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Recent Trend in Chromatography for Pharmaceutical Analysis
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Recent Trend in Chromatography for Pharmaceutical Analysis (Closed)

A topical collection in Chemosensors (ISSN 2227-9040). This collection belongs to the section "Analytical Methods, Instrumentation and Miniaturization".

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Editors

Dr. Cláudia Maria Rosa Ribeiro

E-Mail Website
Collection Editor
1. Associate Laboratory i4HB—Institute for Health and Bioeconomy, University Institute of Health Sciences—CESPU, 4585-116 Gandra, Portugal
2. UCIBIO—Applied Molecular Biosciences Unit, Translational Toxicology Research Laboratory, University Institute of Health Sciences (1H-TOXRUN, IUCS-CESPU), 4585-116 Gandra, Portugal
Interests: chromatography; chiral drugs; pharmaceuticals; environmental contaminants
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Maria Elizabeth Tiritan

E-Mail Website1 Website2
Collection Editor
1. Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal
2. TOXRUN–Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal
Interests: organic and pharmaceutical chemistry; chromatography; chirality; organic environmental pollutants
Special Issues, Collections and Topics in MDPI journals

Topical Collection Information

Dear colleagues,

Pharmaceuticals are synthetic or natural chemicals that can be found in prescription medicines, over-the-counter therapeutic drugs, and veterinary drugs. Nevertheless, due to their biological properties, use of off-label pharmaceuticals and their misuse is widespread (e.g., in aquaculture, agriculture, doping in sport). Therefore, the separation, detection, and quantification of pharmaceuticals is required in different areas. Further, many pharmaceuticals are chiral and, thus, enantiomeric analysis is required in many fields and for different purposes.

Chromatography is the elected methodology for routine and research laboratories for the analysis of pharmaceuticals and their metabolites using both non-enantioselective and enantioselective methods. It is among the most advanced and versatile methodology concerning equipment, stationary phases, and chromatographic elution modes allowing good selectivity/specificity, short analysis time, and beyond accurate and precise data.

A variety of chromatographic techniques coupled with different detectors have been developed for both preparation and analysis of pharmaceuticals. For example, in manufacturing processes to assess the stability of drugs and test for impurities and degradation products as well as in clinical analysis for pharmacokinetic studies or therapeutic monitoring. However, chromatographic methods for the analysis of pharmaceuticals have also been reported in other fields such as forensic toxicology and food and environmental analysis.

Therefore, this Topical Collection aims to focus on recent and innovative preparative and analytical chromatographic methods used for the analysis of pharmaceuticals in different areas covering industry, clinical and medical purposes, forensic toxicology, and food and environmental analysis.

Prof. Dr. Cláudia Maria Rosa Ribeiro
Prof. Dr. Maria Elizabeth Tiritan
Collection Editors

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Keywords

  • chromatography
  • pharmaceuticals
  • industry
  • forensic toxicology
  • food analysis
  • environment

Published Papers (11 papers)

