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Chemical Compound Review

Emulphor     2-[(Z)-octadec-9-enoxy]ethanol

Synonyms: Oleth-4, Oleth-6, Oleth-7, Oleth-8, Oleth-9, ...
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Disease relevance of Oleth-7

  • The use of aqueous Emulphor emulsions appears more appropriate in acute toxicity studies of VOC drinking water contaminants such as CCl4, in that the emulsion did not substantially alter the toxicity of CCl4 from that of undiluted CCl4 or CCl4 ingested in water [1].
  • Ninety-day-old male Fischer 344 rats were gavaged with either 0.125, 0.1875, 0.25, 0.5, 0.75, 1.0, or 1.5 mmol CHCl3 or BDCM/kg body weight in 10% Alkamuls EL-620 (5 ml/kg body weight) [2].
  • Thrombocytopenia occurred in Emulphor-treated dogs but increased platelet counts occurred in Cremophor-treated dogs [3].

High impact information on Oleth-7

  • Anti-CD28 stimulation of in vitro kinase activity was detergent-dependent, occurring in immune complexes prepared with Brij 96 but not Nonidet P-40 [4].
  • In this study, we reveal that in Brij 96-based cell lysates, anti-CD5 antibodies coprecipitated TCR zeta chain (TCR zeta)/CD3 subunits as well as the protein-tyrosine kinases p56lck and p59fyn [5].
  • Only CD9 is coprecipitated with CD36 from platelets that were solubilized in Brij 96 [6].
  • We performed immunoprecipitation of the porcine FcgammaRIIIaalpha multisubunit complex from Brij 96 lysates of polymorphonuclear leukocytes using the G7 mAb, which binds to FcgammaRIIIaalpha on the surface of porcine NK cells and phagocytes [7].
  • CD5 and CD6 co-immunoprecipitate from Brij 96 but not Nonidet P-40 cell lysates, independently of both the co-expression of other lymphocyte surface receptors and the integrity of CD5 cytoplasmic region [8].

Chemical compound and disease context of Oleth-7

  • Groups of 6 male Wistar rats, of about 400 g body weight, were dosed with 14C-labeled pyrene, dissolved in an Emulphor/water solvent vehicle, at 5 different dose levels by the intravenous or oral routes [9].

Biological context of Oleth-7


Anatomical context of Oleth-7

  • The 6H1 monoclonal antibody (mAb) indirectly coprecipitated alpha 3 beta 1 and/or alpha 6 beta 1, but not alpha 2 beta 1, or alpha 5 beta 1 from Brij 96 detergent lysates of multiple cell lines [15].
  • Most of the lipopolysaccharide was selectively removed from the membranes by treatment with the nonionic detergent Brij-96 [16].
  • Brij 96 DIGs floated to a lower density than other detergents tested, possibly representing a subpopulation of DIGs in myelin [17].
  • Phosphatidylinositol anchors give cell membrane insertion, self-aggregation and detergent (Triton X-100, Brij 97) interaction [18].
  • In this paper, we present a multi-compartmental description of the gastrointestinal (GI) tract linked to a physiologically based pharmacokinetic (PB-PK) model to describe the complex oral uptake of carbon tetrachloride (CCl4) administered in corn oil and 0.25% Emulphor [19].

Associations of Oleth-7 with other chemical compounds


Gene context of Oleth-7

  • A novel Ig superfamily protein, EWI-2, was co-purified with tetraspanin protein CD81 under relatively stringent Brij 96 detergent conditions and identified by mass spectrometric protein sequencing [24].
  • This association of Lyn with receptor components was stable in the detergent Brij 96, but was readily disrupted by Nonidet P-40, suggesting the involvement of hydrophobic interactions in stabilizing formation of the Lyn-receptor complex [25].
  • In moderately stringent Brij 96 lysis conditions, CD81 and CD9 complexes are virtually identical to each other, but clearly distinct from other TM4SF complexes [26].
  • Analysis of the soluble fractions obtained from RPE in the gradients made with Brij 96 revealed 16.0S (asymmetric A12), 10.5-10.0S (globular G4H + G4A), 4.5S (G2A), and 3.0S (G1A) AChE forms in S1, whereas G4A, G2A, and G1A enzyme molecules predominated in S2 [27].
  • We demonstrate that Brij-96 can selectively isolate the Pgp domains, separating them from the caveolar and classical lipid rafts [28].

