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At least 1,333 records · Page 74Linked to original sources
PubMed2004

Solid-phase synthesis of a small library of 3-phenylthio-3-nicotinyl propionic acid derivatives acting as antagonists of the integrin alphaVbeta3.

We describe the synthesis of a series of low molecular weight inhibitors of the alphavbeta3 integrin obtained by modifying a high-throughput screening hit with micromolar activity. A solid phase synthesis to prepare 3-phenylthio-3-nicotinyl propionic acid derivatives, exemplified by 13c, was set up. Compounds with nanomolar activity in the biochemical assay and able to efficiently inhibit cell adhesion mediated by vitronectin have been obtained.

Cell Adhesion↗
PubMed2004

Novel anthraquinone conjugate of 2,2-bis(hydroxymethyl)propionic acid incorporated to a TFO with phosphodiester linkage facilitates triplex formation with dsDNA bearing a pyrimidine-gapped polypurine sequence.

An anthraquinone derivative conjugated with 2,2-bis(hydroxymethyl)propionic acid as a novel non-nucleosidic component was synthesized and successfully incorporated into an internal region of 14-mer triplex-forming oligonucleotide (TFO) via the phosphoramidite method. The resulted novel TFO exhibits remarkable enhancement effect on the thermal stability of a DNA triplex upon binding to a pyrimidine-gap containing polyprurine sequence.

Anthraquinones↗
PubMed2005

Non-peptidic alpha(v)beta3 antagonists containing indol-1-yl propionic acids.

We describe the synthesis and structure/activity relationship of RGD mimetics that are potent inhibitors of the integrin alpha(v)beta3. Indol-1-yl propionic acids containing a variety of basic moieties at the 5-position, as well as substitutions alpha and beta to the carboxy terminus were synthesized and evaluated. Novel compounds with improved potency have been identified.

Indoles↗
PubMed2006

3-[6-(2-Dimethylamino-1-imidazol-1-yl-butyl)-naphthalen-2-yloxy]-2,2-dimethyl-propionic acid as a highly potent and selective retinoic acid metabolic blocking agent.

3-[6-(2-Dimethylamino-1-imidazol-1-yl-butyl)-naphthalen-2-yloxy]-2,2-dimethyl-propionic acid and analogs were designed and synthesized as highly potent and selective CYP26 inhibitors, serving as retinoic acid metabolic blocking agents (RAMBAs), with demonstrated in vivo efficacy to increase the half-life of exogenous atRA.

Chromatography, High Pressure Liquid↗
PubMed2006

Effect of initial pH control on enhanced biological phosphorus removal from wastewater containing acetic and propionic acids.

In the literature most of the studies on the effect of pH on enhanced biological phosphorous removal were conducted with the acetate wastewater, and the pH was controlled during the entire anaerobic and aerobic stages. This paper investigated the influence of anaerobic initial pH control, which will be more practical than the entire process pH control strategy, on enhanced biological phosphorus removal from wastewater containing acetic and propionic acids. Typical pH profile showed that both the initial alkaline and acidic pH tended to neutralize due to the consumption of short-chain fatty acid (SCFA) and intracellular pH regulation by polyphosphate accumulating organisms (PAOs). It was observed that the glycogen degradation and polyhydroxyalkanoates (PHA) accumulation decreased with increasing initial pH, which disagreed with previous reports. In the literature the metabolisms of both glycogen and PHA by PAOs in the acetate wastewater were independent of pH. An anaerobic mechanism model was proposed to explain the intra- and extra-cellular pH buffer nature of PAOs, and to address the reasons for increased polyphosphate degradation and decreased PHA synthesis and glycogen degradation at higher pH. The optimal initial pH for higher soluble ortho-phosphorus (SOP) removal efficiency should be controlled between 6.4 and 7.2. This pH control strategy will be easier to use in practice of wastewater treatment plant.

Acetates↗
PubMed2004

Molar mass distribution of a commercial aliphatic hyperbranched polyester based on 2,2-bis(methylol)propionic acid.