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2023

Jump to: 2022, 2021

17 pages, 2784 KiB  
Article
Identification of Degradation Products of the New Anticancer Drug Substance ONC201 by Liquid Chromatography–High-Resolution Multistage Mass Spectrometry
by Maxime Annereau, Marina Vignes, Tahar Sif Eddine Bouchema, Lucas Denis, Audrey Solgadi, Victoire Vieillard, Muriel Paul, André Rieutord, Jacques Grill, Philippe-Henri Secretan and Bernard Do
Chemosensors 2023, 11(5), 294; https://doi.org/10.3390/chemosensors11050294 - 15 May 2023
Cited by 1 | Viewed by 2609
Abstract
ONC201 (dordaviprone) is a new drug substance used in a compassionate manner to treat patients with glioblastoma. Given the clinical context and the particularly promising preclinical results, we have been asked by the medical authorities to make a first treatment available throughout France [...] Read more.
ONC201 (dordaviprone) is a new drug substance used in a compassionate manner to treat patients with glioblastoma. Given the clinical context and the particularly promising preclinical results, we have been asked by the medical authorities to make a first treatment available throughout France as a hospital preparation to allow access to treatment and to conduct clinical trials. However, to control the quality and safety conditions inherent in this academic manufacturing process, while there is virtually no data available to date to understand the stability of ONC201, we had to determine the stability profile of ONC201, i.e., its sensitivity to different stressors and the types of impurities that could form during its degradation. We found that ONC201 was sensitive to oxidation in the presence of hydrogen peroxide or under light irradiation. Both conditions resulted in the formation of 20 degradation products detected and identified by liquid chromatography–high-resolution mass spectrometry. Their structural elucidation required an in-depth study of the fragmentation pattern of protonated ONC201, described for the first time. The product ions of the degradation products were compared to those of ONC201 protonated ion to assign the most plausible structures for all the detected degradation products. Of these degradation products, those that were rapidly produced, of high intensity and/or identified as potentially having a different toxicity profile to ONC201 by in silico studies, were selected to be monitored during batch release testing and stability studies. Full article
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13 pages, 1012 KiB  
Article
Suspect Screening and Semi-Quantification of Macrolide Antibiotics in Municipal Wastewater by High-Performance Liquid Chromatography—Precursor Ion Scan Tandem Mass Spectrometry
by Ilya S. Voronov, Danil I. Falev, Nikolay V. Ul’yanovskii and Dmitry S. Kosyakov
Chemosensors 2023, 11(1), 44; https://doi.org/10.3390/chemosensors11010044 - 3 Jan 2023
Cited by 4 | Viewed by 2262
Abstract
Macrolides are widely used in medicine and veterinary medicine, and are the leading antibiotics in terms of consumption. The release of macrolides and their metabolites into the environment through municipal wastewater can have an adverse effect on aquatic ecosystems and human health. In [...] Read more.
Macrolides are widely used in medicine and veterinary medicine, and are the leading antibiotics in terms of consumption. The release of macrolides and their metabolites into the environment through municipal wastewater can have an adverse effect on aquatic ecosystems and human health. In the present study, a method for the non-targeted screening and semi-quantitative determination of macrolide antibiotics and their derivatives in wastewater based on a combination of chromatographic separation and tandem mass spectrometric detection in precursor ion scan (PrecIS) mode has been proposed. Product ions with m/z 158 and 174 related to specific desosamine fragments were used as diagnostic ions for the PrecIS detection of the macrolide structures without (14- and 15-membered macrocycles) and with a (16-membered macrocycle) glycosylated desosamine moiety, respectively. The combination of the optimized solid phase extraction procedure and HPLC-MS/MS analysis in PrecIS mode allowed for the suspect screening of macrolides in municipal wastewater with limits of detection in the range of 4–150 ng L−1. The developed approach made it possible to detect and tentatively identify in municipal wastewater 17 compounds belonging to the macrolide class, including azithromycin, clarithromycin, josamycin and 14 metabolites with a total concentration of 1450 ng L−1. Full article
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2022

