TY - JOUR AU - Vágvölgyi, Máté AU - Laczkó, Dávid AU - Santa Maria, Anaraquel AU - Vigh, Judit Piroska AU - Walter, Fruzsina AU - Berkecz, Róbert AU - Deli, Mária Anna AU - Tóth, Gábor AU - Hunyadi, Attila TI - 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 JF - PLOS ONE J2 - PLOS ONE VL - 19 PY - 2024 IS - 2 PG - 15 SN - 1932-6203 DO - 10.1371/journal.pone.0290526 UR - https://m2.mtmt.hu/api/publication/34691003 ID - 34691003 N1 - Institute of Pharmacognosy, University of Szeged, Szeged, Hungary Institute of Biophysics, HUN-REN Biological Research Centre, Szeged, Hungary Wyss Institute for Biologically Inspired Engineering, Harvard University, Boston, MA, United States Doctoral School of Biology, University of Szeged, Szeged, Hungary Institute of Pharmaceutical Analysis, University of Szeged, Szeged, Hungary NMR Group, Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Budapest, Hungary Interdisciplinary Centre of Natural Products, University of Szeged, Szeged, Hungary HUN-REN-SZTE Biologically Active Natural Products Research Group, Szeged, Hungary Export Date: 18 March 2024 CODEN: POLNC Correspondence Address: Hunyadi, A.; Institute of Pharmacognosy, Hungary; email: hunyadi.attila@szte.hu AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - AHMED, Sara Hassan Hassan AU - Tayeb, Bizhar Ahmed AU - Gonda, Tímea AU - Girst, Gábor AU - Szőri, Kornél AU - Berkecz, Róbert AU - Zupkó, István AU - Minorics, Renáta AU - Hunyadi, Attila TI - Thymoquinone-protoflavone hybrid molecules as potential antitumor agents JF - PLOS ONE J2 - PLOS ONE VL - 19 PY - 2024 IS - 1 PG - 13 SN - 1932-6203 DO - 10.1371/journal.pone.0291567 UR - https://m2.mtmt.hu/api/publication/34541373 ID - 34541373 AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Németi, Gábor AU - Berkecz, Róbert AU - Le Minh, Tam AU - Szakonyi, Zsolt AU - Péter, Antal AU - Ilisz, István TI - High-performance liquid chromatographic enantioseparation of azole analogs of monoterpene lactones and amides focusing on the separation characteristics of polysaccharide-based chiral stationary phases JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1717 PY - 2024 PG - 9 SN - 0021-9673 DO - 10.1016/j.chroma.2024.464660 UR - https://m2.mtmt.hu/api/publication/34535772 ID - 34535772 N1 - Institute of Pharmaceutical Analysis, Interdisciplinary Excellence Centre, University of Szeged, Somogyi u. 4, Szeged, H-6720, Hungary Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Export Date: 5 February 2024 CODEN: JCRAE Correspondence Address: Ilisz, I.; Institute of Pharmaceutical Analysis, Somogyi u. 4, Hungary; email: ilisz.istvan@szte.hu Funding details: 6752 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding details: Innovációs és Technológiai Minisztérium Funding details: National Research, Development and Innovation Office, K137607, TKP2021-EGA-32 Funding text 1: This work was supported by the National Research, Development and Innovation Office-NKFIA through project K137607. Project no. TKP2021-EGA-32 has been implemented with the support provided by the Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund, financed under the TKP2021-EGA funding scheme. This work was supported by the ÚNKP-21-4 New National Excellence Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund. The publication was funded by the University of Szeged Open Access Fund (No. 6752). LA - English DB - MTMT ER - TY - JOUR AU - Püski, Péter AU - Körmöczi, Tímea AU - Berkecz, Róbert AU - Barta, Anita AU - Bajtel, Ákos AU - Kiss, Tivadar TI - Rapid Detection of Adulteration in Boswellia Extracts with Citric Acid by UPLC–HRMS and 1 H NMR JF - JOURNAL OF DIETARY SUPPLEMENTS J2 - J DIETARY SUPPLEMENTS PY - 2024 PG - 16 SN - 1939-022X DO - 10.1080/19390211.2023.2299886 UR - https://m2.mtmt.hu/api/publication/34474822 ID - 34474822 LA - English DB - MTMT ER - TY - CHAP AU - Zahraa, Ali AU - Csilla, Zsuzsanna Dávid AU - Andrea, Vasas AU - Ilisz, István AU - Berkecz, Róbert ED - Tünde, Alapi ED - Berkecz, Róbert ED - Ilisz, István TI - SIMULTANEOUS ANALYSIS OF STILBENES, CHROMATOGRAPHIC DESIGN AND APPLICATION T2 - Proceedings of the 29th International Symposium on Analytical and Environmental Problems PB - University of Szeged CY - Szeged SN - 9789633069639 PY - 2023 SP - 57 EP - 58 PG - 2 UR - https://m2.mtmt.hu/api/publication/34391766 ID - 34391766 LA - English DB - MTMT ER - TY - CHAP AU - Németi, Gábor AU - Dániel, Ozsvár AU - Berkecz, Róbert AU - Péter, Antal AU - Wolfgang, Lindner AU - Ilisz, István ED - Tünde, Alapi ED - Berkecz, Róbert ED - Ilisz, István TI - Enantioselective separation of substituted amino acids utilizing cinchona alkaloid-based chiral stationary phases T2 - Proceedings of the 29th International Symposium on Analytical and Environmental Problems PB - University of Szeged CY - Szeged SN - 9789633069639 PY - 2023 SP - 42 EP - 42 PG - 1 UR - https://m2.mtmt.hu/api/publication/34391565 ID - 34391565 LA - English DB - MTMT ER - TY - GEN AU - Berkecz, Róbert AU - Ilisz, István AU - D., Csupor TI - Targeted UHPLC-HRMS/MS Method for Analysis Cannabinoids in CBD Hemp Oils PY - 2023 PG - 1 UR - https://m2.mtmt.hu/api/publication/34386938 ID - 34386938 LA - English DB - MTMT ER - TY - GEN AU - Ilisz, István AU - G., Németi AU - Berkecz, Róbert AU - T.M., Le AU - Z., Szakonyi AU - Péter, Antal TI - HPLC study of the separation characteristics of polysaccharide-based chiral stationary phases with particular emphasis on the hysteretic behavior PY - 2023 PG - 1 UR - https://m2.mtmt.hu/api/publication/34386896 ID - 34386896 LA - English DB - MTMT ER - TY - GEN AU - Péter, Antal AU - D., Tanács AU - Berkecz, Róbert AU - D.W., Armstrong AU - Ilisz, István TI - Characteristics of chiral stationary phases utilizing superficially porous silica particles for the HPLC enantioseparation of unusual amino acid analogs PY - 2023 SP - P-CHIR05 PG - 1 UR - https://m2.mtmt.hu/api/publication/34386802 ID - 34386802 LA - English DB - MTMT ER - TY - BOOK AU - Körmöczi, Tímea AU - Evelin, Fehér AU - Nóra, Gödör AU - Tamás, Farkas AU - Ilisz, István AU - Ferenc, Domoki AU - Berkecz, Róbert TI - Monitoring tryptophan metabolites in mouse plasma PY - 2023 SP - 1 UR - https://m2.mtmt.hu/api/publication/34380352 ID - 34380352 LA - English DB - MTMT ER -