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PubMed1998

Molecular Structures of Three-, Four-, and Five-Coordinate Phosphorus Compounds Containing Salicylate Ligands(1).

The new cyclic compound 2,2'-sulfurylbis(4-methyl-6-tert-butylphenyl) methyl 2-benzoate phosphite, O(2)S[(t-Bu)MeC(6)H(4)O](2)(OC(6)H(4)CO(2)Me)P (3), containing a salicylate ligand was synthesized from 2,2'-sulfurylbis(4-methyl-6-tert-butylphenyl) chlorophosphite and methyl salicylate in the presence of triethylamine in ether solution. X-ray analyses of bis(methyl salicylate-O)phenylphosphine, (OC(6)H(4)CO(2)Me)(2)PPh (1), and bis(methylsalicylato-O)phenyl(tetrachlorophenylene-1,2-dioxy)phosphorane, (O(2)C(6)Cl(4))(OC(6)H(4)CO(2)Me)(2)PPh (2), as well as that for 3 were obtained. The phosphane 1 has a pseudo trigonal bipyramidal (TBP) structure due to coordination of a carbonyl oxygen atom at an axial site. The cyclic phosphorane 2 and the phosphite 3 lack any coordination from salicylate ligands. This results in a TBP geometry and a pyramidal geometry respectively for 2 and 3. Comparisons with X-ray structures for carboxylate-containing phosphorus compounds exhibiting oxygen coordination show the formation of four- and five-membered cyclic systems. Thus, 1 appears to be the first example of formation of a six-membered ring via carbonyl oxygen coordination. Reference is made to the tyrosyl-tRNA synthetase system where it is proposed that carbonyl oxygen atom coordination is a likely occurrence in the transition state on the basis of the analysis presented in this work.

Journal Article↗
PubMed1989

Fate and effects of salicylic acid compounds in freshwater systems.

The comparative fates and effects of salicylic acid (SA) and Na salicylate in algae (Scenedesmus subspicatus, Monoraphidium minutum), in Lemna minor, and in Daphnia magna were examined. Test methods were principally based on the OECD testing guidelines with modifications in the procedures. The influence of fulvic acid (FA) on bioconcentration and on toxic effects was studied. FA addition significantly reduced the bioavailability of SA in L. minor and the algae species. SA was more toxic to Lemnaceae, algae, and daphnids than to its Na salt. Bioconcentration factors in S. subspicatus, M. minutum, and L. minor were about 10(3) in 72-96 hr. The reproducibility of D. magna was reduced by 38% at a concentration of 20 mg SA/liter.

Eukaryota↗
PubMed1981

Characterization of the inhibition of k absorption in oat roots by salicylic Acid.

The phenolic compounds salicylic acid (o-hydroxybenzoic acid) and ferulic acid (4-hydroxy-3-methoxycinnamic acid) inhibited K(+) ((86)Rb(+)) absorption in excised oat (Avena sativa L. cv. Goodfield) root tissue. Salicylic acid was the most inhibitory. The degree of inhibition was both concentration- and pH-dependent. With decreasing pH, the inhibitory effect of the phenolic increased. During the early stages of incubation, the time required to inhibit K(+) absorption was also pH- and concentration-dependent. At pH 4.0, 5x10(-4) molar salicylic acid inhibited K(+) absorption about 60% within 1 minute; whereas, at pH 6.5, this concentration affected absorption only after 10 to 15 minutes. However, at 5 x 10(-3) molar and pH 6.5, salicylic acid was inhibitory within 1 minute. The capacity of the tissue to recover following a 1-hour treatment in 5 x 10(-4) molar salicylic acid ranged from no recovery at pH 4.5 to complete recovery at pH 7.5. The absorption of salicylic acid was pH-dependent, also. As pH decreased, more of the phenolic compound was absorbed by the tissue. The increased absorption of the compound at low pH most likely contributed to apparent tissue damage at pH 4.5 and might have accounted for the lack of recovery of K(+) absorption as pH decreased.Under the proper conditions of pH and concentration, phenolic acids such as salicylic acid could significantly affect mineral absorption by plants in the field.

Journal Article↗
PubMed2006

Transvalencin Z, a new antimicrobial compound with salicylic acid residue from Nocardia transvalensis IFM 10065.