The determination of absolute molar mass averages (MMA) and molar mass distribution (MMD) of the fourth generation hyperbranched polyester Boltorn H40 (Perstorp Specialty Chemicals AB), synthesized from 2,2-bis(methylol)propionic acid (bis-MPA) as the AB2 monomer and ethoxylated pentaerythritol as the B4 core molecule was studied in dependence on the type of solvent, preparation procedure and solution concentration. Due to a large number of polar hydroxyl groups, ester, and also some residual carboxyl groups, a very stable H-bond network is formed at room temperature, that can-not be completely disrupted by dissolving the sample in solvents such as tetrahydrofuran (THF), N,N-dimethylacetamide (DMAc), a mixture of THF and methanol (9:1, v/v), and a solution of 0.7% LiBr in DMAc. The H-bonds between the polar groups break down completely and the dissolution of Boltorn H40 on the molecular level is achieved only when the sample is thermally pretreated at a minimum 140 C for at least 20 min prior to dissolution in solvents THF/methanol or LiBr/DMAc. Thus, determined MMA and molar mass distribution (MMD) of Boltorn H40 are independent on the kind of the solvent and solution concentration.

Acetamides↗
PubMed2006

Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid.

To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of Metamasius hemipterus, was resolved using (S)-MalphaNP acid. As a chiral-resolving agent, MalphaNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MalphaNP esters was observed when n-hexane-THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MalphaNP esters gave (R)-2-methyl-4-heptanol and its enantiomer; enantiopure (S)-MalphaNP acid was also recovered. In addition, the preferred conformation of the MalphaNP ester was confirmed using methyl (R)-3-hydroxyvalerate as an authentic compound.

Animals↗
PubMed2006

Structural determination of dihydro- and tetrahydrogeranylgeranyl groups at the 17-propionate of bacteriochlorophylls-a.

In the final stage of bacteriochlorophyll (BChl) biosynthesis, the presence of BChl-a molecules possessing dihydrogeranylgeranyl and tetrahydrogeranylgeranyl groups at the 17-propionate has been reported. However, the molecular structures of such BChls-a have not yet been determined in terms of the positions of CC double bonds in the 17(2)-ester. In this study, we isolated significant amounts of such pure BChls-a from Rhodopseudomonas palustris and determined their structures by both mass spectrometry and (1)H and (13)C NMR spectroscopy. The determined structures enable us to discuss a stepwise reduction from a geranylgeranyl to phytyl substituent.

Bacteriochlorophyll A↗
PubMed2005

N-terminal isotope tagging with propionic anhydride: proteomic analysis of myogenic differentiation of C2C12 cells.

N-Terminal isotope tagging (NIT) is an important proteomic tool for quantifying proteins in complex mixtures. Here we describe a modified version of the isotope-coded propionylation procedure of Zhang et al. [Zhang et al., Rapid Commun. Mass Spectom. 16 (2002) 2325], which uses 'light' D0 and 'heavy' D10-propionic anhydride. The method has been extensively modified to improve both the kinetics and overall yield of propionylation. Using albumin as a model protein, the overall variation in quantification yields, calculated using several tryptic peptides, was within +/-10% (S.D. +/-0.2) error. The efficacy of the method is demonstrated by the quantitative differences obtained for vimentin in cell lysates of C2C12 myoblasts upon their myogensis to myotubules.

Amino Acid Sequence↗
PubMed2005

HPLC method development for testosterone propionate and cipionate in oil-based injectables.

Two isocratic liquid chromatographic methods for the determination of testosterone propionate (TP) and cipionate (TC) in oil-based injectables using methyltestosterone and bolasterone as internal standards, respectively, have been developed and validated. Mobile phases 57% water:acetonitrile 43% (v:v) and 54% water:acetonitrile 46% (v:v) were used for TP and TC, respectively. For both methods, a bonded-silica Luna CN (250 mm x 4.6 mm i.d., 5 microm) (25 degrees C) column, a flow-rate 1 ml min(-1) and UV absorbance detection at 245 nm were used and two separations up to base line were achieved. Prior to HPLC analysis, sample preparation was required, including extraction of TP and TC from oil-based injectables using the surfactant sodium dodecyl sulphate.

