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At least 217 records · Page 12Linked to original sources
PubMed1997

Effects of 3-phenylamino-1,2-propanediol and its mono- and dioleylesters on the production of reactive oxygen metabolites in human polymorphonuclear leukocytes.

Human polymorphonuclear leukocytes (PMNL) were exposed to 3-phenylamino-1,2-propanediol (PAP) or to its mono- or dioleylesters. The dioleylester of PAP (140 microM) slightly increased the production of reactive oxygen metabolites (ROM) from 8 +/- 2 mV to 18 +/- 3 mV, whereas PAP and its mono-oleylester were without any effect on ROM production in PMNL. None of the compounds were able to modulate formyl-Methionyl-Leucyl-Phenylalanine-induced production of ROM. Moreover, PAP did not have any effect on the production of ROM induced by phorbol myristate acetate (PMA). On the other hand, both mono- and dioleylesters of PAP dose-dependently inhibited PMA-induced production of ROM. The dioleylester of PAP, at a concentration of 14 microM, inhibited PMA-induced production of ROM by 79%, whereas a 2.3 mM concentration of mono-oleylester of PAP was required for 65% inhibition of PMA-induced production of ROM. Moreover, both esters of PAP shifted the peak production of ROM by PMA to a later time-point. Our results suggest that mono- and dioleylesters of PAP modulate the responses of PMNL upon stimulation with PMA, whereas PAP does not have any effect on PMA-induced ROM production in PMNL.

Analysis of Variance↗
PubMed2001

Purification and characterisation of an ester hydrolase from a strain of Arthrobacter species: its application in asymmetrisation of 2-benzyl-1,3-propanediol acylates.

An ester hydrolase (ABL) has been isolated from a strain of Arthrobacter species (RRLJ-1/95) maintained in the culture collection of this laboratory. The purified enzyme has a specific activity of 1700 U/mg protein and is found to be composed of a single subunit (Mr 32,000), exhibiting both lipase and esterase activities shown by hydrolysis of triglycerides and p-nitrophenyl acetate respectively. Potential application of the enzyme concerns the asymmetrisation of prochiral 2-benzyl-1,3-propanediol esters besides enantioselective hydrolysis of alkyl esters of unsubstituted and substituted 1-phenyl ethanols.

Arthrobacter↗
PubMedDate not supplied

Conversion of sugars to 1,2-propanediol by Thermoanaerobacterium thermosaccharolyticum HG-8.

The purpose of this study was to explore a fermentation route for the production of 1,2-propanediol (1,2-PD) from renewable sugars: lactose found in cheese whey, and D-glucose, D-galactose, L-arabinose, and D-xylose found in corn and wood byproducts. Thermoanaerobacterium thermosaccharolyticum, a naturally occurring organism, was found to ferment a wider range of sugars to 1,2-PD than previously reported. The specific sugar had a significant effect on the selectivity for 1,2-PD vs other fermentation products such as ethanol, D- and L-lactate, and acetate. T. thermosaccharolyticum potentially provides an environmentally friendly route to a major commodity chemical now made from petrochemicals.

Bacteria, Anaerobic↗
PubMedDate not supplied

A multiphasic hollow fiber reactor for the whole-cell bioconversion of 2-methyl-1,3-propanediol to (r)-beta-hydroxyisobutyric acid.

This paper describes the bioconversion of 2-methyl-1,3-propanediol to (R)-beta-hydoxyisobutyric acid (HIBA) by Acetobacter ALEI in a hollow fiber membrane bioreaction system arrangement that allows the integration of three liquid phases: the aqueous bioconversion phase, the organic phase consisting of a solution of trioctyl phosphine oxide (TOPO) in isooctane, and the third phase consisting of a basic stripping solution that allows reextraction of HIBA from the organic phase. A comparison of HIBA mass transfer experiments was carried out in the membrane reactor with two and three phases for different pH and TOPO concentrations. The use of the three-phase arrangement allows the extraction of high quantities of HIBA from the aqueous medium (higher than 85%) independently of the pH, whereas in the two-phase system the percentage of HIBA extracted from the aqueous medium was lower, 42% in the best case, and strongly influenced by the pH. The percentage of the extractive agent TOPO in the organic phase influenced on the mass transfer rate in both bi- and triphasic arrangements. By simply integrating the re-extraction phase in the system it was possible to increase the extraction yield by 2-fold, reduce the amount of TOPO by 4-fold, and operate at the more favorable pH 4. A bioconversion experiment was done in these conditions (pH = 4, TOPO = 5%) to confirm the advantages of including the third stripping solution. Fed-batch operation of the triphasic membrane reactor was maintained for more than 20 h, reaching an HIBA concentration in the stripping solution of 29 g L(-)(1).