Transvalencin Z was isolated from a culture broth of Nocardia transvalensis IFM 10065, a clinical isolate from a Japanese patient with actinomycotic mycetoma. The transvalencin Z structure was determined using NMR and mass spectrometric analyses. The structure is similar to a partial structure of siderophores such as mycobactins and nocobactins, but the compound has no cytotoxic activity. Transvalencin Z shows a strong antimicrobial activity against Gram-positive bacteria, but shows no activity against Gram-negative bacteria, fungi and tumor cells.

Anti-Bacterial Agents↗
PubMedDate not supplied

Studies on the mechanism of salicylate-induced increase of insulin secretion in man.

Salicylate compounds are known to increase basal and stimulated insulin secretion in man. In our studies, infusion of lysine acetylsalicylate (72 mg/min) increased basal insulin levels and amplified insulin responses to glucose (5 g i.v.), arginine (5 g i.v.) and tolbutamide (1 g i.v.). Verapamil, an organic calcium antagonist, did not modify LAS-induced increase of basal insulin levels, but reduced the effect of LAS on glucose-induced insulin secretion. Calcitonin and somatostatin, two agents that inhibit basal and glucose-stimulated insulin secretion, inhibited the insulin response to glucose in presence of LAS infusion. The ability of salicylate compounds to augment insulin secretion might be due to multiple sites of action in the Beta-cells.

Adult↗
PubMed1989

Theophylline assay on Kodak Ektachem DTSC--performance and interference by structurally-related compounds and salicylate.

Theophylline was measured with a Kodak Ektachem DTSC using its property of uncompetitive inhibition of alkaline phosphatase. Within- and between-batch reproducibility was satisfactory. Agreement with consensus mean values on quality assessment samples was good as was agreement on patients' samples with a high performance liquid chromatography reference method and an automated fluorescence polarisation immunoassay. At therapeutic theophylline concentrations, no interference was seen with caffeine, theobromine, 1,7-dimethylxanthine, 1,3-dimethyluric acid or 3-propylxanthine. 3-methylxanthine (a theophylline metabolite) gave a positive bias but the concentrations of this metabolite found in serum are such that the clinical significance of this finding is questionable. Salicylate at concentrations which might be found during therapy for paediatric rheumatoid arthritis also gave a positive bias.

Alkaline Phosphatase↗
PubMed1989

Tolerability profile of the antiinflammatory compound imidazole salicylate: a metanalysis of safety data in 1408 patients.

In order to evaluate the incidence of side-effects (S.E.), the withdrawal rate and the type of S.E. of the new antiinflammatory agent imidazole salicylate, we performed an analysis of 33 clinical trials involving 1408 patients treated with 750 mg t.i.d. (tablets or solution) or 1000 mg b.i.d. (granulated powder), taking into account all the factors (treatment duration, pharmaceutical form, indications, etc.) that could influence the type and incidence of S.E. Slight and transient episodes of pyrosis or epigastric pain represented the great majority of S.E. The overall rate of withdrawal was 1.8%. According to the duration of therapy, the incidence of S.E. was: 2-3 days, 3.3%; 5-7 days, 5.6%; 10-14 days, 8.8%; 30 days, 10.2%. The pharmaceutical forms, the treated pathologies and the various experimental designs adopted (double-blind, open, etc.) did not influence the S.E. rate. With imidazole salicylate the overall incidence of S.E. was always lower than other NSAID's ranging from 10% to 64% of that observed with the reference drugs (other salicylates, ibuprofen, naproxen, flurbiprofen, piroxicam, diclofenac). In conclusion, this analysis showed a linear relationship between S.E. and exposure time up to 10-12 days, followed by a clear trend toward a plateau of 10% of S.E. with treatments up to 30 days. Therefore the risk-benefit ratio, particularly when compared with that of the reference drugs, seems to be very favourable.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed1997

Mechanism of helix induction by trifluoroethanol: a framework for extrapolating the helix-forming properties of peptides from trifluoroethanol/water mixtures back to water.

