TY - JOUR AU - May, Nóra Veronika AU - Gál, Gyula Tamás AU - Holczbauer, Tamás AU - Nagyné Bereczki, Laura AU - Di Marco, Valerio B. AU - Bombicz, Petra TI - Gradual Changes in the Aromaticity in a Series of Hydroxypyridine-Carboxylic Acid Derivatives and Their Effect on Tautomerism and Crystal Packing JF - CRYSTAL GROWTH & DESIGN J2 - CRYST GROWTH DES VL - 24 PY - 2024 IS - 3 SP - 1096 EP - 1109 PG - 14 SN - 1528-7483 DO - 10.1021/acs.cgd.3c01118 UR - https://m2.mtmt.hu/api/publication/34616122 ID - 34616122 AB - The keto-enol tautomerism of hydroxypyridine-carboxylic acid (HPC) derivatives with proton transfer between the hydroxyl or carboxyl oxygen atoms was investigated in the case of three 3-hydroxy-4-pyridine-carboxylic acid (3HPC) and eight 4-hydroxy-3-pyridine-carboxylic acid (4HPC) derivatives containing altered pyridine ring substituents. Due to the vicinal position of hydroxyl and carboxylate groups, the hydroxyl proton is involved in an intramolecular H-bond and can very easily transform into the keto or enol tautomer. The proton position was found to correlate with the aromaticity of the pyridine ring, which was described by the Bird index, calculated on the basis of the measured atomic distances. Due to the planar shape of the molecules, pi & sdot;& sdot;& sdot;pi stacking and/or C-O & sdot;& sdot;& sdot;pi interactions were found in all investigated compounds. The molecular properties along with their main supramolecular interactions were compared. Packing arrangements and the main hydrogen-bonding schemes were further compared by using Hirshfeld surface analysis. In the case of the four N-methyl-substituted 4HPC derivatives, the synthon consisting of hydrogen bonds was preserved in the plane of the molecules despite the presence of the various ring substituents. Pairing the 3HPC and 4HPC derivatives, the corresponding compounds exhibited the same molecular shape but different nitrogen positions in the pyridine ring. This gave us the opportunity to examine how the difference in the electron distribution affects only and exclusively the secondary interactions and the arrangement of the molecules in the crystals. The electrostatic potential was calculated and mapped over the Hirshfeld surface, and the calculations of pairwise interaction energies and total energy frameworks were performed using the B3LYP/6-31G-(d,p) energy model. LA - English DB - MTMT ER - TY - JOUR AU - Ayyubov, Ilgar AU - Borbáth, Irina AU - Pászti, Zoltán AU - Sebestyén, Zoltán AU - Mihály, Judith AU - Szabó, Tamás AU - Nyergesné Illés, Erzsébet AU - Domján, Attila AU - Florea, Mihaela AU - Radu, Dana AU - Kuncser, Andrei AU - Tompos, András AU - Tálas, Emília TI - Synthesis and Characterization of Graphite Oxide Derived TiO2-Carbon Composites as Potential Electrocatalyst Supports JF - TOPICS IN CATALYSIS J2 - TOP CATAL PY - 2024 SN - 1022-5528 DO - 10.1007/s11244-021-01513-1 UR - https://m2.mtmt.hu/api/publication/32327556 ID - 32327556 N1 - Research Centre for Natural Sciences, Institute of Materials and Environmental Chemistry, Eötvös Loránd Research Network (ELKH), Magyar Tudósok körútja 2, Budapest, 1117, Hungary Department of Physical Chemistry and Materials Science, University of Szeged, Rerrich Béla tér 1, Szeged, 6720, Hungary Department of Food Engineering, Faculty of Engineering, University of Szeged, Mars tér 7, Szeged, 6724, Hungary Research Centre for Natural Sciences, Centre for Structural Science, Eötvös Loránd Research Network (ELKH), Magyar Tudósok Körútja 2, Budapest, 1117, Hungary National Institute of Materials Physics, 405A Atomistilor Street, Magurele, 077125, Romania Cited By :1 Export Date: 12 February 2024 Correspondence Address: Tálas, E.; Research Centre for Natural Sciences, Magyar Tudósok körútja 2, Hungary; email: talas.emilia@ttk.hu Correspondence Address: Florea, M.; National Institute of Materials Physics, 405A Atomistilor Street, Romania; email: mihaela.florea@chimie.unibuc.ro Funding details: NET-2018, NNE 131270 Funding details: European Commission, EC Funding details: Magyar Tudományos Akadémia, MTA Funding details: European Regional Development Fund, ERDF, NNE130004 Funding text 1: The research within project