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Analysis of Xenobiotics and their Residues in Food, Biological and Environmental Samples by Chromatographic Techniques Coupled with Modern Detection Techniques (DAD, FLD, MS, MS/MS)

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Analytical Chemistry".

Deadline for manuscript submissions: closed (30 September 2020) | Viewed by 41312

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Prof. Dr. Tomasz Tuzimski

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Department of Physical Chemistry, Medical University of Lublin, Chodźki 4a, 20-093 Lublin, Poland
Interests: liquid chromatography with modern detection techniques; sample preparation; analysis of xenobiotics in various biological samples; analysis of ionic compounds in plant extracts; biological activity of plant extracts
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Dear Colleagues,

In their daily life, humans constantly encounter a huge amount of different substances, including xenobiotics, which are typically synthetic chemicals that are foreign to the body and/or to an ecological system. Xenobiotics can exert adverse effects on human health and increase the incidence of chronic diseases, including cancer, Parkinson’s, Alzheimer’s, multiple sclerosis, diabetes, cardiovascular, chronic kidney disease, and others. As a consequence, the development and validation of analytical methods for xenobiotics has become essential.

The choice of an appropriate extraction and analytical method for separation and final determination is closely related to the properties of the target compounds and matrices.

Common steps of sample treatment in most of the analytical methods reported for mixtures of xenobiotics and derivatives include sample pretreatment, extraction of analytes from the matrix, clean-up of the extracts to remove interferences, and concentration to achieve the desired sensitivity. Incontestable progress has been made during the past years regarding the development of techniques for the preparation of samples for analysis such as QuEChERS (Quick, Easy, Cheap, Effective, Rugged, and Safe), Solid Phase Extraction (SPE), Solid Phase Microextraction (SPME), Stir Bar Sorptive Extraction (SBSE), Hallow-Fiber Liquid Phase Microextraction (HFLPME), Dispersive Liquid–Liquid Microextraction (DLLME) or Focused Ultrasonic Solid-Liquid Extraction (FUSLE), and others.

The challenge for the analyst is to develop effective and validated analytical strategies for the analysis of hundreds of different xenobiotics on hundreds of different sample types, quickly, accurately and at acceptable cost. The most efficient approach to xenobiotic analysis involves the use of chromatographic methods. The following chromatographic methods are most frequently applied in environmental/biological samples and food analysis: high-performance liquid chromatography (HPLC), ultrahigh-performance liquid chromatography (UPLC), gas chromatography (GC) and multidimensional chromatographic techniques.

This Special Issue will present in a structured manner state-of-the-art information on the very important field of high-performance chromatographic techniques coupled with modern detection techniques, i.e., high resolution mass spectrometry (HRMS). It is a well-established fact that chromatographic techniques with high resolution mass spectrometry (HRMS) find broad application in the separation, identification, and quantification of important components such as xenobiotics (drugs and veterinary drugs, vitamins, dyes, mycotoxins, environmental bioindicators, allergens, and others).

I warmly invite our colleagues to submit their original contributions to this Special Issue in order to provide updates regarding chromatographic methods for xenobiotics analysis of food, biological and environmental samples that will be of interest to our readers.

I would be delighted if you could respond to confirm your contribution and the proposed title by 30 June 2019 to assist in planning the whole project. In the case of review articles, an additional brief (1–2 page) description of the topic including a draft index is required. This preliminary step is essential to avoid the overlapping of topics. The degree of novelty and the significance of the research will be scrutinized prior to the peer-review process.

