymes. Mol Cell Biochem. 2012;365:85-92 pubmed publisher
    The antioxidant properties of organoselenium compounds have been extensively investigated because oxidative stress is a hallmark of a variety of chronic human diseases...
  6. Meinerz D, De Paula M, Comparsi B, Silva M, Schmitz A, Braga H, et al. Protective effects of organoselenium compounds against methylmercury-induced oxidative stress in mouse brain mitochondrial-enriched fractions. Braz J Med Biol Res. 2011;44:1156-63 pubmed
    We evaluated the potential neuroprotective effect of 1-100 µM of four organoselenium compounds: diphenyl diselenide, 3'3-ditri-fluoromethyldiphenyl diselenide, p-methoxy-diphenyl diselenide, and p-chloro-diphenyl diselenide, against ..
  7. Wang H, Riahi M, Pothen J, Bayse C, Riggs Gelasco P, Brumaghim J. Interactions of Cu(I) with selenium-containing amino acids determined by NMR, XAS, and DFT studies. Inorg Chem. 2011;50:10893-900 pubmed publisher
    Cu(I) coordination by organoselenium compounds was recently reported as a mechanism for their prevention of copper-mediated DNA damage...
  8. Klein M, Ouerdane L, Bueno M, Pannier F. Identification in human urine and blood of a novel selenium metabolite, Se-methylselenoneine, a potential biomarker of metabolization in mammals of the naturally occurring selenoneine, by HPLC coupled to electrospray hybrid linear ion trap-orbital io. Metallomics. 2011;3:513-20 pubmed publisher
    ..The analytical tool developed here will be of a great importance to further study the occurrence and the potential metabolic role in mammalian organelles, cells and fluids of these very particular and promising redox metabolites. ..
  9. Sinha I, Null K, Wolter W, Suckow M, King T, Pinto J, et al. Methylseleninic acid downregulates hypoxia-inducible factor-1? in invasive prostate cancer. Int J Cancer. 2012;130:1430-9 pubmed publisher
    ..Our study illustrates the efficacy of MSeA in controlling growth of hormone refractory prostate cancer by downregulating HIF-1?, which is possibly occurring through stabilization or increase in prolyl hydroxylase activity. ..

More Information

Publications92

  1. Sharma A, Kline C, Berg A, Amin S, Irby R. The Akt inhibitor ISC-4 activates prostate apoptosis response protein-4 and reduces colon tumor growth in a nude mouse model. Clin Cancer Res. 2011;17:4474-83 pubmed publisher
    ..Inhibition of Akt with ISC-4 inhibited tumor growth and had a greater effect on cells overexpressing Par-4. The data indicate ISC-4 alone or in combination with Par-4 can greatly reduce tumor growth. ..
  2. Lu J, Vlamis Gardikas A, Kandasamy K, Zhao R, Gustafsson T, Engstrand L, et al. Inhibition of bacterial thioredoxin reductase: an antibiotic mechanism targeting bacteria lacking glutathione. FASEB J. 2013;27:1394-403 pubmed publisher
    ..39 ?g/ml. These results demonstrate that bacterial Trx and TrxR are viable antibacterial drug targets using benzisoselenazol and benzisothiazol derivates. ..
  3. Zhang G, Nitteranon V, Guo S, Qiu P, Wu X, Li F, et al. Organoselenium compounds modulate extracellular redox by induction of extracellular cysteine and cell surface thioredoxin reductase. Chem Res Toxicol. 2013;26:456-64 pubmed publisher
    ..The effects of organoselenium compounds on extracellular redox may contribute to the known, but inadequately understood, biological effects of ..
  4. Bhabak K, Vernekar A, Jakka S, Roy G, Mugesh G. Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues. Org Biomol Chem. 2011;9:5193-200 pubmed publisher
    ..Interestingly, substitution of an oxazoline moiety on the phenyl ring stabilizes the selenoxide, and therefore, enhances the isomerization of PN to nitrate. ..
  5. Santofimia Castaño P, Salido G, Gonzalez A. Ebselen alters mitochondrial physiology and reduces viability of rat hippocampal astrocytes. DNA Cell Biol. 2013;32:147-55 pubmed publisher
    ..These may be early effects that do not involve caspase-3 activation. We conclude that, depending on the concentration used, ebselen might exert deleterious actions on astrocyte physiology that could compromise cell function. ..