Acetobacter↗
PubMedDate not supplied

Improving 1,3-propanediol production from glycerol in a metabolically engineered Escherichia coli by reducing accumulation of sn-glycerol-3-phosphate.

High levels of glycerol significantly inhibit cell growth and 1,3-propanediol (1,3-PD) production in anaerobic glycerol fermentation by genetically engineered Escherichia coli (E. coli) strains expressing genes from the Klebsiella pneumoniae dha (K.pneumoniae) regulon. We have previously demonstrated that 1,3-PD production by the engineered E. coli can be improved by reducing the accumulation of methylglyoxal. This study focuses on investigation of another lesser-known metabolite in the pathways related to 1,3-PD production-glycerol-3-phosphate (G3P). When grown anaerobically on glycerol in the absence of an exogenous acceptor, the engineered E. coli strains have intracellular G3P levels that are significantly higher than those in K. pneumoniae, a natural 1,3-PD producer. Furthermore, in the engineered E. coli strains, the G3P levels increase with increasing glycerol concentrations, whereas, in K. pneumoniae, the concentrations of G3P remain relatively constant. Addition of fumarate, which can stimulate activity of anaerobic G3P dehydrogenase, into the fermentation medium led to a greater than 30-fold increase in the specific activity of anaerobic G3P dehydrogenase and a significant decrease in concentrations of intracellular G3P and resulted in better cell growth and an improved production of 1,3-PD. This indicates that the low activity of G3P dehydrogenase in the absence of an exogenous electron acceptor is one of the reasons for G3P accumulation. In addition, spent media from E.coli Lin61, a glycerol kinase (responsible for conversion of glycerol to G3P) mutant, contains greatly decreased concentrations of G3P and shows improved production of 1,3-PD (by 2.5-fold), when compared to media from its parent strain E. coli K10. This further suggests that G3P accumulation is one of the reasons for the inhibition of 1,3-PD production during anaerobic fermentation.

Anaerobiosis↗
PubMed2001

Automated strong cation exchange extraction of fatty acid esters of 3-(N-phenylamino)-1,2-propanediol from oil samples for routine quantification by HPLC-APCI/MS/MS.

Fatty acid esters of 3-(N-phenylamino)-1,2-propanediol are currently considered the best chemical markers of toxic oils related to the Spanish toxic oil syndrome. Recent research in this area has undertaken the exhaustive and quantitative characterization of these compounds in oils collected during the epidemic outbreak. Current methods developed in this laboratory are based on solid phase extraction (SPE) using SCX cartridges followed by HPLC-APCI/MS/MS quantification. To circumvent the long and tedious extraction procedure, the SPE protocol was adapted for automatic extraction and the problems derived from the use of the immiscible solvents required for the SCX extraction were solved. Linearity of the analytical method was found in the same range as for the manual method. Extraction recoveries were 87 and 75% for 2-hydroxy-3-(N-phenylamino)propyl linoleate and 2-(linoleyloxy)-3-(N-phenylamino)propyl linoleate, respectively, and the corresponding coefficients of variation were approximately 1%, greatly improving reproducibility over manual procedures.

Cation Exchange Resins↗
PubMed2004

Biodegradation of 3-chloro-1,2-propanediol with Saccharomyces cerevisiae.

A novel enzymatic dehalogenating activity of 3-chloro-1,2-propanediol (3-MCPD) with Saccharomyces cerevisiae (baker's yeast) is reported. All bioconversion assays were carried out under aerobic conditions, at 28 degrees C, and the kinetics were monitored. The biodegradation was performed at different pH values (6.2, 7.0, and 8.2), in the presence and absence of glucose, using racemic 3-MCPD at two different concentrations (7.3 micromol/L and 27 mmol/L). Optimal conversion (68%) of racemic (R,S)-3-MCPD at a concentration of 27 mmol/L was achieved after 48 h of reaction time, at pH 8.2, and in the presence of glucose. At a concentration of 7.3 micromol/L, 73% degradation was observed after 72 h, at pH 8.2 and in the absence of glucose. Under the same experimental conditions, the conversion of pure (S)-3-MCPD (85%) was higher than that of the (R)-enantiomer (60%).

Biodegradation, Environmental↗
PubMed1991

2-[(arylmethyl) amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding.

