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Query: CAS:3349-08-4 (propionic acid)
 6,283 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The dependence of the ionic forms of haematoporphyrin(LX) dihydrochloride (HpdiCl) on solvent composition was investigated. In 2.8 x 10(-4) M solutions of HpdiCl in apolar (C6H6) and polar (CH3CN) solvents, HpdiCl exists in dicationic form. In hydrogen-bonding solvents, such as CH3OH, HpdiCl can exist in neutral, monocationic and dicationic forms. In C6H6-CH3OH solvent mixtures, the ionic forms in which HpdiCl is present depend on the composition of the solvent and on the acidity of the solution. The rate of oxidative photodegradation of HpdiCl excitation in its Q bands (WBI) and the ability to produce free radicals are different for the different ionic species. The highest values correspond to the dicationic form of HpdiCl and the lowest values correspond to the neutral species. In the absence of oxygen, the formation of free radicals due to the reaction of 3(Hp dication) is detected in the following solvent mixtures: CH3OH-toluene, CH3OH-ethylbenzene, CH3OH-hexane. The data obtained indicate that interaction of 3(Hp dication) with methine groups is an intermediate step in the formation of free radicals. In the HpdiCl concentration range studied, the presence of a phenolic antioxidant, such as beta-naphtol, inhibits the oxidative photodegradation of the dicationic form in a treated solution, but has little effect on the oxidative photobleaching of the monocation. The rate of oxidative photodegradation of the monocationic form increases with the addition of propionic acid to the solution.
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PMID:Solvents effects in the photodegradation and reactivity of the various ionic forms of haematoporphyrin. 195 42

The effects were studied of sodium monensinate dosed 125 mg on the metabolic profile of rumen fluid. The experiment was conducted under current farming conditions in a pavilion cattle fattening house. The experiment, which lasted 367 days, comprised 985 bulls of the Bohemian Spotted breed. The feed ration was based on silage with an additive of dried poultry litter and concentrates. The additive was administered in concentrate mixture, 125 mg per head/day. After the start of the experiment want of appetite to sodium monensinate was observed. The animals took approximately four weeks to adapt completely to the additive. The following characteristics were investigated to study the metabolic profile of rumen fluid: actual acidity, total titration acidity, ammonia, total nitrogen, lactic acid, total volatile fatty acids, per cent acetic acid, per cent propionic acid, molar ratio acetic acid: propionic acid, per cent iso- and n-butyric acid, absolute number of infusoria and energy net yield of volatile fatty acids. Increased levels of the clinico-biochemical parameters of the metabolic profile of rumen fluid were found in lactic acid, propionic acid and energy net yield of volatile fatty acids. The per cent of propionic acid increased at some samplings by up to 116%. A drop was recorded in total nitrogen, per cent acetic acid, per cent butyric acid, molar ratio C2 : C3 and total number of infusoria. The decrease in the per cent of acetic acid ranged around 16% and the drop in butyric acid level amounted at some samplings up to 78%. No response to the additive was observed in the other characteristics of the metabolic profile of rumen fluid.
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PMID:[The effect of Rumensin on the metabolic profile of rumen fluid in feedlot cattle]. 677 40

