@article{MTMT:36096691,
	title = {Enantioseparation of Mirabegron Using Cyclodextrin-based Chiral Columns: High-performance Liquid Chromatography and Molecular Modeling Study},
	url = {https://m2.mtmt.hu/api/publication/36096691},
	author = {Mhammad, Ali and Dombi, Gergely and Dobó, Máté and Szabo, Zoltan-Istvan and Fiser, Béla and Tóth, Gergő},
	doi = {10.1002/jssc.70132},
	journal-iso = {J SEP SCI},
	journal = {JOURNAL OF SEPARATION SCIENCE},
	volume = {48},
	unique-id = {36096691},
	issn = {1615-9306},
	abstract = {A novel high-performance liquid chromatography method for the enantioseparation of mirabegron (R-mirabegron), a selective beta-3 adrenergic receptor agonist, using cyclodextrin (CD)-based chiral stationary phases (CSPs) was developed. Seven different CSPs containing beta-, gamma-, hydroxypropyl-beta-, sulfobutyl-beta-, carboxymethyl-beta-, permethyl-beta-, and phenylcarbamate-beta-cyclodextrin were evaluated under both polar organic and reversed-phase conditions. Only the phenylcarbamate-beta-cyclodextrin containing the Chiral CD-Ph column displayed enantiorecognition. Optimization of conditions using a full factorial design led to the determination of the most suitable conditions: a mobile phase composition of 90:10:0.1 methanol:water:diethylamine, a flow rate of 0.8 mL/min, and a column temperature of 40 degrees C with enantiomeric elution order, where the impurity S-mirabegron elutes first. Using the optimized conditions, enantioseparation with Rs = 1.9 was achieved within 10 min. The developed method was validated according to current guidelines and successfully applied for the determination of S-mirabegron, as a chiral impurity in pharmaceutical formulations. The enantiorecognition mechanism was investigated by molecular docking and thermodynamic analysis. Using molecular modeling, the interactions between CDs and the analyte were analyzed at the molecular level, revealing that mirabegron interacts primarily with the phenylcarbamate groups on the outer surface of the structure. Enthalpy-controlled enantioseparation was consistently observed across all eluent compositions, regardless of the conditions. The developed and validated method is highly suitable for routine determination of the enantiomeric purity of mirabegron, offering a reliable tool for regulatory compliance.},
	keywords = {CHIRAL SEPARATION; VALIDATION; STATIONARY-PHASE; CHIRAL RECOGNITION; cyclodextrin; LC-MS/MS; Betmiga},
	year = {2025},
	eissn = {1615-9314},
	orcid-numbers = {Fiser, Béla/0000-0003-0603-4626; Tóth, Gergő/0000-0001-5341-319X}
}