The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs with DNA increases as the intercalating ring system grows in area, with three distinct binding levels evident. Isomers from a specific ring system appear to bind DNA similarly. DNA binding is not the sole criterion for antitumor activity for the AMAPs studied; the magnitude of the delta Tm does not correlate with the antitumor activity observed. Significant in vivo P388 activity was seen for AMAP congeners from several tetracyclic ring systems. However, isomers from each of the specific ring systems produced a wide range of in vivo P388 activity. Thus, AMAP antitumor activity is not a function of the ring system per se, but rather appears to be related to the shape of the specific molecule. Three AMAP congeners (crisnatol (770U82, 773U82, and 502U83) are currently in clinical trials.

Animals↗
PubMed1989

Water-soluble third generation antitumor platinum complexes, [2,2-bis (aminomethyl)-1,3-propanediol-N,N']-[1,1-cyclobutanedicarboxylato (2-)-O,O']platinum(II) and [1,1-cyclobutanedicarboxylato(2-)-O,O'] [tetrahydro-4H-pyran-4,4-dimethanamine-N,N']platinum(II).

The synthesis, stability, and antitumor activity of a series of water-soluble third generation platinum(II) complexes have been described. Among these complexes, [2,2-bis(aminomethyl)-1,3- propanediol-N,N'] [1,1-cyclobutanedicarboxylato(2-)-O,O']platinum(II) and [1,1-cyclobutanedicarboxylate(2-)-O,O'](tetrahydro-4H-pyran-4,4- dimethanamine-N,N'-)platinum(II) have shown the greatest promise for further investigation and are currently under clinical evaluation.

Animals↗
PubMed2002

Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate.

An efficient lipase-catalyzed desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols was developed using 1-ethoxyvinyl 2-furoate 1b, for which the well-known method using vinyl or isopropenyl acetate has had limited success due to low reactivity and easy racemization of the products through acyl group migration. The reagent 1b is highly reactive and converts various prochiral 1,3-diols to the monoesters having a chiral quaternary carbon center with 82-99% ee. These products were stable against racemization under acidic conditions, and their furoyl groups were compatible with oxidative conditions. Prolonging the reaction time led to the kinetic resolution of the monoesters resulting in an increase of their optical purity. The similar desymmetrization of meso cis-1,2-cycloalkanediols gave the monoesters with 82-97% ee without racemization.

Benzoates↗
PubMedDate not supplied

Biotransformation of 3-(phenylamino)-1,2-propanediol to 3-(phenylamino)alanine: a chemical link between toxic oil syndrome and eosinophilia-myalgia syndrome.

During late 1989, the eosinophilia-myalgia syndrome (EMS) developed as an epidemic in the United States, with numerous additional cases reported in several other countries worldwide. Eight years earlier, a closely-related disease, the toxic oil syndrome (TOS), occurred in Spain as a massive food-borne epidemic. Although EMS was linked to the ingestion of tainted L-tryptophan, and TOS to aniline-denatured rapeseed oil, the etiologic agent(s) responsible for both diseases remains undetermined. Contaminants in these foodstuffs are believed to have triggered the diseases. Aniline contaminants, including 3-(phenylamino)-1,2-propanediol (PAP), have been reported in oil used by patients who developed TOS. A related aniline derivative, 3-(phenylamino)-L-alanine (PAA), was recently isolated from L-tryptophan associated with the onset of EMS. Here, we demonstrate the biotransformation of PAP into PAA by both rat hepatocytes and human liver tissue. The structural characterization of PAA was unequivocally determined using on-line HPLC coupled with atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS). This finding is the first reported chemical link between TOS and EMS and suggests that these two related diseases share a common etiology, namely, PAA.

Alanine↗
PubMed2003

Comparison of 1,2-propanediol and ethylene glycol for cryopreservation of slow-cooled mouse zygotes and their subsequent development.

PURPOSE: This study was conducted on cryoprotective activity of ethylene glycol (ETG) and propanediol (PROH) on cleavage rate of mouse zygotes. METHODS: Mouse oocytes were excised from fallopian tube of gonadotropin-treated mice, then inseminated with spermatozoa. After 16.5-17.5 h, zygotes were randomly allocated into three groups; control, toxicity, and frozen. In the latter, zygotes were slowly cooled with ETG and PROH similar to those used for human embryo cryopreservation. The survived zygotes cultured for 120 h and their later stages of development were compared with nonfrozen embryos. RESULTS: The toxicity test showed that no differences were observed in cleavage rate between exposed and nonexposed embryos. The survival and expanded hatching blastocyst rate of embryos frozen with PROH was significantly better than with ETG (92.8 vs. 58.2% and 68.2 vs. 39.1%, respectively). CONCLUSIONS: ETG does not appear to be a good alternative to the classical PROH for freezing of mouse zygotes.

