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PubMedDate not supplied

Disposition and metabolism of [2-14C]epichlorohydrin after oral administration to rats.

A comprehensive disposition and metabolism study of epichlorohydrin (ECH) has not been previously reported. In this study, male Fischer 344 rats were dosed (6 mg/kg) orally with [2-14C]ECH (98% radiochemically pure) as an aqueous solution and killed after 3 days. Approximately 38% of the radioactive dose was exhaled as CO2, 50% was excreted as metabolites in the urine, and 3% was present in the feces. Radioactivity in tissues accounted for the remainder of the administered dose. When expressed per gram of tissue, radioactivity was highest in liver, kidney, and forestomach. The half-life of initial elimination of radioactivity in both the urine and exhaled air was about 2 hr, indicating that ECH was rapidly absorbed and metabolized. The major metabolites in the urine were identified as N-acetyl-S-(3-chloro-2-hydroxypropyl)-L-cysteine and alpha-chlorohydrin, about 36 and 4% of the administered dose, respectively. Finding these metabolites, which have not been previously reported, is consistent with the initial metabolic reactions being conjugation of the epoxide with glutathione and hydration of the epoxide.

Administration, Oral↗
PubMed1985

A method for assessing damage to mitochondrial DNA caused by radiation and epichlorohydrin.

This paper describes a rapid and reliable method for quantification of damage to mitochondrial DNA (mtDNA), especially strand breaks. The degree of damage to mtDNA is assessed by the proportion of physical forms (i.e., supercoiled versus open-circular and linear forms) upon agarose gel electrophoresis, blotting, and visualization by hybridization with [32P]mtDNA probes. The use of a radiolabeled probe is a crucial step in the procedure because it provides both a means to quantify by radioautography and to obtain the mtDNA specificity required to eliminate misinterpretation due to nuclear DNA contamination. To demonstrate the utility of this technique, X-irradiation and epichlorohydrin are shown to damage both isolated mtDNA and mtDNA in whole cells in a dose-dependent fashion.

Animals↗
PubMed1998

Rejoining of DNA strand breaks induced by propylene oxide and epichlorohydrin in human diploid fibroblasts.

The repair kinetics of DNA single- and double-strand breaks (SSBs, DSBs) induced with two carcinogenic epoxides, propylene oxide (PO) and epichlorohydrin (ECH), was studied in human diploid fibroblasts. The methods used were: alkaline DNA unwinding (ADU), the comet assay, and pulsed field gel electrophoresis (PFGE). About 70% of SSBs, measured by ADU, were rejoined after the treatment with 5 mMh and 10 mMh of PO within 20 hr, and the half-life was estimated to be approximately 15 hr. On the other hand, effective rejoining of SSBs after ECH treatment was observed only at a dose of 1 mMh (a half-life of approximately 15 hr), whereas after 2 mMh treatment, only 26% of SSBs could be rejoined within 20 hr. Furthermore, the use of the comet assay demonstrated that DNA strand breaks were effectively rejoined after PO and ECH treatment at doses of 5-10 mMh and 0.5-1 mMh, respectively. About 76% and 83% of DSBs induced by 5 and 10 mMh of PO, respectively, were rejoined within 4 hr after the treatment (a half-life of approximately 2.5 hr), with little further repair thereafter. At lower dose of ECH (1 mMh) a half-life for DSBs rejoining was estimated to be approximately 2 hr; however, only 29% of DSBs were rejoined within 2 hr at the higher dose of 2 mMh. After 18 hr, the rejoining following treatment with a lower dose was negligible. At a higher dose, a rapid accumulation of DSBs was observed, probably as the result of cell death and DNA degradation. The results demonstrate the capability of human diploid fibroblasts to repair DNA SSBs and DSBs at low-to-moderate doses of the epoxides. A weak capacity to rejoin DNA strand breaks induced by higher doses of ECH may be a consequence of its higher DNA alkylation activity and approximately 10 times higher toxicity compared to PO.

Carcinogens↗
PubMed2002

Determination of boron by using a quartz crystal resonator coated with N-methyl-D-glucamine-modified poly(epichlorohydrin).

A nongravimetric quartz crystal resonator for determination of boron was proposed. The key step is the preparation of a polymer that forms a complex with boron (from borate ion). The polymeric film is deposited on one face of an electrode-separated quartz crystal. The backbone of the polymer is poly(epichlorohydrin), which is modified to anchor N-methyl-D-glucamine. After reticulation and reduction, the film presents high stability and sensitivity to boron at pH 8.5. A carrier solution containing 50 mM EDTA ensures high conductivity and the elimination of several interfering metal ions. Boron is strongly retained by the film, and a positive shift of the oscillating frequency is proportional to its concentration. Boron is eluted with 1 mL of a 1 M mannitol solution. For a 0.160-mL sample loop and concentration up to 600 microM, the calibration sensitivity was 1.67 Hz/microM and the LOD was 2 microM. This limit could be lowered to 0.3 microM by using a 1.00-mL sample loop. In both cases, it was possible to detect 3 ng of boron. It was estimated that the nongravimetric sensor is at least 10 times more sensitive that a hypothetical gravimetric sensor.

Journal Article↗
PubMed1988

Bile acid binding and hypocholesterolemic activity of a new anion exchange resin from 2-methylimidazol and epichlorohydrin.

