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At least 631 records · Page 35Linked to original sources
PubMed1988

Synthesis and characterization of deoxy analogues of diphytanylglycerol phospholipids.

Novel analogues of diphytanyl phospholipids, 2,3-diphytanyl sn-1-glycerol-1-phosphoryl-1'-(1',3'-propanediol) (dPG), 2,3-diphytanyl-sn-glycerol-1-phosphoryl-1'-propanol (ddPG) and 2,3-diphytanyl-sn-glycerol-1-phosphoryl-1'-(1',3'-propanediol-3'-p hosphate) (dPGP), were synthesized according to modifications of previously published procedures. The samples were TLC and analytically pure and were characterized by 13C- and 1H-NMR and negative FAB/MS. The pK values of dPGP in aqueous dispersions or in methanol/water (1:1, v/v) were determined by potentiometric titration and compared with those of 2,3-diphytanyl-sn-glycerol-1-phosphoryl-3'-sn-glycerol-1'-phosphat e (PGP). The dissociation constant of the third ionizable POH group of dPGP was more than 2 pK units higher than that of PGP, indicating that the free glycerol hydroxyl group plays an important role in headgroup conformation and stabilization, perhaps through hydrogen bonding with the phosphate group(s).

Chemical Phenomena↗
PubMed1988

Cryoprotection of red blood cells by 1,3-butanediol and 2,3-butanediol.

1,3-Butanediol and 2,3-butanediol have been used in buffered solutions with 20, 30, or 35% (w/w) alcohol to cool erythrocytes to -196 degrees C at different cooling rates between 1 to 3500 degrees C/min, followed by slow or rapid rewarming. 1,3-butanediol shows the same shapes of red blood cell survival curves as 1,2-propanediol. Having nearly the same physical properties, they have comparable effects on cell survival. The classical maximum of survival for intermediate cooling rates and an increase for the highest cooling rates are observed. This increase seems to be correlated with the glass-forming tendency of the solution. After the fastest cooling rates, a warming rate of 5000 degrees C/min is sufficient to avoid cell damage, but a warming rate of 100-200 degrees C/min is not. Yet both of these rates would be insufficient to avoid the intracellular ice crystallization on warming. The damage on warming after fast cooling seems once again to be correlated with the transition from cubic to hexagonal ice. For all our results, 1,3-butanediol is like a "second" 1,2-propanediol and could be useful as a cryoprotectant for preservation by total vitrification. 2,3-Butanediol always gives extremely low survival rates, though it presents good physical properties. The crystallization of its hydrate seems to be lethal on cooling or on rewarming.

Blood Preservation↗
PubMed1993

Methylglyoxal and the polyol pathway. Three-carbon compounds are substrates for sheep liver sorbitol dehydrogenase.

Methylglyoxal, 1,2-propanediol and glycerol are shown to be substrates for sheep liver sorbitol dehydrogenase. With 1,2-propanediol the enzyme-catalyzed reaction occurs specifically with the R(-)-enantiomer. The maximum velocities and the specificity constants obtained for the three-carbon substrates are considerably lower than those reported previously for sorbitol, and suggest that rate-determination is imposed by catalytic steps other than the enzyme-coenzyme product dissociation. The present findings are discussed in terms of substrate specificity and stereospecificity, and may indicate novel aspects of sorbitol dehydrogenase function in relation to glucose metabolism and diabetic pathogenesis.

Acetone↗
PubMed1988

Some factors affecting successful vitrification of mouse blastocysts.

The effects of temperature and exposure time to vitrification solutions on In vitro survival of mouse blastocysts were investigated. Blastocysts were first exposed for 10 min to vitrification Solution 1 (VS1) containing 10% glycerol-20% 1,2 propanediol in phosphate buffered saline (PBS), then to vitrification Solution 2 (VS2) with 25 % glycerol-25% 1,2 propanediol for various periods either at room temperature or at 4 degrees C. At room temperature survival dropped quickly, while at 4 degrees C an increase in survival was observed. It is concluded that the viability of mouse blastocyts after vitrification is dependent on the temperature and duration of equilibration in vitrification solutions.

Journal Article↗
PubMed1989

Stage-dependent viability of vitrified rabbit embryos.