Analytical, diagnostic and therapeutic context of Oleth-7


  1. Effect of oral dosing vehicles on the acute hepatotoxicity of carbon tetrachloride in rats. Kim, H.J., Odend'hal, S., Bruckner, J.V. Toxicol. Appl. Pharmacol. (1990) [Pubmed]
  2. NOAEL and LOAEL determinations of acute hepatotoxicity for chloroform and bromodichloromethane delivered in an aqueous vehicle to F344 rats. Keegan, T.E., Simmons, J.E., Pegram, R.A. J. Toxicol. Environ. Health Part A (1998) [Pubmed]
  3. Cremophor and Emulphor induced alterations of serum lipids and lipoprotein electrophoretic patterns of dogs. Hacker, M., Koeferl, M., Hong, C.B., Fagan, M.A. Res. Commun. Chem. Pathol. Pharmacol. (1981) [Pubmed]
  4. Activation-dependent phosphorylation of the T-lymphocyte surface receptor CD28 and associated proteins. Hutchcroft, J.E., Bierer, B.E. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  5. CD5 acts as a tyrosine kinase substrate within a receptor complex comprising T-cell receptor zeta chain/CD3 and protein-tyrosine kinases p56lck and p59fyn. Burgess, K.E., Yamamoto, M., Prasad, K.V., Rudd, C.E. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  6. CD36 associates with CD9 and integrins on human blood platelets. Miao, W.M., Vasile, E., Lane, W.S., Lawler, J. Blood (2001) [Pubmed]
  7. Identification of a novel Fc gamma RIIIa alpha-associated molecule that contains significant homology to porcine cathelin. Sweeney, S.E., Kim, Y.B. J. Immunol. (2004) [Pubmed]
  8. The accessory molecules CD5 and CD6 associate on the membrane of lymphoid T cells. Gimferrer, I., Farnós, M., Calvo, M., Mittelbrunn, M., Enrich, C., Sánchez-Madrid, F., Vives, J., Lozano, F. J. Biol. Chem. (2003) [Pubmed]
  9. Pharmacokinetics and bioavailability of pyrene in the rat. Withey, J.R., Law, F.C., Endrenyi, L. Journal of toxicology and environmental health. (1991) [Pubmed]
  10. Effect of dosing vehicles on the pharmacokinetics of orally administered carbon tetrachloride in rats. Kim, H.J., Bruckner, J.V., Dallas, C.E., Gallo, J.M. Toxicol. Appl. Pharmacol. (1990) [Pubmed]
  11. Use of human keratinocyte and fibroblast cultures for toxicity studies of topically applied compounds. Ponec, M., Haverkort, M., Soei, Y.L., Kempenaar, J., Bodde, H. Journal of pharmaceutical sciences. (1990) [Pubmed]
  12. A fluorescence-based detergent binding assay for protein hydrophobicity. London, E. Anal. Biochem. (1986) [Pubmed]
  13. Effect of cationic surfactant on transport of surface-active and non-surface-active model drugs and emulsion stability in triphasic systems. Chidambaram, N., Burgess, D.J. AAPS PharmSci (2000) [Pubmed]
  14. Effect of dosing vehicle on the developmental toxicity of bromodichloromethane and carbon tetrachloride in rats. Narotsky, M.G., Pegram, R.A., Kavlock, R.J. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1997) [Pubmed]
  15. Specific association of CD63 with the VLA-3 and VLA-6 integrins. Berditchevski, F., Bazzoni, G., Hemler, M.E. J. Biol. Chem. (1995) [Pubmed]
  16. Protection against group B Neisseria meningitidis disease: preparation of soluble protein and protein-polysaccharide immunogens. Frasch, C.E., Peppler, M.S. Infect. Immun. (1982) [Pubmed]