Animals↗
PubMed1975

Voluntary selection of and tolerance to 1,2 propanediol (propylene glycol) by high and low ethanol-selecting mouse strains.

Fifteen male mice from each of 4 inbred strains (C57BL/6J, BALB/cJ, CBA/J, and DBA/2J) were tested to determine their voluntary self-selection of a 10% solution of 1,2 propanediol (1,2 PD), A 3-carbon alcohol of low toxicity. As with ethanol, the C57BL/6J strain consumed significantly greater amounts that the 3 other low ethanol-selecting strains. A second experiment determined that the 3 low selecting strains suffered significantly greater depression of the central nervous system from 1,2 PD than the high selecting C57BL strain. It was also found that ethanol is a much more potent depressant that 1,2 PD. These results are discussed in terms of the possible role of neural sensitivity in regulating consumption levels of the 2 alcohols.

Alcohol Drinking↗
PubMed2003

Molecular characterization of the 1,3-propanediol (1,3-PD) operon of Clostridium butyricum.

The genes encoding the 1,3-propanediol (1,3-PD) operon of Clostridium butyricum VPI1718 were characterized from a molecular and a biochemical point of view. This operon is composed of three genes, dhaB1, dhaB2, and dhaT. When grown in a vitamin B12-free mineral medium with glycerol as carbon source, Escherichia coli expressing dhaB1, dhaB2, and dhaT produces 1,3-PD and high glycerol dehydratase and 1,3-PD dehydrogenase activities. dhaB1 and dhaB2 encode, respectively, a new type of glycerol dehydratase and its activator protein. The deduced proteins DhaB1 and DhaB2, with calculated molecular masses of 88,074 and 34,149 Da, respectively, showed no homology with the known glycerol dehydratases that are all B12 dependent but significant similarity with the pyruvate formate lyases and pyruvate formate lyases activating enzymes and their homologues. The 1,158-bp dhaT gene codes for a 1,3-PD dehydrogenase with a calculated molecular mass of 41,558 Da, revealing a high level of identity with other DhaT proteins from natural 1,3-PD producers. The expression of the 1,3-PD operon in C. butyricum is regulated at the transcriptional level, and this regulation seems to involve a two-component signal transduction system DhaASDhaA, which may have a similar function to DhaR, a transcriptional regulator found in other natural 1,3-PD producers. The discovery of a glycerol dehydratase, coenzyme B12 independent, should significantly influence the development of an economical vitamin B12-free biological process for the production of 1,3-PD from renewable resources.

Alcohol Dehydrogenase↗
PubMed1999

Highly cross-linked networks for dental applications obtained by photocuring of tris[2-(acryloyloxy)ethyl]isocyanurate, 2-ethyl-2-(hydroxymethyl)-1,3-propanediol triacrylate, and pentaerythritol triacrylate.

Highly cross-linked networks have been obtained by photoinitiated camphorquinone-amine polymerization of tris[2-(acryloyloxy)ethyl]isocyanurate alone and/or with 2-ethyl-2-(hydroxymethyl)-1,3-propanediol triacrylate or pentaerythritol triacrylate, which can be considered a new class of dental restorative resins. The most effective coinitiators in this system are amines such as ethyl-4-dimethylaminobenzoate, N,N-dimethyl-benzylamine, and 2,4,6-tris(dimethylaminomethyl)phenol. The volume shrinkages of polymerized samples were 8%-13%. The hardness of photocured resins in the presence of an inorganic filler (aluminum/fluoro/silicate glass, Ketac-Fil was slightly less than that of a restorative composite material (Z100 MP).

Acrylates↗
PubMed2006

Removal of 1,3-dichloro2-propanol and 3-chloro1,2-propanediol by the whole cell system of pseudomonas putida DSM 437.