Dr. Tomasz Tuzimski (Ph.D., Adjunct Professor)
Guest Editor

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Keywords

xenobiotics (drugs and veterinary drugs, vitamins, dyes, mycotoxins, environmental bioindicators, allergens, pesticides, and others)
extraction techniques (QuEChERS/d-SPE, SPE, SPME, SBSE, HFLPME, DLLME, FUSLE, and others)
chromatographic methods (HPLC, UPLC, GC, GC x GC, and others)
detection techniques (DAD, FLD, MS, MS/MS, and others)

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Published Papers (11 papers)

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Research

15 pages, 1484 KiB

Open AccessArticle

Determination of Endocrine Disrupting Chemicals in Water and Wastewater Samples by Liquid Chromatography-Negative Ion Electrospray Ionization-Tandem Mass Spectrometry

by Ghada Aborkhees, Renata Raina-Fulton and Ondiveerapan Thirunavokkarasu

Molecules 2020, 25(17), 3906; https://doi.org/10.3390/molecules25173906 - 27 Aug 2020

Cited by 6 | Viewed by 3213

Abstract

A liquid chromatography-negative ion electrospray ionization-tandem mass spectrometry method was developed for the simultaneous analysis of bisphenol A, 4-octylphenol, 4-nonylphenol, diethylstilbestrol, 17β-estradiol, estriol, estrone, 17α-ethinylestradiol, prednisone, and prednisolone. This method used solid-phase extraction with an elution solvent of acetonitrile to improve the stability of the analytes. To maintain the stability of analytes analyses were completed within five days. The recoveries ranged from 84 to 112% and the relative standard deviation of analysis of duplicate samples was <10%. The limits of quantitation were 1–10 ng/L. Surface water and wastewater were obtained from five wastewater treatment plants in Saskatchewan. Matrix effects were moderate to severe. Using standard addition calibration, all analytes except diethylstilbestrol and 17α-ethinyl estradiol were detected. There was a low frequency of detection of the target analytes in upstream and downstream water, indicating good removal efficiency during the wastewater treatment process. Bisphenol A and 4-nonylphenol were the only analytes detected downstream. Bisphenol A was the most frequently detected in raw wastewater (133 to 403 ng/L). Estriol was detected more often in raw wastewater than estrone or 17β-estradiol. This is the first Canadian study with the detection of prednisone and prednisolone with concentrations at 198–350 ng/L in raw wastewater at 60% of the wastewater treatment plants. Full article

(This article belongs to the Special Issue Analysis of Xenobiotics and their Residues in Food, Biological and Environmental Samples by Chromatographic Techniques Coupled with Modern Detection Techniques (DAD, FLD, MS, MS/MS))

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18 pages, 3039 KiB

Open AccessFeature PaperArticle

Comparison of Various Chromatographic Systems for Identification of Vortioxetine in Bulk Drug Substance, Human Serum, Saliva, and Urine Samples by HPLC-DAD and LC-QTOF-MS

by Anna Petruczynik, Karol Wróblewski, Krzysztof Wojtanowski, Tomasz Mroczek, Dariusz Juchnowicz, Hanna Karakuła-Juchnowicz and Tomasz Tuzimski

Molecules 2020, 25(11), 2483; https://doi.org/10.3390/molecules25112483 - 27 May 2020

Cited by 10 | Viewed by 3799

Abstract

Background: Determination of psychotropic drugs in clinical study is significant, and the establishment of methodologies for these drugs in biological matrices is essential for patients’ safety. The search for new methods for their detection is one of the most important challenges of modern scientific research. The methods for analyzing of psychotropic drugs and their metabolites in different biological samples should be based on combining a very efficient separation technique including high-performance liquid chromatography (HPLC), with a sensitive detection method and effectively sample preparation methods. Objective: Retention, peaks symmetry and system efficiency of vortioxetine on Hydro RP, Polar RP, HILIC A (with silica stationary phase), HILIC-B (with aminopropyl stationary phase), and ACE HILIC-N (with polyhydroxy stationary phase and SCX columns were investigated. Various mobile phases containing methanol or acetonitrile as organic modifiers and different additives were also applied to obtained optimal retention, peaks shape, and systems efficiency. The best chromatographic procedure was used for simultaneous analysis of vortioxetine and its metabolites in human serum, urine and saliva samples. Methods: Analysis of vortioxetine was performed in various chromatographic systems: Reversed phase (RP) systems on alkylbonded or phenyl stationary phases, hydrophilic interaction liquid chromatography (HILIC), and ion-exchange chromatography (IEC). Based on the dependence of log k vs the concentration of the organic modifier, log kw values for vortioxetine in various chromatographic systems were determined and compared with calculated log P values. Solid phase extraction (SPE) method was applied for sample pre-treatment before HPLC analysis. HPLC-QTOF-MS method was applied for confirmation of presence of vortioxetine and some its metabolites in biological samples collected from psychiatric patient. Conclusions: Differences were observed in retention parameters with a change of the applied chromatographic system. The various properties of stationary phases resulted in differences in vortioxetine retention, systems’ efficiency, and peaks’ shape. Lipophilicity parameters were also determined using different HPLC conditions. The most optimal systems were chosen for the analysis of vortioxetine in biological samples. Both serum and urine or saliva samples collected from patients treated with vortioxetine can be used for the drug determination. For the first time, vortioxetine was detected in patient’s saliva. Obtained results indicate on possibility of application of saliva samples, which collection are non-invasive and painless, for determination and therapeutic drug monitoring in patients. Full article