A new anion exchange resin with an imidazolium salt on a epoxide polymer skeleton was synthesized. This white powder material was odorless and tasteless. The in vitro sodium cholate binding of this resin was much more potent than that of cholestyramine. The hypocholesterolemic activity of this resin in cholesterol-fed rabbits proved to be 4.3 times more potent than that of cholestyramine. These results suggest that effective reduction of plasma cholesterol may be achieved with lower doses of this resin.

Animals↗
PubMed1983

Evaluation of a testicular sperm head counting technique using rats exposed to dimethoxyethyl phthalate (DMEP), glycerol alpha-monochlorohydrin (GMCH), epichlorohydrin (ECH), formaldehyde (FA), or methyl methanesulphonate (MMS).

Single dosages of DMEP (1,000-2,000 mg/kg), GMCH (50 mg/kg), ECH (25 and 50 mg/kg), FA (100 and 200 mg/kg), and MMS (100-400 mg/kg) were administered orally to 10 week old male Wistar rats. The rats were necropsied on the 11th day following dosing. The testes were weighed, homogenised and sonicated; numbers of sperm heads (total and abnormal) were counted and percentage sperm head abnormalities were calculated. Testes weights were significantly reduced only in rats exposed to 1,500 and 2,000 mg DMEP/kg. Compared with controls, there were significant increases in the incidence of abnormal sperm at all dose levels of MMS and the higher dose levels of DMEP (1,500 and 2,000 mg/kg), ECH and FA. No toxicologically significant effects upon total sperm counts were seen following the oral administration of any of the five chemicals tested. However, an additional group of rats given 100 mg MMS/kg intraperitoneally (i.p.) showed significant reductions in testes weight and total sperm head counts compared with control animals. It is concluded that this testicular sperm head counting technique is a useful tool in the detection of selective adverse effects of chemicals upon testicular sperm but requires further evaluation.

Animals↗
PubMed2006

A novel composite nanofiltration (NF) membrane prepared from graft copolymer of trimethylallyl ammonium chloride onto chitosan (GCTACC)/poly(acrylonitrile) (PAN) by epichlorohydrin cross-linking.

A novel composite nanofiltration (NF) membrane was prepared by over-coating the PAN ultrafiltration (UF) membrane with a GCTACC thin layer. The effects of membrane preparation techniques and operating conditions on the performance of the composite membrane were studied. The results indicate that a composite NF membrane from 1.0wt% GCTACC casting solution, vaporized for 2h at 50 degrees C, cross-linked for 20h at 50 degrees C and pH approximately 12 with ethanol/epichlorohydrin (50/0.45 wt/wt) had optimum performance. The resultant GCTACC/PAN composite membrane was positively charged. Scanning electron microscopy showed its asymmetric and composite features. At 25 degrees C and 30L/h of cycling flow, the permeability of pure water through this membrane is 6.3L/hm(2)MPa. At 25 degrees C, 1.2MPa and 30L/h of cycling flow, the rejection of 1000mg/L MgCl(2), CaCl(2), MgSO(4), Na(2)SO(4), and NaCl solutions is 0.976, 0.972, 0.897, 0.65, and 0.407, respectively, with fluxes of 6.8, 6.12, 6.12, 5.57, and 5.51L/hm(2), respectively. The order of rejection of different salts follows the decreasing order of MgCl(2), CaCl(2), MgSO(4), NaCl, KCl, Na(2)SO(4), and K(2)SO(4), which reveals the characteristics of the positively charged NF membrane. In addition, the curve for the streaming potential also illustrates the positively charged characteristics of this membrane, with a pressure osmotic coefficient of 11.7mVMPa(-1).

Acrylonitrile↗
PubMed2004

Use of epichlorohydrin-treated chitosan resin as an adsorbent to isolate kappa-casein glycomacropeptide from sweet whey.

This study was undertaken to develop a method to isolate glycomacropeptide (GMP), a bioactive compound, from sweet whey by using chitosan resins as anion exchangers. Shrimp shells were used to prepare two chitosan (polyglucosamine) resins, one with the primary amine (-NH(2)) (resin A) and the other with the secondary amine (-NH-) (resin B) as the major functional group. These resins were tested as adsorbents for the isolation of GMP from sweet whey, and the results obtained were compared with those obtained with commercial anion exchangers. The most important finding in this experiment was that the GMP binding capacity of resin A was much higher than that of resin B. Resin A may be the anion exchanger to be tested for industrial scale production of GMP. Amino acid analysis of the GMP-depleted whey fraction suggests that this product can replace sweet whey as an ingredient in various food products including infant formulas, bakery products, and beverages.

Adsorption↗
PubMedDate not supplied

Formulation of epichlorohydrin cross-linked starch microspheres.

The present work describes a water/oil emulsion technique for the production of microspheres by cross-linking soluble starch with epichlorohyrin, which is a very efficient divalent cross-linking agent for starch. Because they are important features for potential applications, such as pulmonary administration, special attention has been paid to control the mean particle size and size distribution. Microspheres ranging from 0.3-250 microm with narrow size distributions could be obtained. Due to the strongly basic nature of the aqueous phase, no stable emulsions could be obtained in the water/oil emulsion domains. In this context, the stirring rate during the emulsification step was crucial for controlling the particle size. Additionally, a high organic-to-aqueous phase ratio and the presence of a surfactant agent helped to prevent the coalescence of the droplets during the formation of the microspheres. The process was not sensitive to odifications of the chemical conditions, such as the cross-linking ratio, which allows variation of the chemical nature of the polymer forming the core of the microspheres without modifying their morphological characteristics.

Cross-Linking Reagents↗