Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

The synthesis of a library of structurally variable aromatic esters of (benzyloxycarbonylamino)(aryl)methylphosphonic acids is described by means of the Oleksyszyn reaction. The library was enlarged by the application of a Suzuki–Miayra approach and by preparation of mixed esters.

Metabolomics provides new information on the changes occurring in thyroid tumours

Metabolomics is a part of systems biology dealing with the determination of qualitative and quantitative profile of low molecular weight compounds (metabolites) present in body fluids and tissues of living organisms. Metabolic composition is strongly dependent on the state of homeostasis and any deregulation should affect it. For this reason, there is now increased interest in metabolomics as a potential tool to support cancer research. At the same time the analysis of metabolic pathways involved in the process of carcinogenesis provides the possibility of a more complete understanding of the mechanisms that are critical for tumour biology. In this study, 1H NMR measurements were performed …

Application of 1H NMR-based serum metabolomic studies for monitoring female patients with rheumatoid arthritis

AbstractRheumatoid arthritis is a chronic autoimmune-based inflammatory disease that leads to progressive joint degeneration, disability, and an increased risk of cardiovascular complications, which is the main cause of mortality in this population of patients. Although several biomarkers are routinely used in the management of rheumatoid arthritis, there is a high demand for novel biomarkers to further improve the early diagnosis of rheumatoid arthritis, stratification of patients, and the prediction of a better response to a specific therapy.In this study, the metabolomics approach was used to provide relevant biomarkers to improve diagnostic accuracy, define prognosis and predict and mon…

Follicular adenomas exhibit a unique metabolic profile. ¹H NMR studies of thyroid lesions.

Thyroid cancer is the most common endocrine malignancy. However, more than 90% of thyroid nodules are benign. It remains unclear whether thyroid carcinoma arises from preexisting benign nodules. Metabolomics can provide valuable and comprehensive information about low molecular weight compounds present in living systems and further our understanding of the biology regulating pathological processes. Herein, we applied ¹H NMR-based metabolic profiling to identify the metabolites present in aqueous tissue extracts of healthy thyroid tissue (H), non-neoplastic nodules (NN), follicular adenomas (FA) and malignant thyroid cancer (TC) as an alternative way of investigating cancer lesions. Multivar…

Differences in metabolic profiles of planktonic and biofilm cells in Staphylococcus aureus - (1)H Nuclear Magnetic Resonance search for candidate biomarkers.

Staphylococcus aureus is responsible for many types of infections related to biofilm presence. As the early diagnostics remains the best option for prevention of biofilm infections, the aim of the work presented was to search for differences in metabolite patterns of S. aureus ATCC6538 biofilm vs. free-swimming S. aureus planktonic forms. For this purpose, Nuclear Magnetic Resonance (NMR) spectroscopy was applied. Data obtained were supported by means of Scanning Electron Microscopy, quantitative cultures and X-ray computed microtomography. Metabolic trends accompanying S. aureus biofilm formation were found using Principal Component Analysis (PCA). Levels of isoleucine, alanine and 2,3-but…

Interactions of N-heteroalkylaminomethylenebisphosphonic acids with Cd(II) ions: Electrochemical and spectroscopic investigations

The aminomethylenebisphosphonates are known to be excellent chelators for many metal ions. In this work, the coordination properties of three different aminomethylenebisphosphonates with N-substituted heteroalkyl moieties (L1, L2 and L3) and their N-pyridyl derivative (L4) toward cadmium(II) ions are described. Due to their coordination abilities over a broad range of pH, the compounds of this group are good candidates for heavy metal detoxification. To determine the stability constants and the coordination mode of formed aminomethylenebisphosphonate-cadmium(II) complexes, four analytical methods were employed: potentiometry, pulse polarography (DPP), nuclear magnetic resonance spectroscopy…

Electrochemical and spectroscopic investigations of selected N -heteroalkylaminomethylenebisphosphonic acids with Pb(II) ions

Abstract The coordination properties of aminomethylenebisphosphonic acids towards various metal ions have been exploited during the last decade. These compounds are good chelators for biologically important metal ions, such as Cu(II), Fe(II), Zn(II), Ca(II), and Mg(II), as well as a toxic ion (i.e., Cd(II)). In this study, the interactions of five aminomethylenebisphosphonates with N-substituted heteroalkyl moieties (L1, L2 and L3) and their N-pyridyl (L4) and N-benzylpiperazine (L5) derivatives with Pb(II) ions were investigated. A wide range of analytical methods were employed, including potentiometry, pulse polarography (DPP), nuclear magnetic resonance (NMR) spectroscopy and electrospra…

Serum and urine 1H NMR-based metabolomics in the diagnosis of selected thyroid diseases