  6. Hort M, Straliotto M, Netto P, da Rocha J, de Bem A, Ribeiro do Valle R. Diphenyl diselenide effectively reduces atherosclerotic lesions in LDLr -/- mice by attenuation of oxidative stress and inflammation. J Cardiovasc Pharmacol. 2011;58:91-101 pubmed publisher
    ..Our results reveal the antiatherogenic actions of DD by modulating intracellular signaling pathways related to antioxidant and anti-inflammatory responses. ..
  7. Zhang J, Wang L, Li G, Anderson L, Xu Y, Witthuhn B, et al. Mouse prostate proteomes are differentially altered by supranutritional intake of four selenium compounds. Nutr Cancer. 2011;63:778-89 pubmed publisher
    ..We propose that the balance of oncogenic vs. suppressor protein patterns in the prostate may impact the direction of PCa risk modification by a given selenium...
  8. Nogueira C, Rocha J. Toxicology and pharmacology of selenium: emphasis on synthetic organoselenium compounds. Arch Toxicol. 2011;85:1313-59 pubmed publisher
    ..In this review, we shall cover a wide range of toxicological and pharmacological effects, in which organoselenium compounds are involved but the effects of inorganic compounds were not discussed in detail here...
  9. de Freitas A, Rocha J. Diphenyl diselenide and analogs are substrates of cerebral rat thioredoxin reductase: a pathway for their neuroprotective effects. Neurosci Lett. 2011;503:1-5 pubmed publisher
    ..However, ebselen was not reduced by brain TrxR, indicating that the neuroprotective properties of this compound is possibly mediate by its glutathione peroxidase-like activity. ..
  10. Gammelgaard B, Jackson M, Gabel Jensen C. Surveying selenium speciation from soil to cell--forms and transformations. Anal Bioanal Chem. 2011;399:1743-63 pubmed publisher
  11. Bhattacharya A, Toth K, Sen A, Seshadri M, Cao S, Durrani F, et al. Inhibition of colon cancer growth by methylselenocysteine-induced angiogenic chemomodulation is influenced by histologic characteristics of the tumor. Clin Colorectal Cancer. 2009;8:155-62 pubmed publisher
    ..Such regions constitute a physical barrier to chemotherapy and can confer drug resistance. Our results indicate that MSC could enhance chemotherapeutic efficacy in human CRC, especially in CRC with few or no hypoxic regions. ..
  12. Husbeck B, Bhattacharyya R, Feldman D, Knox S. Inhibition of androgen receptor signaling by selenite and methylseleninic acid in prostate cancer cells: two distinct mechanisms of action. Mol Cancer Ther. 2006;5:2078-85 pubmed
    ..In conclusion, we have found that selenite and MSeA disrupt AR signaling by distinct mechanisms. The inhibition of AR expression and activity by selenite occurs via a redox mechanism involving GSH, superoxide, and Sp1. ..
  13. Moroder H, Kreutz C, Lang K, Serganov A, Micura R. Synthesis, oxidation behavior, crystallization and structure of 2'-methylseleno guanosine containing RNAs. J Am Chem Soc. 2006;128:9909-18 pubmed
    ..Moreover, we determined the crystal structures of model RNA helices and showed that the Se modification can affect crystal packing interactions, thus potentially expanding the possibilities for obtaining the best crystal form. ..
  14. Sarma B, Mugesh G. Antioxidant activity of the anti-inflammatory compound ebselen: a reversible cyclization pathway via selenenic and seleninic acid intermediates. Chemistry. 2008;14:10603-14 pubmed publisher
    ..This indicates that the regeneration of ebselen under a variety of conditions protects the selenium moiety from irreversible inactivation, which may be responsible for the biological activities of ebselen. ..
  15. Johnson W, Morrissey R, Kapetanovic I, Crowell J, McCormick D. Subchronic oral toxicity studies of Se-methylselenocysteine, an organoselenium compound for breast cancer prevention. Food Chem Toxicol. 2008;46:1068-78 pubmed
    ..5mg/kg/day. Based on alterations in hematology parameters and liver morphology in male dogs in all dose groups, the NOAEL for MSC in dogs is <0.15 mg/kg/day. ..
  16. Posser T, Kaster M, Baraúna S, Rocha J, Rodrigues A, Leal R. Antidepressant-like effect of the organoselenium compound ebselen in mice: evidence for the involvement of the monoaminergic system. Eur J Pharmacol. 2009;602:85-91 pubmed publisher
    ..It may be concluded that ebselen produces an antidepressant-like effect in the forced swimming test that seems to be dependent on its interaction with the noradrenergic and dopaminergic systems, but not with the serotonergic system. ..
