The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Oxirane     oxirane

Synonyms: Amprolene, Anprolene, Anproline, Oxiraan, Oxyfume, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of oxirane


Psychiatry related information on oxirane


High impact information on oxirane


Chemical compound and disease context of oxirane


Biological context of oxirane


Anatomical context of oxirane

  • To determine whether anaphylactoid reactions during dialysis are the result of allergy to ethylene oxide (EtO) used for sterilisation of dialysis equipment, EtO-specific cytophilic antibodies on basophils were detected by means of a sensitive protease-release assay [17].
  • Ethylene oxide gas is used to sterilize plastic medical equipment including capillary flow dialysis membranes [18].
  • Since ethylene oxide is toxic to the human peripheral nervous system, it is proposed that ethylene oxide in dialyzers may contribute to the progressive neuropathy observed in patients on long-term hemodialysis [18].
  • Incubations of the enantiomerically pure 8,9- and 14,15-epoxides with lung or liver cytosol, followed by chiral analysis of the resulting diols demonstrate selective cleavage of the oxirane ring at C9 and C15, respectively [19].
  • The stereoselectivity of vitamin K-epoxide reductase for the oxirane ring configuration was determined by recovery of the partially resolved unreacted substrate following incubations of racemic vitamin K epoxide with rat liver microsomes [20].

Associations of oxirane with other chemical compounds

  • To test whether ethylene oxide retained in the dialyzers might be neurotoxic, tissue culture medium was incubated in the blood compartment of dialyzers [18].
  • Appropriate methods for sterilizing endoscopes are reviewed, including sterilization with 2.5 per cent glutaraldehyde solution and ethylene oxide gas [21].
  • For each case patient and control patient, we conducted a chart review; a parental interview; skin prick testing with latex, anesthetics, aeroallergens, and banana extract; ELISA and RAST for latex-specific IgE; a total serum IgE; and an ELISA for IgE antibody to ethylene oxide [22].
  • The main reasons for the high solubility and formation of the microemulsions may be that the surfactant has four CO(2)-philic groups (propylene oxide) and five hydrophilic groups (ethylene oxide) and its molecular weight are relatively low [23].
  • Inactivation of the enzyme by (17S)-spiro[estra-1,3,5(10),6,8-pentaene-17,2'-oxiran-18O]-3-ol, followed by mass spectral analysis of the diacetate of the steroid released upon hydrolysis of the enzyme-inhibitor bond, reveals that TPS1 is formed by attack of Asp-38 at the methylene carbon of the oxirane [24].

Gene context of oxirane

  • In this experiment individuals carrying GSTT1 showed lower adduct level increments from ethylene oxide than individuals lacking GSTT1 [25].
  • CONCLUSIONS: This result is in accordance with the finding that ethylene oxide is a substrate for GSTT1 but not for GSTM1 [26].
  • These findings may be explained by reduced detoxification capacity rendered by the altered gene and may be linked with exposure to, for example, heterocyclic amines in the case of NAT2 and endogenously formed ethylene oxide in the case of GSTT1 [27].
  • Relative to control cells, those expressing GSTA1-1 showed the highest rate (about 50-fold increase) to perform GSH-conjugation of (-)-anti-DBPDE (R-absolute configuration at the benzylic oxirane carbon in the fjord-region) followed by GSTM1-1 (25-fold increase) and GSTP1-1 (10-fold increase) [28].
  • In contrast to GSTM1-1 and as previously shown for GSTA1-1, GSTP1-1 showed an exclusive preference for conjugation of the enantiomers with R-configuration at the benzylic oxirane carbon [29].