@article{MTMT:35799034,
	title = {Chiral Recognition Mechanism of Benzyltetrahydroisoquinoline Alkaloids: Cyclodextrin-Mediated Capillary Electrophoresis, Chiral HPLC, and NMR Spectroscopy Study},
	url = {https://m2.mtmt.hu/api/publication/35799034},
	author = {Várnagy, Erzsébet and Tóth, Gergő and Hosztafi, Sándor and Dobó, Máté and Fejős, Ida and Béni, Szabolcs},
	doi = {10.3390/molecules30051125},
	journal-iso = {MOLECULES},
	journal = {MOLECULES},
	volume = {30},
	unique-id = {35799034},
	issn = {1431-5157},
	abstract = {The tetrahydroisoquinoline skeleton is a pharmacologically significant core structure containing chiral centers, making enantiomeric separation crucial due to the potentially distinct biological effects of each enantiomer. In this study, laudanosine (N-methyl-tetrahydropapaverine) and its three derivatives (6′-bromo-laudanosine, norlaudanosine, and N-propyl-norlaudanosine) were synthesized and used as model compounds to investigate chiral recognition mechanisms. Screening over twenty cyclodextrins (CyDs) as chiral selectors in capillary electrophoresis (CE), we found anionic CyDs to be the most effective, with sulfated-γ-CyD (S-γ-CyD) achieving a maximum Rs of 10.5 for laudanosine. Notably, octakis-(6-deoxy-6-(2-carboxyethyl)-thio)-γ-CyD (sugammadex, SGX), heptakis-(2,3-O-diacetyl-6-O-sulfo)-β-CD (HDAS), heptakis-(2,3-O-dimethyl-6-O-sulfo)-β-CD (HDMS), and octakis-(2,3-O-dimethyl-6-O-sulfo)-γ-CD (ODMS) provided excellent enantioseparation for all four analytes. Following HPLC screening on CyD-based and polysaccharide-based chiral stationary phases, semi-preparative HPLC methods using amylose and cellulose-based columns were optimized to isolate enantiomers. The purity of the isolated enantiomers was evaluated by HPLC, and their configurations were confirmed via circular dichroism spectroscopy. The isolated enantiomers allowed us to explore enantiomer migration order reversals in CE and enantiomer elution order reversal in HPLC. Further 1H and 2D ROESY NMR experiments provided atomic-level insights into enantioselective complex formation, confirming enantiomer differentiation by SGX and elucidating the inclusion complex structure, where the ring C immersion into the CyD cavity is prevalent.},
	year = {2025},
	eissn = {1420-3049},
	orcid-numbers = {Várnagy, Erzsébet/0009-0004-8348-4545; Tóth, Gergő/0000-0001-5341-319X; Hosztafi, Sándor/0000-0003-3793-4651; Fejős, Ida/0000-0002-3458-0854; Béni, Szabolcs/0000-0001-7056-6825}
}

@article{MTMT:35578246,
	title = {Possibilities and limitations of computer assisted chiral HPLC method development for ozanimod on polysaccharide based chiral stationary phases},
	url = {https://m2.mtmt.hu/api/publication/35578246},
	author = {Ferencz, E. and Szabó, Z.-I. and Zöldhegyi, A. and Dombi, Gergely and Molnár, G. and Dobó, Máté and Varga, E. and Molnár, I. and Tóth, Gergő},
	doi = {10.1038/s41598-024-78415-1},
	journal-iso = {SCI REP},
	journal = {SCIENTIFIC REPORTS},
	volume = {14},
	unique-id = {35578246},
	abstract = {In this study, a direct HPLC method was developed to determine the enantiomeric purity of the immunomodulatory drug, ozanimod. A systematic method development process was followed, incorporating risk assessment, identification of critical analytical procedure parameters, initial screening of stationary phases, and software-assisted optimization of method parameters. Eight different polysaccharide-based chiral columns were selected to assess chiral separation of enantiomers under polar organic elution mode. The most promising results were obtained using a methanol:2-propanol mixture on the amylose-based Chiralpak AD column. Following this, systematic modeling was conducted using DryLab software to optimize method conditions, including isocratic eluent composition, temperature, and flow rate. Baseline separation was achieved within fifteen minutes using the optimized parameters: Chiralpak AD column thermostated at 10 °C, and a mobile phase of methanol:2-propanol: diethylamine, 70:30:0.1 (v/v/v %), delivered at a flow rate of 0.8 mL/min. The developed method was validated according to current guidelines and in silico robustness testing was conducted to determine tolerance limits for critical separation parameters and their impact on enantioresolution. Our findings demonstrate the utility of DryLab, typically employed for reversed-phase achiral separations, in optimizing chiral methods even in polar organic mode. Limitations of the selected approach the development of chiral separation methods are also highlighted. © The Author(s) 2024.},
	keywords = {CHIRAL SEPARATION; METHANOL; METHANOL; 2-PROPANOL; Chemistry; Software; Software; AMYLOSE; AMYLOSE; Chromatography, High Pressure Liquid; high performance liquid chromatography; Stereoisomerism; Stereoisomerism; Polysaccharides; polysaccharide; carbamic acid derivative; 2 propanol; procedures; Drylab; ozanimod; AQbD; Computer-assisted method development; Polysaccharide-type chiral column; Chiralpak AD; Phenylcarbamates},
	year = {2024},
	eissn = {2045-2322},
	orcid-numbers = {Tóth, Gergő/0000-0001-5341-319X}
}