To establish a framework for extrapolating the helix-forming properties of peptides from TFE/H2O mixtures (TFE = 2,2, 2-trifluoroethanol) back to water, the thermal unfolding curves have been measured by circular dichroism for four repeating-sequence peptides, with chain lengths from 7 to 22 residues. The unfolding curves were measured between 0 and 50 volume percent TFE and were fitted to the modified Lifson-Roig theory. A single set of helix-coil parameters fits the results for the four peptides at each TFE concentration; only two of the basic helix-coil parameters, , the mean helix propagation parameter of residues in the sequence repeat, and DeltaH, the enthalpy change per residue on unfolding the helix, are allowed to vary with TFE molarity. The success in fitting these curves over a wide range of experimental variables shows that helix formation is basically the same in TFE/H2O mixtures as in water. Moreover, a simple model based on a linear dependence of ln and DeltaH on TFE molarity can be used to extrapolate the results from 25% TFE (approximately 4 M) back to water. The results also give curves of helix formation induced by TFE at constant temperature, and the properties of these helix induction curves explain some of the puzzling results shown by other peptides in the literature. The average helix propensity increases regularly from 0 to 25% TFE but levels off at higher TFE concentrations, which explains why the extent of helix formation levels off in this range. The change in the apparent cooperativity of thermal unfolding curves in concentrated TFE solutions results from the decrease of the enthalpy change for helix unfolding at higher TFE concentrations. The rapid decrease in the plateau values of apparent helix content with increasing temperature results mainly from the strong temperature dependence of the ellipticity of the complete helix. To determine whether the helix-stabilizing effect of TFE arises from strengthening the hydrogen bonds in the helix backbone, the strength of the hydrogen bond in a model compound, salicylic acid, has been measured in TFE/H2O mixtures from the pKa difference between salicylic acid and a similar compound which cannot form the hydrogen bond. The curve of hydrogen bond strength versus increasing TFE concentration matches both in shape and magnitude the increase in average helix propensity in TFE/H2O mixtures.

Circular Dichroism↗
PubMed1982

Inhibition of hepatic lipogenesis by salicylate.

Salicylate has been found to be an inhibitor of fatty acid synthesis in isolated rat hepatocytes. Half-maximal inhibition of fatty acid synthesis occurs at approximately 2 mM. The inhibitory effect of salicylate on fatty acid synthesis is not relieve by the addition of acetate, suggesting that salicylate inhibits the conversion of acetate into fatty acids. Acetyl-CoA carboxylase activity in homogenates of hepatocytes is not influenced by previous exposure of the intact cells to salicylate. Partially purified acetyl-CoA carboxylase, isolated and assayed in the absence of citrate, is markedly inhibited by salicylate. However, in the presence of 0.5 mM citrate, which is the concentration of this metabolite in the cytosol of the liver cell, salicylate activates the enzyme. Upon treatment of acetyl-CoA carboxylase with salicylate (in the absence or presence of citrate), followed by separation of enzyme and effector on a Sephadex G-25 column, the enzyme activity is enhanced as compared to the salicylate-free control, demonstrating that the inhibitory effect of salicylate (in the absence of citrate) is reversible, but not the stimulatory effect (in the presence of citrate). Salicylate inhibition of fatty acid synthesis by hepatocytes is not rapidly reversible; hepatocytes preincubated with salicylate followed by a wash procedure (centrifugation and resuspension) still show depressed rates of fatty acid synthesis from acetate upon further incubation. Salicylate was found to prevent pyruvate accumulation in hepatocyte suspensions observed in the absence of this compound; salicylate even induces the disappearance of pyruvate and lactate initially present in the cell suspension. This suggests that salicylate activates pyruvate and lactate consumption, which is most likely related to the well-known fact that salicylate uncouples oxidative phosphorylation. The latter action of the drug will stimulate citric acid-cycle activity. This causes an inhibition of fatty acid and cholesterol synthesis since acetyl units will be specifically channelled into the citric acid cycle and not into the lipogenic pathway. It is concluded that part of the inhibitory effect of salicylate on fatty acid biosynthesis is exerted at (a) step(s) in the conversion of acetate into fatty acids, acetyl-CoA carboxylase not being a target of this compound. In addition, salicylate prevents that pyruvate, generated by glycolysis, enters the lipogenic pathway. The latter effect of salicylate would also explain the observed inhibition of cholesterol synthesis by this compound.

Acetyl-CoA Carboxylase↗
PubMed1995

Transdermal iontophoresis and solute penetration across excised human skin.

The potential of transdermal iontophoresis to facilitate drug delivery was evaluated by studying the transport kinetics of model compounds salicylate (anion), phenylethylamine (cation), mannitol (polar neutral compound of low molecular weight), and inulin (polar neutral compound of high molecular weight) using an excised human skin model. The transport kinetics of solutes were determined across both intact and cellophane-tape-stripped dermatomed skin both in the presence and absence of applied current to probe the mechanisms of iontophoretic delivery. Iontophoresis effectively enhanced delivery of all compounds relative to passive transport. The skin is shown to be both ion selective and size selective. On the basis of results from present work and other studies, the "aqueous pathway" of iontophoretic transport is further reinforced.

