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PubMed1992

Determination of salicylic acid by HPLC in plasma and saliva from children with juvenile chronic arthritis.

A high performance liquid chromatography (HPLC) method has been developed for measuring salicylic acid in the plasma and saliva of children with juvenile chronic arthritis (JCA). Samples were extracted with diethyl ether and, after drying, redissolved in methanol to be chromatographed. Quantitation of salicylic acid was performed by reverse phase HPLC on a spherisorb ODS-2 column, using methanol: water: acetic acid as mobile phase. Phenolic was monitored by absorbance at 237 nm. Linearity between the amount of mass injected and the response in the detector was determined. This method was applied to compare concentrations of salivary and plasma salicylic acid. The method also permitted the quantitation of salivary salicylate as a non-invasive, indirect method for monitoring the concentration of plasma salicylate in patients with JCA.

Adolescent↗
PubMed1987

Determination of aspirin and salicylic acid in uremic patients' plasma using reversed-phase high-performance liquid chromatography.

A simple, rapid, and sensitive method for the determination of aspirin and salicylic acid in plasma of uremic patients is reported. After extraction with hexane, aspirin (ASA) and salicylic acid (SA) were quantified by high-performance liquid chromatography (HPLC) with ultraviolet detection at 229 nm. ASA and SA concentrations and peak-height ratios were linearly related up to 20 micrograms/ml. The lower limit of sensitivity was 0.1 microgram/ml for both compounds. The average recoveries of aspirin and salicylic acid were 27 and 54%, respectively. This procedure offers better performance than do previously described methods. The sample clean-up allows quantitation of a low concentration of aspirin in uremic patients' plasma, commonly rich in interfering endogenous substances.

Aspirin↗
PubMed1995

Salicylic acid inhibits ultraviolet- and cis-platinum-induced human immunodeficiency virus expression.

Previous studies have shown that exposure of HeLa cells stably transfected with an HIV-long terminal repeat-chloramphenicol acetyltransferase (HIV-LTR-CAT) construct to many DNA-damaging agents (such as UV light) induces expression from the HIV LTR. By culturing the cells with salicylic acid we demonstrated dose-dependent repression of this UV-or cis-platinum (cis-Pt)-induced HIV expression. While salicylic acid treatment, indomethacin treatment, UV exposure, or cis-Pt treatment alone decreased viability by up to 50%, equal numbers of viable cells were used for the CAT assays. Repression was evident if salicylic acid was administered 2 h before, at the same time as, or up to 6 h after exposure to the DNA-damaging agent. The kinetics were similar for UV- and for cis-Pt-induced HIV expression, and induction was dependent on the UV dose or cis-Pt concentration added to the culture. pH changes of the media alone in the absence of salicylic acid did not affect HIV expression. Indomethacin (100 microM) did not affect UV- or cis-Pt-induced HIV expression. These results suggest a role for the prostaglandins or the cyclo-oxygenase pathway or both in HIV induction mediated by DNA-damaging agents.

Chloramphenicol O-Acetyltransferase↗
PubMed1975

[Chronic percutaneous salicylic acid poisoning].

The uncontrolled, long-term (18 months), widespread (almost 3/4 total body skin surface), application of a concentrated (10%) salicylic acid ointment in a 62 year old psoriatic female led to chronic percutaneous salicylism. Salicylic acid levels in the urine (200 mg %) and serum (223 mg %), the highest values ever recorded in this type of intoxication, contrasted with the discrete clinical picture. The acute and chronic percutaneous salicylism is discussed with a review of the literature. It is warned against the uncontrolled use of topicals containing salicylic acid.

Administration, Topical↗
PubMed1996

Experimental study of the antithrombogenic behavior of Dacron vascular grafts coated with hydrophilic acrylic copolymers bearing salicylic acid residues.

