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 - CONF 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 ED - Hohmann, Judit TI - Thymoquinone-protoflavone hybrids T2 - 4th Symposium of Young Researchers on Pharmacognosy PB - Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged C1 - Szeged PY - 2023 SP - 13 EP - 13 PG - 1 DO - 10.14232/syrmpnpr.2023.7 UR - https://m2.mtmt.hu/api/publication/33947701 ID - 33947701 LA - English DB - MTMT ER - TY - JOUR AU - AHMED, Sara Hassan Hassan AU - Gonda, Tímea AU - Agbadua, Orinamhe Godwin AU - Girst, Gábor AU - Berkecz, Róbert AU - Kúsz, Norbert AU - Tsai, Meng-Chun AU - Wu, Chin-Chung AU - Balogh, György Tibor AU - Hunyadi, Attila TI - Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents JF - ANTIOXIDANTS J2 - ANTIOXIDANTS-BASEL VL - 12 PY - 2023 IS - 3 PG - 18 SN - 2076-3921 DO - 10.3390/antiox12030744 UR - https://m2.mtmt.hu/api/publication/33709440 ID - 33709440 N1 - Institute of Pharmacognosy, University of Szeged, Szeged, H-6720, Hungary Institute of Pharmaceutical Analysis, University of Szeged, Szeged, H-6720, Hungary Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, 807, Taiwan Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, H-6720, Hungary Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, H-1111, Hungary Interdisciplinary Centre of Natural Products, University of Szeged, Szeged, H-6720, Hungary Export Date: 11 April 2023 Correspondence Address: Hunyadi, A.; Institute of Pharmacognosy, Hungary; email: hunyadi.attila@szte.hu AB - Ginger (Zingiber officinale) is widely used as a spice and a traditional medicine. Many bioactivities have been reported for its extracts and the isolated compounds, including cardiovascular protective effects. Different pathways were suggested to contribute to these effects, like the inhibition of platelet aggregation. In this study, we synthesised fourteen 6-gingerol derivatives, including eight new compounds, and studied their antiplatelet, COX-1 inhibitor, and antioxidant activities. In silico docking of selected compounds to h-COX-1 enzyme revealed favourable interactions. The investigated 6-gingerol derivatives were also characterised by in silico and experimental physicochemical and blood–brain barrier-related parameters for lead and preclinical candidate selection. 6-Shogaol (2) was identified as the best overall antiplatelet lead, along with compounds 3 and 11 and the new compound 17, which require formulation to optimize their water solubility. Compound 5 was identified as the most potent antioxidant that is also promising for use in the central nervous system (CNS). LA - English DB - MTMT ER - TY - CONF AU - Ferreira, Ricardo J. F. AU - Lopes, Francisca AU - Girst, Gábor AU - Hunyadi, Attila AU - M. M. Santos, Maria ED - Hohmann, Judit TI - Hybrid molecules of tryptophan derivatives and protoflavones totackle colon cancer T2 - 4th Symposium of Young Researchers on Pharmacognosy PB - Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged C1 - Szeged PY - 2023 SP - 10 EP - 10 PG - 1 DO - 10.14232/syrmpnpr.2023.4 UR - https://m2.mtmt.hu/api/publication/33963403 ID - 33963403 LA - English DB - MTMT ER - TY - JOUR AU - Girst, Gábor AU - Lopes, Elizabeth A. AU - Goncalves, Lidia M. AU - Espadinha, Margarida AU - Kúsz, Norbert AU - Wang, Hui-Chun AU - Santos, Maria M. M. AU - Hunyadi, Attila TI - Hybrid molecules of protoflavones and spirooxindole derivatives with selective cytotoxicity against triple-negative breast cancer cells JF - RSC MEDICINAL CHEMISTRY J2 - RSC MED CHEM VL - 14 PY - 2023 IS - 9 SP - 1778 EP - 1786 PG - 9 SN - 2632-8682 DO - 10.1039/d3md00251a UR - https://m2.mtmt.hu/api/publication/34261677 ID - 34261677 AB - The combination of compounds with complementary bioactivities into hybrid molecules is an emerging concept in drug discovery. In this study, we aimed to synthesize new hybrid compounds based on p53-MDM2/X protein-protein interaction spiropyrazoline oxindole-based inhibitors and ataxia telangiectasia and Rad3-related (ATR) protoflavone-based inhibitors through copper(i) catalysed azide-alkyne cycloaddition. Five new hybrids were prepared along with three representative reference fragments. The compounds were tested against human breast cancer cell lines MCF-7 (hormone-dependent, wild-type p53) and MDA-MB-231 (triple-negative, mutant p53). Most of the new hybrids were more cytotoxic than their reference fragments and several showed 2-4 times selective toxicity against MDA-MB-231 