  17. Meotti F, Borges V, Perottoni J, Nogueira C. Toxicological evaluation of subchronic exposure to diphenyl diselenide in rats. J Appl Toxicol. 2008;28:638-44 pubmed
    ..Taken together, these results demonstrated that subchronic exposure to diphenyl diselenide at high doses induced minor toxicological effects. ..
  18. Freeman J, Zhang L, Marcus M, Fakra S, McGrath S, Pilon Smits E. Spatial imaging, speciation, and quantification of selenium in the hyperaccumulator plants Astragalus bisulcatus and Stanleya pinnata. Plant Physiol. 2006;142:124-34 pubmed
    ..The high concentration of Se in the plant periphery may contribute to Se tolerance and may also serve as an elemental plant defense mechanism...
  19. Yin Z, Lee E, Ni M, Jiang H, Milatovic D, Rongzhu L, et al. Methylmercury-induced alterations in astrocyte functions are attenuated by ebselen. Neurotoxicology. 2011;32:291-9 pubmed publisher
    ..In addition, the protective effects elicited by ebselen reinforce the idea that organic selenocompounds represent promising strategies to counteract MeHg-induced neurotoxicity. ..
  20. Lee S, Yeon Chun J, Nadiminty N, Trump D, Ip C, Dong Y, et al. Monomethylated selenium inhibits growth of LNCaP human prostate cancer xenograft accompanied by a decrease in the expression of androgen receptor and prostate-specific antigen (PSA). Prostate. 2006;66:1070-5 pubmed
    ..These findings suggest that selenium (MSC) can serve as a therapeutic agent aimed at disruption of AR signaling for prostate cancer. ..
  21. Prigol M, Schumacher R, WayneNogueira C, Zeni G. Convulsant effect of diphenyl diselenide in rats and mice and its relationship to plasma levels. Toxicol Lett. 2009;189:35-9 pubmed publisher
    ..p.>p.o.>s.c.), vehicle solutions (DMSO>canola oil) and animal species (mice>rat). ..
  22. Olm E, Fernandes A, Hebert C, Rundlöf A, Larsen E, Danielsson O, et al. Extracellular thiol-assisted selenium uptake dependent on the x(c)- cystine transporter explains the cancer-specific cytotoxicity of selenite. Proc Natl Acad Sci U S A. 2009;106:11400-5 pubmed publisher
  23. Usuki F, Yamashita A, Fujimura M. Post-transcriptional defects of antioxidant selenoenzymes cause oxidative stress under methylmercury exposure. J Biol Chem. 2011;286:6641-9 pubmed publisher
    ..Treatment with ebselen, a seleno-organic compound, effectively suppressed oxidative stress and protected cells against MeHg-induced relative selenium deficiency and cytotoxicity. ..
  24. Li Z, Carrier L, Belame A, Thiyagarajah A, Salvo V, Burow M, et al. Combination of methylselenocysteine with tamoxifen inhibits MCF-7 breast cancer xenografts in nude mice through elevated apoptosis and reduced angiogenesis. Breast Cancer Res Treat. 2009;118:33-43 pubmed publisher
    ..Organic selenium may provide added benefit when combined with tamoxifen in adjuvant therapy or prevention...
  25. Braga A, Alberto E, Soares L, Rocha J, Sudati J, Roos D. Synthesis of telluroamino acid derivatives with remarkable GPx like activity. Org Biomol Chem. 2009;7:43-5 pubmed publisher
    ..A series of modular telluroamino acid derivatives with remarkable GPx-like behavior was prepared in an efficient and short two-step synthesis. ..
  26. Larabee J, Hocker J, Hanas J. Mechanisms of inhibition of zinc-finger transcription factors by selenium compounds ebselen and selenite. J Inorg Biochem. 2009;103:419-26 pubmed publisher
  27. Gammelgaard B, Gabel Jensen C, Sturup S, Hansen H. Complementary use of molecular and element-specific mass spectrometry for identification of selenium compounds related to human selenium metabolism. Anal Bioanal Chem. 2008;390:1691-706 pubmed publisher
    ..Hence, selenium metabolites identified in relation to absorption, metabolism and excretion are included. ..
  28. Zeng H, Wu M, Botnen J. Methylselenol, a selenium metabolite, induces cell cycle arrest in G1 phase and apoptosis via the extracellular-regulated kinase 1/2 pathway and other cancer signaling genes. J Nutr. 2009;139:1613-8 pubmed publisher
    ..The regulation of these genes is likely to play a key role in G1 cell cycle arrest and apoptosis, which may contribute to the inhibition of tumor cell invasion. ..