The objective of the present work was study of the behavior of active coatings of hydrophilic acrylic polymers bearing salicylic acid residues linked covalently to the macromolecular chains, after their application to woven and knitted Dacron vascular grafts. In vitro tests were carried out under dynamic flow conditions using equipment especially designed to reproduce physiologic conditions, to determine the retention of the coating using a saline solution. Ex vivo tests were carried out in an extracorporeal circuit using the dog as an animal model. The study of the deposition of platelets was followed by labeling of autologous platelets with 111In-oxine, as well as by analysis of the surfaces of the prostheses by scanning electron microscopy. An application of thin coatings of hydrophilic acrylic copolymers improves the antithrombogenicity of the vascular grafts with respect to the uncoated prosthesis. The presence of relatively small amounts of units bearing salicylic acid residues in the copolymer chains (5-20 wt %) gives good results when they are applied to woven and knitten Dacron meshes which have been quantified by analysis of the percentage of radiotracer on the surface of the vascular grafts tested in ex vivo experiments. The salicylic acid residues are released slowly to the medium by hydrolysis of the reversible covalent bonds of this compound to the acrylic macromolecular chains, which provides an additional antiaggregating effect for platelets. The polymeric coating forms a thin active film which improves the antithrombogenic properties of the surface of woven or knitted Dacron vascular grafts in ex vivo experiments.

Animals↗
PubMed1998

Coordinated expression of defense-related genes by TMV infection or salicylic acid treatment in tobacco.

To understand the coordinated functions of the different classes of defense-related genes expressed in plant disease resistance, the expression patterns of pathogenesis related (PR) protein genes and genes involved in antioxidation and the production of secondary metabolites were examined. The expression patterns of the respective defense-related genes were monitored following TMV infection or salicylic acid treatment. Northern blot analyses showed that PR genes such as PR-1, beta-1,3-glucanase and chitinase were strongly induced in tobacco leaves upon TMV infection or salicylic acid treatment. 3-Hydroxy-3-methylglutaryl CoA reductase (HMGR) and phenylalanine ammonialyase (PAL), involved in isoprenoid and phenylpropanoid biosynthesis, respectively, were mildly induced at the late stage of normal hypersensitive response (HR) or after salicylic acid treatment when compared with the PR-gene expressions. However, in acute HR, they were strongly expressed at the early stage. Interestingly, the expression of the antioxidative genes, anionic peroxidase and ascorbate peroxidase, were inversely expressed following TMV infection and salicylic acid treatment. Differential expression of 3 groups of genes involved in plant defense responses are discussed in relation to different signal transduction pathways.

Anti-Infective Agents↗
PubMed1999

S-Adenosyl-L-methionine:salicylic acid carboxyl methyltransferase, an enzyme involved in floral scent production and plant defense, represents a new class of plant methyltransferases.

S-Adenosyl-L-methionine:salicylic acid carboxyl methyltransferase (SAMT) was partially purified from petals of the annual California plant Clarkia breweri. SAMT catalyzes the formation of methylsalicylate, an important floral scent compound in C. breweri, from salicylic acid and S-adenosyl-L-methionine (SAM). The native enzyme is a dimer with a subunit molecular weight of 40.3 kDa, and it has a Km for salicylic acid of 24 microM and a Km for SAM of 9 microM. A cDNA encoding SAMT was isolated from a C. breweri cDNA library prepared from floral mRNA. The sequence of the protein encoded by SAMT cDNA shows no significant sequence similarity to any protein in the data bank whose biochemical function is known. It does show significant sequence similarity (20-40% identity) to proteins encoded by at least seven Arabidopsis thaliana genes whose sequences have recently been determined in large-scale sequencing projects. The C. breweri SAMT cDNA was expressed in E. coli and the bacterial cells synthesized a functional SAMT protein with properties nearly identical to those of the plant-purified enzyme.

Amino Acid Sequence↗
PubMedDate not supplied

[Iontophoresis of forced skin absorption of indomethacin and salicylic acid].

Cutaneous absorption of ionized substances is forced by iontophoresis. This was shown by Pratzel and Hillmeier's investigation of the permeation of salicylic acid (increasing factor 150) and Pratzel and Dittrich's experiments with indomethacin (factor 10) in pigs. In the present paper it is shown that in human volunteers iontophoretic application of indomethacin for one hour onto the skin of the back (surface 1380 cm2) increased indomethacin plasma levels after 2 hours to a maximum of 221 ng/ml, and increased urinary excretion of indomethacin from 24 micrograms (control) to 138.7 micrograms in 5 hours. Iontophoretic application of salicylic acid for one hour daily in human volunteers onto a skin area of 400 cm2 increased serum levels in five days to 690 ng/ml and urinary excretion of salicylic acid and salicyluric acid to 24 mg, as opposed to 2.5 mg by control without current. However, after 30 min iontophoresis only 4 mg is excreted in the urine. In conclusion, if the iontophoresis is practised over a long period of time on large skin areas, systemic effects can be expected.

Administration, Topical↗
PubMed1983

[Therapy of erythrosquamous dermatoses. Betamethasone dipropionate plus salicylic acid in comparison with betamethasone dipropionate solution].