Jump to: 2023, 2021

11 pages, 6316 KiB  
Article
Fabric Phase Sorptive Extraction Combined with HPLC-UV for the Quantitation of Amphotericin B in Human Urine
by Evmorfia Asimakopoulou, Natalia Manousi, Nikoleta Anaxagorou, Abuzar Kabir, Kenneth G. Furton and Constantinos K. Zacharis
Chemosensors 2022, 10(12), 537; https://doi.org/10.3390/chemosensors10120537 - 15 Dec 2022
Cited by 2 | Viewed by 2378
Abstract
Herein, a fabric phase sorptive extraction-based scheme was reported for the determination of amphotericin B in human urine. The developed method allowed the direct extraction of the analyte from the biological matrix with improved selectivity, repeatability and recovery. Due to the membrane’s engineered [...] Read more.
Herein, a fabric phase sorptive extraction-based scheme was reported for the determination of amphotericin B in human urine. The developed method allowed the direct extraction of the analyte from the biological matrix with improved selectivity, repeatability and recovery. Due to the membrane’s engineered affinity towards the analyte, extraction equilibrium was achieved in 30 min. Moreover, no additional sample pretreatment was required due to the high permeability of the FPSE membrane and the small volume of eluting solvent required for quantitative back-extraction of the analytes. The hydrophobic sol–gel polydimethylphenylsiloxane (sol–gel PDMDPheS) coated membrane provided the optimum extraction performance. Important parameters that affect the extraction efficiency (such as sample volume, extraction time, membrane size, stirring rate, ion strength, elution solvent and time) were thoroughly investigated. The analyte was separated from the internal standard (nimesulide) and endogenous compounds of the human urine using a gradient elution program. The proposed assay was linear within the range of 0.10–10.0 μg mL−1 while the relative standard deviation of the repeatability (sr) and within-laboratory reproducibility (sR) were less than 12.7% in all cases. The method exhibited good accuracy which varied between 88.1 to 110.3%. The developed method was successfully applied for the monitoring of amphotericin B concentration in human urine. Full article
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10 pages, 1411 KiB  
Communication
A New Method for Enantiomeric Determination of 3,4-Methylenedioxymethamphetamine and p-Methoxymethamphetamine in Human Urine
by Wei-Jay Chen, Ren-Jang Wu, Hsueh-Hui Yang, Ahai-Chang Lua, Yin-Jeh Tzeng, Shun-Hsing Tuan, Liang Chen and Tsong-Yung Chou
Chemosensors 2022, 10(2), 50; https://doi.org/10.3390/chemosensors10020050 - 28 Jan 2022
Cited by 3 | Viewed by 2688
Abstract
The abuse of paramethoxymethamphetamine (PMMA) and 3,4-methylenedioxymethamphetamine (MDMA) among young people is increasingly serious and has become a public health problem. Since enantiomers of MDMA and PMMA are metabolized at different rates in the body and exhibit different neurotoxicity in tissues, we have [...] Read more.
The abuse of paramethoxymethamphetamine (PMMA) and 3,4-methylenedioxymethamphetamine (MDMA) among young people is increasingly serious and has become a public health problem. Since enantiomers of MDMA and PMMA are metabolized at different rates in the body and exhibit different neurotoxicity in tissues, we have developed a simple method for simultaneous enantiomeric determination of PMMA and MDMA, using parallel dual capillary immunoaffinity columns coupled with tandem mass spectrometry. Linear calibration curves were obtained in concentration ranges of 100–1000 ng/mL, with a limit of quantitation of <22 ng/mL. Good interday accuracy and precision were achieved with this method. Besides filtering the urine sample through a 0.45 μm MILLIPORE membrane, no other sample pretreatment was needed, and no toxic organic solvent was used. It is a rapid, environmentally friendly safe method, and could be applied for routine enantiomeric analysis of PMMA and MDMA in the pharmaceutical industry, forensic science, and environmental analysis. Full article
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2021