Biliverdin and bilirubin are naturally-occurring tetrapyrrolic bile pigments containing two propionic acid side chains. These side chains, and their propensity for ionization, are critical in the biological disposition of the pigments. Surprisingly, accurate dissociation constants for the propionic acid groups of biliverdin are unknown, and a wide range of values, extending over some 4 orders of magnitude, has been suggested for the Ka values of the propionic acid groups of bilirubin in aqueous solutions. Recently, pKa values of 6.7-9.3 have been reported for bilirubin--values much greater than the value of approximately 5 typical of propionic acid groups. These curiously high values, currently being used to explain the biological transport and metabolism of bilirubin and related compounds, have been attributed to intramolecular hydrogen bonding. We have determined the pKa values of 99% 13C-enriched (13CO2H) [8(3),12(3)-13C2]mesobilirubin-XIII, alpha, the corresponding biliverdin, and several monopropionic model compounds by 13C NMR spectroscopy. This technique allows direct observation and quantitative measurement of the carboxylic acid and carboxylate anion carbon signals. Analysis of the variation of carboxyl 13C NMR chemical shift with pH gave rubin pKa values of 4.2 and 4.9 and verdin pKa values of 3.9 and 5.3 in aqueous buffers containing only a very small quantity (0.086 mol fraction) of dimethyl sulfoxide. When extrapolated to water, the pKa values are essentially unchanged. The data provide the first experimentally-determined pKa values for a biliverdin. They indicate that intramolecular hydrogen bonding has little effect on the acid dissociation of bilirubin and suggest that the equilibrium acidity of the bilirubin carboxylic acid groups is not abnormally high but similar to the thermodynamic acidity found in other carboxylic acids, as originally suggested by Overbeek et al. (Overbeek, J. T. G., Vink, C. L. J., and Deenstra, H. (1955) Recl. Trav. Chim. Pays-Bas 74, 81-84).
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PMID:On the acid dissociation constants of bilirubin and biliverdin. pKa values from 13C NMR spectroscopy. 857 98

Observations were carried out of actual acidity, volatile fatty acid (VFA) concentrations, enzyme activity in the rumen, total protein, urea, total lipid and glucose in the serum of conventional (CL) and gnotobiotic lambs (GL) in the period of milk nutrition. The inoculum of gnotobiotic lambs contained Streptococcus bovis, Prevoxella ruminicola, Butyrivibrio fibrisolvens and Selenomonas ruminantium at a concentration of 1.10(6) each. Throughout the observation period the pH of the rumen contents of gnotobiotic lambs ranged within 6.5-6.8 with a significant difference at an age of 7 weeks. Total VFA concentrations in the rumen contents were increased in the CL throughout milk nutrition: the differences at 4 and 5 weeks of age were significant. Total VFA in the conventional lambs revealed an increasing tendency between weeks 4 and 7, reaching higher levels at 7 weeks of age (57.1 mmol.l-1), whereas in the gnotobiotic animals the range (24.3-30.1 mmol.l-1) was narrow and the peak occurred at 6 weeks of age. In GL significantly increased molar proportions of acetic acid were observed whereas in CL the molar proportions of propionic acid proved to be significant increased. The molar proportions of butyric and valeric acids were increased in CL but the group differences were not significant. In GL no isoacids were found. Alpha amylase (E.C.3.2.1.1.) activity of the rumen contents was significantly increased in GL between weeks 2 and 6 of age whereas cellulase (endoglucanase E.C.3.2.1.4. and cellobiohydrolase E.C.3.2.1.91.) activity was significantly increased in 4-week-old CL. Over the whole period of milk nutrition no significant differences were observed in urease (E.C.3.5.1.5.) activity of the rumen contents in the examined groups. At 5 weeks of age significantly increased total protein levels were observed in the conventional animals with maximum levels occurring at 4 weeks of age (CL-59.5 g.l-1 GL-55.3 g.l-1). Urea levels in 6-week old conventional lambs were significantly higher than in the gnotobiotic animals (CL-6.4 mmol.l-1 vs. GL-1.9 mmol.l-1). As to glycaemia no significant group differences were recorded. In the conventional animals total lipid levels were significantly increased at 1 and 6 weeks of age with a peak occurring in the first week of life (7.5 g.l-1) whereas in the gnotobiotic lambs a significant increase was observed at 3 weeks of age, the peak being recorded in 4 week-old animals (4.3 g.l-1). Throughout the period of interest the mean daily weight gains in the conventional and gnotobiotic lambs presented 0.164 and 0.162 kg, respectively.(ABSTRACT TRUNCATED AT 400 WORDS)
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PMID:Rumen fermentation and metabolic profile in conventional and gnotobiotic lambs. 858 97