cells. Relevant pharmacological benefit gained from the hybrid coupling was further confirmed by virtual combination index calculations using the Chou method. Compound 13 modulated doxorubicin-induced DNA damage response through inhibiting the ATR-dependent activation of Chk-1, while increasing the activation of Chk-2. Our results suggest that the new hybrids may serve as new leads against triple negative breast cancer. LA - English DB - MTMT ER - TY - CONF AU - Girst, Gábor AU - Balogh, György Tibor AU - Hunyadi, Attila ED - Hohmann, Judit TI - Antioxidant and pharmacokinetic studies on new semi-syntheticnitrogen-containing diarylheptanoids derived from curcumin T2 - 4th Symposium of Young Researchers on Pharmacognosy PB - Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged C1 - Szeged PY - 2023 SP - 21 EP - 21 PG - 1 DO - 10.14232/syrmpnpr.2023.14 UR - https://m2.mtmt.hu/api/publication/33963590 ID - 33963590 LA - English DB - MTMT ER - TY - JOUR AU - Najem, Ayoub AU - Campos, Othon S. AU - Girst, Gábor AU - Mounir, Raji AU - Hunyadi, Attila AU - García-Antón, José AU - Bellaouchou, Abdelkbir AU - Amin, Hatem M. A. AU - Boudalia, Maria TI - Experimental and DFT Atomistic Insights into the Mechanism of Corrosion Protection of Low-Carbon Steel in an Acidic Medium by Polymethoxyflavones from Citrus Peel Waste JF - JOURNAL OF THE ELECTROCHEMICAL SOCIETY J2 - J ELECTROCHEM SOC VL - 170 PY - 2023 IS - 9 PG - 14 SN - 0013-4651 DO - 10.1149/1945-7111/acfa69 UR - https://m2.mtmt.hu/api/publication/34167387 ID - 34167387 AB - Developing green anticorrosive films is gaining great attention in science and engineering. Citrus fruit peels are mainly discarded as waste, although they can be an excellent repository of phytochemicals, that can be exploited as mitigating agents for corrosion. Herein, we report the high anticorrosion activity of a citrus extract for low-carbon steel in 1 M HCl solution at different temperatures. The main extract constituents were identified by MS and NMR. Two polymethoxyflavones (PMFs), namely nobiletin and heptamethoxyflavone, were identified as major constituents of the extract and the crude PMFs-based extract was investigated for corrosion protection. Using potentiodynamic polarization, weight loss and electrochemical impedance spectroscopy (EIS) methods, this extract revealed improved inhibition efficiency of 94%. The inhibition mechanism was elucidated by considering electrochemical kinetics and adsorption thermodynamics. SEM and UV–vis supported the electrochemical results. PMFs-based extract acted as a mixed-type inhibitor with a Langmuir model of adsorption. Importantly, DFT simulations provided atomic-level insights into the inhibition mechanism and unraveled donor-acceptor interactions between the methoxy groups of PMFs and iron atoms, facilitating the formation of a stable inhibition adsorption layer, and thus supporting the experimental findings. In addition to the physical barrier effect of PMF inhibitor, π -back bonding effect between PMF and steel was suggested. LA - English DB - MTMT ER - TY - JOUR AU - Ahmed, SHH AU - Gonda, Tímea AU - Agbadua, Orinamhe Godwin AU - Girst, Gábor AU - Berkecz, Róbert AU - Kúsz, Norbert AU - Tsai, M-C AU - Wu, C-C AU - Balogh, György Tibor AU - Hunyadi, Attila TI - 6-Gingerol Derivatives as Promising Antiplatelet Leads JF - PLANTA MEDICA: NATURAL PRODUCTS AND MEDICINAL PLANT RESEARCH J2 - PLANTA MED VL - 88 PY - 2022 IS - 15 SP - 1514 SN - 0032-0943 DO - 10.1055/s-0042-1759193 UR - https://m2.mtmt.hu/api/publication/33686916 ID - 33686916 LA - English DB - MTMT ER - TY - CONF AU - Girst, Gábor ED - Kiss, Tivadar ED - Hohmann, Judit TI - Structural modification of hydrocurcumins in the aim of increased antioxidant activity T2 - 3rd Symposium of Young Researchers on Pharmacognosy PB - Szegedi Tudományegyetem, Gyógyszerésztudományi Kar, Farmakognóziai Intézet C1 - Szeged PY - 2022 SP - 25 EP - 25 PG - 1 DO - 10.14232/syrpharmacognosy.2022.b10 UR - https://m2.mtmt.hu/api/publication/33100243 ID - 33100243 LA - English DB - MTMT ER - TY - CONF AU - Girst, Gábor ED - Kiss, Tivadar ED - Hohmann, Judit TI - Study on peroxynitrite-induced oxidation of hydrocurcumins T2 - 2nd Symposium of Young Researchers on Pharmacognosy PB - Szegedi Tudományegyetem, Gyógyszerésztudományi Kar, Farmakognóziai Intézet C1 - Szeged PY - 2021 PG - 1 DO - 10.14232/syrpharmacognosy.2021.a6 UR - https://m2.mtmt.hu/api/publication/32012961 ID - 32012961 LA - English DB - MTMT ER -