  29. Chen T, Wong Y. Selenocystine induces reactive oxygen species-mediated apoptosis in human cancer cells. Biomed Pharmacother. 2009;63:105-13 pubmed publisher
    ..Our results suggest a possible role of ROS as a mediator of the signaling pathway of selenocystine-induced, DNA damage-mediated apoptosis in susceptible cancer cells. ..
  30. Yamashita Y, Yamashita M. Identification of a novel selenium-containing compound, selenoneine, as the predominant chemical form of organic selenium in the blood of bluefin tuna. J Biol Chem. 2010;285:18134-8 pubmed publisher
    ..Selenoneine was measurable at 2-4 orders of magnitude lower concentration in a limited set of tissues from squid, tilapia, pig, and chicken. Quantitatively, selenoneine is the predominant form of organic selenium in tuna tissues. ..
  31. Corte C, Fachinetto R, Puntel R, Wagner C, Nogueira C, Soares F, et al. Chronic treatment with fluphenazine alters parameters of oxidative stress in liver and kidney of rats. Basic Clin Pharmacol Toxicol. 2009;105:51-7 pubmed publisher
    ..Moreover, our data point to the relationship between the oxidative stress and fluphenazine treatment in liver and kidney of rats. ..
  32. Brandao R, Santos F, Farina M, Zeni G, Bohrer D, Rocha J, et al. Antioxidants and metallothionein levels in mercury-treated mice. Cell Biol Toxicol. 2006;22:429-38 pubmed
    ..Mercuric chloride poisoning caused an increase in hepatic and renal MT levels and antioxidant treatments did not modify this parameter. Our data indicated a lack of therapeutic effect of the antioxidants tested. ..
  33. Kumar B, Kunwar A, Ahmad A, Kumbhare L, Jain V, Priyadarsini K. In vitro radioprotection studies of organoselenium compounds: differences between mono- and diselenides. Radiat Environ Biophys. 2009;48:379-84 pubmed publisher
    b>Organoselenium compounds belonging to the class of monoselenides, such as selenomethionine (SeM) and methylselenocysteine (MSeCys) and diselenides including selenocystine (SeCys) and selenopropionic acid (SePA), were examined for their ..
  34. Brüning C, Prigol M, Barancelli D, Nogueira C, Zeni G. Disubstituted diaryl diselenides inhibit delta-ALA-D and Na+, K+-ATPase activities in rat brain homogenates in vitro. Mol Cell Biochem. 2009;332:17-24 pubmed publisher
    ..The mechanism through which diselenides inhibit delta-ALA-D and Na(+), K(+)-ATPase activities involves the oxidation of thiol groups. ..
  35. Pinto J, Sinha R, Papp K, Facompre N, Desai D, El Bayoumy K. Differential effects of naturally occurring and synthetic organoselenium compounds on biomarkers in androgen responsive and androgen independent human prostate carcinoma cells. Int J Cancer. 2007;120:1410-7 pubmed
    ..and synthetic 1,4-phenylenebis(methylene)selenocyanate (p-XSC) and p-xylylbis(methylselenide) p-XMS) organoselenium compounds in androgen responsive (AR) LNCaP and its androgen independent clone (AI) LNCaP C4-2 human prostate ..
  36. Ohta Y, Kobayashi Y, Konishi S, Hirano S. Speciation analysis of selenium metabolites in urine and breath by HPLC- and GC-inductively coupled plasma-MS after administration of selenomethionine and methylselenocysteine to rats. Chem Res Toxicol. 2009;22:1795-801 pubmed publisher
    ..These results suggest that MeSeCys is converted to methylselenol more efficiently than is SeMet and that urinary TMSe and exhaled DMSe might be useful biomarkers for the generation of cancer chemopreventive forms of Se. ..
  37. Zu K, Bihani T, Lin A, Park Y, Mori K, Ip C. Enhanced selenium effect on growth arrest by BiP/GRP78 knockdown in p53-null human prostate cancer cells. Oncogene. 2006;25:546-54 pubmed
    ..Collectively, the above findings support the idea that UPR could be an important mechanism in mediating the anticancer activity of selenium. ..
  38. Kumar B, Tiwari S, Saikant R, Manoj G, Kunwar A, Sivaram G, et al. Antibacterial and ulcer healing effects of organoselenium compounds in naproxen induced and Helicobacter pylori infected Wistar rat model. J Trace Elem Med Biol. 2010;24:263-70 pubmed publisher
    ..vitro toxicity and in vivo antibacterial, anti-inflammatory, antiulcer, and antioxidant activities of two organoselenium compounds, selenocystine (SeCys) and ebselen (Ebs)...