Chromatography, High Pressure Liquid↗
PubMed2004

The importance of gut motility in the metabolic control of propionic acidemia.

We hypothesized that gut motility likely plays a critical role in the metabolic stability in propionic acidemia (PA). Therefore, 4 known patients with PA (aged 47 months to 185 months) were prospectively studied over 7 days in the Clinical Research Center at Children's Hospital, Boston. Determinations of ammonia, bicarbonate, and amino acids in blood; organic acids and propionylglycine in urine; and a lactulose breath test were conducted under two study conditions: on regular therapy (for 4 days) and on regular therapy plus Senekot (Purdue Frederick Company, Norwalk, Conn), an intestinal motility agent (for 3 days). The total gastrointestinal transit time was calculated using 20 nonabsorbable, inert, radio-opaque markers. The addition of an intestinal motility agent resulted in a significant decrease in blood ammonia, urinary excretion of propionylglycine, and a rise in the ratio of free to total carnitine over baseline. We concluded that enhancement of gut motility can improve metabolic stability in patients with PA.

Adolescent↗
PubMed2005

Effects of Na+-Ca2+ exchanger activity on the alpha-amino-3-hydroxy-5-methyl-4-isoxazolone-propionate-induced Ca2+ influx in cerebellar Purkinje neurons.

Variations in intracellular calcium activity ([Ca2+]i) play crucial roles in information processing in Purkinje neurons such as synaptic plasticity. Although Na+-Ca2+ exchanger (NCX) has been shown to participate in the regulation of homeostasis and secretion in neuronal cells, the physiological role of NCX in Purkinje neurons, such as a role in cerebellar synaptic plasticity, is not well understood. NCX in acutely dissociated rat Purkinje neurons was identified by double staining with anti-calbindin D-28k antibody and anti-NCX antibody. The physiological activity of NCX was examined by measuring transient intracellular Ca2+ changes resulting from the Ca2+ influx via reverse mode of NCX (with 0 mM Na+/2.5 mM Ca2+ solutions) and the efflux via the forward mode of NCX (with 140 mM Na+/0 mM Ca2+ solutions). This transient increase in Ca2+ concentration was not elicited in the cells pretreated with NCX antisense oligodeoxynucleotides. And the Ca2+ influx resulting from the reverse mode of NCX was significantly reduced by 2-[2-[4-(4-nitrobenyloxy) phenyl] ethyl] isothiourea methanesulfonate, while the Ca2+ efflux via forward mode was inhibited by bepridil. The physiological role of NCX in synaptic function was studied by measuring Ca2+ transients induced by alpha-amino-3-hydroxy-5-methyl-4-isoxazolone-propionate (AMPA) receptor activation. This AMPA-evoked response was decreased with the inhibition of NCX forward mode and also, to less degree, with the inhibition of reverse mode. In antisense oligodeoxynucleotides pretreated cells, the AMPA-evoked response was also reduced, as was the case in NCX-inhibitor treated cells. The inhibition of NCX activity had depressant effects on Ca2+ transients induced by AMPA receptor activation. These results suggest that NCX plays a physiological role in modulating the activity of cerebellar Purkinje neurons, such as synaptic plasticity, via interaction with AMPA receptors in Purkinje neurons.

Agatoxins↗
PubMed2005

Comparative study of the H-bond and FTIR spectra between 2,2-hydroxymethyl propionic acid and 2,2-hydroxymethyl butanoic acid.

