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PubMed1999

Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: the case of two contiguous propionate units.

[formula: see text] Using triol 1 as a representative example of natural products containing two contiguous propionate units, 13C and 1H NMR databases for the stereochemical assignment of acyclic compounds have been created. Chemical shift increments due to the presence of additional functional groups as well as solvent effects are discussed.

Databases, Factual↗
PubMed1999

Synthesis of four diastereomeric 3,5-dialkoxy-2,4-dimethylalkanals by a simple extension of the non-aldol aldol process to bis(propionates).

[formula: see text] The synthesis of all four diastereomers of bis(propionates), 3,5-dialkoxy-2,4-dimethylalkanals, by non-aldol aldol chemistry is described. The epoxy alcohols (3, 4) were converted into the mesylates (9, 11) which were cleanly rearranged to the desired 3,5-bis(oxygenated)-2,4-dimethylalkanals (10, 12) in high yield. The epoxy mesylates (13, 16) gave the desired products (14, 17) in good yield on treatment with TMSOTf and a hindered base.

Aldehydes↗
PubMed1997

Essential fatty acids in clinically stable children with propionic acidaemia.

Disturbances of fatty acid metabolism with accumulation of odd-chain fatty acids have been reported in propionic acidaemia (PA). It is not known whether the synthesis of long-chain polyunsaturated fatty acids (LCPUFA) is also affected. In five clinically stable children with PA (median age 8 years, range 3.5-9.5 years; median percentage fibroblast propionyl-CoA carboxylase activity 0.8, range 0.8-1.5), we determined the fatty acid composition of plasma phospholipids, triglycerides and sterol esters and compared the results with those of 18 age-matched healthy controls. Odd-numbered fatty acids were found in all samples of PA patients but in controls median values were zero. Percentage contributions of substrate (linoleic acid, C18:2 omega-6) and principal product (arachidonic acid, C20:4 omega-6) of omega-6 LCPUFA synthesis did not differ between patients and controls. Similarly, there were no differences between both groups in the substrate (alpha-linolenic acid, C18:3 omega-3) and principal product (docosahexaenoic acid, C22:6 omega-3) of omega-3 LCPUFA formation. We conclude that disturbances of fatty acid metabolism in clinically stable children with PA do not affect LCPUFA synthesis.

Amino Acid Metabolism, Inborn Errors↗
PubMed2002

Gas chromatographic-mass spectrometric newborn screening for propionic acidaemia by targeting methylcitrate in dried filter-paper urine samples.

Propionic acidaemia (PCCD) or deficiency of propionyl-CoA carboxylase (PCC) is one of the most common organic acidaemias. Recent studies have suggested that this disease can cause somatic or cognitive deterioration even in patients without ketosis or metabolic acidosis, or in cases with unusually late onset. This suggests that for this disease a sensitive yet practical screening procedure is required to achieve early treatment. We conducted a pilot study of gas chromatographic-mass spectrometric screening of 12,000 newborns for PCCD using eluates from dried filter-paper urine collected at 4-7 days of age. Methylcitrate (MC) was targeted for PCCD. For bulk screening, 2-hydroxyundecanoate was used as internal standard; for quantification, stable-isotope-labelled MC was used. Urease pretreatment without fractionation allowed satisfactory recovery and reproducibility of the highly polar MC. We detected an asymptomatic male infant with distinctly elevated MC: the creatinine-corrected level relative to 2-hydroxyundecanoate was 4.8 SD above the normal mean. The MC concentration calculated using the stable-isotope-labelled internal standard was 70.6 mmol/mol creatinine 14.7 SD above the normal mean of 3.70. Parallel analysis of the dried blood spot at 4 days of age by tandem MS showed only borderline elevation of propionylcarnitine. The activity of PCC in lymphocytes was 7% of control. Gene analysis revealed that a single missense mutation, TAT to TGT, resulting in Y435C in the beta chain was present in a homozygous form. Dietary treatment including carnitine supplementation decreased this infant's MC level and to date (at 13 months of age), he shows no neurological or somatic abnormalities.

Carboxy-Lyases↗
PubMed1997

Successful topical dissolution of cholesterol gallbladder stones using ethyl propionate.

