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PubMed1987

Comparison of labeled propanediol and urea as markers of lung vascular injury.

The purpose of these studies was a comparison of [14C]urea (U) and 1,3-[14C]propanediol (Pr) as measures of lung vascular permeability-surface area (PS) under base-line conditions and after lung injury caused by alloxan infusion in isolated perfused dog lungs. Indicator mixtures of 125I-albumin, 51Cr-red blood cells, 3HOH, and U or Pr were injected under base-line conditions, after 1.2 g of alloxan, and after an additional 0.8 g of alloxan. Indicator-dilution curves were analyzed from sampled outflow blood to provide PS, the square root of effective extravascular diffusivity multiplied by exchange surface area (D1/2S), and extravascular lung water (EVLW) from the tracer mean transit times (VW). Results show that alloxan increases PS and D1/2S for U, D1/2S for Pr, and VW and EVLW by desiccation. All indicator-dilution parameters correlate significantly with alloxan dose. Interpretation of Pr transport suggests that materials with lipid and hydrophilic pathways might be used in conjunction with U to minimize the effects of surface area changes and increase the sensitivity of these tracers to permeability alteration. In addition Pr may be a useful alternative to U as a marker of vascular damage.

Alloxan↗
PubMedDate not supplied

Carcinogenic activity of the flame retardant, 2,2-bis(bromomethyl)-1,3-propanediol in rodents, and comparison with the carcinogenicity of other NTP brominated chemicals.

Several brominated chemicals have been shown to be multisite-multispecies carcinogens in laboratory animals, and in this paper we report that the flame retardant, 2,2-bis(bromomethyl)-1,3-propanediol (BMP) is also a multisite carcinogen in both sexes of Fischer 344 rats and B6C3F1 mice. BMP was administered continuously in the diet for up to 2 yr to rats at doses of 0, 2,500, 5,000, or 10,000 ppm and to mice at doses of 0, 312, 625, or 1,250 ppm. Interim groups of rats were examined at 15 mo. An additional recovery group of male rats received the chemical for 3 mo at 20,000 ppm in the feed, and then the control diet for the remainder of the study. Chemical exposure caused neoplasms of the skin, subcutaneous tissue, mammary gland, Zymbal's gland, oral cavity, esophagus, forestomach, small intestine, large intestine, mesothelium, kidney, urinary bladder, lung, thyroid gland, seminal vesicle, hematopoietic system, and pancreas in the male rat; mammary gland, oral cavity, esophagus, and thyroid gland in the female rat; lung, kidney, and Harderian gland in male mice; and subcutaneous tissue, lung, and Harderian gland in the female mouse. The recovery group of male rats presented with the same spectrum of treatment-related neoplasms as in the core study. In this recovery group, BMP (at 20,000 ppm) caused irreversible effects at numerous sites after 90 days of exposure that was not detectable by histologic examination, but without further exposure resulted in carcinogenic responses at 2 yr. BMP is mutagenic in the salmonella test, but it was not determined if the BMP-induced effects that eventually lead to development of neoplasms at multiple sites are the same in both species and in all organ systems affected.

Animals↗
PubMed2000

Lipase-catalyzed asymmetric desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl benzoate.

The lipase-catalyzed asymmetric desymmetrization of the prochiral 2,2-disubstituted 1,3-propanediols was studied using various types of 1-ethoxyvinyl esters (1a-i). Although 1a-e with aliphatic acyl groups were not sufficient, use of the benzoate (1f) in combination with Candida rugosa lipases converted acyclic diols (2, 6) and cyclic diols (11-14) to the optically active compounds (3f, 7f, 15f-18f), bearing a quaternary carbon center, with moderate-to-high optical yields. These products were fairly stable against racemization under acidic conditions.

Benzoates↗
PubMed2001

Practical production of (S)-1,2-propanediol and its derivative through baker's yeast-mediated reduction.

The enantiomeric excess (ee) of (S)-1,2-propanediol produced by baker's yeast-mediated reduction of 1-acetoxy-2-propanone was improved to 96% ee by a fed-batch operation of the substrate. A similar reduction of 1-benzoyloxy-2-propanone stopped because of the inhibition toward the enzymes for NADPH regeneration by the reduction product. The inhibition was prevented using resin that adsorbs the product from the reaction mixture, and 70 g/l substrate was reduced yielding (S)-1-benzoyloxy-2-propanol at > 99% ee.