@article{MTMT:35429645,
	title = {Enantioselective Binding of Proton Pump Inhibitors to Alpha1-Acid Glycoprotein and Human Serum Albumin—A Chromatographic, Spectroscopic, and In Silico Study},
	url = {https://m2.mtmt.hu/api/publication/35429645},
	author = {Dombi, Gergely and Tyukodi, Levente and Dobó, Máté and Molnár, Gergely and Rozmer, Zsuzsanna and Szabó, Zoltán-István and Fiser, Béla and Tóth, Gergő},
	doi = {10.3390/ijms251910575},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {25},
	unique-id = {35429645},
	issn = {1661-6596},
	abstract = {The enantioselective binding of three proton pump inhibitors (PPIs)—omeprazole, rabeprazole, and lansoprazole—to two key plasma proteins, α1-acid glycoprotein (AGP) and human serum albumin (HSA), was characterized. The interactions between PPI enantiomers and proteins were investigated using a multifaceted analytical approach, including high-performance liquid chromatography (HPLC), fluorescence and UV spectroscopy, as well as in silico molecular docking. HPLC analysis demonstrated that all three PPIs exhibited enantioseparation on an AGP-based chiral stationary phase, suggesting stereoselective binding to AGP, while only lansoprazole showed enantioselective binding on the HSA-based column. Quantitatively, the S-enantiomers of omeprazole and rabeprazole showed higher binding affinity to AGP, while the R-enantiomer of lansoprazole displayed greater affinity for AGP, with a reversal in the elution order observed between the two protein-based columns. Protein binding percentages, calculated via HPLC, were greater than 88% for each enantiomer across both transport proteins, with all enantiomers displaying higher affinity for AGP compared to HSA. Thermodynamic analysis indicated that on the HSA, the more common, enthalpy-controlled enantioseparation was found, while in contrast, on the AGP, entropy-controlled enantioseparation was observed. The study also identified limitations in using fluorescence titration due to the high native fluorescence of the compounds, whereas UV titration was effective for both proteins. The determined logK values were in the range of 4.47–4.83 for AGP and 4.02–4.66 for HSA. Molecular docking supported the experimental findings by revealing the atomic interactions driving the binding process, with the predicted enantiomer elution orders aligning with experimental data. The comprehensive use of these analytical methods provides detailed insights into the enantioselective binding properties of PPIs, contributing to the understanding of their pharmacokinetic differences and aiding in the development of more effective therapeutic strategies.},
	year = {2024},
	eissn = {1422-0067},
	orcid-numbers = {Tyukodi, Levente/0000-0002-8983-1876; Szabó, Zoltán-István/0000-0002-8740-0212; Fiser, Béla/0000-0003-0603-4626; Tóth, Gergő/0000-0001-5341-319X}
}

@misc{MTMT:35264360,
	title = {Bioactivity and biosynthesis of halogenated isocoumarins produced by a dark septate endophytic (DSE) fungus},
	url = {https://m2.mtmt.hu/api/publication/35264360},
	author = {S., Csíkos and S., Dekimpe and M., Kraszni and Tóth, Gergő and L., Lakatos and Bősze, Szilvia and B., Pályi and Z., Farkas and F., Ősz and R., Wicik and L., Castagnetti and A., Darázs and Németh Z., Márk and H., Gerstmans and Vellainé Takács, Krisztina and I., Boldizsár and J., Masschelein and Kovács, M. Gábor},
	unique-id = {35264360},
	year = {2024},
	orcid-numbers = {Tóth, Gergő/0000-0001-5341-319X; Bősze, Szilvia/0000-0001-9555-699X; Németh Z., Márk/0000-0001-9521-8421; Vellainé Takács, Krisztina/0000-0002-4472-0363; Kovács, M. Gábor/0000-0001-9509-4270}
}

