@article{MTMT:34688029,
	title = {Simultaneous Determination of Enantiomeric Purity and Organic Impurities of Dexketoprofen Using Reversed-Phase Liquid Chromatography—Enhancing Enantioselectivity through Hysteretic Behavior and Temperature-Dependent Enantiomer Elution Order Reversal on Polysaccharide Chiral Stationary Phases},
	url = {https://m2.mtmt.hu/api/publication/34688029},
	author = {Dobó, Máté and Dombi, Gergely and Köteles, István and Fiser, Béla and Kis, Csenge and Szabó, Zoltán-István and Tóth, Gergő},
	doi = {10.3390/ijms25052697},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {25},
	unique-id = {34688029},
	issn = {1661-6596},
	abstract = {A reversed-phase high-performance liquid chromatographic (HPLC) method was developed for the simultaneous determination of the potential impurities of dexketoprofen, including the distomer R-ketoprofen. After screening the separation capability of four polysaccharide columns (Lux Amylose-1, Lux Amylose-2, Lux Cellulose-1 and Lux Cellulose-2) in polar organic and in reversed-phase modes, appropriate enantioseparation was observed only on the Lux Amylose-2 column in an acidified acetonitrile/water mixture. A detailed investigation of the mobile phase composition and temperature for enantio- and chemoselectivity showed many unexpected observations. It was observed that both the resolution and the enantiomer elution order can be fine-tuned by varying the temperature and mobile phase composition. Moreover, hysteresis of the retention times and enantioselectivity was also observed in reversed-phase mode using methanol/water mixtures on amylose-type columns. This could indicate that the three-dimensional structure of the amylose column can change by transitioning from a polar organic to a reversed-phase mode, which affects the enantioseparation process. Temperature-dependent enantiomer elution order and rare enthalpic/entropic controlled enantioseparation in the operative temperature range were also observed in reversed-phase mode. To find the best methodological conditions for the determination of dexketoprofen impurities, a full factorial optimization design was performed. Using the optimized parameters (Lux Amylose-2 column with water/acetonitrile/acetic acid 50/50/0.1 (v/v/v) at a 1 mL/min flow rate at 20 °C), baseline separations were achieved between all compounds within 15 min. Our newly developed HPLC method was validated according to the current guidelines, and its application was tested on commercially available pharmaceutical formulations. According to the authors’ knowledge, this is the first study to report hysteretic behavior on polysaccharide columns in reversed-phase mode.},
	year = {2024},
	eissn = {1422-0067},
	orcid-numbers = {Köteles, István/0000-0002-1678-233X; Fiser, Béla/0000-0003-0603-4626; Szabó, Zoltán-István/0000-0002-8740-0212; Tóth, Gergő/0000-0001-5341-319X}
}

@article{MTMT:34448514,
	title = {Chiral Separation of Vildagliptin by Capillary Electrophoresis—The Study of Enantiomeric Complexation},
	url = {https://m2.mtmt.hu/api/publication/34448514},
	author = {Papp, L.A. and Hancu, G. and Szabó, Z.I. and Székely-Szentmiklósi, B. and Gáti, T. and Fiser, Béla and Mazákné Kraszni, Márta and Tóth, Gergő},
	doi = {10.3390/sym16010017},
	journal-iso = {SYMMETRY-BASEL},
	journal = {SYMMETRY (BASEL)},
	volume = {16},
	unique-id = {34448514},
	year = {2024},
	eissn = {2073-8994},
	orcid-numbers = {Fiser, Béla/0000-0003-0603-4626; Mazákné Kraszni, Márta/0000-0003-4364-9486; Tóth, Gergő/0000-0001-5341-319X}
}

@article{MTMT:34285588,
	title = {The Applicability of Chromatographic Retention Modeling on Chiral Stationary Phases in Reverse-Phase Mode: A Case Study for Ezetimibe and Its Impurities},
	url = {https://m2.mtmt.hu/api/publication/34285588},
	author = {Ferencz, Elek and Kelemen, Éva-Katalin and Obreja, Mona and Tóth, Gergő and Urkon, Melinda and Zöldhegyi, Arnold and Sipos, Emese and Szabó, Zoltán-István},
	doi = {10.3390/ijms242216097},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {24},
	unique-id = {34285588},
	issn = {1661-6596},
	abstract = {Mechanistic modeling is useful for predicting and modulating selectivity even in early chromatographic method development. This approach is also in accordance with current analytical quality using design principles and is highly welcomed by the authorities. The aim of this study was to investigate the separation behavior of two different types of chiral stationary phases (CSPs) for the separation of ezetimibe and its related substances using the mechanistic retention modeling approach offered by the Drylab software (version 4.5) package. Based on the obtained results, both CSPs presented with chemoselectivity towards the impurities of ezetimibe. The cyclodextrin-based CSP displayed a higher separation capacity and was able to separate seven related substances from the active pharmaceutical ingredient, while the cellulose-based column enabled the baseline resolution of six impurities from ezetimibe. Generally, the accuracy of predicted retention times was lower for the polysaccharide CSP, which could indicate the presence of additional secondary interactions between the analytes and the CSP. It was also demonstrated that the combination of mechanistic modeling and an experimental design approach can be applied to method development on CSPs in reverse-phase mode. The applicability of the methods was tested on spiked artificial placebo samples, while intraday and long-term (2 years) method repeatability was also challenged through comparing the obtained retention times and resolution values. The results indicated the excellent robustness of the selected setpoints. Overall, our findings indicate that the chiral columns could offer orthogonal selectivity to traditional reverse-phase columns for the separation of structurally similar compounds.},
	year = {2023},
	eissn = {1422-0067},
	orcid-numbers = {Ferencz, Elek/0000-0001-8916-1780; Kelemen, Éva-Katalin/0000-0002-8285-1567; Tóth, Gergő/0000-0001-5341-319X; Urkon, Melinda/0000-0002-8197-3992; Szabó, Zoltán-István/0000-0002-8740-0212}
}