Journal Article↗
PubMed2002

Metabolism of propionate and 1,2-propanediol absorbed from the washed reticulorumen of lactating cows.

To investigate the metabolism of 1,2-propanediol (PPD) in lactating cows independently of normal rumen microbial metabolism, three ruminally cannulated lactating Holstein cows were subjected to three experimental infusion protocols under washed reticulo-ruminal conditions in a Latin square design. Reticulo-ruminal absorption rates were maintained for 420 min by continuous intraruminal infusion of VFA and PPD. With the control treatment, 1,246 +/- 39 mmol/ h of acetate and 213 +/- 5 mmol/h of butyrate were absorbed from the reticulorumen. With the propionate treatment, 1,148 +/- 39 mmo/h of acetate, 730 +/- 23 mmol/h of propionate and 196 +/- 5 mmol/h of butyrate were absorbed from the reticulorumen. With PPD treatment, 1,264 +/- 39 mmol/h of acetate, 220 +/- 5 mmol/h of butyrate and 721 +/- 17 mmol/h of PPD were absorbed from the reticulorumen. Glucose irreversible loss rate (ILR), as well as the relative enrichment of plasma lactate and alanine, were determined by primed continuous infusion of [U-13C]glucose in a jugular vein. Treatments did not affect (P > 0.10) the plasma concentrations of glucose (4.2 +/- 0.1 mmoVL), alanine (0.14 +/- 0.01 mmol/L), or insulin (80 +/- 25 pmol/L). The plasma concentration of lactate was higher (P < 0.05) with both propionate (0.84 +/- 5 mmol/L) and PPD treatment (0.81 +/- 5 mmol/ L) compared with the control treatment (0.29 +/- 0.5 mmol/L). The plasma concentration of pyruvate was higher (P < 0.05) with the propionate treatment (0.09 +/- 0.01 mmol/L) compared with the control treatment (0.03 +/- 0.01 mmol/L). The plasma concentration of 3-hydroxybutyrate was lower (P < 0.05) with the propionate treatment (0.15 +/- 0.03 mmol/L) compared with the control treatment (0.40 +/- 0.03). With the PPD treatment, the plasma concentrations of pyruvate and 3-hydroxybutyrate were in between the other treatments and tended (P < 0.10) to be different from both. The plasma concentration of PPD increased throughout the infusion period with the PPD treatment and reached a concentration of 4.9 +/- 0.6 mmol/L at 420 min. The ILR of glucose was not affected (P > 0.10) by treatments (441 +/- 35 mmol/h). The relative 13C enrichment of plasma lactate compared with that of glucose decreased (P < 0.05) with the PPD treatment compared with the control treatment (44 to 21 +/- 3%). It was concluded that PPD has a low rate of metabolism in cows without a normal functioning rumen, although about 10% of the absorbed PPD was metabolized into lactate.

Absorption↗
PubMed1976

Effects of 1,3-butanediol and 1,2-propanediol on growth, blood metabolites, and liver glycogen broiler chickens.

Control diets, and diets containing 4% 1,3-butanediol (BD), 8% BD, 4% 1,2-propanediol (PD) and 8% PD were offered ad libitum to broilers from 1 to 28 days of age. Body weight gain and feed intake were recorded, and plasma metabolites and liver glycogen were measured. When compared to the control diet, the synthetic compounds depressed (p less than 0.01) growth at the 4% level, but the effect was more pronounced (p less than 0.01) at the 8% level. The test compounds had no effect (p less than 0.05) on the efficiency of feed utilization. Four percent BD elevated (p less than 0.01) plasma beta-hydroxybutyrate and acetoacetate concentrations, and the ratio of beta-hydroxybutyrate to acetoacetate. The influence was more pronounced at the 8% level; PD did not affect (p greater than or equal to 0.05) ketone body concentrations. Neither BD, nor PD caused changes (p greater than or equal to) in plasma glucose, free fatty acids, cholesterol, or liver glycogen. Results are discussed with reference to feeding these compounds to monogastric and ruminant animals.

Acetoacetates↗
PubMed1976

Acute toxicity of various solvents in the mouse and rat. LD50 of ethanol, diethylacetamide, dimethylformamide, dimethylsulfoxide, glycerine, N-methylpyrrolidone, polyethylene glycol 400, 1,2-propanediol and Tween 20.