Efficacy and tolerance of an alcoholic solution containing 0.64 mg betamethasone-dipropionate plus 20 mg salicylic acid (Diprosalic Solution) were compared with an alcoholic solution containing 0,64 mg betamethasone-dipropionate in a 3 week double blind study in 100 patients with psoriasis and other steroid-responsive dermatoses of dry nature, comprising scalp and other hairy and non-hairy areas of the body. This double blind study was followed by a 3 week open study in another 100 patients with similar diagnosis, using Diprosalic Solution only. Although the therapeutic results of the double blind study showed no significant differences between both treatment groups, distinct advantages of the drug containing salicylic acid could be clearly demonstrated, such as: 1. More rapid onset of action, 2. rapid clearing of scaling, pruritus and inflammation, 3. these advantages are in compliance with the fact that topically applied salicylic acid softens keratin, loosens cornified epithelium and desquamates the epidermis, making the underlying layers more accessible to the antiinflammatory steroid.

Administration, Topical↗
PubMed2006

Changes in lipid composition of Blumeria graminis f.sp. tritici conidia produced on wheat leaves treated with heptanoyl salicylic acid.

Treatment of wheat leaves with heptanoyl salicylic acid (HS) and trehalose at concentrations of 0.1 and 15 g l(-1), prior to fungal inoculation, resulted in 40% and 60% protection, respectively, against powdery mildew. The total lipid composition of Blumeria graminis f.sp. tritici (Bgt) conidia, the causal agent of wheat powdery mildew, was compared when produced on wheat leaves, respectively, untreated and treated with the two elicitors, HS and trehalose. An obvious effect was observed on lipid composition (sterol and fatty acid (FA)) of Bgt conidia produced on wheat leaves treated with HS. A total of 16 FA (C12-C24 saturated and unsaturated) as well as unusual methoxylated Fatty Acids (mFA) (3-methoxydocosanoic and 3-methoxytetracosanoic acids) were detected in the conidia. Medium chain FA were predominant in HS treated conidia (64.65%) while long chain fatty acids constituted the major compounds in untreated conidia (62%). The long chain/medium chain FA ratio decreased from 1.8 in the conidia produced on untreated leaves to 0.5 in the conidia obtained from HS treated leaves. When comparing the sterol composition of Bgt conidia produced on leaves treated with HS versus conidia obtained from untreated ones, very important changes within the two major classes can be seen. In particular, 24-methylsterols, e.g., 24-methylenecholesterol and 24-methylcholesta-7,24-dien were reduced by about 82% whereas 24-ethylsterols, e.g., 24-ethylcholesterol and 24-ethylcholesta-5,22-dienol were increased by about 85%. The 24-methylsterols/24-ethylsterols ratio was reduced by ninefold in the conidia produced from HS treated leaves.

Ascomycota↗
PubMed2003

Loss of non-host resistance of Arabidopsis NahG to Pseudomonas syringae pv. phaseolicola is due to degradation products of salicylic acid.

In plants carrying the NahG transgene, salicylate hydroxylase converts salicylic acid (SA) to catechol. Arabidopsis NahG plants are defective in non-host resistance to Pseudomonas syringae pv. phaseolicola strain 3121 (Psp), suggesting that resistance requires SA signaling. However, several mutants with defects in SA signaling, including eds1, pad4, eds5, sid2, and npr1, remain resistant to Psp, demonstrating that susceptibility of NahG plants is not due to absence of SA. SA synthesis is blocked in sid2NahG double mutants, but resistance to Psp is retained. Therefore, it must be the degradative action of NAHG on SA that causes the loss of resistance of NahG to Psp. Treatment of plants with catechol compromised Psp resistance suggesting that the effect of NahG on resistance results from catechol production. Application of catalase to NahG or catechol-treated wild-type plants partially restored resistance to Psp, suggesting that the deleterious effect of catechol results from inappropriate production of hydrogen peroxide. These results indicate that conclusions about SA requirements based solely on phenotypes of NahG plants should be re-evaluated.

Arabidopsis↗
PubMed1985

Interactions between sodium salicylate and acetyl salicylic acid evaluated using ADP induced platelet aggregation and bleeding time.