@article{MTMT:34281522,
	title = {Untargeted metabolomic analyses support the main phylogenetic groups of the common plant-associated Alternaria fungi isolated from grapevine (Vitis vinifera)},
	url = {https://m2.mtmt.hu/api/publication/34281522},
	author = {Molnár, Anna and Knapp, Dániel and Lovas, Miklós and Tóth, Gergő and Boldizsár, Imre and Váczy, Kálmán Zoltán and Kovács, M. Gábor},
	doi = {10.1038/s41598-023-46020-3},
	journal-iso = {SCI REP},
	journal = {SCIENTIFIC REPORTS},
	volume = {13},
	unique-id = {34281522},
	issn = {2045-2322},
	abstract = {Alternaria , a cosmopolitan fungal genus is a dominant member of the grapevine ( Vitis vinifera ) microbiome. Several Alternaria species are known to produce a variety of secondary metabolites, which are particularly relevant to plant protection and food safety in field crops. According to previous findings, the majority of Alternaria species inhabiting grapevine belong to Alternaria sect. Alternaria . However, the phylogenetic diversity and secondary metabolite production of the distinct Alternaria species has remained unclear. In this study, our aim was to examine the genetic and metabolic diversity of endophytic Alternaria isolates associated with the above-ground tissues of the grapevine. Altogether, 270 Alternaria isolates were collected from asymptomatic leaves and grape clusters of different grapevine varieties in the Eger wine region of Hungary. After analyses of the nuclear ribosomal DNA internal transcribed spacer (ITS) and RNA polymerase second largest subunit ( rpb2 ) sequences, 170 isolates were chosen for further analyses. Sequences of the Alternaria major allergen gene ( Alt a 1 ), endopolygalacturonase ( endoPG ), OPA10-2, and KOG1058 were also included in the phylogenetic analyses. Identification of secondary metabolites and metabolite profiling of the isolates were performed using high-performance liquid chromatography (HPLC)–high-resolution tandem mass spectrometry (HR-MS/MS). The multilocus phylogeny results revealed two distinct groups in grapevine, namely A . alternata and the A . arborescens species complex (AASC). Eight main metabolites were identified in all collected Alternaria isolates, regardless of their affiliation to the species and lineages. Multivariate analyses of untargeted metabolites found no clear separations; however, a partial least squares-discriminant analysis model was able to successfully discriminate between the metabolic datasets from isolates belonging to the AASC and A. alternata . By conducting univariate analysis based on the discriminant ability of the metabolites, we also identified several features exhibiting large and significant variation between A. alternata and the AASC. The separation of these groups may suggest functional differences, which may also play a role in the functioning of the plant microbiome.},
	year = {2023},
	eissn = {2045-2322},
	orcid-numbers = {Molnár, Anna/0000-0002-0919-0512; Knapp, Dániel/0000-0002-7568-238X; Tóth, Gergő/0000-0001-5341-319X; Boldizsár, Imre/0000-0001-7852-8364; Kovács, M. Gábor/0000-0001-9509-4270}
}

@CONFERENCE{MTMT:34163455,
	title = {Inclusion complexation of the novel antipsoriatic drug apremilast with cyclodextrins},
	url = {https://m2.mtmt.hu/api/publication/34163455},
	author = {Benkő, Beáta Mária and Tóth, Gergő and Tóth, Bence and I. Szabó, Zoltán and Szente, Lajos and Szabó, Edina and Zelkó, Romána and Sebe, István},
	booktitle = {EUROCD 2023 7th European Cyclodextrin Conference},
	unique-id = {34163455},
	year = {2023},
	orcid-numbers = {Benkő, Beáta Mária/0000-0002-3608-6219; Tóth, Gergő/0000-0001-5341-319X; Zelkó, Romána/0000-0002-5419-9137; Sebe, István/0000-0003-0752-781X}
}

@CONFERENCE{MTMT:34163447,
	title = {Exploring enantiomer migration order alterations in capillary electrophoretic studies with cyclodextrin chiral selectors},
	url = {https://m2.mtmt.hu/api/publication/34163447},
	author = {Tóth, Gergő and Szőcs, Levente and Szabó, Zoltán-István},
	booktitle = {EUROCD 2023 7th European Cyclodextrin Conference},
	unique-id = {34163447},
	year = {2023},
	orcid-numbers = {Tóth, Gergő/0000-0001-5341-319X}
}