  39. Rosa R, Moura D, Romano E Silva A, Saffi J, Pegas Henriques J. Antioxidant activity of diphenyl diselenide prevents the genotoxicity of several mutagens in Chinese hamster V79 cells. Mutat Res. 2007;631:44-54 pubmed
    ..Our results clearly demonstrate that DPDS at low concentrations presents antimutagenic properties, which are most probably due to its antioxidant properties. ..
  40. Prigol M, Wilhelm E, Stangherlin E, Barancelli D, Nogueira C, Zeni G. Diphenyl diselenide-induced seizures in rat pups: possible interaction with glutamatergic system. Neurochem Res. 2008;33:996-1004 pubmed
  41. Lugokenski T, Müller L, Taube P, Rocha J, Pereira M. Inhibitory effect of ebselen on lactate dehydrogenase activity from mammals: a comparative study with diphenyl diselenide and diphenyl ditelluride. Drug Chem Toxicol. 2011;34:66-76 pubmed publisher
    ..Our results also indicate that the use of LDH, as a marker of cell viability, may be biased by a direct inhibitory effect of ebselen or other chalcogenides on LDH, resulting in false protection in an in vitro system. ..
  42. Funchal C, Moretto M, Vivian L, Zeni G, Rocha J, Pessoa Pureur R. Diphenyl ditelluride- and methylmercury-induced hyperphosphorilation of the high molecular weight neurofilament subunit is prevented by organoselenium compounds in cerebral cortex of young rats. Toxicology. 2006;222:143-53 pubmed
    ..In contrast, organoselenium compounds are considered to exert neuroprotective actions on such effects...
  43. Bhabak K, Mugesh G. Synthesis, characterization, and antioxidant activity of some ebselen analogues. Chemistry. 2007;13:4594-601 pubmed
    ..In contrast to the effect of peroxides, the nature of thiols appears to have a dramatic effect on the catalytic activity of ebselen and its related derivatives. ..
  44. Hu H, Jiang C, Li G, Lu J. PKB/AKT and ERK regulation of caspase-mediated apoptosis by methylseleninic acid in LNCaP prostate cancer cells. Carcinogenesis. 2005;26:1374-81 pubmed
    ..These findings support the differential involvement of these protein kinase pathways in regulating apoptosis induction by different forms of selenium. ..
  45. Bhattacharya A, Seshadri M, Oven S, Toth K, Vaughan M, Rustum Y. Tumor vascular maturation and improved drug delivery induced by methylselenocysteine leads to therapeutic synergy with anticancer drugs. Clin Cancer Res. 2008;14:3926-32 pubmed publisher
  46. Tsuji Y, Suzuki N, T Suzuki K, Ogra Y. Selenium metabolism in rats with long-term ingestion of Se-methylselenocysteine using enriched stable isotopes. J Toxicol Sci. 2009;34:191-200 pubmed
    ..The results suggest that MeSeCys was transformed into selenide via methylselenol by beta-lyase. Consequently, it is surmised that MeSeCys is a precursor of methylselenol under long-term ingestion...
  47. Li S, Zhou Y, Dong Y, Ip C. Doxorubicin and selenium cooperatively induce fas signaling in the absence of Fas/Fas ligand interaction. Anticancer Res. 2007;27:3075-82 pubmed
    ..Doxorubicin and selenium cooperatively activate Fas signaling by targeting key regulatory steps. ..
  48. Brandão R, Borges L, de Oliveira R, Rocha J, Nogueira C. Diphenyl diselenide protects against hematological and immunological alterations induced by mercury in mice. J Biochem Mol Toxicol. 2008;22:311-9 pubmed publisher
    ..In conclusion, (PhSe)(2) was effective in protecting against hematological and immunological alterations induced by mercury in mice. ..
  49. de Bem A, Farina M, Portella R, Nogueira C, Dinis T, Laranjinha J, et al. Diphenyl diselenide, a simple glutathione peroxidase mimetic, inhibits human LDL oxidation in vitro. Atherosclerosis. 2008;201:92-100 pubmed publisher
    ..Taken together, such data render (PhSe)(2) a promising molecule for pharmacological studies with respect to the atherogenic process. ..
  50. Sinha R, Pinto J, Facompre N, Kilheffer J, Baatz J, El Bayoumy K. Effects of naturally occurring and synthetic organoselenium compounds on protein profiling in androgen responsive and androgen independent human prostate cancer cells. Nutr Cancer. 2008;60:267-75 pubmed publisher
    ..Using 2D gel electrophoresis, both organoselenium compounds altered the expression, to a varied extent, of several unrecognized selenium-responsive proteins...