Topical dissolution of cholesterol gallbladder stones using methyl tert-butyl ether (MTBE) is useful in symptomatic patients judged too ill for surgery. Previous studies showed that ethyl propionate (EP), a C5 ester, dissolves cholesterol gallstones rapidly in vitro, but differs from MTBE in being eliminated so rapidly by the liver that blood levels remain undetectable. Our aim was to test EP as a topical dissolution agent for cholesterol gallbladder stones. Five high-risk patients underwent topical dissolution of gallbladder stones by EP. In three patients, the solvent was instilled via a cholecystostomy tube placed previously to treat acute cholecystitis; in two patients, a percutaneous transhepatic catheter was placed in the gallbladder electively. Gallstone dissolution was assessed by chromatography, by gravimetry, and by catheter cholecystography. Total dissolution of gallstones was obtained in four patients after 6-10 hr of lavage; in the fifth patient, partial gallstone dissolution facilitated basketing of the stones. In two patients, cholesterol dissolution was measured and averaged 30 mg/min. Side effects were limited to one episode of transient hypotension and pain at the infusion site; no patient developed somnolence or nausea. Gallstone elimination was associated with relief of symptoms. EP is an acceptable alternative to MTBE for topical dissolution of cholesterol gallbladder stones in high-risk patients. The lower volatility and rapid hepatic extraction of EP suggest that it may be preferable to MTBE in this investigational procedure.

Aged↗
PubMed2004

Energy expenditure in patients with propionic and methylmalonic acidaemias.

Resting energy expenditure (REE) was investigated in 8 children with propionic and methylmalonic acidaemias because a lowered REE has been reported in the literature. We observed a marginally elevated REE and think that adequate caloric intake and the use of a synthetic amino acid mixture are responsible for this.

Amino Acid Metabolism, Inborn Errors↗
PubMed2025

Imidazole propionate is a driver and therapeutic target in atherosclerosis.

Atherosclerosis is the main underlying cause of cardiovascular diseases. Its prevention is based on the detection and treatment of traditional cardiovascular risk factors1. However, individuals at risk for early vascular disease often remain unidentified2. Recent research has identified new molecules in the pathophysiology of atherosclerosis3, highlighting the need for alternative disease biomarkers and therapeutic targets to improve early diagnosis and therapy efficacy. Here, we observed that imidazole propionate (ImP), produced by microorganisms, is associated with the extent of atherosclerosis in mice and in two independent human cohorts. Furthermore, ImP administration to atherosclerosis-prone mice fed with chow diet was sufficient to induce atherosclerosis without altering the lipid profile, and was linked to activation of both systemic and local innate and adaptive immunity and inflammation. Specifically, we found that ImP caused atherosclerosis through the imidazoline-1 receptor (I1R, also known as nischarin) in myeloid cells. Blocking this ImP-I1R axis inhibited the development of atherosclerosis induced by ImP or high-cholesterol diet in mice. Identification of the strong association of ImP with active atherosclerosis and the contribution of the ImP-I1R axis to disease progression opens new avenues for improving the early diagnosis and personalized therapy of atherosclerosis.

Atherosclerosis↗
PubMed2006

On the energy landscapes of 3-indole acetic acid and 3-indole propionic acid. A study of side chain flexibilities in their S(0) and S(1) electronic states.

The tandem of 3-indole acetic acid (IAA) and 3-indole propionic acid (IPA) is ideally suited for a detailed study of the intramolecular forces responsible for the conformational properties of species containing side chains. Toward this end, high resolution S(1)<-- S(0) excitation spectra of the three origin bands in IAA and the two origin bands in IPA were recorded and analyzed. Each origin is assigned to a unique conformer. A discussion of the resulting energy landscape is given.

Indoleacetic Acids↗
PubMed2005

Modified alpha-beta chimeric oligoDNA bearing a multi-conjugate of 2,2-bis(hydroxymethyl)propionic acid-anthraquinone-polyamine exhibited improved and stereo-nonspecific triplex-forming ability.

Novel alpha-beta chimeric oligonucleotides bearing a propionic acid derivative of an anthraquinone-polyamine conjugate in the "linker" region sequence-specifically formed a substantially stable alternate-stranded triplex with dsDNA almost regardless of the stereochemistry of the derivative.

Anthraquinones↗
PubMed1981

Tritiation of alpha-bungarotoxin with N-succinimidyl [2,3-3H]propionate. A useful reagent for labelling proteins.