Jump to: 2023, 2022

19 pages, 785 KiB  
Review
A Review of the Analytical Methods for the Determination of 4(5)-Methylimidazole in Food Matrices
by Panagiota-Kyriaki Revelou, Marinos Xagoraris, Eleftherios Alissandrakis, Christos S. Pappas and Petros A. Tarantilis
Chemosensors 2021, 9(11), 322; https://doi.org/10.3390/chemosensors9110322 - 18 Nov 2021
Cited by 7 | Viewed by 5229
Abstract
4(5)-Methylimidazole (4(5)MEI) is a product of the Maillard reaction between sugars and amino acids, which occurs during the thermal processing of foods. This compound is also found in foods with caramel colorants additives. Due to its prevalence in foods and beverages and its [...] Read more.
4(5)-Methylimidazole (4(5)MEI) is a product of the Maillard reaction between sugars and amino acids, which occurs during the thermal processing of foods. This compound is also found in foods with caramel colorants additives. Due to its prevalence in foods and beverages and its potent carcinogenicity, 4(5)MEI has received federal and state regulatory agency attention. The aim of this review is to present the extraction procedures of 4(5)MEI from food matrices and the analytical methods for its determination. Liquid and gas chromatography coupled with mass spectrometry are the techniques most commonly employed to detect 4(5)MEI in food matrices. However, the analysis of 4(5)MEI is challenging due to the high polarity, water solubility, and the absence of chromophores. To overcome this, specialized sample pretreatment and extraction methods have been developed, such as solid-phase extraction and derivatization procedures, increasing the cost and the preparation time of samples. Other analytical methods for the determination of 4(5)MEI, include capillary electrophoresis, paper spray mass spectrometry, micellar electrokinetic chromatography, high-performance cation exchange chromatography, fluorescence-based immunochromatographic assay, and a fluorescent probe. Full article
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34 pages, 5063 KiB  
Review
Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends
by Tony Cardoso, Ana Sofia Almeida, Fernando Remião and Carla Fernandes
Chemosensors 2021, 9(11), 304; https://doi.org/10.3390/chemosensors9110304 - 25 Oct 2021
Cited by 12 | Viewed by 3947
Abstract
The interaction between proteins and drugs or other bioactive compounds has been widely explored over the past years. Several methods for analysis of this phenomenon have been developed and improved. Nowadays, increasing attention is paid to innovative methods, such as high performance affinity [...] Read more.
The interaction between proteins and drugs or other bioactive compounds has been widely explored over the past years. Several methods for analysis of this phenomenon have been developed and improved. Nowadays, increasing attention is paid to innovative methods, such as high performance affinity liquid chromatography (HPALC) and affinity capillary electrophoresis (ACE), taking into account various advantages. Moreover, the development of separation methods for the analysis and resolution of chiral drugs has been an area of ongoing interest in analytical and medicinal chemistry research. In addition to bioaffinity binding studies, both HPALC and ACE al-low one to perform other type of analyses, namely, displacement studies and enantioseparation of racemic or enantiomeric mixtures. Actually, proteins used as chiral selectors in chromatographic and electrophoretic methods have unique enantioselective properties demonstrating suitability for the enantioseparation of a large variety of chiral drugs or other bioactive compounds. This review is mainly focused in chromatographic and electrophoretic methods using human serum albumin (HSA), the most abundant plasma protein, as chiral selector for binding affinity analysis and enantioresolution of drugs. For both analytical purposes, updated examples are presented to highlight recent applications and current trends. Full article
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19 pages, 3015 KiB  
Article
Comprehensive Characterization of 76 Pharmaceuticals and Metabolites in Wastewater by LC-MS/MS
by Cristian Gómez-Canela, Sílvia Edo, Natalia Rodríguez, Gemma Gotor and Sílvia Lacorte
Chemosensors 2021, 9(10), 273; https://doi.org/10.3390/chemosensors9100273 - 24 Sep 2021
Cited by 28 | Viewed by 4111
Abstract
Wastewaters are considered one of the main sources of pollution in the aquatic environment as release a large number of contaminants every day. Emerging contaminants such as pharmaceuticals have special interest due to the high levels of consumption by the global population, their [...] Read more.