The aim of the work was to determine the susceptibility of rabbit embryos to vitrification at different developmental stages. The experiment was carried out on 676 embryos at 1-, 2- and 8-to 16-cell stages as well as the morula and blastocyst stages. As a vitrification medium, a mixture of 30% 1,2-propanediol + 30% glycerol (Solution I), or 35% 1,2-propanediol + 35% glycerol (Solution II), was used. The embryos were frozen in glass ampules placed in nitrogen vapour for 5 min before being plunged into liquid nitrogen. Dilution after rapid thawing was done in one step in a 1-M sucrose solution. After vitrification in Solution I, none of the 1- or 2-cell embryos survived, whereas the survival rate of 8-to 16-cell embryos, morula and blastocysts, was 23.0, 82.7 and 78.5%, respectively. After vitrification in Solution II, the survival rate of 1-, 2- and 8-to 16-cell embryos was 20.0, 43.8 and 92.9%, respectively. The proportion of live offspring on the Day 28 after transfer of 68 vitrified morula was 26.5% compared with 24.0% in the control group. Thus, the proposed vitrification procedures can be useful in the cryopreservation of rabbit embryos.

Journal Article↗
PubMed1981

Detection of Neisseria gonorrhoeae by ultraviolet illumination of NADH generated by an immobilized antibody-gonococcal enzyme complex.

Frozen, cervical swabs were placed in a lysis buffer containing an immobilized antibody to the gonococcal enzyme, 1,2-propanediol oxidoreductase. The immobilized antibody--enzyme complex that formed was active after the addition of substrate (1,2-propanediol and NAD) and this activity could be detected by visual inspection of NADH fluorescence under ultraviolet illumination.

Alcohol Oxidoreductases↗
PubMed1995

Comparison of the energetic efficiencies of hydrogen and oxychemicals formation in Klebsiella pneumoniae and Clostridium butyricum during anaerobic growth on glycerol.

Data for the anaerobic growth of Klebsiella pneumoniae DSM 2026 and Clostridium butyricum DSM 5431 on glycerol have been analyzed using the concept of material and available electron balances with consideration for hydrogen production. Models for the kinetics of energetic efficiencies of product formation under low residual glycerol are presented. For Klebsiella pneumoniae, the specific rates of electron transfer to the products were mainly significantly dependent on specific growth rate with the exception of ethanol and hydrogen which were also significantly non-growth associated. In the case of Clostridium butyricum, the rates were only growth rate dependent, except for hydrogen formation. The analysis also indicated that the production of 1,3-propanediol by Klebsiella pneumoniae was favoured by limitations other than glycerol limitation, while hydrogen generation was best under low residual glycerol and particularly in the presence of external 1,3-propanediol. Klebsiella pneumoniae appeared to be able to incorporate more of the available electrons of glycerol into hydrogen as compared with the Clostridium butyricum. The study demonstrates the need for properly considering H2 in models describing anaerobic processes.

Clostridium↗
PubMed1990

Short chain diol metabolism in human disease states.

Recent clinical studies have shown the presence of two short chain diols, meso-2,3-butanediol and D/L-2,3-butanediol, and in most cases 1,2-propanediol in either serum or urine collected from humans in several apparently unrelated disease states: congenital propionic and methylmalonic acidemia, premature infants, and alcoholics both in the presence and absence of ethanol. In addition 1,2-propanediol has been shown in patients during prolonged starvation, and in patients with diabetic keto-acidosis. No common defect is known to exist in these metabolic states. Understanding how these compounds are produced in clinically well-defined diseases such as methyl malonic and propionic aciduria, however, may help explain how and why these compounds are produced in alcoholics.

Acetoin↗
PubMed2004

Thermal properties of ethylene glycol aqueous solutions.

Preventing ice crystallization by transforming liquids into an amorphous state, vitrification can be considered as the most suitable technique allowing complex tissues, and organs cryopreservation. This process requires the use of rapid cooling rates in the presence of cryoprotective solutions highly concentrated in antifreeze compounds, such as polyalcohols. Many of them have already been intensively studied. Their glass forming tendency and the stability of their amorphous state would make vitrification a reality if their biological toxicity did not reduce their usable concentrations often below the concentrations necessary to vitrify organs under achievable thermal conditions. Fortunately, it has been shown that mixtures of cryoprotectants tend to reduce the global toxicity of cryoprotective solutions and various efficient combinations have been proposed containing ethanediol. This work reports on the thermal properties of aqueous solutions with 40, 43, 45, 48, and 50% (w/w) of this compound measured by differential scanning calorimetry. The glass forming tendency and the stability of the amorphous state are evaluated as a function of concentration. They are given by the critical cooling rates v(ccr)above which ice crystallization is avoided, and the critical warming rates v(cwr) necessary to prevent ice crystallization in the supercooled liquid state during rewarming. Those critical rates are calculated using the same semi-empirical model as previously. This work shows a strong decrease of averaged critical cooling and warming rates when ethanediol concentration increases, V(ccr) and V(cwr) = 1.08 x 10 (10) K/min for 40% (w/w) whereas V(ccr) = 11 and V(cwr) = 853 K/min for 50% (w/w). Those results are compared with the corresponding properties of other dialcohols obtained by the same method. Ethylene glycol efficiency is between those of 1,2-propanediol and 1,3-propanediol.