Mono[3H]propionyl-alpha-bungarotoxin, prepared with N-succinimidyl [2,3-3H]propionate (sp. radioactivity 50 Ci/mmol) and purified to homogeneity by electrofocusing, retains its biological activity and stability. Rate constants for its binding to acetylcholine receptor were 4.4-fold lower than for unlabelled toxin; no dissociation was detectable. Analysis of enzymic digests of toxin showed 3H is located mainly of entirely in epsilon-propionyl-lysine.

Bungarotoxins↗
PubMed1996

Enzyme-to-enzyme channelling of Krebs cycle metabolic intermediates in Caco-2 cells exposed to [2-13c]propionate.

The generation of 13C-labelled lactate by colon carcinoma cells of the Caco-2 line incubated for 120 min in the presence of [2-13C]propionate (10 mM) was assessed by 13C NMR. About 10% of the total amount of 13C-labelled lactate was recovered in the cell pellet and displayed a [2-13C]lactate/[3-13C]lactate isotopomer ratio of 1.18 +/- 0.01. An even higher isotopomer ratio of 1.53 +/- 0.14 was observed in the case of 13C-labelled lactate released by the cells into the incubation medium. These findings indicate that, in the Caco-2 cells, metabolic intermediates of the Krebs cycle undergo enzyme-to-enzyme channelling in the sequence of reactions catalysed by succinyl-CoA synthetase, succinate dehydrogenase and fumarase.

Caco-2 Cells↗
PubMed1997

Perturbation of fluid reabsorption in the efferent ducts of the rat by testosterone propionate, 17beta-oestradiol 3-benzoate, flutamide and tamoxifen.

The regulation by oestradiol and testosterone of fluid reabsorption in the efferent ducts of the rat was investigated by determining the effects of administering the hormones and their antagonists. Untreated rats were compared to animals treated for 7 days with testosterone propionate (1 mg d(-1)), oestradiol benzoate (400 microg d(-1)), flutamide (10 mg d(-1)) or tamoxifen (1 mg d(-1)). Two procedures were used to measure perturbation of transepithelial fluid fluxes in vivo. The first procedure used cannulation of the proximal epididymal duct and micropuncture of the rete testis to compare the rate at which fluid enters and leaves the efferent ducts. Oestradiol administration increased (p < 0.001) the volume of fluid entering the epididymal duct from the efferent ducts (i.e. reduced reabsorption) while flutamide and tamoxifen decreased (p < 0.05) the amount of fluid entering the epididymal duct (i.e. increased fluid reabsorption). Testosterone did not have a statistically significant effect, although it produced a small increase in fluid reabsorption. There was some perturbation of the concentration of electrolytes and the osmotic pressure of the fluid leaving the efferent ducts, but as these were not large, it is suggested that the treatments had little effect on the basic mechanisms of osmotic water transport via solute-solvent coupling. The second procedure used to test the effect of the steroids involved microperfusing individual efferent ducts, and the results were consistent with those of the first study. Oestradiol decreased fluid reabsorption by the efferent ducts (p < 0.05), and testosterone (p < 0.05, lowest perfusion rate only), flutamide (p < 0.001) and tamoxifen (p < 0.01) increased reabsorption. The similar responses to flutamide and testosterone administration suggest that flutamide acted as an androgenic agonist by elevating systemic and luminal androgen. It is concluded that fluid reabsorption in the efferent ducts is perturbed by oestrogens and androgens. Although their actions have not been completely resolved, it is proposed that they are involved in a chronic regulation, with androgens stimulating and oestrogens suppressing fluid reabsorption by the ducts.

Androgen Antagonists↗
PubMed2003

Effect of dietary formic and propionic acids on salmonella pullorum shedding and mortality in layer chicks after experimental infection.