1 g acetyl salicylic acid orally significantly enhanced the initial rate of platelet aggregation induced by 1 mumol/l and 2.5 mumol/l ADP. Sodium salicylate was without effects on the platelet aggregation and specifically it did not prevent acetylsalicylic acid from inhibiting the secondary aggregation. Sodium salicylate was without effect on the bleeding time and did not inhibit the prolongation induced by acetyl salicylic acid. Our study does not lend support to the concept of an important interaction in vivo between acetyl salicylic acid and its first metabolite salicylate in man.

Adenosine Diphosphate↗
PubMed1983

Effect of salicylic acid on the activity of betamethasone-17,21-dipropionate in the treatment of erythematous squamous dermatoses.

Forty adult out-patients with erythematous squamous dermatoses of the scalp were treated in this 21-day double-blind study with an alcohol base lotion containing either 0.05% betamethasone-17,21-dipropionate, 2% salicylic acid, 0.05% betamethasone-17,21-dipropionate + 2% salicylic acid or their respective placebo. The four treatments were assigned randomly to the patients according to a 2 x 2 orthogonal factorial design. Changes in severity of redness, scaling, pruritus and size of lesions were evaluated. Since very few patients presented with excoriation and lichenification, these symptoms could not be ascertained. Results were assessed for significance by covariance analysis where initial status was used as regressor. A potentiation of the betamethasone-17,21-dipropionate activity by salicylic acid was observed for scaling. An additive effect was noted for redness and pruritus. According to the physician's global evaluation, patients treated with the combination drug showed a better evolution than those treated with placebo. The results suggest that addition of a keratolytic agent enhances the corticosteroid effect in the treatment of erythematous squamous dermatoses.

Administration, Topical↗
PubMed1993

In-vitro permeability to salicylic acid of human, rodent, and shed snake skin.

In-vitro permeability to salicylic acid of human, rodent, and shed snake skin has been examined for the purpose of selecting model membranes for human skin corresponding to different anatomic sites, since a marked regional variation is suggested among the different sites. The greatest permeability to salicylic acid was observed in the scrotum, that of the sole was negligible. The cheek, neck, and inguinal skin seemed more permeable than the breast, back, thigh, lower leg, or foot skin. Shed snake and skin of hairless rat were found to show similar permeability to human breast and thigh skin. Wistar rat and nude mouse skin showed similar permeability to human cheek, neck, and inguinal skin.

Animals↗
PubMed2006

Ab initio quantum chemical investigation of the ground and excited states of salicylic acid dimer.

The structure and stability of different forms of salicylic acid dimer have been examined by Hartree-Fock and density functional theoretic calculations using 6-31G(d,p) and 6-311++g(d,p) basis sets. Vertical excitation energies for the monomer as well as the dimer have been computed using the time-dependent density functional theory using 6-311++G(d,p) basis set. The predicted absorption maxima for the first excited singlet state of salicylic acid monomer and the dimer of the primary form are in reasonable agreement with the experimental result. There is a slight red shift (approximately 6 nm) in the absorption maximum in going from the monomer to the dimer, in accord with the experimental observation. Configuration-interaction calculations including single excitation have been carried out to map the potential-energy profile for the intra- as well as the intermolecular proton transfer in different forms of the dimer. The barrier for proton transfer in the ground state as well as the excited states makes it clear that most of the processes take place in the primary form and largely by intramolecular proton transfer.

Journal Article↗
PubMed2002

Chemiluminescence associated with the oxidative metabolism of salicylic acid in rat liver microsomes.

Rat liver microsomal suspension (1 mg protein per ml) was incubated at 37 degrees C with 5 mM salicylic acid and 0.2 mM NADPH. The amounts of thiobarbituric acid reactive substances (TBARS) and 2,5-dihydroxybenzoic acid (2,5-DHB), an oxidative metabolite of salicylic acid increased with the incubation time. Simultaneously spontaneous chemiluminescence (CL) was found to be generated there. The addition of SKF-525A, an inhibitor of cytochrome P450 (P450), to the reaction mixture inhibited the CL generation together with the inhibition of the oxidative metabolism. The anti-oxidants and singlet oxygen scavengers like N,N-diphenylphenylenediamine (DPPD) and histidine suppressed the CL generation. The addition of 1,4-diazabicyclo [2.2.2] octane (DABCO), a singlet oxygen quencher, to the reaction mixture generating CL enhanced CL transiently and then CL decreased markedly. Thus CL observed here may possibly originate from the singlet oxygen. The CL generation was suggested to be closely related with salicylic acid-induced lipid peroxidation, and to be coupled with the oxidative metabolism mediated by P450 in rat liver microsomes.

Animals↗