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15 pages, 1906 KiB

Open AccessArticle

Mimicking of Phase I Metabolism Reactions of Molindone by HLM and Photocatalytic Methods with the Use of UHPLC-MS/MS

by Maciej Gawlik, Vladimir Savic, Milos Jovanovic and Robert Skibiński

Molecules 2020, 25(6), 1367; https://doi.org/10.3390/molecules25061367 - 17 Mar 2020

Cited by 5 | Viewed by 3211

Abstract

Establishing the metabolism pathway of the drug undergoing the hepatic biotransformation pathway is one of the most important aspects in the preclinical discovery process since the presence of toxic or reactive metabolites may result in drug withdrawal from the market. In this study, we present the structural elucidation of six, not described yet, metabolites of an antipsychotic molecule: molindone. The elucidation of metabolites was supported with a novel photocatalytical approach with the use of WO₃ and WS₂ assisted photochemical reactions. An UHPLC-ESI-Q-TOF combined system was used for the registration of all obtained metabolite profiles as well as to record the high resolution fragmentation spectra of the observed transformation products. As a reference in the in vitro metabolism simulation method, the incubation with human liver microsomes was used. Chemometric comparison of the obtained profiles pointed out the use of the WO₃ approach as being more convenient in the field of drug metabolism studies. Moreover, the photocatalysis was used in the direction of the main drug metabolite synthesis in order to further isolation and characterization. Full article

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15 pages, 3511 KiB

Open AccessArticle

Comparative Study on Pharmacokinetics of Four Active Compounds in Rat Plasma after Oral Administration of Raw and Wine Processed Chuanxiong Rhizoma

by Yan Ning, Ke Pei, Gang Cao, Hao Cai, Xiao Liu, Lilong Cao, Shuosheng Zhang and Baochang Cai

Molecules 2020, 25(1), 93; https://doi.org/10.3390/molecules25010093 - 25 Dec 2019

Cited by 17 | Viewed by 2991

Abstract

In Chinese medicine, the effect of promoting blood circulation and removing stasis could be enhanced after Chuanxiong Rhizoma is processed by wine. However, the relevant mechanism remains unclear. In this manuscript, a rapid and sensitive quantification method employing ultrahigh performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was established and validated to simultaneously determine butylidenephthalide, ligustilide, senkyunolide A and ferulic acid in rat plasma after oral administration of raw Chuanxiong Rhizoma (RCR) and wine-processed Chuanxiong Rhizoma (WCR) respectively. All analytes were extracted from plasma by proteins precipitation with methanol. Chromatographic separation was carried out on a Hypersil GOLD C₁₈ column by using a gradient mobile phase system of acetonitrile and water with 0.01% formic acid, the flow rate was 0.3 mL/min. For exact mass detecting, quick switching mode was used, positive and negative ions could be detected in one injection. The pharmacokinetic profiles of four components in the two groups were evaluated and compared. The results showed that, compared to the RCR group, the V_d and AUC_0→t values of four active compounds were increased and decreased respectively in WCR group, which revealed the effect of wine processing to Chuanxiong Rhizoma: the stronger the effect, the wider the distribution. Full article