In the present paper, the FTIR band and H-bond differences between the two dihydroxy-based carboxyls, 2,2-hydroxymethyl butanoic acid (hereinafter abbreviated to DMBA) and 2,2-hydroxymethyl propionic acid (hereinafter abbreviated to DMPA), were analyzed based on the crystal structure as well as the relation between H-bond and FTIR band of DMPA. In addition, the energy and length of the H-bonds formed between COOH, between OH, between COOH and OH were also calculated via molecular modeling. The results showed that three H-bond types existing in DMPA while only two in DMBA. The COOH pattern and H-bond type in DMBA and DMPA can be preliminarily judged according to the band position and relative strength of the nuOH and nuCOOH in FTIR spectrum. The H atom in COOH is a stronger H-bond donor than that in primary OH, while the O atom in primary OH is a stronger H-bond acceptor than that in COOH. The H-bond formed by two COOH is, therefore, weaker than that formed by COOH (as donor) and OH (as acceptor), which makes nuC=O shift to lower frequency in DMPA than in DMBA.

Butyrates↗
PubMedDate not supplied

Improved growth and nutrition status in children with methylmalonic or propionic acidemia fed an elemental medical food.

BACKGROUND: Failure-to-thrive (FTT) has been described in patients with organic acidemias treated with low protein diets. OBJECTIVE: To determine if patients with methylmalonic (MMA) or propionic acidemia (PA) can achieve normal growth and nutrition status. METHODS: A 6-month multicenter outpatient study was conducted with infants and toddlers treated with Propimex-1 Amino Acid-Modified Medical Food With Iron (Ross Products Division, Abbott Laboratories, Columbus, OH). Main outcome measures were anthropometrics, protein status indices, plasma retinol, and alpha-tocopherol. RESULTS: Sixteen patients completed the study. Mean baseline age was 0.54 +/- 0.02 years (range 0.03-3.00 years). By study end, mean National Center for Health Statistics (NCHS) weight centile increased from 26 to 49%; mean crown-heel length centile from 25 to 33%; and mean head circumference centile from 43 to 54%. Mean (+/- SE) protein and energy intakes by <6-month-old, 6<12-month-old, and 1<4-year-old patients were 15.3 +/- 0.9 g and 645 +/- 10 kcal; 18.3 +/- 1.1 g and 741 +/- 92 kcal; and 25.1 +/- 2.46 g and 1062 +/- 100 kcal, respectively. Plasma glycine concentrations were significantly and negatively correlated with energy intake (r=-0.77, p<0.0005). No correlation was found between dietary protein intakes and plasma ammonia concentrations. Protein status indices, retinol and alpha-tocopherol concentrations were within reference ranges at study end. CONCLUSIONS: Propimex-1 improved growth and nutrition status in patients with MMA or PA in just 6 months when fed in sufficient amounts. Providing energy and protein for patients with FTT at intakes recommended for catch-up growth may have resulted in even better growth.

Amino Acids↗
PubMedDate not supplied

Propionic acidemia: mutation update and functional and structural effects of the variant alleles.

Mutations in the PCCA or PCCB genes, encoding both subunits of propionyl-CoA carboxylase, result in propionic acidemia, a life-threatening inborn error of metabolism with autosomal recessive inheritance. To date, 41 mutations in the PCCA gene and 54 in the PCCB gene have been reported, most of them single base substitutions causing amino acid replacements, and a variety of small insertions and deletions and splicing defects. A greater heterogeneity is observed in the PCCA gene, specially in Caucasians, with no prevalent mutations, while in the Japanese population three mutations account for more than half of the alleles studied. For the PCCB gene a limited number of mutations is responsible for the majority of the alleles characterized in both Caucasian and Oriental populations. These two populations show a different mutational spectrum, only sharing some involving CpG dinucleotides probably as recurrent mutational events. Functional characterization of the mutant missense alleles has been accomplished using different prokaryotic and eukaryotic systems, and the structural consequences have been analyzed in the available crystal models. For the PCCA gene, the main molecular effect of the expressed mutations is related to protein instability, except two mutations in the active site predictably affecting ATP binding. In the PCCB gene the majority of the analyzed mutations are predicted to alter the active site conformation resulting in diminished activity. A few carboxy-terminal PCCB mutations affect the interaction between subunits and the assembly with PCCA to form a functional PCC oligomer. The amount of normal transcripts resulting from some PCCA and PCCB splicing mutations has also been analyzed. Overall, the data generated from the expression analysis reveal potential genotype-phenotype correlations for this clinically heterogeneous disorder.