  51. Lee S, Nadiminty N, Wu X, Lou W, Dong Y, Ip C, et al. Selenium disrupts estrogen signaling by altering estrogen receptor expression and ligand binding in human breast cancer cells. Cancer Res. 2005;65:3487-92 pubmed
    ..Thus, differential regulation of ERalpha and ERbeta in breast cancer cells may represent a novel mechanism of selenium action and provide a rationale for selenium breast cancer prevention trial. ..
  52. Lunøe K, Gabel Jensen C, Sturup S, Andresen L, Skov S, Gammelgaard B. Investigation of the selenium metabolism in cancer cell lines. Metallomics. 2011;3:162-8 pubmed publisher
    ..MeSeA, MeSeCys and selenite showed noticeable protein binding. Correlations between cell death induction and the Se compounds transformations could not be demonstrated. ..
  53. Li G, Hu H, Jiang C, Schuster T, Lu J. Differential involvement of reactive oxygen species in apoptosis induced by two classes of selenium compounds in human prostate cancer cells. Int J Cancer. 2007;120:2034-43 pubmed
    ..nongenotoxic classes of selenium may exert differential apoptosis efficacy depending on the p53 status of the cancer cells. ..
  54. Prigol M, Wilhelm E, Schneider C, Rocha J, Nogueira C, Zeni G. Involvement of oxidative stress in seizures induced by diphenyl diselenide in rat pups. Brain Res. 2007;1147:226-32 pubmed
    ..Taken together, this paper could add to our understanding of diphenyl diselenide neurotoxic effect demonstrated by the appearance of seizures which are, at least in part, related to the oxidative stress. ..
  55. Pinto J, Lee J, Sinha R, Macewan M, Cooper A. Chemopreventive mechanisms of ?-keto acid metabolites of naturally occurring organoselenium compounds. Amino Acids. 2011;41:29-41 pubmed publisher
  56. Suzuki K, Doi C, Suzuki N. Metabolism of 76Se-methylselenocysteine compared with that of 77Se-selenomethionine and 82Se-selenite. Toxicol Appl Pharmacol. 2006;217:185-95 pubmed
    ..TMSe was produced much efficiently from MeSeCys than from SeMet and selenite, suggesting a role of methylselenol through the beta-lyase reaction in the metabolism of Se-methylated selenoamino acids. ..
  57. Naithani R. Organoselenium compounds in cancer chemoprevention. Mini Rev Med Chem. 2008;8:657-68 pubmed
    ..The metabolism of selenium compounds , carcinogenesis studies, epidemiological data, and various proposed chemopreventive mechanisms of selenium compounds along with results of human intervention trials have been discussed. ..
  58. Li G, Lee H, Wang Z, Hu H, Liao J, Watts J, et al. Superior in vivo inhibitory efficacy of methylseleninic acid against human prostate cancer over selenomethionine or selenite. Carcinogenesis. 2008;29:1005-12 pubmed publisher
    ..In summary, our data demonstrated superior in vivo growth inhibitory efficacy of MSeA over SeMet and selenite, against two human PCa xenograft models without the genotoxic property of selenite. ..
  59. Ohta Y, Suzuki K. Methylation and demethylation of intermediates selenide and methylselenol in the metabolism of selenium. Toxicol Appl Pharmacol. 2008;226:169-77 pubmed
    ..Organ-dependent differences in the methylation and demethylation reactions were characterized for the liver, kidney and lung...
  60. Puffer B, Moroder H, Aigner M, Micura R. 2'-Methylseleno-modified oligoribonucleotides for X-ray crystallography synthesized by the ACE RNA solid-phase approach. Nucleic Acids Res. 2008;36:970-83 pubmed
    ..Thus far, preparation of 2'-methylseleno-modified oligoribonucleotides has been restricted to the 2'-O-[(triisopropylsilyl)oxy]methyl (TOM) and 2'-O-tert-butyldimethylsilyl (TBDMS) RNA synthesis methods. ..
  61. Straliotto M, Mancini G, de Oliveira J, Nazari E, Müller Y, Dafre A, et al. Acute exposure of rabbits to diphenyl diselenide: a toxicological evaluation. J Appl Toxicol. 2010;30:761-8 pubmed publisher
    ..These results indicated that acute toxicology to (PhSe)(2) in rabbit is dependent on the dose, which should motivate further experiments on the therapeutic properties of this compound. ..
