@article{MTMT:34830921, title = {Liquid Chromatographic Enantioseparation of Newly Synthesized Fluorinated Tryptophan Analogs Applying Macrocyclic Glycopeptides-Based Chiral Stationary Phases Utilizing Core-Shell Particles}, url = {https://m2.mtmt.hu/api/publication/34830921}, author = {Tanács, Dániel and Berkecz, Róbert and Bozsó, Zsolt and Tóth, Gábor and Armstrong, Daniel W. and Péter, Antal and Ilisz, István}, doi = {10.3390/ijms25094719}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {25}, unique-id = {34830921}, issn = {1661-6596}, abstract = {Due to the favorable features obtained through the incorporation of fluorine atom(s), fluorinated drugs are a group with emerging pharmaceutical importance. As their commercial availability is still very limited, to expand the range of possible candidates, new fluorinated tryptophan analogs were synthesized. Control of enantiopurity during the synthesis procedure requires that highly efficient enantioseparation methods be available. In this work, the enantioseparation of seven fluorinated tryptophans and tryptophan was studied and compared systematically to (i) develop analytical methods for enantioselective separations and (ii) explore the chromatographic features of the fluorotrytophans. For enantioresolution, macrocyclic glycopeptide-based selectors linked to core-shell particles were utilized, applying liquid chromatography-based methods. Application of the polar-ionic mode resulted in asymmetric and broadened peaks, while reversed-phase conditions, together with mobile-phase additives, resulted in baseline separation for all studied fluorinated tryptophans. The marked differences observed between the methanol and acetonitrile-containing eluent systems can be explained by the different solvation abilities of the bulk solvents of the applied mobile phases. Among the studied chiral selectors, teicoplanin and teicoplanin aglycone were found to work effectively. Under optimized conditions, baseline separations were achieved within 6 min. Ionic interactions were semi-quantitatively characterized and found to not influence enantiorecognition. Interestingly, fluorination of the analytes does not lead to marked changes in the chromatographic characteristics of the methanol-containing eluents, while larger differences were noticed when the polar but aprotic acetonitrile was applied. Experiments conducted on the influence of the separation temperature indicated that the separations are enthalpically driven, with only one exception. Enantiomeric elution order was found to be constant on both teicoplanin and teicoplanin aglycone-based chiral stationary phases (L < D) under all applied chromatographic conditions.}, year = {2024}, eissn = {1422-0067}, orcid-numbers = {Tanács, Dániel/0000-0003-1011-8638; Berkecz, Róbert/0000-0002-9076-2177; Bozsó, Zsolt/0000-0002-5713-3096; Tóth, Gábor/0000-0002-3604-4385; Armstrong, Daniel W./0000-0003-0501-6231; Ilisz, István/0000-0001-8282-457X} } @article{MTMT:34691003, title = {17-Oxime ethers of oxidized ecdysteroid derivatives modulate oxidative stress in human brain endothelial cells and dose-dependently might protect or damage the blood-brain barrier}, url = {https://m2.mtmt.hu/api/publication/34691003}, author = {Vágvölgyi, Máté and Laczkó, Dávid and Santa Maria, Anaraquel and Vigh, Judit Piroska and Walter, Fruzsina and Berkecz, Róbert and Deli, Mária Anna and Tóth, Gábor and Hunyadi, Attila}, doi = {10.1371/journal.pone.0290526}, journal-iso = {PLOS ONE}, journal = {PLOS ONE}, volume = {19}, unique-id = {34691003}, issn = {1932-6203}, abstract = {20-Hydroxyecdysone and several of its oxidized derivatives exert cytoprotective effect in mammals including humans. Inspired by this bioactivity of ecdysteroids, in the current study it was our aim to prepare a set of sidechain-modified derivatives and to evaluate their potential to protect the blood-brain barrier (BBB) from oxidative stress. Six novel ecdysteroids, including an oxime and five oxime ethers, were obtained through regioselective synthesis from a sidechain-cleaved calonysterone derivative 2 and fully characterized by comprehensive NMR techniques revealing their complete 1 H and 13 C signal assignments. Surprisingly, several compounds sensitized hCMEC/D3 brain microvascular endothelial cells to tert -butyl hydroperoxide (tBHP)-induced oxidative damage as recorded by impedance measurements. Compound 8 , containing a benzyloxime ether moiety in its sidechain, was the only one that exerted a protective effect at a higher, 10 μM concentration, while at lower (10 nM– 1 μM) concentrations it promoted tBHP-induced cellular damage. Brain endothelial cells were protected from tBHP-induced barrier integrity decrease by treatment with 10 μM of compound 8 , which also mitigated the intracellular reactive oxygen species production elevated by tBHP. Based on our results, 17-oxime ethers of oxidized ecdysteroids modulate oxidative stress of the BBB in a way that may point towards unexpected toxicity. Further studies are needed to evaluate any possible risk connected to dietary ecdysteroid consumption and CNS pathologies in which BBB damage plays an important role.