Alleles↗
PubMed2001

A comparison of short-term treatment with inhaled fluticasone propionate and zafirlukast for patients with persistent asthma.

PURPOSE: To compare the short-term efficacy and safety of low-dose fluticasone propionate with that of oral zafirlukast therapy for patients previously treated with beta-2-agonists alone, and to evaluate the potential therapeutic benefit of switching from zafirlukast to a low-dose inhaled corticosteroid. SUBJECTS AND METHODS: This study consisted of a 4-week randomized, double-blind treatment period followed by a 4-week open-label period. Two hundred ninety-four patients > or =12 years old with asthma previously uncontrolled with beta-2-agonists alone were randomly assigned to treatment with low-dose inhaled fluticasone (88 microg twice daily) or oral zafirlukast (20 mg twice daily). After 4 weeks, all patients discontinued their double-blind therapy and received open-label fluticasone (88 microg twice daily). Outcomes included pulmonary function, asthma symptoms, albuterol use, asthma exacerbations, and adverse events. RESULTS: During the double-blind treatment period, fluticasone patients had significantly greater improvements in morning peak flow (29.3 L/min vs. 18.3 L/min), percentage of symptom-free days (19.8% vs. 11.6%), and daily albuterol use (-1.8 puffs per day vs. -1.1 puffs per day) compared with zafirlukast patients (P < or =0.025, each comparison). During the open-label treatment period, patients switched from zafirlukast to fluticasone experienced additional improvements in morning peak flow (17.2 L/min), evening peak flow (13.6 L/min), and FEV(1) (0.11 liter) and daily albuterol use (-0.9 puffs daily) compared with values obtained at the end of the double-blind treatment period (P < or =0.001, each comparison). CONCLUSION: Low-dose fluticasone was more effective than zafirlukast in improving pulmonary function and symptoms in patients with persistent asthma. In addition, switching patients from zafirlukast to fluticasone further improved clinical outcomes.

Administration, Inhalation↗
PubMed1998

Useful 1O2 (1delta g) generator, 3-(4'-methyl-1'-naphthyl)-propionic acid, 1',4'-endoperoxide (NEPO), for dioxygenation of squalence (a skin surface lipid) in an organic solvent and bacterial killing in aqueous medium.

3-(4'-Methyl-1'-naphthyl)-propionic acid, 1',4'-endoperoxide (NEPO) provides singlet state of oxygen (1O2, 1delta g) at 37 degrees C in sodium phosphate buffer (pH 7.2), acetate buffer (pH 4.5), methanol or chloroform, through the retro-Diels-Alder reaction. The total amount of 1O2 generated by NEPO was calculated using the following equation: [1O2]= [NEPO]0[1-exp(-kt)], where [1O2], [NEPO]0 and k are the total amount of 1O2 produced during the time t, initial concentration of NEPO and the first-order reaction rate constant, respectively. When squalene was exposed to 1O2 which was generated thermolytically from NEPO, it was oxidized to three hydroperoxides, mono-, di- and tri-hydroperoxides, in amounts proportional to the dose of NEPO. The oxidizability of squalene was much more extensive compared with unsaturated phospholipids. Additionally, when wild-type E. coli and lycopene-producing mutant E. coli were exposed to NEPO-derived 1O2, there was significant loss of viability of wild-type E. coli but no significant loss of viability in lycopene-producing strain, suggesting that lycopene by scavenging 1O2 protected E. coli against 1O2 toxicity.

Anti-Bacterial Agents↗