Calorimetry, Differential Scanning↗
PubMed2005

Modulation of the rheological and mucoadhesive properties of thermosensitive poloxamer-based hydrogels intended for the rectal administration of quinine.

The aim of this work was to formulate and characterize thermosensitive gels based on poloxamer 407, a thermosensitive polymer, and hydroxypropylmethylcellulose (HPMC), a bioadhesive polymer, intended for the rectal delivery of quinine in children. In order to avoid the macroscopic phase separation between the two polymers it was necessary to add propanediol-1,2. After the formulation of stable ternary systems, their rheological properties were studied as a function of temperature. It was thus possible to obtained the gelation temperature of the systems as well as their elastic modulus, G', at 37 degrees C. It appeared that HPMC in the presence of propanediol-1,2 had a synergistic effect on the gelation of poloxamer 407. Tests on the rabbit rectal mucous membrane, founded on a technique of traction of the adhesive/adhered joint, made it possible to characterize the bioadhesive properties of the gels by measuring the work of adhesion, W, and the maximum detachment force, F(max). Over small concentration ranges of poloxamer and HPMC, very important variations of the viscoelastic and mucoadhesives properties were observed. It was shown that the viscoelastic and the bioadhesive properties were tightly correlated. Indeed, an empirical equivalence relation was established between the shear frequency and the rate of deformation in traction and allowed to describe all our samples by a master curve. This master curve would make it possible to predict the values of W at various rates of traction by the simple non-destructive measurement of the elastic modulus, G', at an equivalent shear frequency.

Adhesiveness↗
PubMed2005

Novel microbial epoxide hydrolases for biohydrolysis of glycidyl derivatives.

Microbial isolates from biofilters and petroleum-polluted bioremediation sites were screened for the presence of enantioselective epoxide hydrolases active towards tert-butyl glycidyl ether, benzyl glycidyl ether, and allyl glycidyl ether. Out of 270 isolated strains, which comprised bacteria, yeasts, and filamentous fungi, four were selected based on the enantioselectivities of their epoxide hydrolases determined in biotransformation reactions. The enzyme of Aspergillus niger M200 preferentially hydrolyses (S)-tert-butyl glycidyl ether to (S)-3-tert-butoxy-1,2-propanediol with a relatively high enantioselectivity (the enantiomeric ratio E is about 30 at a reaction temperature of 28 degrees C). Epoxide hydrolases of Rhodotorula mucilaginosa M002 and Rhodococcus fascians M022 hydrolyse benzyl glycidyl ether with relatively low enantioselectivities, the former reacting predominantly with the (S)-enantiomer, the latter preferring the (R)-enantiomer. Enzymatic hydrolysis of allyl glycidyl ether by Cryptococcus laurentii M001 proceeds with low enantioselectivity (E=3). (R)-tert-Butyl glycidyl ether with an enantiomeric excess (ee) of over 99%, and (S)-3-tert-butoxy-1,2-propanediol with an ee-value of 86% have been prepared on a gram-scale using whole cells of A. niger M200. An enantiomeric ratio of approximately 100 has been determined under optimised biotransformation conditions with the partially purified epoxide hydrolase from A. niger M200. The regioselectivity of this enzyme was determined to be total for both (S)-tert-butyl glycidyl ether and (R)-tert-butyl glycidyl ether.

Aspergillus niger↗
PubMed2005

Physical characterizations of microemulsion systems using tocopheryl polyethylene glycol 1000 succinate (TPGS) as a surfactant for the oral delivery of protein drugs.