  17. Detergent-insoluble glycosphingolipid/cholesterol microdomains of the myelin membrane. Taylor, C.M., Coetzee, T., Pfeiffer, S.E. J. Neurochem. (2002) [Pubmed]
  18. Acetylcholinesterase at high catalytic efficiency and substrate specificity in the optic lobe of Eledone moschata (Cephalopoda: Octopoda): biochemical characterization and histochemical localization. Talesa, V., Romani, R., Calvitti, M., Rosi, G., Giovannini, E. Neurochem. Int. (1998) [Pubmed]
  19. A pharmacokinetic model describing pulsatile uptake of orally-administered carbon tetrachloride. Semino, G., Lilly, P., Andersen, M.E. Toxicology (1997) [Pubmed]
  20. Crystallization of Ca2+-ATPase in detergent-solubilized sarcoplasmic reticulum. Dux, L., Pikula, S., Mullner, N., Martonosi, A. J. Biol. Chem. (1987) [Pubmed]
  21. Microbial transformations of natural antitumor agents: use of solubilizing agents to improve yields of hydroxylated ellipticines. Chien, M.M., Rosazza, J.P. Appl. Environ. Microbiol. (1980) [Pubmed]
  22. The principal difference in regulation of the catalytic activity of water-soluble and membrane forms of enzymes in reversed micelles. Gamma-glutamyltransferase and aminopeptidase. Kabanov, A.V., Nametkin, S.N., Levashov, A.V. FEBS Lett. (1990) [Pubmed]
  23. Evidence of redox-linked signaling for producing a giant signal complex. Katano, Y., Pu, M.Y., Akhand, A.A., Hamaguchi, M., Koga, Y., Isobe, K., Fukuda, Y., Hayakawa, T., Nakashima, I. J. Cell. Biochem. (1995) [Pubmed]
  24. EWI-2 is a major CD9 and CD81 partner and member of a novel Ig protein subfamily. Stipp, C.S., Kolesnikova, T.V., Hemler, M.E. J. Biol. Chem. (2001) [Pubmed]
  25. Interactions of Lyn with the antigen receptor during B cell activation. Burg, D.L., Furlong, M.T., Harrison, M.L., Geahlen, R.L. J. Biol. Chem. (1994) [Pubmed]
  26. FPRP, a major, highly stoichiometric, highly specific CD81- and CD9-associated protein. Stipp, C.S., Orlicky, D., Hemler, M.E. J. Biol. Chem. (2001) [Pubmed]
  27. Acetyl- and butyrylcholinesterase activities in the rat retina and retinal pigment epithelium. Sánchez-Chávez, G., Vidal, C.J., Salceda, R. J. Neurosci. Res. (1995) [Pubmed]
  28. P-Glycoprotein is localized in intermediate-density membrane microdomains distinct from classical lipid rafts and caveolar domains. Radeva, G., Perabo, J., Sharom, F.J. FEBS J. (2005) [Pubmed]
  29. The integrins alpha3beta1 and alpha6beta1 physically and functionally associate with CD36 in human melanoma cells. Requirement for the extracellular domain OF CD36. Thorne, R.F., Marshall, J.F., Shafren, D.R., Gibson, P.G., Hart, I.R., Burns, G.F. J. Biol. Chem. (2000) [Pubmed]
  30. Radioprotective and locomotor responses of mice treated with nimodipine alone and in combination with WR-151327. Landauer, M.R., Castro, C.A., Benson, K.A., Hogan, J.B., Weiss, J.F. Journal of applied toxicology : JAT. (2001) [Pubmed]
  31. Combined chemical and enzymatic stable isotope labeling for quantitative profiling of detergent-insoluble membrane proteins isolated using Triton X-100 and Brij-96. Blonder, J., Yu, L.R., Radeva, G., Chan, K.C., Lucas, D.A., Waybright, T.J., Issaq, H.J., Sharom, F.J., Veenstra, T.D. J. Proteome Res. (2006) [Pubmed]
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