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Chemical Compound Review

Oxirane     oxirane

Synonyms: Amprolene, Anprolene, Anproline, Oxiraan, Oxyfume, ...
 
 
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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

References

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  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]
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  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]
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  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]
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  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]
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  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]
 
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