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24 pages, 8255 KiB

Open AccessArticle

Determination of Chemical Stability of Two Oral Antidiabetics, Metformin and Repaglinide in the Solid State and Solutions Using LC-UV, LC-MS, and FT-IR Methods

by Anna Gumieniczek, Anna Berecka-Rycerz, Tomasz Mroczek and Krzysztof Wojtanowski

Molecules 2019, 24(24), 4430; https://doi.org/10.3390/molecules24244430 - 4 Dec 2019

Cited by 19 | Viewed by 6306

Abstract

Firstly, metformin and repaglinide were degraded under high temperature/humidity, UV/VIS light, in different pH and oxidative conditions. Secondly, a new validated LC-UV method was examined, as to whether it validly determined these drugs in the presence of their degradation products and whether it is suitable for estimating degradation kinetics. Finally, the respective LC-MS method was used to identify the degradation products. In addition, using FT-IR method, the stability of metformin and repaglinide was scrutinized in the presence of polyvinylpyrrolidone (PVP), mannitol, magnesium stearate, and lactose. Significant degradation of metformin, following the first order kinetics, was observed in alkaline medium. In the case of repaglinide, the most significant and quickest degradation, following the first order kinetics, was observed in acidic and oxidative media (0.1 M HCl and 3% H₂O₂). Two new degradation products of metformin and nine new degradation products of repaglinide were detected and identified when the stressed samples were examined by our LC-MS method. What is more, the presence of PVP, mannitol, and magnesium stearate proved to affect the stability of metformin, while repaglinide stability was affected in the presence of PVP and magnesium stearate. Full article

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10 pages, 1331 KiB

Open AccessArticle

Analysis of the Heterogeneous Distribution of Amiloride and Propranolol in Dried Blood Spot by UHPLC-FLD and MALDI-IMS

by Beatriz Uribe, Oskar González, María Encarnación Blanco, Oihane Elena Albóniga, María Luz Alonso and Rosa María Alonso

Molecules 2019, 24(23), 4320; https://doi.org/10.3390/molecules24234320 - 26 Nov 2019

Cited by 5 | Viewed by 3447

Abstract

Dried blood spot (DBS) has lately experienced an increase in its use in bioanalysis due to its several advantages compared with traditional blood sampling methods. Nevertheless, the use of DBS with quantitative purposes is hindered by the heterogeneous distribution of some compounds in the supporting matrix and the dependence of the response on different factors, such as the hematocrit, blood volume, and sampling position. In this study the effect of those factors in the analytical response was investigated by ultra high performance liquid chromatography coupled to fluorescence detection, using amiloride and propranolol as model compounds. The results showed a heterogeneous and drug-dependent distribution of the compounds in the blood spot. While amiloride concentration was higher in the center, propranolol concentration was higher in the periphery of the spot. Besides, the influence of the hematocrit on the quantitative results was observed. MALDI mass spectrometry imaging (MALDI-IMS) has allowed study of the distribution of the two cardiovascular drugs when they were placed in the DBS card using water:methanol solutions, demonstrating that they followed a similar distribution pattern as in blood. This work has showed the potentiality of the MALDI-IMS technique to predict the distribution of the drugs in the DBS card. Full article

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12 pages, 1485 KiB

Open AccessArticle

Analysis of Multiclass Antibiotics in Lettuce by Liquid Chromatography–Tandem Mass Spectrometry to Monitor Their Plant Uptake

by Beatriz Albero, José L. Tadeo, María del Mar Delgado, Esther Miguel and Rosa Ana Pérez

Molecules 2019, 24(22), 4066; https://doi.org/10.3390/molecules24224066 - 10 Nov 2019