Attempts were to develop microemulsion systems using medium chain triglyceride, deionized water, and TPGS as surfactant for the oral delivery of protein drugs or poorly water-soluble drugs. Phase diagrams were constructed to elucidate the phase behavior of systems composed of Captex 300 and water with D-alpha-tocopheryl polyethylene glycol 1000 succinate (TPGS) as main surfactant, polysorbates (Tween 20, Tween 40, Tween 60 and Tween 80) as adjuvant surfactants, and polyethylene glycols (PEG 400 and PEG 600) and polyols (ethanediol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol and glycerin) as cosurfactants. The ratios of TPGS to Tweens, PEGs or polyols (K(m)) were set at 4/1, 2/1, 1/1, 1/2, and 1/4. The phase diagram for H(2)O/Captex 300/TPGS system reveals that when TPGS was used as a sole surfactant, it is not capable of producing isotropic solutions of water and oil over a wide range of the compositions. H(2)O/Captex 300/TPGS/Tweens systems with various K(m), regardless of the adjuvant surfactant used were capable of producing an isotropic phase. The extension of microemulsion phase and the presence and extension of the gel phase were found to be dependent on the surfactant mixture. The phase diagrams of H(2)O/Captex 300/TPGS systems using polyols as cosurfactants demonstrate that the types of polyols have a slight effect on the region of existence of the microemulsions. Comparison between the isotropic regions for the polyols system reveals that as the relative concentration of polyols increase, the isotropic region decrease in size. This decrease is towards the S(mix)-water axis indicating that as the relative concentration of polyols increases the maximum amount of oil solubilized decreases. The gel region decreased in size with the increase of polyols weight ratio. All polyols do not solubilized Captex 300 without using TPGS as surfactant.

Chemical Phenomena↗
PubMed2006

Extraction of berberine from rhizome of Coptis chinensis Franch using supercritical fluid extraction.

Supercritical fluid was used to extract berberine from rhizome of Coptis chinensis Franch. The recovery of berberine was compared with various modifiers, i.e. methanol and 95% ethanol with and without surfactant Tween 80, and 1,2-propanediol. The results show that the yield obtained after 3 h extraction with 1,2-propanediol-modified supercritical carbon dioxide was the highest (from 6.91%, w/w at 200 bar to 7.53%, w/w at 500 bar), while that obtained with 95% ethanol modified-supercritical carbon dioxide was the lowest (from 0.15%, w/w at 300 bar to 0.19%, w/w at 600 bar). The recovery of berberine was not improved by adding 5% Tween 80 in supercritical fluid.

Berberine↗
PubMed1988

Chromosome analysis of two-cell mouse embryos frozen by slow and ultrarapid methods using two different cryoprotectants.

Three freezing methods (slow-1,2 propanediol; ultrarapid-dimethyl sulphoxide; ultrarapid-1,2 propanediol) were used to assess the effects of low temperature storage on morphologic features and chromosome make-up of 2-cell mouse embryos. Weekly batches (15 weeks) of 2-cell mouse embryos were frozen for a period of 7 days using these three freezing methods, then thawed and subjected to chromosome analysis. After thawing, all three freezing regimens yielded 70.2% to 75.8% of healthy intact 2-cell embryos, and 5.5% to 8.1% of embryos with one healthy blastomere intact, respectively, out of 817 embryos examined. Chromosome analysis was possible in all 1- and 2-cell embryos. The incidence of aneuploidy and polyploidy in frozen-thawed embryos of all three methods (2.8% to 3.4%; 4.0% to 6.5%) was not significantly different from that of control unfrozen embryos (3.0%; 6.0%) (P greater than 0.01). Mitotic crossing over was observed in 3.5% of embryos frozen-thawed by the ultrarapid-dimethyl sulphoxide method only. It is not clear how the mitotic crossing over was induced by ultrarapid freezing in the presence of dimethyl sulphoxide.

Animals↗
PubMed1997

Chromosome and spindle configurations of human oocytes matured in vitro after cryopreservation at the germinal vesicle stage.

OBJECTIVE: To investigate effects of cryoprotectant and cryopreservation on the chromosome and microtubule configuration of human immature oocytes. DESIGN: Intact cumulus-enclosed immature oocytes were collected from unstimulated ovaries and divided into three groups: group 1, no treatment (control); group 2, only 1,2-propanediol treatment, and group 3, cryopreserved oocytes. Oocytes in groups 1 and 2, and oocytes that survived after cryopreservation in group 3 were cultured for 48 hours. SETTING: Infertility Medical Center at the CHA General Hospital, Seoul, Korea. PATIENT(S): Oocytes were obtained from patients undergoing gynecologic surgery. MAIN OUTCOME MEASURE(S): Maturation rate and abnormality in chromosomes by fluorescence in situ hybridization and in the spindle by immunostaining for tubulin. RESULT(S): There was no effect of propanediol-only treatment on the chromosomal (41.4%) and spindle abnormalities (35.3%) in group 2 compared with control oocytes (31.8% and 22.2%, respectively), whereas a statistically significant increase in abnormalities in chromosomes (77.8%) and spindles (70%) was found in group 3. CONCLUSION(S): Human oocytes matured in vitro after cryopreservation at the germinal vesicle stage showed increased incidence of chromosomal and spindle abnormalities. These abnormalities may impair the capacity for further development of the embryos derived from frozen-thawed oocytes.