Wastewaters are considered one of the main sources of pollution in the aquatic environment as release a large number of contaminants every day. Emerging contaminants such as pharmaceuticals have special interest due to the high levels of consumption by the global population, their bioactive properties and because actual directives do not include the monitoring of pharmaceuticals. Moreover, it is well-known that pharmaceuticals can be degraded to metabolites or transformation products (TPs), which could be more toxic than the parental compound. In this study, we have developed an analytical method based on solid-phase extraction (SPE) and liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) to determine 76 highly consumed pharmaceuticals, including metabolites and TPs in wastewater effluents. In the 10 wastewaters analysed, the mean concentrations were in the µg L−1 levels, being mycophenolic acid, levodopa, ibuprofen, 4-aminoantypirine, losartan, amylmetacresol, amoxicillin, fluticasone, tramadol, budesonide, chlorpheniramine and diclofenac the pharmaceuticals with the highest concentrations. This study provides a comprehensive optimization on the MS conditions to determine pharmaceutical compounds and their metabolites and provides a spectral characterization to be used for the identification of these compounds in water. Full article
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11 pages, 1261 KiB  
Article
Enantioselective Monitoring of Biodegradation of Ketamine and Its Metabolite Norketamine by Liquid Chromatography
by Ariana Pérez-Pereira, Alexandra Maia, Virgínia Gonçalves, Cláudia Ribeiro and Maria Elizabeth Tiritan
Chemosensors 2021, 9(9), 242; https://doi.org/10.3390/chemosensors9090242 - 30 Aug 2021
Cited by 2 | Viewed by 3598
Abstract
Ketamine (K) and its main metabolite, norketamine (NK), are chiral compounds that have been found in effluents from wastewater treatment plants (WWTPs) and aquatic environments. Little is known about their enantioselective biodegradation during sewage treatment; however, this information is pivotal for risk assessment, [...] Read more.
Ketamine (K) and its main metabolite, norketamine (NK), are chiral compounds that have been found in effluents from wastewater treatment plants (WWTPs) and aquatic environments. Little is known about their enantioselective biodegradation during sewage treatment; however, this information is pivotal for risk assessment, the evaluation of WWTP performance and wastewater epidemiological studies. The aim of this study was to investigate the biodegradation pattern of the enantiomers of K by activated sludge (AS) from a WWTP. For that, an enantioselective liquid chromatography with diode array detection (LC-DAD) method was developed and validated to quantify the enantiomers of K and NK. Both K and NK enantiomers were separated, in the same chromatographic run, using a Lux® 3 µm cellulose-4 analytical column under isocratic elution mode. The method was demonstrated to be linear (r2 > 0.99) and precise (<11.3%). Accuracy ranged between 85.9 and 113.6% and recovery ranged between 50.1 and 86.9%. The limit of quantification was 1.25 µg/mL for the enantiomers of NK and 2.5 µg/mL for K. The method was applied to monitor the biodegradation assay of the enantiomers of K by AS for 14 days. K was poorly biodegraded, less than 15% for both enantiomers, and enantioselectivity in the biodegradation was not observed. The metabolite NK and other possible degradation products were not detected. This work reports, for the first time, the behavior of both enantiomers of K in biodegradation studies. Full article
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17 pages, 19500 KiB  
Article
Gas Chromatography Multiresidue Method for Enantiomeric Fraction Determination of Psychoactive Substances in Effluents and River Surface Waters
by Ivan Langa, Maria Elizabeth Tiritan, Diana Silva and Cláudia Ribeiro
Chemosensors 2021, 9(8), 224; https://doi.org/10.3390/chemosensors9080224 - 13 Aug 2021
Cited by 12 | Viewed by 3018
Abstract
Determination of psychoactive substances (PAS) and/or their metabolites in surface waters is crucial for environmental risk assessment, and disclosure of their enantiomeric fractions (EF) allows discrimination between consumption, direct disposal, and synthesis pathways. The aim of this study was to develop and validate [...] Read more.
Determination of psychoactive substances (PAS) and/or their metabolites in surface waters is crucial for environmental risk assessment, and disclosure of their enantiomeric fractions (EF) allows discrimination between consumption, direct disposal, and synthesis pathways. The aim of this study was to develop and validate an indirect method by gas chromatography coupled to mass spectrometry (GC–MS) based on derivatization using (R)-(−)-α-methoxy-α-(trifluoromethyl) phenylacetyl chloride as chiral derivatization reagent, for enantiomeric quantification of amphetamine (AMP), methamphetamine (MAMP), 3,4-methylenedioxymethamphetamine (MDMA), norketamine, buphedrone (BPD), butylone, 3,4-dimethylmethcathinone (3,4-DMMC), 3-methylmethcathinone, and quantification of 1-benzylpiperazine and 1-(4-metoxyphenyl)-piperazine. The method allowed to evaluate the occurrence, spatial distribution, and the EF of the target chiral PAS in Portuguese surface waters and in effluents from 2 wastewater treatment plants (WWTP). For that, water samples were pre-concentrated by solid phase extraction using OASIS® MCX cartridges, derivatized and further analyzed by GC–MS. Both enantiomers of AMP, (R)-MDMA, (S)-MAMP, and the first eluted enantiomer of BPD (configuration not assigned) were found in surface waters, while effluent samples showed both enantiomers of MDMA, (S)-MAMP, (R)-AMP, and the first eluted enantiomer of BPD and 3,4-DMMC. According to our knowledge, this is the first multiresidue analytical method by CG–MS enrolling cathinones, amphetamines, and piperazines. The presence of illicit synthetic cathinones in Douro River estuary is here reported for the first time, along with other amphetamine derivatives. The potential of the method to monitor consumption of the target PAS was demonstrated. Full article