The removal of 1,3-dichloro-2-propanol (1,3-DCP), 3-chloro-1,2-propanediol (3-CPD) and their mixtures at concentrations up to 1,000 mg . L(-1) by the whole cell system of Pseudomonas putida DSM 437 was investigated. The 1,3-DCP removal rates ranged from 2.36 to 10.55 mg . L(-1) . h(-1); 3-CPD exhibited approximately two times higher removal rates compared to 1,3-DCP for all concentrations tested. Removal of 1,3-DCP and 3-CPD followed first-order kinetics with rate constants of 0.0109 h(-1) and 0.0206 h(-1), respectively. When the whole cell system of P. putida DSM 437 was applied to mixtures of the two halohdrins, complete removal of 1,3-DCP was achieved at 144 h while removal of 3-CPD was completed at times ranging from 72 to 144 h. Time to achieve 50% removal of both halohydrins depends on the initial concentration of each in the mixture. For 1,3-DCP, it ranged from 40.55 h at 200 mg . L(-1) to 53.28 h at 500 mg . L(-1) while the respected values for 3-CPD were 33.39 and 68.91 h.

Biodegradation, Environmental↗
PubMed2004

Mechanism of antifertility in male rats treated with 3-monochloro-1,2-propanediol (3-MCPD).

3-Monochloro-1,2-propanediol (3-MCPD) is a food contaminant that is often found in foods containing acid-hydrolyzed (AH) protein, like seasonings and savory food products. The purpose of the present study was to investigate the effects of 3-MCPD on male fertility, sperm, and hormonal levels and its antifertility mechanism. In vivo male fertility testing was performed to observe the adverse effects of 3-MCPD on the functioning of the male reproductive system and pregnancy outcome. 3-MCPD (0.01-5 mg/kg) was administered daily by gavage to Sprague-Dawley (SD) male rats for 4 wk. At the end of the pretreatment period, male rats were mated overnight with untreated females. Males successfully inducing pregnancy were sacrificed to assess sperm parameters, reproductive organ histopathology, and spermatogenesis. The resulting pregnant females were sacrificed on 20 of gestation to evaluate pregnancy outcome. The paternal administration of 3-MCPD (5 mg/kg) was found to result in adverse effects on male fertility and pregnancy outcome without inducing remarkable histopathological changes in testes and epididymides. Additionally, 3-MCPD (5 mg/kg) significantly reduced sperm motility, copulation, fertility indices, and the number of live fetuses showed steep dose-response curves. 3-MCPD did not affect spermatogenesis or induce hormonal changes in the blood and testes of male rats. An in vitro hormone assay using primary isolated Leydig cells showed no significant changes in related hormone levels after 3-MCPD treatment. To evaluate the effects of 3-MCPD on apoptotic induction and H+-ATPase levels in the testis and epididymis, 10 or 100 mg/kg of 3-MCPD was administered by gavage to male rats and testes and epididymides were examined at 3, 6, 12, and 24 h later. Apoptosis was not detected in the testes of animals treated with 100 mg/kg 3-MCPD. However, the level of H+-ATPase in the cauda epididymis was reduced by 3-MCPD treatment. These results indicate that 3-MCPD induced a spermatotoxic effect, which was mediated by reduced H+-ATPase expression in the cauda epididymis, and suggest that an altered pH level in the cauda epididymis might lead to a disruption of sperm maturation and the acquisition of motility.

Animals↗
PubMed1998

Formaldehyde in cryoprotectant propanediol and effect on mouse zygotes.

Cryopreservation of human zygotes and embryos has been routinely performed by in-vitro fertilization clinics for many years. Karran and Legge (1996) first reported that formaldehyde (FA) present in the cryoprotective solutions can have a deleterious effect on mouse oocytes. FA is a cytotoxic, carcinogenic and mutagenic chemical. The effect of FA on mouse zygotes was investigated. In addition, the concentrations of FA in propanediol (PROH) obtained from various sources were determined. Pooled 1-cell embryos were dispensed into droplets of modified Ham's F10 or human tubal fluid containing various concentrations of FA. Since bovine serum albumin (BSA) may minimize toxicity additional trials were done as above in the absence of BSA. FA concentration in the standard 1.5 M PROH, from different sources in water, was measured in the same assay using a standard curve of 0-100 microM FA. FA in a complex medium had a significant deleterious effect on embryo development and hatching but only at 1 mM concentration (P < 0.000001; see Tables I-III). There was no significant effect of FA at 100 microM. However, in a simple medium even 50 microM FA decreased embryo hatching. FA was present in 1.5 M PROH from different sources (range 1.0-35.3 microM concentration). It appears that FA concentrations do not increase with storage because FA concentrations were low even after opening and storage for 3 years on the shelf. This suggests that FA is a contaminant during the manufacturing process and may vary from manufacturer to manufacturer and batch to batch. Until further studies are done to confirm the lack of toxicity to embryos during cryopreservation (with or without FA scavengers) it may be prudent to screen all batches of cryoprotectants for FA as part of quality control.

Animals↗