Adult↗
PubMed2000

Effects of valproate derivatives I. Antiepileptic efficacy of amides, structural analogs and esters.

Derivatives of the antiepileptic drug valproate (VPA, 2-propylpentanoic acid) have been synthesized and tested in order to improve the intracellular availability of VPA. The buccal ganglia of Helix pomatia were used as a test nervous system and antiepileptic efficacies were reconfirmed using rat cortex in vivo. Epileptiform activities consisted of typical paroxysmal depolarization shifts (PDS) which appeared in the identified neuron B3 with application of pentylenetetrazol. Epileptiform activities were found to be accelerated, unaffected or blocked. (i) The Amide-derivatives 2-propylpentanamide and N,N-dipropyl-2-propylpentanamide, and short chain ester derivatives 1-O-(2-propylpentanoyl)-2,3-propandiol, 2,2-di(hydroxymethyl)-1-O-(2-propylpentanoyl)-1,3-propanediol and 2,2-di(hydroxymethyl)-1,3-di-O-(2-propylpentanoyl)-1,3-propanediol accelerated epileptiform activities. Membrane potential often shifted to a permanent depolarization which corresponded to the PDS-inactivation level. (ii) The structural analogs 1-cycloheptene-1-carboxylic acid and cyclooctanecarboxylic acid accelerated epileptiform activities only slightly or were without effects. (iii) The small VPA-ester, 2-propylpentanoic acid ethyl ester, decreased the epileptiform activities in a way that is comparable to the effects of VPA well known from previous studies. It thus could be thought as a VPA-pro-drug. (iv) The mannitol-esters 1-O-(2-propylpentanoyl)-D-mannitol and 3,4;5,6-Di-O-isopropylidene-1-O-(2-propylpentanoyl)-D-mannitol blocked the PDS in a way which is different from the known effects of VPA. These substances are interpreted not to exert their effects after being metabolized to VPA and thus they are thought to be new antiepileptic substances.

Amides↗
PubMed2001

Storage time and deodorization temperature influence the formation of aniline-derived compounds in denatured rapeseed oils.

In 1981 an epidemic, named Toxic Oil Syndrome, occurred in Spain as a result of ingestion of rapeseed oil denatured with 2% aniline, which had been imported for industrial use but was fraudulently diverted and processed for human consumption. Two groups of chemical compounds have been identified in the ingested toxic oil: fatty acid anilides and amino-propanediol derivatives. The objective of this work was to assess the effect of several refining process variables on the formation of 3-(N-phenylamino)-1,2-propanediol (PAP) esters. The amount of PAP esters in aniline-denatured oil increased dramatically when oil was heated from 250 degrees C to 300 degrees C. However, the ones formed when 300 degrees C was reached were lost during processing at that temperature. The level maintained during the operation time at 300 degrees C was higher in denatured samples stored for 3 weeks before refining than in denatured samples stored only for 1 week. Anilides were also analyzed. We found that anilides decreased very little with distillation time. In this paper we discuss the influence of storage time prior to refining and of elevated refining temperature, such as temperatures that might occur in close proximity to a deodorizer coil.

Aniline Compounds↗
PubMed2003

Efficient synthesis of glyceroyl beta-lactoside and its derivatives through a condensation reaction by cellulase.

Condensation reaction between lactose and glycerol was effectively catalyzed by utilizing a commercially available cellulase preparation from Trichoderma reesei. The enzyme induced the formation of 1-O-beta-lactosyl-(R,S)-glycerol (1) and 2-O-beta-lactosyl glycerol (2) in a molar ratio of 7:3 and in a 20% yield based on lactose added. The enzyme also induced the condensation of lactose with 1,3-propanediol to produce O-beta-lactosyl propanediol (3) in a yield of 15%. When various alkanols (N: 2-8) and allyl alcohol were used in the condensation reaction, the corresponding alkyl and allyl beta-lactoside were obtained in the yields of 0.9-3.8% of the desired compounds.

Cellulase↗