@article{MTMT:35188022,
	title = {Author Correction: 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/35188022},
	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/s41598-024-69306-6},
	journal-iso = {SCI REP},
	journal = {SCIENTIFIC REPORTS},
	volume = {14},
	unique-id = {35188022},
	year = {2024},
	eissn = {2045-2322},
	orcid-numbers = {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:35186956,
	title = {Grapevine-associated Alternaria phylogenetic groups are supported by untargeted metabolomic profiling},
	url = {https://m2.mtmt.hu/api/publication/35186956},
	author = {Molnár, Anna and Knapp, Dániel and Lovas, Miklós and Tóth, Gergő and Boldizsár, Imre and Váczy, Kálmán Zoltán and Kovács, M. Gábor},
	booktitle = {International Mycological Congress IMC12 (2024)},
	unique-id = {35186956},
	year = {2024},
	pages = {n.a},
	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:35135901,
	title = {Elucidating the Enantioseparation Mechanism of Laudanosine Derivatives: CE, HPLC and NMR Spectroscopic Study},
	url = {https://m2.mtmt.hu/api/publication/35135901},
	author = {Várnagy, Erzsébet and Tóth, Gergő and Hosztafi, Sándor and Malanga, Milo and Fejős, Ida and Béni, Szabolcs},
	booktitle = {PhD Scientific Days 2024},
	unique-id = {35135901},
	year = {2024},
	orcid-numbers = {Várnagy, Erzsébet/0009-0004-8348-4545; Tóth, Gergő/0000-0001-5341-319X; Hosztafi, Sándor/0000-0003-3793-4651; Fejős, Ida/0000-0002-3458-0854; Béni, Szabolcs/0000-0001-7056-6825}
}

@CONFERENCE{MTMT:35011349,
	title = {Egy sötét szeptált endofiton (DSE) gomba klórozott izokumarinjai - bioaktivitás és bromináció},
	url = {https://m2.mtmt.hu/api/publication/35011349},
	author = {Csíkos, Sándor and Kraszni, M. and Tóth, Gergő and Lakatos, Levente and Bősze, Szilvia and Pályi, B. and Darázs, A. and Németh Z., Márk and Boldizsár, Imre and Kovács, M. Gábor},
	booktitle = {VII. Magyar Mikológiai Konferencia, 2024. június 5–7. Budapest},
	unique-id = {35011349},
	year = {2024},
	pages = {80-81},
	orcid-numbers = {Tóth, Gergő/0000-0001-5341-319X; Bősze, Szilvia/0000-0001-9555-699X; Németh Z., Márk/0000-0001-9521-8421; Boldizsár, Imre/0000-0001-7852-8364; Kovács, M. Gábor/0000-0001-9509-4270}
}

@CONFERENCE{MTMT:34901794,
	title = {Cyclodextrin-Mediated Capillary Electrophoresis: Enantiomer Separation of Tetrahydrobenzylisoquinoline Alkaloids},
	url = {https://m2.mtmt.hu/api/publication/34901794},
	author = {Várnagy, Erzsébet and Tóth, Gergő and Hosztafi, Sándor and Malanga, Milo and Béni, Szabolcs and Fejős, Ida},
	booktitle = {Congressus Pharmaceuticus Hungaricus XVII. and EUFEPS Annual Meeting 2024},
	unique-id = {34901794},
	year = {2024},
	pages = {437-438},
	orcid-numbers = {Várnagy, Erzsébet/0009-0004-8348-4545; Tóth, Gergő/0000-0001-5341-319X; Hosztafi, Sándor/0000-0003-3793-4651; Béni, Szabolcs/0000-0001-7056-6825; Fejős, Ida/0000-0002-3458-0854}
}