The LD50's of various solvents frequently used in toxicological work to improve the solubility of otherwise poorly soluble compounds were determined in the mouse and rat. The substances investigated were ethanol, dimethylacetamide, dimethylformamide, dimethylsulfoxide, glycerine, N-methylpyrrolidone, polyethylene glycol 400, 1,2-propanediol and Tween 20. The substances were administered under standardized conditions to groups of 10 animals (5 females, 5 males) (mice and rats) at doses that supplied at least 3 values lying between the LD16 and LD84. The median lethal dose and slope were determined with the aid of Finney's programmed probit analysis. The results are tabulated as LD50 ml/kg with 95% confidence limits. It is recommended that when using these solvents for pharmacological and toxicological investigations not more than a quarter of the LD50 should be used because otherwise there will be confusion between the deaths due to the substance being investigated and those due to the solvent.

Acetamides↗
PubMedDate not supplied

Determination of 3-chloro-1,2-propanediol in foods and food ingredients by gas chromatography with mass spectrometric detection: collaborative study.

The results of a collaborative study are reported for the determination of 3-chloro-1,2-propanediol (3-monochloropropane-1,2-diol; 3-MCPD) in a wide range of foods and food ingredients, using gas chromatography with mass spectrometric detection and incorporating the use of a deuterated internal standard. After a pretrial study, 12 laboratories (6 United Kingdom, 1 Switzerland, 1 Japan, 2 United States, 1 The Netherlands, and 1 from the European Commission) were asked to analyze 12 test materials (as known duplicates or split-level samples) by using a prescribed procedure. The test materials consisted of duplicate samples of acid-hydrolyzed vegetable protein (containing 3-MCPD at 0.029 mg/kg), malt extract (0.055 mg/kg), wholemeal bread crumbs (0.030 mg/kg), salami (0.016 mg/kg), cheese alternative (0.043 mg/kg), and soup powder (split levels at 0.045 and 0.041 mg/kg). Repeatability ranged from 0.005 to 0.013 mg/kg and reproducibility, from 0.010 to 0.027 mg/kg, for the samples tested. Precision values were well within statistically predicted levels (HORRAT values of <1 for 5 of the 6 matrixes tested) and within method criteria prepared by a joint working group composed of the United Kingdom Ministry of Agriculture, Fisheries and Food and industry representatives. The study demonstrated the satisfactory validation of the method for quantifying 3-MCPD at levels of > or = 0.010 mg/kg. The limit of detection derived from separate in-house studies was estimated to be 0.005 mg/kg. The method was adopted First Action by AOAC INTERNATIONAL.

Animal Feed↗
PubMedDate not supplied

Three new derivatives of 3-amino-1,2-propanediol; their spectral properties and biological evaluation.

Three new derivatives of 3-amino-1,2-propanediol have been synthesized. Full assignments of signals in their 1H- and 13C-NMR spectra are given. The influence of these compounds on the cardiovascular system in the anaesthetized rat was examined. In contrast to CGP 12177 which induced a strong increase in heart rate and a slight increase in blood pressure, compounds 1, 2 and 3 x HCl at doses up to 1 micromol/kg and compound 3 at doses of 0.01 and 0.1 micromol/kg did not change the cardiovascular parameters. The highest dose of compound 3-1 micromol/kg caused a very short-lasting decrease in heart rate (by 14%) and in blood pressure (by 25%).

Animals↗
PubMed1975

Chemical sterilization: effects of a single high dose of 3-chloro-1,2-propanediol on the testes and epididymides of dog.

A single high dose (70 mg/kg) of 3-chloro-1,2-propanediol (alpha-chlorohydrin) caused pathological degeneration in the testes of dog when examined after 33 days. The seminiferous tubules were depleted of spermatogenic elements. Epididymal epithelium was regressed, the lumen was empty and the passage through the duct was unimpaired. Alpha-chlorohydrin inhibited the synthesis of RNA and sialic acid of the testes and epididymides. A single high dose of alpha-chlorohydrin increased the total cholesterol/g of wet testis tissue which could be correlated with the testicular atrophy. Antiandrogenic nature of the compound has been discussed.

Animals↗
PubMed2002

Production of 1,3-propanediol by Klebsiella pneumoniae.