  62. Moretto M, Funchal C, Zeni G, Rocha J, Pessoa Pureur R. Organoselenium compounds prevent hyperphosphorylation of cytoskeletal proteins induced by the neurotoxic agent diphenyl ditelluride in cerebral cortex of young rats. Toxicology. 2005;210:213-22 pubmed
    ..Furthermore the neuroprotective action of selenium compounds against tellurium effects could be a promising route to be exploited for a possible treatment of organic tellurium poisoning. ..
  63. Dernovics M, García Barrera T, Bierla K, Preud homme H, Lobinski R. Standardless identification of selenocystathionine and its gamma-glutamyl derivatives in monkeypot nuts by 3D liquid chromatography with ICP-MS detection followed by nanoHPLC-Q-TOF-MS/MS. Analyst. 2007;132:439-49 pubmed
    ..This is the first MS and MS/MS-based formal evidence of the presence of these compounds in a biological sample...
  64. Wang Z, Hu H, Li G, Lee H, Jiang C, Kim S, et al. Methylseleninic acid inhibits microvascular endothelial G1 cell cycle progression and decreases tumor microvessel density. Int J Cancer. 2008;122:15-24 pubmed
    ..An inhibition of mitogen-stimulated proliferation of endothelial cells by MSeA may therefore contribute to the inhibition of tumor angiogenesis. ..
  65. Barbosa N, Rocha J, Soares J, Wondracek D, Goncalves J, Schetinger M, et al. Dietary diphenyl diselenide reduces the STZ-induced toxicity. Food Chem Toxicol. 2008;46:186-94 pubmed
    ..Our findings suggest that diphenyl diselenide compound showed beneficial effects against the development of diabetes by exhibiting antioxidant properties. ..
  66. Freeman J, Quinn C, Marcus M, Fakra S, Pilon Smits E. Selenium-tolerant diamondback moth disarms hyperaccumulator plant defense. Curr Biol. 2006;16:2181-92 pubmed
    ..In a broader context, this study provides insight into the possible ecological implications of using Se-enriched crops as a source of anti-carcinogenic selenocompounds and for the remediation of Se-polluted environments. ..
  67. El Sayed W, Aboul Fadl T, Roberts J, Lamb J, Franklin M. Murine hepatoma (Hepa1c1c7) cells: a responsive in vitro system for chemoprotective enzyme induction by organoselenium compounds. Toxicol In Vitro. 2007;21:157-64 pubmed
    ..Thus, Hepa1c1c7 cells appear to provide a viable platform for the study of protective enzyme regulation by selenocompounds, and with the exception of Ugt1a6, the mRNA elevations from selenazolidines are transcriptionally dependent. ..
  68. Brandão R, Moresco R, Bellé L, Leite M, de Freitas M, Bianchini A, et al. Diphenyl diselenide potentiates nephrotoxicity induced by mercuric chloride in mice. J Appl Toxicol. 2011;31:773-82 pubmed publisher
    ..The results demonstrated that (PhSe)? did not modify mercury levels in mice. In conclusion, (PhSe)? potentiated damage caused by HgCl? affecting mainly the renal tissue...
  69. Liu S, Zhang H, Zhu L, Zhao L, Dong Y. Kruppel-like factor 4 is a novel mediator of selenium in growth inhibition. Mol Cancer Res. 2008;6:306-13 pubmed publisher
    ..Taken together, our results suggest that KLF4 plays a key role in mediating the growth-inhibitory effect of selenium in prostate cancer cells. ..
  70. Sausen de Freitas A, de Souza Prestes A, Wagner C, Haigert Sudati J, Alves D, Oliveira Porciúncula L, et al. Reduction of diphenyl diselenide and analogs by mammalian thioredoxin reductase is independent of their gluthathione peroxidase-like activity: a possible novel pathway for their antioxidant activity. Molecules. 2010;15:7699-714 pubmed publisher
    ..been concerted efforts geared towards understanding the precise mechanism of action of ebselen and other organoselenium compounds, especially the diorganyl diselenides such as diphenyl diselenide, and its analogs...
  71. Suzuki M, Endo M, Shinohara F, Echigo S, Rikiishi H. Differential apoptotic response of human cancer cells to organoselenium compounds. Cancer Chemother Pharmacol. 2010;66:475-84 pubmed publisher
  72. Bhabak K, Mugesh G. Functional mimics of glutathione peroxidase: bioinspired synthetic antioxidants. Acc Chem Res. 2010;43:1408-19 pubmed publisher
    ..In this Account, we demonstrate the effect of amide and amine substituents on the GPx activity of various organoselenium compounds. The existence of strong Se···O/N interactions in the selenenyl sulfide intermediates significantly ..