@article{MTMT:34144177,
	title = {Enantioseparation and molecular docking study of selected chiral pharmaceuticals on a commercialized phenylcarbamate-β-cyclodextrin column using polar organic mode},
	url = {https://m2.mtmt.hu/api/publication/34144177},
	author = {Dobó, Máté and Ádám, M. and Fiser, Béla and Papp, L.A. and Dombi, Gergely and Sekkoum, K. and Szabó, Z.-I. and Tóth, Gergő},
	doi = {10.1038/s41598-023-41941-5},
	journal-iso = {SCI REP},
	journal = {SCIENTIFIC REPORTS},
	volume = {13},
	unique-id = {34144177},
	issn = {2045-2322},
	year = {2023},
	eissn = {2045-2322},
	orcid-numbers = {Fiser, Béla/0000-0003-0603-4626; Tóth, Gergő/0000-0001-5341-319X}
}

@CONFERENCE{MTMT:34122754,
	title = {TAXONOMIC AND METABOLIC CHARACTERIZATION OF ALTERNARIA SPECIES IN GRAPEVINE (VITIS VINIFERA) IN HUNGARY},
	url = {https://m2.mtmt.hu/api/publication/34122754},
	author = {Molnár, Anna and Knapp, Dániel and Lovas, Miklós and Boldizsár, Imre and Tóth, Gergő and Váczy, Kálmán Zoltán and Kovács, M. Gábor},
	booktitle = {Abstracts of the 19th International Congress of the Hungarian Society for Microbiology},
	unique-id = {34122754},
	year = {2023},
	pages = {72-72},
	orcid-numbers = {Molnár, Anna/0000-0002-0919-0512; Knapp, Dániel/0000-0002-7568-238X; Boldizsár, Imre/0000-0001-7852-8364; Tóth, Gergő/0000-0001-5341-319X; Kovács, M. Gábor/0000-0001-9509-4270}
}

@article{MTMT:33963988,
	title = {Chiral Separation of Oxazolidinone Analogs by Capillary Electrophoresis Using Anionic Cyclodextrins as Chiral Selectors. Emphasis on Enantiomer Migration Order},
	url = {https://m2.mtmt.hu/api/publication/33963988},
	author = {Szabó, Zoltán-István and Boda, Francisc and Fiser, Béla and Dobó, Máté and Szőcs, Levente and Tóth, Gergő},
	doi = {10.3390/molecules28114530},
	journal-iso = {MOLECULES},
	journal = {MOLECULES},
	volume = {28},
	unique-id = {33963988},
	issn = {1420-3049},
	year = {2023},
	eissn = {1420-3049},
	orcid-numbers = {Fiser, Béla/0000-0003-0603-4626; Szőcs, Levente/0000-0002-9521-3628; Tóth, Gergő/0000-0001-5341-319X}
}

@article{MTMT:33741526,
	title = {Chiral Separation of Apremilast by Capillary Electrophoresis Using Succinyl-β-Cyclodextrin—Reversal of Enantiomer Elution Order by Cationic Capillary Coating},
	url = {https://m2.mtmt.hu/api/publication/33741526},
	author = {Szabó, Zoltán-István and Benkő, Beáta Mária and Bartalis-Fábián, Ágnes and Iványi, Róbert and Varga, Erzsébet and Szőcs, Levente and Tóth, Gergő},
	doi = {10.3390/molecules28083310},
	journal-iso = {MOLECULES},
	journal = {MOLECULES},
	volume = {28},
	unique-id = {33741526},
	issn = {1420-3049},
	abstract = {A stereospecific capillary electrophoresis method was developed for the separation of the novel, antipsoriatic agent, apremilast (APR). Six anionic cyclodextrin (CD) derivatives were screened for their ability to discriminate between the uncharged enantiomers. Only succinyl-β-CD (Succ-β-CD) presented chiral interactions; however, the enantiomer migration order (EMO) was unfavorable, and the eutomer, S-APR, migrated faster. Despite the optimization of all possible parameters (pH, cyclodextrin concentration, temperature, and degree of substitution of CD), the method was unsuccessful for purity control due to the low resolution and the unfavorable enantiomer migration order. Changing the direction of electroosmotic flow (EOF) by the dynamic coating of the inner surface of the capillary with poly(diallyldimethylammonium) chloride or polybrene resulted in EMO reversal, and the developed method could be applied for the determination of R-APR as the enantiomeric purity. Thus, the application of the dynamic capillary coating offers a general opportunity for enantiomeric migration order reversal in particular cases when the chiral selector is a weak acid.},
	year = {2023},
	eissn = {1420-3049},
	orcid-numbers = {Benkő, Beáta Mária/0000-0002-3608-6219; Szőcs, Levente/0000-0002-9521-3628; Tóth, Gergő/0000-0001-5341-319X}
}