A series of (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) analogues were evaluated for activity at homo-oligomeric glutamate1-flop (Glu1-flop) receptors expressed in Xenopus oocytes, using the two-electrode voltage clamp technique. (RS)-2-Amino-3-(3-carboxy-5-methyl-4-isoxazolyl)propionic acid (ACPA) (EC50, 2.4 microM), a homologue of AMPA having a carboxyl group as the terminal acidic functionality, was five times more potent than AMPA (EC50, 12 microM) and 20 times more potent than kainate (EC50, 46 microM). (RS)-2-Amino-3(3-hydroxy-5-trifluoromethyl-4-isoxazolyl)propionic acid (Tri-F-AMPA), in which an electronegative trifluoromethyl group is substituted for the methyl group on the isoxazole ring in the AMPA structure, was three times more potent than AMPA, whereas (RS)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-5-carboxylic acid (5-HPCA), a bicyclic analogue of AMPA with highly restricted conformational flexibility was 10 times less potent than AMPA. The limiting slope of log-log plots of Glu1-flop receptor currents versus low agonist concentrations had a value of 1.7 for ACPA and kainate compared to 1.5 for Tri-F-AMPA and 1.3 for 5-HPCA and AMPA. The amplitude of responses evoked by near saturating concentrations of the agonists varied more than 7-fold. The sequence of efficacy was ACPA = kainate > Tri-F-AMPA > AMPA > 5-HPCA. Moreover, when saturating concentrations of Tri-F-AMPA and kainate were co-applied, the response was significantly greater than when each of the agonists was applied separately. The potency of the antagonist 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo(f)quinoxaline (NBQX) (estimated KB, approximately 200 nM), to block currents mediated by Glu1-flop receptors was similar for all of the agonists tested in this study. These results indicate that relatively minor changes in the molecular structure of AMPA are associated with marked effects on potency and efficacy. In particular, it is suggested that the acidity of the terminal group plays a major role in determining the degree of receptor activation in the steady state.
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PMID:Different characteristics of AMPA receptor agonists acting at AMPA receptors expressed in Xenopus oocytes. 884 Jan 34

In slices kept at 33 degrees C, N-methyl-D-aspartate (NMDA) receptor- and (+/-)-alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptor-mediated field excitatory post-synaptic potentials (EPSPs) were pharmacologically isolated in CA1. Both types of EPSPs were reversibly blocked by 3 min of hypoxia (95% N2/5% CO2); but NMDA receptor-mediated EPSPs were consistently blocked earlier and recovered later than AMPA receptor-mediated EPSPs, recorded in the same slice. This difference may be due to inactivation of NMDA receptors by hypoxia-induced acidity and/or rise in internal [Ca2+].
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PMID:In rat hippocampal slices, NMDA receptor-mediated EPSPs are more sensitive to hypoxia than AMPA receptor-mediated EPSPs. 960 74

A symmetrical difluorinated bilirubin analog, 8,12-bis(2-carboxy-2-fluoroethyl)-3,17-diethyl-2,7,13,18-tetramethyl-10H,21H,23H,24H-biline-1,19-dione (9), was synthesized from methyl 3-[2,4-dimethyl-5-(methoxycarbonyl)-1H-pyrrol-3-yl] propionate (1) in nine steps. Fluorine was introduced by reaction of an intermediate methyl 3-[1-(tert-butoxycarbonyl)-2,4-dimethyl-5-(methoxycarbonyl)-1H-pyrrol-3-yl]-2-hydroxypropionate (5), with (diethylamino)sulfur trifluoride (DAST). The fluorinated rubin exhibited the expected IR, UV-vis, and NMR spectroscopic properties, similar to those of the unfluorinated parent, mesobilirubin XIIIalpha. However, the solubility properties unexpectedly differed, with the fluorinated rubin being less soluble in organic solvents than its parent. While this phenomenon may be attributed to the much increased acidity of the carboxylic acid hydrogens in 9, it probably also arises from less effective intramolecular hydrogen bonding due to a decreased basicity of the propionic acid carbonyl groups.
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PMID:Synthesis of the First Fluorinated Bilirubin. 1167 15