Administration, Cutaneous↗
PubMed2006

Salicylate modulates oxidative stress in the rat colon: a proteomic approach.

The dietary phenolic compound, salicylic acid, decreases oxidative stress and pro-inflammatory and potentially neo-plastic prostaglandins with a concomitant increase in glutathione peroxidase activity. Salicylic acid, a dietary plant-based phenolic compound and also the main metabolite of aspirin, may contribute to the colon protective effects of plant-based diets. Oxidative stress is a characteristic of pre-cancerous and cancerous colon and inflammatory bowel diseases (IBD) that increase colon cancer risk. The mechanism(s) whereby salicylic acid modulates potentially pro-cancerous activity associated with oxidative stress is further investigated here using a proteomic approach. A rat model of oxidative stress was supplemented with salicylic acid (1 mg/kg diet, mean plasma levels 310+/-32 micromol/l). Soluble colon protein extracts were subjected to 2D PAGE. Salicylic acid modulated proteins, identified using MALDI-TOF and LC/MS/MS, are involved in protein folding, transport, redox, energy metabolism and cytoskeletal regulation. A partial least squares (PLS) analysis approach was used to assist biological interpretation of the altered protein profiles via their associations between previously published biochemical measurements of oxidative stress, prostaglandin levels and increased glutathione peroxidase activity. Early detection of altered homeostasis in colon may assist in identifying pre-pathological features preceding colon tumorigenesis and contribute to an understanding of epidemiological evidence supporting a protective effect of plant-based diets.

Animals↗
PubMed2000

Catabolic and Genetic Diversity of Degradative Bacteria from Fuel-Hydrocarbon Contaminated Aquifers.

A BSTRACTSubsurface sediments were recovered from two aquifers contaminated with petroleum hydrocarbons in order to isolate and characterize indigenous microorganisms capable of biodegrading fuel-related compounds. These sediments had been previously studied using catabolic gene probes providing putative demonstration of significant biodegradation potential. Based on 16S rDNA sequence analysis, the isolates were phylogenetically similar to common soil microorganisms, including members of the genera Pseudomonas, Ralstonia, Burkholderia, Sphingomonas, Flavobacterium, and Bacillus. A total of 26 isolates were obtained using a vapor-plate enrichment technique with the volatile aromatic hydrocarbons toluene, ethylbenzene, p-xylene, naphthalene, and JP-4 jet fuel. JP-4, toluene, and ethylbenzene served as growth substrates for more than 80% of the isolates, while less than 10% of the organisms grew on the aromatic compounds benzene and o-xylene. Subsequent assays monitoring the evolution of (14)CO(2) indicated that only seven isolates were able to completely mineralize target compounds. One isolate, designated CAFB-naph-5, was able to completely mineralize the monoaromatic compounds salicylate and toluene, as well as the polyaromatic compound naphthalene. Molecular probing of the isolates showed four isolates hybridized with DNA probes targeting genes commonly associated with hydrocarbon-degrading bacteria. The isolates also demonstrated broad ability to grow in the presence of the antimicrobial agents streptomycin, tetracycline rifampicin, carbenicillin, nalidixic acid, kanamycin, and ampicillin. The results of the study demonstrate the biochemical and biodegradative capabilities of microorganisms isolated from contaminated aquifer systems and provide closure for indirect molecular monitoring of degradative potential in contaminated environments.

Journal Article↗
PubMedDate not supplied

Salsalate intoxication and ramifications of utilizing nonspecific analytical methods in estimating quantitative blood concentrations.

In a case involving poisoning with salsalate, a salicylate analogue, the initial blood concentration of the parent drug was underestimated because of the low cross-reactivity of the immunoassay used for the analysis. This resulted in unnecessary additional clinical and laboratory evaluations to find the cause of metabolic acidosis exhibited by the patient. Additional findings led to the conclusion that parent salsalate contributed to patient toxicity. For testing purposes, all salicylate compounds should not necessarily be classified into one salicylic acid category, and there must be detailed communication between the caregiver and the laboratory regarding the specific drug history.

Adolescent↗