  73. Suzuki K, Ohta Y, Suzuki N. Availability and metabolism of 77Se-methylseleninic acid compared simultaneously with those of three related selenocompounds. Toxicol Appl Pharmacol. 2006;217:51-62 pubmed
    ..However, TMSe was not detected in the liver. The organ- and selenium source-specific production of TMSe was discussed as to the differences in selenium sources, and demethylation and methylation activity. ..
  74. de Freitas A, Funck V, Rotta M, Bohrer D, Mörschbächer V, Puntel R, et al. Diphenyl diselenide, a simple organoselenium compound, decreases methylmercury-induced cerebral, hepatic and renal oxidative stress and mercury deposition in adult mice. Brain Res Bull. 2009;79:77-84 pubmed publisher
    ..We posit that formation of a selenol intermediate, which possesses high nucleophilicity and high affinity for MeHg, accounts for the ability of diphenyl diselenide to ameliorate MeHg-induced toxicity. ..
  75. Snider G, Grout L, Ruggles E, Hondal R. Methaneseleninic acid is a substrate for truncated mammalian thioredoxin reductase: implications for the catalytic mechanism and redox signaling. Biochemistry. 2010;49:10329-38 pubmed publisher
    ..The data presented here support this assertion. The results also imply that the redox signaling function of the thioredoxin system can remain active under oxidative stress. ..
  76. Ibrahim M, Prigol M, Hassan W, Nogueira C, Rocha J. Protective effect of binaphthyl diselenide, a synthetic organoselenium compound, on 2-nitropropane-induced hepatotoxicity in rats. Cell Biochem Funct. 2010;28:258-65 pubmed publisher
    ..Results presented here indicate that the protective mechanism of (NapSe)(2) against 2-NP hepatotoxicity is possibly linked to its antioxidant activity. ..
  77. Hassan W, Ibrahim M, Rocha J. Diphenyl diselenide behaves differently than ebselen under different pH media in rat's liver preparations. Pathol Res Pract. 2010;206:357-60 pubmed publisher
    ..The anti-oxidant potential of diphenyl diselenide is confirmed against acidosis-catalyzed oxidative stress in rat liver homogenates. ..
  78. Nogueira C, Zeni G, Rocha J. Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem Rev. 2004;104:6255-85 pubmed
  79. Hu H, Li G, Wang L, Watts J, Combs G, Lu J. Methylseleninic acid enhances taxane drug efficacy against human prostate cancer and down-regulates antiapoptotic proteins Bcl-XL and survivin. Clin Cancer Res. 2008;14:1150-8 pubmed publisher
    ..MSeA may be a novel agent to improve taxane combination therapy. ..
  80. Jüliger S, Goenaga Infante H, Lister T, Fitzgibbon J, Joel S. Chemosensitization of B-cell lymphomas by methylseleninic acid involves nuclear factor-kappaB inhibition and the rapid generation of other selenium species. Cancer Res. 2007;67:10984-92 pubmed
    ..These data encourage the further clinical development of selenium as a potential modulator of cytotoxic drug activity in B-cell lymphomas. ..
  81. Borges V, Rocha J, Nogueira C. Effect of diphenyl diselenide, diphenyl ditelluride and ebselen on cerebral Na(+), K(+)-ATPase activity in rats. Toxicology. 2005;215:191-7 pubmed
    ..Cerebral Na(+), K(+)-ATPase is a potential molecular target for the toxic effect of organochalcogens and the inhibition may occur through a change in the crucial thiol groups of this enzyme. ..
  82. Yamaguchi K, Uzzo R, Pimkina J, Makhov P, Golovine K, Crispen P, et al. Methylseleninic acid sensitizes prostate cancer cells to TRAIL-mediated apoptosis. Oncogene. 2005;24:5868-77 pubmed
    ..These results suggest that selenium-based dietary compounds may help to overcome resistance to TRAIL-mediated apoptosis in prostate cancer cells. ..
  83. Lynch E, Gu R, Pierce C, Kil J. Reduction of acute cisplatin ototoxicity and nephrotoxicity in rats by oral administration of allopurinol and ebselen. Hear Res. 2005;201:81-9 pubmed
    ..Further evaluation of the chemoprotective effects of ebselen and allopurinol on cisplatin side effects in the presence of tumor appears warranted. ..