Substitution of electron-withdrawing groups at the alpha-position of an aliphatic carboxylic acid can be expected to increase the acidity of the acid. Methoxy and methylthio groups are especially effective; they increase the acidity of acetic acid by approximately 1.1 pK(a) units. Bilirubin, the water-insoluble pigment of jaundice, has two propionic acids, and an alpha-methoxy or alpha-methylthio substituent in each propionic acid can be expected to lower the pK(a) similarly and thus alter its solubility properties. (A previously synthesized analogue, alpha,alpha'-difluororubin (4), is soluble in water.) Two new analogues of bilirubin, alpha,alpha'-dimethoxyrubin (1) and alpha,alpha'-bis(methylthio)rubin (2), have been synthesized, separated into diastereomers, and analyzed. The isomers are shown by NMR to adopt intramolecularly hydrogen-bonded ridge-tile-shaped conformations. Like bilirubin, both 1 and 2 are insoluble in water. Unlike bilirubin, 1 is soluble in dilute aqueous bicarbonate, but 2 is insoluble, which would not be predicted from the expectation that 1 and 2 have the same pK(a). The data hint at a much larger steric size of SCH(3) relative to OCH(3).
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PMID:Altering the Acidity and Solution Properties of Bilirubin. Methoxy and Methylthio Substituents. 1167 52

The secondary structure of bilirubin, with a ridge-tile shape and six intramolecular hydrogen bonds, is more stable than any other conformation and perhaps the most important determinant of its solubility and properties in solution and its hepatic metabolism/excretion. Uncoupling the intramolecular hydrogen bonding, increasing the acidity of the propionic acid, or even increasing its length can decrease the pigment's hydrophobicity and permit its excretion intact across the liver into bile; less intuitively obvious, so can subtle modifications at C(10), the pivotal carbon in the ridge tile.
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PMID:Structure and metabolism of natural and synthetic bilirubins. 1180 9

(1) The 2-(p-chlorophenoxy)propionic acid (CPP) modulates in a stereoselective manner the macroscopic chloride conductance (gCl), the electrical parameter sustained by the CLC-1 channel, of skeletal muscle. In order to determine the structural requirements for modulating native gCl and to identify high-affinity ligands, the effects of newly synthesised CPP analogues have been evaluated on gCl of rat EDL muscle fibres by means of the two-microelectrode current-clamp technique. (2) Each type of the following independent modification of CPP structure led to a three- to 10-fold decrease or to a complete lack of gCl-blocking activity: replacement of the electron-attractive chlorine atom of the aromatic ring, substitution of the oxygen atom of the phenoxy group, modification at the chiral centre and substitution of the carboxylic function with a phosphonate one. (3) The analogues bearing a second chlorophenoxy group on the asymmetric carbon atom showed a significant gCl-blocking activity. Similar to racemate CPP, the analogue with this group, spaced by an alkyl chain formed by three methylenic groups, blocked gCl by 45% at 100 micro M. (4) These latter derivatives were tested on heterelogously expressed CLC-1 performing inside-out patch-clamp recordings to further define how interaction between drug and channel protein could take place. Depending on the exact chemical nature of modification, these derivatives strongly blocked CLC-1 with K(D) values at -140 mV ranging from about 4 to 180 micro M. (5) In conclusion, we identified four molecular determinants pivotal for the interaction with the binding site on muscle CLC-1 channels: (a) the carboxylic group that confers the optimal acidity and the negative charge; (b) the chlorophenoxy moiety that might interact with a hydrophobic pocket; (c) the chiral centre that allows the proper spatial disposition of the molecule; (d) an additional phenoxy group that remarkably stabilises the binding by interacting with a second hydrophobic pocket.
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PMID:Structural requisites of 2-(p-chlorophenoxy)propionic acid analogues for activity on native rat skeletal muscle chloride conductance and on heterologously expressed CLC-1. 1289 Jul 4


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