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20 pages, 3115 KiB  
Article
Expediting Disulfiram Assays through a Systematic Analytical Quality by Design Approach
by João Basso, Maria Luísa Ramos, Alberto Pais, Rui Vitorino, Ana Fortuna and Carla Vitorino
Chemosensors 2021, 9(7), 172; https://doi.org/10.3390/chemosensors9070172 - 6 Jul 2021
Cited by 8 | Viewed by 3840
Abstract
An Analytical Quality by Design (AQbD) approach is presented, aiming at the development and validation of an HPLC method for the quantification of disulfiram and copper diethyldithiocarbamate in lipid nanoparticles. Following the definition of the analytical target profile (ATP), encompassing the critical analytical [...] Read more.
An Analytical Quality by Design (AQbD) approach is presented, aiming at the development and validation of an HPLC method for the quantification of disulfiram and copper diethyldithiocarbamate in lipid nanoparticles. Following the definition of the analytical target profile (ATP), encompassing the critical analytical attributes (CAA), a two-level risk assessment strategy (Ishikawa diagram—failure mode and effect analysis (FMEA)) was employed to identify the critical method parameters (CMPs) with an extensive impact on method performance. The behavior of the CMPs (flow rate and mobile phase composition) was further characterized by experimental design, resorting to a face-centered central composite design (FcCCD). Statistical modeling, response surface analysis, and Monte Carlo simulations led to the definition of the Method Operable Design Region (MODR), associated with a negligible risk of failing the predefined CAA specifications. The optimal method was validated according to international regulatory recommendations. Apart from guaranteeing linearity, accuracy, precision, specificity, robustness, and stability, these conditions were found to be suitable for analysis using a different HPLC column and equipment. In a nutshell, the development and optimization strategies, under the comprehensive framework of AQbD, provided an effective, simple, rapid, reliable, and flexible method for routine analysis of the compounds in research or industrial environments. Full article
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19 pages, 2111 KiB  
Review
Recent Advances in Solid-Phase Extraction (SPE) Based on Molecularly Imprinted Polymers (MIPs) for Analysis of Hormones
by Anele Mpupa, Shirley Kholofelo Selahle, Boris Mizaikoff and Philiswa Nosizo Nomngongo
Chemosensors 2021, 9(7), 151; https://doi.org/10.3390/chemosensors9070151 - 22 Jun 2021
Cited by 15 | Viewed by 4359
Abstract
Steroid hormones are active substances that are necessary in the normal functioning of all physiological activities in the body, such as sexual characteristics, metabolism, and mood control. They are also widely used as exogenous chemicals in medical and pharmaceutical applications as treatments and [...] Read more.
Steroid hormones are active substances that are necessary in the normal functioning of all physiological activities in the body, such as sexual characteristics, metabolism, and mood control. They are also widely used as exogenous chemicals in medical and pharmaceutical applications as treatments and at times growth promoters in animal farming. The vast application of steroid hormones has resulted in them being found in different matrices, such as food, environmental, and biological samples. The presence of hormones in such matrices means that they can easily come into contact with humans and animals as exogenous compounds, resulting in abnormal concentrations that can lead to endocrine disruption. This makes their determination in different matrices a vital part of pollutant management and control. Although advances in analytical instruments are constant, it has been determined that these instruments still require some sample preparation steps to be able to determine the occurrence of pollutants in the complex matrices in which they occur. Advances are still being made in sample preparation to ensure easier, selective, and sensitive analysis of complex matrices. Molecularly imprinted polymers (MIPs) have been termed as advanced solid-phase (SPE) materials for the selective extraction and preconcentration of hormones in complex matrices. This review explores the preparation and application of MIPs for the determination of steroid hormones in different sample types. Full article
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