Cited by 14 | Viewed by 3215

Abstract

The main entry routes of antibiotics in the environment are the application of organic wastes to improve soil quality and the irrigation with recycled water. Once in the environment, antibiotics can be introduced in the food chain through their uptake by crops. This paper describes the development of an analytical method based on ultrasound-assisted extraction for the determination of seven antibiotics in lettuce. The developed method was applied to evaluate antibiotic uptake by lettuce grown in pots fertilized with composted poultry litter doped with a mixture of antibiotics to reach a final concentration of 2.5 µg/g in soil. Lettuce were harvested after 21, 36, and 55 days. Five of the seven studied antibiotics were found in all samples. The highest uptake was found for lincomycin (51 ng/g fresh weight) followed by sulfamethoxazole (44 ng/g fresh weight) and sulfamethazine (21 ng/g fresh weight) in lettuce harvested after 21 days. An important decrease of their levels was observed after 36 days, but these levels remained similar after 55 days. Although levels found in lettuce were low, the presence of antibiotics demonstrates the need for further assessing food safety risks related with the use of soil amendments or irrigation water contaminated with antibiotics. Full article

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8 pages, 872 KiB

Open AccessArticle

The Usefulness of MS³ to Confirm Poisoning on the Example of Dog Poisoning with Strychnine

by Tomasz Śniegocki, Bartosz Sell and Andrzej Posyniak

Molecules 2019, 24(20), 3765; https://doi.org/10.3390/molecules24203765 - 19 Oct 2019

Cited by 4 | Viewed by 3043

Abstract

Strychnine is an alkaloid with strong toxic properties. Poisoning results in muscular contractions and death through asphyxiation. Intentional or accidental poisonings with strychnine occur mainly in small animals, especially dogs and occasionally cats. Strychnine can be detected in the liver or stomach contents. Unfortunately, the determination of strychnine in these matrices, especially in postmortem examination, is subject to a significant matrix effect that makes it difficult to confirm the presence of the substance being determined. Therefore, we developed a new liquid chromatography method combined with mass spectrometry. One-gram homogenized samples were extracted and partitioned after adding acetonitrile and 5-mol solution of ammonium acetate. After extraction, the samples were analyzed using high-pressure liquid chromatography-MS/MS/MS. The results of validation fulfil the requirement of the confirmatory criteria according to SANTE/11945/2015 regarding apparent recoveries (98.97% to 104.0%), repeatability (2.9%–4.1%), and within-laboratory reproducibility (3.3%–4.6%). The method can be successfully applied to confirm strychnine poisoning cases. Full article

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21 pages, 5159 KiB

Open AccessArticle

A Complete Study of Farrerol Metabolites Produced In Vivo and In Vitro

by Jintuo Yin, Yinling Ma, Caijuan Liang, Hairong Wang, Yupeng Sun, Lantong Zhang and Qingzhong Jia

Molecules 2019, 24(19), 3470; https://doi.org/10.3390/molecules24193470 - 24 Sep 2019

Cited by 6 | Viewed by 3023

Abstract

Although farrerol, a characteristically bioactive constituent of Rhododendron dauricum L., exhibits extensive biological and pharmacological activities (e.g., anti-oxidant, anti-immunogenic, and anti-angiogenic) as well as a high drug development potential, its metabolism remains underexplored. Herein, we employed ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry coupled with multiple data post-processing techniques to rapidly identify farrerol metabolites produced in vivo (in rat blood, bile, urine and feces) and in vitro (in rat liver microsomes). As a result, 42 in vivo metabolites and 15 in vitro metabolites were detected, and farrerol shown to mainly undergo oxidation, reduction, (de)methylation, glucose conjugation, glucuronide conjugation, sulfate conjugation, N-acetylation and N-acetylcysteine conjugation. Thus, this work elaborates the metabolic pathways of farrerol and reveals the potential pharmacodynamics forms of farrerol. Full article

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13 pages, 1290 KiB

Open AccessArticle

Comparison of Anticancer Activity and HPLC-DAD Determination of Selected Isoquinoline Alkaloids from Thalictrum foetidum, Berberis sp. and Chelidonium majus Extracts

by Anna Petruczynik, Tomasz Tuzimski, Tomasz Plech, Justyna Misiurek, Karolina Szalast and Grażyna Szymczak