AbstractEarly detection of nodular thyroid diseases including thyroid cancer is still primarily based on invasive procedures such as fine-needle aspiration biopsy. Therefore, there is a strong need for development of new diagnostic methods that could provide clinically useful information regarding thyroid nodular lesions in a non-invasive way. In this study we investigated 1H NMR based metabolic profiles of paired urine and blood serum samples, that were obtained from healthy individuals and patients with nodular thyroid diseases. Estimation of predictive potential of metabolites was evaluated using chemometric methods and revealed that both urine and serum carry information sufficient to d…

Rapid determination of ibotenic acid and muscimol in human urine

1H NMR-based metabolomics studies of urine reveal differences between type 1 diabetic patients with high and low HbAc1 values

Abstract The aim of this study was to investigate relation between level of HbAc1 and concentration of metabolites in urine of T1D patients. To test this hypothesis the 1 H NMR (proton nuclear magnetic resonance) target analysis of crucial urine metabolites combined with chemometric approach were applied. Urine samples were collected from 30 children and teenagers aged 4–19 with T1D and 12 healthy children, aged 9, as control group. Patients were divided into two groups according to their level of glycated hemoglobin (HbA1c): below (L-T1D) and above 6.5% (H-T1D). The multivariate data analysis (OPLS-DA) was used to explore data and generate the models for selected groups of patients. Two ta…

Metabolomics of chronic obstructive pulmonary disease and obstructive sleep apnea syndrome : response to Maniscalco and Motta

We appreciate Maniscalco and Motta’s comments on our recently published article “Fusion of the 1H NMR data of serum, urine and exhaled breath condensate in order to discriminate chronic obstructive pulmonary disease and obstructive sleep apnea syndrome” (Zabek et al. 2015) and we are grateful for the opportunity to clarify a number of points from our work. We are glad that the authors appreciated our data analysis and interpretation. Fusion of metabolomic data is an outstanding tool for a comprehensive description of patient’s phenotype that combines metabolic profiles acquired in different domains. Such an integrative approach is highly valued in the so-called ‘breathomics’ (Smolinska et a…

Phosphorus NMR as a tool to study mineralization of organophosphonates—The ability of Spirulina spp. to degrade glyphosate

Abstract A commercially available mixed culture of Spirulina spp. exhibited a remarkable ability to degrade the widely used organophosphorus herbicide glyphosate, that served as sole source of either phosphorus or nitrogen for cyanobacterial growth. 31P NMR analysis of spent media appeared to be an effective and simple technique to follow disappearance of the phosphonate and release of inorganic phosphate in biodegradation process(es).

LC-QTOF-MS and 1H NMR Metabolomics Verifies Potential Use of Greater Omentum for Klebsiella pneumoniae Biofilm Eradication in Rats

Bacterial wound infections are a common problem associated with surgical interventions. In particular, biofilm-forming bacteria are hard to eradicate, and alternative methods of treatment based on covering wounds with vascularized flaps of tissue are being developed. The greater omentum is a complex organ covering the intestines in the abdomen, which support wound recovery following surgical procedures and exhibit natural antimicrobial activity that could improve biofilm eradication. We investigated changes in rats&rsquo

1H NMR-based metabolic profiling for evaluating poppy seed rancidity and brewing

Poppy seeds are widely used in household and commercial confectionery. The aim of this study was to demonstrate the application of metabolic profiling for industrial monitoring of the molecular changes which occur during minced poppy seed rancidity and brewing processes performed on raw seeds. Both forms of poppy seeds were obtained from a confectionery company. Proton nuclear magnetic resonance (1H NMR) was applied as the analytical method of choice together with multivariate statistical data analysis. Metabolic fingerprinting was applied as a bioprocess control tool to monitor rancidity with the trajectory of change and brewing progressions. Low molecular weight compounds were found to be…

Metabolomics of Human Amniotic Fluid and Maternal Plasma during Normal Pregnancy

Metabolic profiles of amniotic fluid and maternal blood are sources of valuable information about fetus development and can be potentially useful in diagnosis of pregnancy disorders. In this study, we applied 1H NMR-based metabolic profiling to track metabolic changes occurring in amniotic fluid (AF) and plasma (PL) of healthy mothers over the course of pregnancy. AF and PL samples were collected in the 2nd (T2) and 3rd (T3) trimester, prolonged pregnancy (PP) until time of delivery (TD). A multivariate data analysis of both biofluids reviled a metabolic switch-like transition between 2nd and 3rd trimester, which was followed by metabolic stabilization throughout the rest of pregnancy proba…

Fusion of the 1H NMR data of serum, urine and exhaled breath condensate in order to discriminate chronic obstructive pulmonary disease and obstructive sleep apnea syndrome

Chronic obstructive pulmonary disease, COPD, affects the condition of the entire human organism and causes multiple comorbidities. Pathological lung changes lead to quantitative changes in the composition of the metabolites in different body fluids. The obstructive sleep apnea syndrome, OSAS, occurs in conjunction with chronic obstructive pulmonary disease in about 10–20 % of individuals who have COPD. Both conditions share the same comorbidities and this makes differentiating them difficult. The aim of this study was to investigate whether it is possible to diagnose a patient with either COPD or the OSA syndrome using a set of selected metabolites and to determine whether the metabolites t…

Do differences in chemical composition of stem and cap of Amanita muscaria fruiting bodies correlate with topsoil type?

