TY - JOUR AU - Ribeiro, Joana R. L. AU - Szemerédi, Nikoletta AU - Gonçalves, Bruno M. F. AU - Spengler, Gabriella AU - Afonso, Carlos A. M. AU - Ferreira, Maria-José U. TI - Nitrogen-containing andrographolide derivatives with multidrug resistance reversal effects in cancer cells JF - RSC MEDICINAL CHEMISTRY J2 - RSC MED CHEM PY - 2024 SN - 2632-8682 DO - 10.1039/D3MD00711A UR - https://m2.mtmt.hu/api/publication/34753868 ID - 34753868 N1 - This study was financially supported by Fundação para a Ciência e a Tecnologia (FCT), Portugal (projects: PTDC/MED-QUI/30591/2017; 2022.05718.PTDC; UIDB/04138/2020, UIDP/ 04138/2020, PhD grant SFRH/BD/139760/2018) and the János Bolyai Research Scholarship (BO/00158/22/5) of the Hungarian Academy of Sciences. We also thank COST Action RSC Medicinal Chemistry Research ArticleOpen Access Article. Published on 26 February 2024. Downloaded on 3/25/2024 5:44:13 AM.This article is licensed under aCreative Commons Attribution 3.0 Unported Licence. View Article Online RSC Med. Chem. This journal is © The Royal Society of Chemistry 2024 CA17104 STRATAGEM. The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project no. 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC). AB - A set of twenty-three new andrographolide derivatives, bearing a nitrogen-containing moiety, is reported. Several derivatives were found to be promising leads for reversing cancer multidrug resistance. LA - English DB - MTMT ER - TY - JOUR AU - Resende, D.I.S.P. AU - Durães, F. AU - Zubarioglu, S. AU - Freitas-Silva, J. AU - Szemerédi, Nikoletta AU - Pinto, M. AU - Pinto, E. AU - Martins, da Costa P. AU - Spengler, Gabriella AU - Sousa, E. TI - Antibacterial Potential of Symmetrical Twin-Drug 3,6-Diaminoxanthones JF - PHARMACEUTICALS J2 - PHARMACEUTICALS-BASE VL - 17 PY - 2024 IS - 2 PG - 18 SN - 1424-8247 DO - 10.3390/ph17020209 UR - https://m2.mtmt.hu/api/publication/34746290 ID - 34746290 N1 - Laboratory of Organic and Pharmaceutical Chemistry (LQOF), Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, Porto, 4050-313, Portugal Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, Matosinhos, 4450-208, Portugal ICBAS—Instituto de Ciências Biomédicas Abel Salazar, University of Porto, Rua de Jorge Viterbo Ferreira, Porto, 228, 4050-313, Portugal Department of Medical Microbiology, Albert Szent-Györgyi Health Center and Albert Szent-Györgyi Medical School, University of Szeged, Semmelweis utca 6, Szeged, 6725, Hungary Laboratory of Microbiology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, Porto, 4050-313, Portugal Export Date: 19 March 2024 Correspondence Address: Sousa, E.; Laboratory of Organic and Pharmaceutical Chemistry (LQOF), Rua de Jorge Viterbo Ferreira, 228, Portugal; email: esousa@ff.up.pt Correspondence Address: Pinto, E.; Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Av. General Norton de Matos s/n, Portugal; email: epinto@ff.up.pt Tradenames: Advance 300, Bruker, United States; ChemDraw, Perkin Elmer; CLARIOstar Plus, BMG Labtech, Germany; DGV-20A5, Shimadzu, Japan; Kofler, Wagner and Munz, Germany; LCMS Lab Solutions software version 3.50 SP2, Shimadzu, Japan; Lux, Phenomenex; Multiscan EX, Thermo Labsystems, United States; Q Exactive, Thermo, Germany; Rheodyne 7725, Shimadzu, Japan; Waterchath B-480, BUCHI; Xcalibur 4.1.31.9 software, Thermo, Germany Manufacturers: BMG Labtech, Germany; BUCHI; Perkin Elmer; Phenomenex; Thermo, Germany; Wagner and Munz, Germany; Shimadzu, Japan; Bruker, United States; Thermo Labsystems, United States Funding details: 2022.00379, BO/00158/22/5 Funding details: European Commission, EC Funding details: Fundação para a Ciência e a Tecnologia, FCT, EXPL/CTA-AMB/0810/2021, PTDC/CTA-AMB/0853/2021, UIDP/04423/2020 Funding details: Magyar Tudományos Akadémia, MTA Funding details: European Regional Development Fund, ERDF, NORTE-01-0145-FEDER-000040 Funding details: Programa Operacional Temático Factores de Competitividade, POFC Funding text 1: This research was supported by national funds through the FCT—Foundation