1,3-Propanediol (1,3-PD) has numerous applications from polymers to cosmetics, foods, lubricants, and medicines. Recently, there are strong industrial interests in a new kind of polyester, polytrimethylene terephthalate, with 1,3-PD as a monomer. This new polyester shows significant promise for use in carpeting and textiles. In this article we introduce a mild aerobic fermentation process using a strain screened from Klebsiella pneumoniae ATCC 25955, which is insensitive to oxygen, to produce 1,3-PD. We also describe a two-step fermentation process starting with glucose that was converted into glycerol with a glycerol-producing yeast, followed by K. pneumoniae that converts glycerol into 1,3-PD without intermediate isolation and purification of glycerol.

Aerobiosis↗
PubMedDate not supplied

Gas chromatographic/mass spectrometric determination of 3-methoxy-1,2-propanediol and cyclic diglycerols, by-products of technical glycerol, in wine: interlaboratory study.

The aim of the present study was to provide the official wine control authorities with an internationally validated method for the determination of 3-methoxy-1,2-propanediol (3-MPD) and cyclic diglycerols (CycDs)-both of which are recognized as impurities of technical glycerol-in different types of wine. Because glycerol gives a sweet flavor to wine and contributes to its full-body taste, an economic incentive is to add glycerol to a wine to mask its poor quality. Furthermore, it is known that glycerol, depending on whether it is produced from triglycerides or petrochemicals, may contain considerable amounts of 3-MPD in the first case or CycDs in the second. However, because these compounds are not natural wine components, it is possible to detect glycerol added to wine illegally by determining the above-mentioned by-products. To this end, one of the published methods was adopted, modified, and tested in a collaborative study. The method is based on gas chromatographic/mass spectrometric analysis of diethyl ether extracts after salting out with potassium carbonate. The interlaboratory study for the determination of 3-MPD and CycDs in wine was performed in 11 laboratories in 4 countries. Wine samples were prepared and sent to participants as 5 blind duplicate test materials and 1 single test material. The concentrations covered ranges of 0.1-0.8 mg/L for 3-MPD and 0.5-1.5 mg/L for CycDs. The precision of the method was within the range predicted by the Horwitz equation. HORRAT values obtained for 3-MPD ranged from 0.8 to 1.7, and those obtained for CycDs ranged from 0.9 to 1.3. Average recoveries were 104 and 109%, respectively.

Diglycerides↗
PubMed2003

[Cloning and expressing of 1,3-propanediol oxidoreductase-encoding gene].

Based on what mentioned above, the gene encoding 1,3-propanediol Oxidoreductase (dhaT) in Clostridium pasteurianum CpN-86 was cloned by using PCR method. The sequence, expressing vector construction and its expression of dhaT in E. coli were accomplished respectively. The recombination protein expressed by dhaT was also isolated and purified. The experimental results showed that: (1) The homogeneity of dhaT cloned by PCR and that in klebsiella pneumoniae strain was 82.9%; (2)The enzymatic activity of the protein expressed by cloned dhaT was 108 microM/ mg; (3)The molecular weight of the protein was 43 kD; (4) The protein expressed by dhaT has the same antigenicity as the natural protein of CpN-86 through Western blotting.

Alcohol Dehydrogenase↗
PubMed2006

[Study on elimination of 3-chloro-1,2-propanediol in hydrolyzed vegetable protein by capillary electrophoresis with electrochemical detection].

A method was developed to estimate 3-chloro-1,2-propanediol (3-MCPD) in hydrolyzed vegetable protein (HVP) by capillary electrophoresis with electrochemical detection. The optimum conditions were investigated to determine 3-MCPD in hydrolyzed vegetable protein. In 30 mmol/L borax (pH 9.24) running buffer, separation of 3-MCPD from glycerol was achieved. A 328 microm copper-disk electrode used as the working electrode exhibited a good response at + 0.65 V (vs. saturated calomel electrode (SCE)) in 0.05 mol/L sodium hydroxide solution. The effects of pH value, temperature and hydrolysis time on the elimination of 3-MCPD in hydrolyzed vegetable protein were studied. By adjusting hydrolyzed vegetable protein to pH value of 8.0 and heating up for 1 h at 90 degrees C, the content of 3-MCPD in hydrolyzed vegetable protein could be controlled under the level of 1.0 mg/kg, which coincides with the criterion of food safety in China.