Fly agaric (Amanita muscaria) was investigated using a 1H NMR-based metabolomics approach. The caps and stems were studied separately, revealing different metabolic compositions. Additionally, multivariate data analyses of the fungal basidiomata and the type of soil were performed. Compared to the stems, A. muscaria caps exhibited higher concentrations of isoleucine, leucine, valine, alanine, aspartate, asparagine, threonine, lipids (mainly free fatty acids), choline, glycerophosphocholine (GPC), acetate, adenosine, uridine, 4-aminobutyrate, 6-hydroxynicotinate, quinolinate, UDP-carbohydrate and glycerol. Conversely, they exhibited lower concentrations of formate, fumarate, trehalose, α- an…

Antifungal activity of the carrot seed oil and its major sesquiterpene compounds.

Carrot seed oil is the source of the carotane sesquiterpenes carotol, daucol and β-caryophyllene. These sesquiterpenic allelochemicals were evaluated against Alternaria alternata isolated from the surface of carrot seeds cultivar Perfekcja, a variety widely distributed in horticultural practise in Poland. Alternaria alternata is one of the most popular phytotoxic fungi infesting the carrot plant. The strongest antifungal activity was observed for the main constituent of carrot seed oil, carotol, which inhibited the radial growth of fungi by 65% at the following concentration.

“Twin” phosphorous atoms of tetraethyl 2-methyl-piperyd-1-ylmethylenebisphosphonates

Recently, bisaminophosphonates found applications as therapeutic agents for curing bone disorders. When trying to relate the structures of substituted piperid-1-ylmethylenebisphosphonic with their biological properties, non-typical findings that in 31P NMR spectra of 2-methyl-piperid-1-ylmethylenebisphosphonic and 2-ethyl-piperid-1-ylmethylenebisphosphonic acids, two separate singlets from each of the phosphonic groups were observed, while their analogues bearing substituent in position 3 exhibit only one signal. Their presence was explained by freezing of the molecular motions by strong hydrogen bonding between NH and P = O atoms. In this work, synthesis as well as spectroscopic and theore…

Follicular Adenomas Exhibit a Unique Metabolic Profile. 1H NMR Studies of Thyroid Lesions

Thyroid cancer is the most common endocrine malignancy. However, more than 90% of thyroid nodules are benign. It remains unclear whether thyroid carcinoma arises from preexisting benign nodules. Metabolomics can provide valuable and comprehensive information about low molecular weight compounds present in living systems and further our understanding of the biology regulating pathological processes. Herein, we applied 1H NMR-based metabolic profiling to identify the metabolites present in aqueous tissue extracts of healthy thyroid tissue (H), non-neoplastic nodules (NN), follicular adenomas (FA) and malignant thyroid cancer (TC) as an alternative way of investigating cancer lesions. Multivar…

Metabolomics provide new insights on lung cancer staging and discrimination from chronic obstructive pulmonary disease

Chronic obstructive pulmonary disease (COPD) and lung cancer are widespread lung diseases. Cigarette smoking is a high risk factor for both the diseases. COPD may increase the risk of developing lung cancer. Thus, it is crucial to be able to distinguish between these two pathological states, especially considering the early stages of lung cancer. Novel diagnostic and monitoring tools are required to properly determine lung cancer progression because this information directly impacts the type of the treatment prescribed. In this study, serum samples collected from 22 COPD and 77 lung cancer (TNM stages I, II, III, and IV) patients were analyzed. Then, a collection of NMR metabolic fingerprin…

Studying the stability of Solvent Red 19 and 23 as excise duty components under the influence of controlled factors

Abstract In this study, we examine the chemical stability of two disazo dyes, namely Solvent Red 19 and 23 (SR 19 and SR 23), under simulated conditions. Both dyes are considered to be chemically stable under normal exploitation conditions and therefore, are used extensively as excise duty components that enable a rapid visual verification of the tax levels that were imposed on fuel products as well as identifying fuel usage. However, the results from this study confirmed that the colour of the samples that had been fortified with either SR 19 or SR 23 fades under the influence of external conditions such as UV-A irradiation and temperature over time. The UV-A irradiation was the dominant f…

Gender-Specific Metabolomics Approach to Kidney Cancer

Renal cell carcinoma (RCC) is the most common form of kidney malignancy. RCC is more common among men with a 2/1 male/female incidence ratio worldwide. Given the underlying epidemiological differences in the RCC incidence between males and females, we explored the gender specific 1H NMR serum metabolic profiles of RCC patients and their matched controls. A number of differential metabolites were shared by male and female RCC patients. These RCC specific changes included lower lactate, threonine, histidine, and choline levels together with increased levels of pyruvate, N-acetylated glycoproteins, beta-hydroxybutyrate, acetoacetate, and lysine. Additionally, serum lactate/pyruvate ratio was a…