Molecules 2019, 24(19), 3417; https://doi.org/10.3390/molecules24193417 - 20 Sep 2019

Cited by 19 | Viewed by 3889

Abstract

Background: Plants are an important origin of natural substances that the raw material for various pharmaceutical and therapeutic applications due to the presence of phytochemicals, such as alkaloids. Alkaloids, which are found in different plant species, possess numerous biological activities. Some alkaloids have strong cytotoxic effects on various cancer cells. The search for new drugs to treat various cancers is one of the most important challenges of modern scientific research. Objective: This study aimed to investigate of cytotoxic activity of extracts that were obtained from Chelidonium Majus; Berberis sp.; Thalictrum foetidum containing various alkaloids on selected cancer cell lines. The aim was also the quantification of selected alkaloids in the investigated extracts by HPLC. Methods: The analysis of alkaloids contents were performed while using HPLC in reversed phase (RP) mode using Polar RP column and mobile phase containing acetonitrile, water, and ionic liquid. The cytotoxic effect of the tested plant extracts and respective alkaloids’ standards were examined while using human pharyngeal squamous carcinoma cells (FaDu), human tongue squamous carcinoma cells (SCC-25), human breast adenocarcinoma cell line (MCF-7), and human triple-negative breast adenocarcinoma cell line (MDA-MB-231). Conclusion: All of the investigated plant extracts possess cytotoxic activity against cancer cell lines: FaDu, SCC-25, MCF-7, and MDA-MB-231. The highest cytotoxic activity against FaDu and MDA-MB-231 cells was observed for Chelidonium majus root extract, while the highest cytotoxic activity against SCC-25 and MCF-7 cells was estimated for the Thalictrum foetidum root extract. There obtained significant differences in the cytotoxic activity of extracts that were obtained from the roots and herbs of Chelidonium majus and Thalictrum foetidum. Based on these results, investigated plant extracts can be recommended for further investigations of anticancer activity. Full article

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12 pages, 845 KiB

Open AccessArticle

Determination of Urinary Pterins by Capillary Electrophoresis Coupled with LED-Induced Fluorescence Detector

by Wojciech Grochocki, Magdalena Buszewska-Forajta, Szymon Macioszek and Michał J. Markuszewski

Molecules 2019, 24(6), 1166; https://doi.org/10.3390/molecules24061166 - 24 Mar 2019

Cited by 9 | Viewed by 3616

Abstract

Urinary pterins have been found as potential biomarkers in many pathophysiological conditions including inflammation, viral infections, and cancer. However, pterins determination in biological samples is difficult due to their degradation under exposure to air, light, and heat. Besides, they occur at shallow concentration levels, and thus, standard UV detectors cannot be used without additional sample preconcentration. On the other hand, ultra-sensitive laser-induced fluorescence (LIF) detection can be used since pterins exhibit native fluorescence. The main factor that limits an everyday use of LIF detectors is its high price. Here, an alternative detector, i.e., light-emitted diode induced fluorescence (LEDIF) detector, was evaluated for the determination of pterins in urine samples after capillary electrophoresis (CE) separation. An optimized method was validated in terms of linearity range, limit of detection (LOD), limit of quantification (LOQ), intra- and interday precision and accuracy, sample stability in the autosampler, and sample stability during the freezing/thawing cycle. The obtained LOD (0.1 µM) and LOQ (0.3 µM) values were three-order of magnitude lower compared to UV detector, and two orders of magnitude higher compared to previously reported house-built LIF detector. The applicability of the validated method was demonstrated in the analysis of urine samples from healthy individuals and cancer patients. Full article

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Analysis of Xenobiotics and their Residues in Food, Biological and Environmental Samples by Chromatographic Techniques Coupled with Modern Detection Techniques (DAD, FLD, MS, MS/MS)

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