China↗
PubMed1988

The use of amniotic fluid and serum with propanediol in freezing of murine 2-cell embryos.

Human and mouse embryos have been cultured in amniotic fluid (AF). Human AF and human serum (HS) are used in the freeze-thaw of 2-cell mouse embryos. Two hundred seventy-five 2-cell embryos were collected into phosphate-buffered saline with 20% HS and 20% AF and into 100% HS and AF. The embryos were cooled with propanediol as cryoprotectant at a controlled rate. After thaw, they were cultured in T6 with 3 mg/ml bovine serum albumin. Blastocyst formation post-thaw was 56/79, 44/70, 51/61, and 56/79 of intact embryos from 20% HS, 20% AF, pure HS, and pure AF (NS). But blastocyst hatching was better from embryos frozen in pure HS (22/61, compared with 16/79 for 20% HS; P less than 0.05). Hence there is no advantage in using AF in freeze-thaw, but pure HS may be of use.

Amniotic Fluid↗
PubMed1986

Analogues of chloramphenicol as mechanism-based inactivators of rat liver cytochrome P-450: modifications of the propanediol side chain, the p-nitro group, and the dichloromethyl moiety.

The importance of the p-nitro group, the propanediol side chain, and the dichloromethyl moiety of chloramphenicol in regulating its effectiveness and selectivity as a mechanism-based inactivator of rat liver cytochromes P-450 has been examined. 1-p-Nitrophenyl-2-dichloroacetamidoethane, 1-p-nitrophenyl-2-dibromoacetamidoethane, and 1-phenyl-2-dichloroacetamidoethane were as effective as chloramphenicol at inactivating the major phenobarbital-inducible isozyme of rat liver cytochrome P-450, whereas 1-p-nitrophenyl-2-difluoroacetamidoethane caused no enzyme inactivation. Unlike chloramphenicol, 1-p-nitrophenyl-2-dichloroacetamidoethane and 1-phenyl-2-dichloroacetamidoethane also inactivated the major beta-naphthoflavone-inducible isozyme of rat liver cytochrome P-450. Alkaline hydrolysis of the adducts formed upon in vitro incubation of liver microsomes from phenobarbital- and beta-naphthoflavone-induced rats with [14C]-1-p-nitrophenyl-2-dichloroacetamidoethane resulted in the release of 4-nitro-1-phenethyl-1,2-dicarboxylic acid amide and oxalic acid. Enzymatic digests of the radio-labeled protein produced by incubation of a reconstituted system containing the major isozymes induced by beta-naphthoflavone or phenobarbital with [14C]-1-p-nitrophenyl-2-dichloroacetamidoethane led to the release of 4-nitro-1-phenethyl-1,2-dicarboxylic acid amide and 4-nitro-1-phenethyl oxamyl lysine. These results suggest that a single oxamyl chloride intermediate is responsible for the covalent modification and, hence, inactivation of both isozymes by 1-p-nitrophenyl-2-dichloroacetamidoethane.

Animals↗
PubMed1978

Cell kinetics of mouse urinary bladder epithelium. VI. Changes in the proportions of cells with various nuclear DNA content after repeated doses of propylene glycol (1,2 propanediol).

A dose of 0.2 ml propylene glycol (1,2 propanediol) was injected subcutaneously into 12 hairless mice three times a week for three months. Four animals were killed at 1, 2 and 3 months and micro-flow fluorometric histograms of the bladder epithelial cells were made. The proportion of cells in diploid S phase was not much altered, but the proportion of tetraploid S-phase cells was significantly reduced and at three months DNA synthesis in tetraploid cells completely disappeared. The proportion of diploid cells increased, the proportion of tetraploids was slightly reduced and almost all octoploid cells disappeared. The changes are qualitatively similar to those seen after the bladder carcinogen dibutylnitrosamine, and after repeated injections of cyclophosphamide, but quantitatively much less pronounced. They can be explained as a result of cell toxicity whereby propylene glycol kills some bladder epithelial cells and disturbs the mechanism of repeated DNA synthesis. Propylene glycol is thus not a completely harmless solvent and when the kinetic effects of bladder carcinogens dissolved in propylene glycol are studied, the effect of the solvent alone must be accounted for.

Animals↗