}, year = {2024}, eissn = {1932-6203}, orcid-numbers = {Vágvölgyi, Máté/0000-0002-2233-9422; Santa Maria, Anaraquel/0000-0003-3505-5477; Walter, Fruzsina/0000-0001-8145-2823; Berkecz, Róbert/0000-0002-9076-2177; Deli, Mária Anna/0000-0001-6084-6524; Hunyadi, Attila/0000-0003-0074-3472} } @article{MTMT:34541373, title = {Thymoquinone-protoflavone hybrid molecules as potential antitumor agents}, url = {https://m2.mtmt.hu/api/publication/34541373}, author = {AHMED, Sara Hassan Hassan and Tayeb, Bizhar Ahmed and Gonda, Tímea and Girst, Gábor and Szőri, Kornél and Berkecz, Róbert and Zupkó, István and Minorics, Renáta and Hunyadi, Attila}, doi = {10.1371/journal.pone.0291567}, journal-iso = {PLOS ONE}, journal = {PLOS ONE}, volume = {19}, unique-id = {34541373}, issn = {1932-6203}, abstract = {We describe herein the synthesis of eight new ester-coupled hybrid compounds from thymoquinone and protoflavone building blocks, and their bioactivity testing against multiple cancer cell lines. Among the hybrids, compound 14 showed promising activities in all cell lines studied. The highest activities were recorded against breast cancer cell lines with higher selectivity to MDA-MB-231 as compared to MCF-7. Even though the hybrids were found to be completely hydrolysed in 24 h under cell culture conditions, compound 14 demonstrated a ca. three times stronger activity against U-87 glioblastoma cells than a 1:1 mixture of its fragments. Further, compound 14 showed good tumour selectivity: it acted 4.4-times stronger on U-87 cells than on MRC-5 fibroblasts. This selectivity was much lower, only ca. 1.3-times, when the cells were co-treated with a 1:1 mixture of its non-coupled fragments. Protoflavone-thymoquinone hybrids may therefore serve as potential new antitumor leads particularly against glioblastoma.}, year = {2024}, eissn = {1932-6203}, orcid-numbers = {Tayeb, Bizhar Ahmed/0000-0001-5197-564X; Szőri, Kornél/0000-0003-3337-8635; Berkecz, Róbert/0000-0002-9076-2177; Zupkó, István/0000-0003-3243-5300; Minorics, Renáta/0000-0001-9685-813X; Hunyadi, Attila/0000-0003-0074-3472} } @article{MTMT:34535772, title = {High-performance liquid chromatographic enantioseparation of azole analogs of monoterpene lactones and amides focusing on the separation characteristics of polysaccharide-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/34535772}, author = {Németi, Gábor and Berkecz, Róbert and Le Minh, Tam and Szakonyi, Zsolt and Péter, Antal and Ilisz, István}, doi = {10.1016/j.chroma.2024.464660}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1717}, unique-id = {34535772}, issn = {0021-9673}, year = {2024}, eissn = {1873-3778}, orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Berkecz, Róbert/0000-0002-9076-2177; Le Minh, Tam/0000-0002-8296-887X; Szakonyi, Zsolt/0000-0003-2432-8409; Ilisz, István/0000-0001-8282-457X} } @article{MTMT:34474822, title = {Rapid Detection of Adulteration in Boswellia Extracts with Citric Acid by UPLC–HRMS and 1 H NMR}, url = {https://m2.mtmt.hu/api/publication/34474822}, author = {Püski, Péter and Körmöczi, Tímea and Berkecz, Róbert and Barta, Anita and Bajtel, Ákos and Kiss, Tivadar}, doi = {10.1080/19390211.2023.2299886}, journal-iso = {J DIETARY SUPPLEMENTS}, journal = {JOURNAL OF DIETARY SUPPLEMENTS}, unique-id = {34474822}, issn = {1939-022X}, year = {2024}, orcid-numbers = {Körmöczi, Tímea/0000-0002-0973-2473; Berkecz, Róbert/0000-0002-9076-2177; Bajtel, Ákos/0000-0003-2128-6522; Kiss, Tivadar/0000-0003-3538-377X} } @article{MTMT:34423770, title = {Protein engineering - a biológiai gyógyszerek racionális tervezése}, url = {https://m2.mtmt.hu/api/publication/34423770}, author = {Szakonyi, Gerda}, journal-iso = {GYÓGYSZERÉSZET}, journal = {GYÓGYSZERÉSZET}, volume = {6}, unique-id = {34423770}, issn = {0017-6036}, year = {2023}, pages = {294-303}, orcid-numbers = {Szakonyi, Gerda/0000-0002-4366-4283} } @{MTMT:34391766, title = {SIMULTANEOUS ANALYSIS OF STILBENES, CHROMATOGRAPHIC DESIGN AND APPLICATION}, url = {https://m2.mtmt.hu/api/publication/34391766}, author = {Zahraa, Ali and Csilla, Zsuzsanna Dávid and Andrea, Vasas and Ilisz, István and Berkecz, Róbert}, booktitle = {Proceedings of the 29th International Symposium on Analytical and Environmental Problems}, unique-id = {34391766}, year = {2023}, pages = {57-58}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Berkecz, Róbert/0000-0002-9076-2177} } @{MTMT:34391565, title = {Enantioselective separation of substituted amino acids utilizing cinchona alkaloid-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/34391565}, author = {Németi, Gábor and Dániel, Ozsvár and Berkecz, Róbert and Péter, Antal and Wolfgang, Lindner and Ilisz, István}, booktitle = {Proceedings of the 29th International Symposium on Analytical and Environmental Problems}, unique-id = {34391565}, year = {2023}, pages = {42-42}, orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X} } @misc{MTMT:34386938, title = {Targeted UHPLC-HRMS/MS Method for Analysis Cannabinoids in CBD Hemp Oils}, url = {https://m2.mtmt.hu/api/publication/34386938}, author = {Berkecz, Róbert and Ilisz, István and D., Csupor}, unique-id = {34386938}, year = {2023}, orcid-numbers = {Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X} } @misc{MTMT:34386896, title = {HPLC study of the separation characteristics of polysaccharide-based chiral stationary phases with particular emphasis on the hysteretic behavior}, url = {https://m2.mtmt.hu/api/publication/34386896}, author = {Ilisz, István and G., Németi and Berkecz, Róbert and T.M., Le and Z., Szakonyi and Péter, Antal}, unique-id = {34386896}, year = {2023}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Berkecz, Róbert/0000-0002-9076-2177} }