This investigation was conducted to study the effect of dietary formic acid (FA) and propionic acid (PA) mixture on inhibitory effect of Salmonella pullorum in layer chicks. Nine equal groups of 1-day-old layer chicks, in addition to positive and negative controls, were fed on day 3 of age with acid-treated feed containing mixture of both acids at concentrations, from 0.5 to 1.5%. Positive and negative controls were fed untreated feed. All groups except the negative control were challenged orally on day 3 with 104 CFU/ml/bird S. pullorum. Cloacal swabs were taken at three successive days and at 7, 14 and 21 days of challenge. After 1, 2 and 3 weeks after challenge, four chicks from each group were killed, and crop and caecal contents were examined for S. pullorum and pH. The numbers of S. pullorum re-isolation from all treated groups, 'except groups treated with mixture of 0.5% and 0.5%, 1% and 0.5% as well as 0.5% and 1% FA and PA', decreased significantly (P < 0.05) compared with the positive control. The mortality rates of all treated groups except the group treated with 0.5% FA and 0.5% PA decreased significantly (P < 0.05) compared with the positive control. The treatment significantly (P < 0.05) lowered the pH of the crop and caecal contents in all groups except the group treated with 0.5% FA and 0.5% PA compared with the control. Also, the treatment significantly (P < 0.05) lowered the pH of the crop and caecal contents in all groups after 3 weeks of treatment compared with the first and second weeks. The treatments significantly (P < 0.05) lowered the frequency of S. pullorum recovery from crop and caecal contents in six groups treated with 1.5 and 0.5, 1 and 1, 1.5 and 1, 0.5 and 1.5, 1 and 1.5, 1.5% and 1.5% FA and PA, respectively. These results indicate that addition of FA and PA mixture in a total concentration of 2% or more to the diet of newly hatched infected layer chicks significantly decreases the crop and caecal colonization by S. pullorum and significantly decreases S. pullorum faecal excretion and reduced the chick mortality rate.

Animal Feed↗
PubMed2004

Glutamate regulates Oct-2 DNA-binding activity through alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate receptors in cultured chick Bergmann glia cells.

Ionotropic glutamate receptors in cerebellar Bergmann glial cells are linked to transcriptional regulation and, by these means, are thought to play an important role in plasticity, learning and memory and in several neuropathologies. Within the CNS, the transcription factors of the POU family bind their target DNA sequences after a growth factor-dependent phosphorylation-dephosphorylation cascade. Exposure of cultured Bergmann glial cells to glutamate leads to a time- and dose-dependent increase in Oct-2 DNA-binding activity. The use of specific pharmacological tools established the involvement of Ca2+-permeable alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate receptors. Furthermore, the signaling cascade includes phosphatidyl inositol 3-kinase as well as protein kinase C activation. Interestingly, transcriptional as well as translational inhibitors abolish the glutamate effect, suggesting a transcriptional up-regulation of the oct-2 gene. These data demonstrate that Oct-2 expression is not restricted to neurons and further strengthen the notion that the glial glutamate receptors participate in the modulation of glutamatergic cerebellar neurotransmission.

Animals↗
PubMedDate not supplied

[Propionic acidemia with myelination disorders of the CNS].

Clinical course and special diagnostic procedures in a 7 1/2 weeks old dystrophic infant with propionic acidemia are described. The disorder manifested with vomiting and diarrhea within the first week of life when the child was on a cow milk formula. Parenteral nutrition with glucose and electrolytes led to improvement. When oral nutrition with a cow milk formula was implemented again, an acute deterioration with diarrhoea and vomiting occurred. Thus, a diagnosis of cow milk allergy was suggested. There was also a severe muscular hypotony. Oral nutrition with a soybean formula did not prevent further clinical deterioration. At 7 1/2 weeks of age the patient died with symptoms of cardiogenic shock. The correct diagnosis was considered too late and confirmed post mortem. Clinical symptoms in the neonatal period like vomiting, muscular hypotony and failure to thrive should alert the physician to a possible diagnosis of a hereditary organic aciduria. Gas chromatography-mass spectrometry of urinary organics acids, in the present case, established the diagnosis. On autopsy, spongy degenerations were found in CNS.

Acidosis↗
PubMed2000

Living-related liver transplantation for neonatal-onset propionic acidemia.

We report a child with neonatal-onset propionic acidemia treated with living-related liver transplantation. Despite minimal improvement in the levels of circulating propionyl CoA metabolites, hyperammonemia was corrected, and no episode of metabolic decompensation was experienced after the transplantation was performed. Natural protein intake could be increased from 0.5 g/kg per day to 2 g/kg per day. Anemia was corrected, and the growth rate and mental development improved significantly.

Carboxy-Lyases↗