for Science and Technology within the scope of UIDB/04423/2020, UIDP/04423/2020 (Group of Marine Natural Products and Medicinal Chemistry CIIMAR), and under the projects EXPL/CTA-AMB/0810/2021 and PTDC/CTA-AMB/0853/2021, co-financed by COMPETE 2020, Portugal 2020 and the European Union through the ERDF and by FCT through national funds, as well as R&D&I ATLANTIDA (reference NORTE-01-0145-FEDER-000040), supported by NORTE2020, through ERDF. D.I.S.P.R. acknowledges her individual researcher contract (2022.00379.CEECIND). Gabriella Spengler was supported by the János Bolyai Research Scholarship (BO/00158/22/5) of the Hungarian Academy of Sciences. AB - Global health faces a significant issue with the rise of infectious diseases caused by bacteria, fungi, viruses, and parasites. The increasing number of multi-drug resistant microbial pathogens severely threatens public health worldwide. Antibiotic-resistant pathogenic bacteria, in particular, present a significant challenge. Therefore, there is an urgent need to identify new potential antimicrobial targets and discover new chemical entities that can potentially reverse bacterial resistance. The main goal of this research work was to create and develop a library of 3,6-disubstituted xanthones based on twin drugs and molecular extension approaches to inhibit the activity of efflux pumps. The process involved synthesizing 3,6-diaminoxanthones through the reaction of 9-oxo-9H-xanthene-3,6-diyl bis(trifluoromethanesulfonate) with various primary and secondary amines. The resulting 3,6-disubstituted xanthone derivatives were then tested for their in vitro antimicrobial properties against a range of pathogenic strains and their efficacy in inhibiting the activity of efflux pumps, biofilm formation, and quorum-sensing. Several compounds have exhibited effective antibacterial properties against the Gram-positive bacterial species tested. Xanthone 16, in particular, has demonstrated exceptional efficacy with a remarkable MIC of 11 µM (4 µg/mL) against reference strains Staphylococcus aureus ATCC 25923 and Enterococcus faecalis ATCC 29212, and 25 µM (9 µg/mL) against methicillin-resistant S. aureus 272123. Furthermore, some derivatives have shown potential as antibiofilm agents in a crystal violet assay. The ethidium bromide accumulation assay pinpointed certain compounds inhibiting bacterial efflux pumps. The cytotoxic effect of the most promising compounds was examined in mouse fibroblast cell line NIH/3T3, and two monoamine substituted xanthone derivatives with a hydroxyl substituent did not exhibit any cytotoxicity. Overall, the nature of the substituent was critical in determining the antimicrobial spectra of aminated xanthones. © 2024 by the authors. LA - English DB - MTMT ER - TY - JOUR AU - Szabó, Diána AU - Janovák, László AU - Abdelghafour, Mohamed M. AU - Takács, Tamás AU - Csanády, Miklós ifj. AU - Spengler, Gabriella AU - Szakács, László AU - Csanády, Miklós AU - Rovó, László TI - Új minimálinvazív kezelési lehetőségek jó- és rosszindulatú fül-orr-gégészeti betegségekben nanoszerkezetű hatóanyag-leadó rendszerek alkalmazásával = New minimally invasive treatment options in benign and malignant otorhinolaryngological diseases using nanostructured drug delivery systems JF - ORVOSI HETILAP J2 - ORV HETIL VL - 165 PY - 2024 IS - 10 SP - 370 EP - 378 PG - 9 SN - 0030-6002 DO - 10.1556/650.2024.32978 UR - https://m2.mtmt.hu/api/publication/34729015 ID - 34729015 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Hegedűs, Dóra AU - Szemerédi, Nikoletta AU - Gábor, Maja AU - Sas, Judit AU - Belasri, Khadija AU - Szatmári, István AU - Spengler, Gabriella TI - Cyclic Amines Coupled to Indole Derivatives With Improved Efflux Pump Inhibiting Activity in Bacteria and Cancer Cells JF - ANTICANCER RESEARCH J2 - ANTICANCER RES VL - 44 PY - 2024 IS - 3 SP - 1149 EP - 1160 PG - 12 SN - 0250-7005 DO - 10.21873/anticanres.16910 UR - https://m2.mtmt.hu/api/publication/34715381 ID - 34715381 N1 - Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Hungary