Analytical, diagnostic and therapeutic context of oxirane


  1. Allergic reactions in healthy plateletpheresis donors caused by sensitization to ethylene oxide gas. Leitman, S.F., Boltansky, H., Alter, H.J., Pearson, F.C., Kaliner, M.A. N. Engl. J. Med. (1986) [Pubmed]
  2. Mortality among workers exposed to ethylene oxide. Steenland, K., Stayner, L., Greife, A., Halperin, W., Hayes, R., Hornung, R., Nowlin, S. N. Engl. J. Med. (1991) [Pubmed]
  3. Association of ethylene-oxide-induced IgE antibodies with symptoms in dialysis patients. Rumpf, K.W., Seubert, S., Seubert, A., Lowitz, H.D., Valentin, R., Rippe, H., Ippen, H., Scheler, F. Lancet (1985) [Pubmed]
  4. Anaphylaxis from the product(s) of ethylene oxide gas. Poothullil, J., Shimizu, A., Day, R.P., Dolovich, J. Ann. Intern. Med. (1975) [Pubmed]
  5. Carcinogenicity and genotoxicity of ethylene oxide: new aspects and recent advances. Thier, R., Bolt, H.M. Crit. Rev. Toxicol. (2000) [Pubmed]
  6. Compliance with the ethylene oxide standard during exhaust system upgrade at a hospital sterilizer. Williamson, C.S., Oransky, J.J. Journal of clinical engineering. (1997) [Pubmed]
  7. Exposure to ethylene oxide at work increases sister chromatid exchanges in human peripheral lymphocytes. Yager, J.W., Hines, C.J., Spear, R.C. Science (1983) [Pubmed]
  8. Epidemiologic support for ethylene oxide as a cancer-causing agent. Hogstedt, C., Aringer, L., Gustavsson, A. JAMA (1986) [Pubmed]
  9. Carcinogenicity of ethylene oxide and 1,2-propylene oxide upon intragastric administration to rats. Dunkelberg, H. Br. J. Cancer (1982) [Pubmed]
  10. Biopsy forceps disinfection technique does not influence Helicobacter pylori culture. Elizalde, J.I., Gómez, J., Ginès, A., Llach, J., Piqué, J.M., Bordas, J.M., Marco, F., Terés, J. Am. J. Gastroenterol. (1998) [Pubmed]
  11. Association between latex sensitization and repeated latex exposure in children. Porri, F., Pradal, M., Lemière, C., Birnbaum, J., Mege, J.L., Lanteaume, A., Charpin, D., Vervloet, D., Camboulives, J. Anesthesiology (1997) [Pubmed]
  12. Recurrent bilateral pleural effusions secondary to superior vena cava obstruction as a complication of central venous catheterization. Dhande, V., Kattwinkel, J., Alford, B. Pediatrics (1983) [Pubmed]
  13. Epoxyalkane: coenzyme M transferase in the ethene and vinyl chloride biodegradation pathways of mycobacterium strain JS60. Coleman, N.V., Spain, J.C. J. Bacteriol. (2003) [Pubmed]
  14. Leukemia in workers exposed to ethylene oxide. Hogstedt, C., Malmqvist, N., Wadman, B. JAMA (1979) [Pubmed]
  15. The role of 3-hydroxyethyldeoxyuridine in mutagenesis by ethylene oxide. Bhanot, O.S., Singh, U.S., Solomon, J.J. J. Biol. Chem. (1994) [Pubmed]
  16. Cytogenetic effects of ethylene oxide, with an emphasis on population monitoring. Preston, R.J. Crit. Rev. Toxicol. (1999) [Pubmed]
  17. Anaphylactoid reactions in dialysis patients: role of ethylene-oxide. Bommer, J., Wilhelms, O.H., Barth, H.P., Schindele, H., Ritz, E. Lancet (1985) [Pubmed]
  18. Residual ethylene oxide in hollow fiber hemodialysis units is neurotoxic in vitro. Windebank, A.J., Blexrud, M.D. Ann. Neurol. (1989) [Pubmed]
  19. Regio- and enantiofacial selectivity of epoxyeicosatrienoic acid hydration by cytosolic epoxide hydrolase. Zeldin, D.C., Kobayashi, J., Falck, J.R., Winder, B.S., Hammock, B.D., Snapper, J.R., Capdevila, J.H. J. Biol. Chem. (1993) [Pubmed]
  20. Stereospecificity of vitamin K-epoxide reductase. Preusch, P.C., Suttie, J.W. J. Biol. Chem. (1983) [Pubmed]
  21. Salmonella oslo. A focal outbreak in a hospital. Chmel, H., Armstrong, D. Am. J. Med. (1976) [Pubmed]
  22. A cluster of anaphylactic reactions in children with spina bifida during general anesthesia: epidemiologic features, risk factors, and latex hypersensitivity. Kelly, K.J., Pearson, M.L., Kurup, V.P., Havens, P.L., Byrd, R.S., Setlock, M.A., Butler, J.C., Slater, J.E., Grammer, L.C., Resnick, A. J. Allergy Clin. Immunol. (1994) [Pubmed]
  23. Formation of water-in-CO(2) microemulsions with non-fluorous surfactant Ls-54 and solubilization of biomacromolecules. Liu, J., Han, B., Zhang, J., Li, G., Zhang, X., Wang, J., Dong, B. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  24. Mechanism of inactivation of 3-oxosteroid delta 5-isomerase by 17 beta-oxiranes. Bantia, S., Bevins, C.L., Pollack, R.M. Biochemistry (1985) [Pubmed]
  25. In vitro studies of the influence of glutathione transferases and epoxide hydrolase on the detoxification of acrylamide and glycidamide in blood. Paulsson, B., Rannug, A., Henderson, A.P., Golding, B.T., Törnqvist, M., Warholm, M. Mutat. Res. (2005) [Pubmed]
  26. Ethylene oxide-protein adduct formation in humans: influence of glutathione-S-transferase polymorphisms. Müller, M., Krämer, A., Angerer, J., Hallier, E. International archives of occupational and environmental health. (1998) [Pubmed]
  27. Cytogenetic biomarkers. Norppa, H. IARC Sci. Publ. (2004) [Pubmed]
  28. Glutathione conjugation and DNA adduct formation of dibenzo[a,l]pyrene and benzo[a]pyrene diol epoxides in V79 cells stably expressing different human glutathione transferases. Sundberg, K., Dreij, K., Seidel, A., Jernström, B. Chem. Res. Toxicol. (2002) [Pubmed]
  29. Glutathione conjugation of bay- and fjord-region diol epoxides of polycyclic aromatic hydrocarbons by glutathione transferases M1-1 and P1-1. Sundberg, K., Widersten, M., Seidel, A., Mannervik, B., Jernström, B. Chem. Res. Toxicol. (1997) [Pubmed]
  30. Formation of a stable surface oxametallacycle that produces ethylene oxide. Linic, S., Barteau, M.A. J. Am. Chem. Soc. (2002) [Pubmed]
  31. A comparison of cutaneous testing and ELISA testing for assessing reactivity to ethylene oxide-human serum albumin in hemodialysis patients with anaphylactic reactions. Grammer, L.C., Roberts, M., Wiggins, C.A., Fitzsimons, R.R., Ivanovich, P.T., Roxe, D.M., Patterson, R. J. Allergy Clin. Immunol. (1991) [Pubmed]
  32. Longitudinal study of specific IgE and IgG antibodies in a patient sensitized to ethylene oxide through dialysis. Wass, U., Belin, L., Delin, K. J. Allergy Clin. Immunol. (1988) [Pubmed]
  33. Molecular dosimetry of endogenous and ethylene oxide-induced N7-(2-hydroxyethyl) guanine formation in tissues of rodents. Wu, K.Y., Ranasinghe, A., Upton, P.B., Walker, V.E., Swenberg, J.A. Carcinogenesis (1999) [Pubmed]
WikiGenes - Universities