Department of Medical Microbiology, Albert Szent-Györgyi Health Center, Albert Szent-Györgyi Medical School, University of Szeged, Szeged, Hungary HUN-REN–SZTE Stereochemistry Research Group, University of Szeged, Szeged, Hungary Department of Medical Microbiology, Albert Szent-Györgyi Health Center, Albert Szent-Györgyi Medical School, University of Szeged, Semmelweis utca 6, Szeged, 6725, Hungary Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Export Date: 3 April 2024 CODEN: ANTRD Correspondence Address: Szatmári, I.; Institute of Pharmaceutical Chemistry, Hungary; email: szatmari.istvan@szte.hu Correspondence Address: Spengler, G.; Department of Medical Microbiology, Hungary; email: spengler.gabriella@med.u-szeged.hu Chemicals/CAS: doxorubicin, 23214-92-8, 25316-40-9; ethidium bromide, 1239-45-8; isoquinoline, 119-65-3; rhodamine 123, 62669-70-9; vemurafenib, 918504-65-1; adamantane, 281-23-2; Adamantane; Amines; Anti-Bacterial Agents; Antipsychotic Agents; Antiviral Agents Funding details: TKP-2021-EGA-32, ÚNKP-23-4-SZTE-347 Funding details: Hungarian Scientific Research Fund, OTKA, K-138871 Funding details: Magyar Tudományos Akadémia, MTA, ÚNKP-23-5-SZTE-677 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA, BO/00158/22/5 Funding details: Innovációs és Technológiai Minisztérium Funding text 1: The Authors thank the Hungarian Research Foundation (OTKA No. K-138871), the Ministry of Human Capacities, Hungary grant, TKP-2021-EGA-32. N. S. was supported by the ÚNKP-23-4-SZTE-347 New National Excellence Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund. G.S. was supported by the János Bolyai Research Scholarship (BO/00158/22/5) of the Hungarian Academy of Sciences and by the ÚNKP-23-5-SZTE-677 New National Excellence Program of the Ministry for Culture and Innovation from the source of the National Research, Development and Innovation Fund. LA - English DB - MTMT ER - TY - JOUR AU - Pivarcsik, Tamás AU - Kiss, Márton Attila AU - Rapuš, Uroš AU - Kljun, Jakob AU - Spengler, Gabriella AU - Nagyné Frank, Éva AU - Turel, Iztok AU - Enyedy, Éva Anna TI - Organometallic Ru(II), Rh(III) and Re(I) complexes of sterane-based bidentate ligands: Synthesis, solution speciation, interaction with biomolecules and anticancer activity JF - DALTON TRANSACTIONS J2 - DALTON T VL - 53 PY - 2024 IS - 11 SP - 4984 EP - 5000 PG - 17 SN - 1477-9226 DO - 10.1039/D3DT04138G UR - https://m2.mtmt.hu/api/publication/34601216 ID - 34601216 AB - In this study, we present the synthesis, characterization and in vitro cytotoxicity of six organometallic [Ru(II)(η6-p-cymene)(N,N)Cl]Cl, [Rh(III)(η5-C5Me5)(N,N)Cl]Cl and [Re(I)(CO)3(N,N)Cl] complexes, in which the (N,N) ligands are sterane-based 2,2’-bipyridine derivatives (4-Me-bpy-St-OH,... LA - English DB - MTMT ER - TY - JOUR AU - Enyedy, Éva Anna AU - Giricz, Anett AU - Petrasheuskaya, Tatsiana AU - Mészáros, János Péter AU - May, Nóra Veronika AU - Spengler, Gabriella AU - Kovács, Ferenc AU - Molnár, Barnabás AU - Nagyné Frank, Éva TI - Comparative Solution Equilibrium Studies on Anticancer Estradiol-Based Conjugates and Their Copper Complexes JF - INORGANICS J2 - INORGANICS VL - 12 PY - 2024 IS - 2 PG - 21 SN - 2304-6740 DO - 10.3390/inorganics12020049 UR - https://m2.mtmt.hu/api/publication/34556458 ID - 34556458 AB - Steroids are often considered valuable molecular tools for the development of anticancer agents with improved pharmacological properties. Conjugation of metal chelating moieties with a lipophilic sterane backbone is a viable option to obtain novel anticancer compounds. In this work, two estradiol-based hybrid molecules (PMA-E2 and DMA-E2) with an (N,N,O) binding motif and their Cu(II) complexes were developed. The lipophilicity, solubility, and acid-base properties of the novel ligands were determined by the combined use of UV-visible spectrophotometry, pH-potentiometry, and 1H NMR spectroscopy. The solution speciation and redox activity of the Cu(II) complexes were also investigated by means of UV-visible and electron paramagnetic resonance spectroscopy. Two structurally analogous ligands (PMAP and DMAP) were also included in the studies for better interpretation of the solution chemical data obtained. Three pKa values were determined for all ligands, revealing the order of the deprotonation steps: pyridinium-NH+ or NH(CH3)2+, secondary NH2+, and OH. The dimethylamine derivatives (DMA-E2, DMAP) are found in their H2L+ forms in solution at pH 7.4, whereas the fraction of the neutral HL species is significant (34–37%) in the case of the pyridine nitrogen-containing derivatives (PMA-E2, PMAP). Both estradiol derivatives were moderately cytotoxic in human breast (MCF-7) and colon adenocarcinoma (Colo-205) cells (IC50 = 30–63 μM). They form highly stable complexes with Cu(II) ions capable of oxidizing ascorbate and glutathione. These Cu(II) complexes are somewhat more cytotoxic (IC50 = 15–45 μM) than their corresponding ligands and show a better selectivity profile. LA - English DB - MTMT ER - TY - JOUR AU - Pósa, Vivien AU - Federa, Anja AU - Cseh, Klaudia AU - Wenisch, Dominik AU - Spengler, Gabriella AU - May, Nóra Veronika AU - Lihi, Norbert AU - Samu, Gergely Ferenc AU - Jakupec, Michael A. AU - Keppler, Bernhard K. AU - Kowol, Christian R. AU - Enyedy, Éva Anna TI - A Comparative Study on the Complexation of the Anticancer Iron Chelator VLX600 with Essential Metal Ions JF - INORGANIC CHEMISTRY J2 - INORG CHEM VL - 63 PY - 2024 IS - 5 SP - 2401 EP - 2417 PG - 17 SN - 0020-1669 DO - 10.1021/acs.inorgchem.3c03259 UR - https://m2.mtmt.hu/api/publication/34536068 ID - 34536068 N1 - Funding Agency and Grant Number: Austrian Science Fund [TKP-2021-EGA-32]; National Research Development and Innovation Office-NKFIA (Hungary) [P31923, UNKP-22-3-SZTE-447, LP2019-6/2019]; Austrian Science Fund (FWF) [6774]; University of Szeged Open Access Fund Funding text: This work was financially supported by the National Research Development and Innovation Office-NKFIA (Hungary) through project TKP-2021-EGA-32 (to E.A.E.), the Austrian Science Fund (FWF) grant P31923 (to C.K.), and the UNKP-22-3-SZTE-447 New National Excellence Program (to V.P.). The support of the "Lendulet" Programme (ELKH, LP2019-6/2019) and University of Szeged Open Access Fund (grant number: 6774) is also acknowledged (to E.A.E.). We thank the Core Facility X-ray Centre of the Faculty of Chemistry, University of Vienna, for crystal structure determination. LA - English DB - MTMT ER - TY - JOUR AU - Kovács, Balázs AU - Szemerédi, Nikoletta AU - Csikós, Orsolya AU - Kiss, Tivadar AU - Veres, Katalin AU - Spengler, Gabriella AU - Csupor-Löffler, Boglárka AU - Csupor, Dezső TI - Chemical composition, antimicrobial and antiproliferative activity of the essential oil from Ambrosia artemisiifolia L JF - JOURNAL OF ESSENTIAL OIL RESEARCH J2 - J ESSENT OIL RES VL - 36 PY - 2024 IS - 1 SP - 30 EP - 42 PG - 13 SN - 1041-2905 DO - 10.1080/10412905.2024.2303449 UR - https://m2.mtmt.hu/api/publication/34501021 ID - 34501021 LA - English DB - MTMT ER - TY - BOOK AU - Burián, Katalin AU - Endrész, Valéria AU - Megyeri, Klára AU - Mosolygó, Tímea AU - Orosz, László AU - Somogyvári, Ferenc AU - Spengler, Gabriella AU - Bogdanov, Anita AU - Virók, Dezső ED - Burián, Katalin TI - MEDICAL MICROBIOLOGY. Practical classes TS - Practical classes PB - SZTE SZAOK Orvosi Mikrobiológiai Intézet CY - Szeged PY - 2023 SN - 9789633069325 UR - https://m2.mtmt.hu/api/publication/34747796 ID - 34747796 N1 - Second edition LA - English DB - MTMT ER - TY - BOOK AU - Burián, Katalin AU - Endrész, Valéria AU - Megyeri, Klára AU - Mosolygó, Tímea AU - Orosz, László AU - Somogyvári, Ferenc AU - Spengler, Gabriella AU - Bogdanov, Anita AU - Virók, Dezső ED - Burián, Katalin TI - ORVOSI MIKROBIOLÓGIA. Gyakorlati jegyzet I-II. kötet TS - Gyakorlati jegyzet I-II. kötet PB - SZTE SZAOK Orvosi Mikrobiológiai Intézet CY - Szeged PY - 2023 SN - 9789633069332 UR - https://m2.mtmt.hu/api/publication/34747744 ID - 34747744 N1 - (2. javított kiadás) LA - Hungarian DB - MTMT ER -