No. VEKOP-2.3.2-16-2017-00013 was supported by the European Union and the State of Hungary, co-financed by the European Regional Development Fund. Project No. NNE130004 has been implemented with the support provided from the National Research, Development and Innovation Fund of Hungary, financed under the TR-NN-17 funding scheme. Project No. NNE 131270 has been implemented with the support provided from the National Research, Development and Innovation Fund of Hungary financed under the M-ERA.NET-2018 funding scheme. The financial supports by the János Bolyai Research Scholarship of the Hungarian Academy of Sciences are gratefully acknowledged (Erzsébet Illés). The authors also thank Dr. Ágnes Szegedi and Dr. Szilvia Klébert for the nitrogen physisorption measurements, and Dr. Zoltán May for the ICP-OES measurements. AB - TiO2-C (carbon) hybrid materials are promising electrocatalyst supports because the presence of TiO2 results in enhanced stability. Use of new types of carbonaceous materials such as reduced graphene oxide instead of traditional active carbon provides certain benefits. Although the rutile polymorph of TiO2 seems to have the most beneficial properties in these hybrid materials, the anatase type is more frequent in TiO2-rGO composites, especially in graphite oxide (GO) derived ones, as GO has several properties which may interfere with rutile formation. To explore and evaluate these peculiarities and their influence on the composite formation, we compared TiO2-C systems formulated with GO and Black Pearls (BP) carbon. Various physicochemical methods, such as attenuated total reflection infrared (ATR-IR)-, solid state NMR-, Raman- and X-ray photoelectron spectroscopy, X-ray powder diffraction (XRD), electron microscopy, etc. were used to characterize the samples from the different stages of our multistep sol–gel synthesis. Our experiments demonstrated that utilization of GO is indeed feasible for composite preparation, although its sodium contamination has to be removed during the synthesis. On the other hand, high temperature treatment and/or solvothermal treatment during composite synthesis resulted in decomposition of the functional groups of the GO and the functional properties of the final product were similar in case of both composites. However, Pt/TiO2-GO derived sample showed higher oxygen reduction reaction activity than Pt/TiO2-BP derived one. Based on the decrease of electrochemical surface area, the stability order was the following: Pt/C (commercial) < Pt/TiO2-BP derived C < Pt/TiO2-GO derived C. © 2021, The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature. LA - English DB - MTMT ER - TY - JOUR AU - Szebényi, Kornélia AU - Füredi, András AU - Bajtai, Eszter AU - Sama, Sai Nagender AU - Csiszar, Agnes AU - Gombos, Balázs AU - Szabó, Pál Tamás AU - Grusch, Michael AU - Szakács, Gergely TI - Effective targeting of breast cancer by the inhibition of P-glycoprotein mediated removal of toxic lipid peroxidation byproducts from drug tolerant persister cells JF - DRUG RESISTANCE UPDATES J2 - DRUG RESIST UPDATE VL - 71 PY - 2023 PG - 12 SN - 1368-7646 DO - 10.1016/j.drup.2023.101007 UR - https://m2.mtmt.hu/api/publication/34163799 ID - 34163799 LA - English DB - MTMT ER - TY - JOUR AU - Orbán, István AU - Ujj, Dóra Viktória AU - Mátravölgyi, Béla AU - Holczbauer, Tamás AU - Rapi, Zsolt TI - d-Idose-Based Monoaza-15-Crown-5 Lariat Ethers: Synthesis of an Elusive d-Hexose and Application of Derived Macrocycles in Enantioselective Syntheses JF - SYMMETRY (BASEL) J2 - SYMMETRY-BASEL VL - 15 PY - 2023 IS - 9 PG - 23 SN - 2073-8994 DO - 10.3390/sym15091714 UR - https://m2.mtmt.hu/api/publication/34133474 ID - 34133474 N1 - Department of organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, 1111, Hungary Centre for Structural Research, Eötvös Loránd Research Network, Magyar Tudósok Körútja 2, Budapest, 1117, Hungary Export Date: 13 October 2023 Correspondence Address: Rapi, Z.; Department of organic Chemistry and Technology, Hungary; email: rapi.zsolt@vbk.bme.hu AB - Carbohydrate-based macrocycles can be enantioselective catalysts in certain reactions. Previously, it was proven that the carbohydrate moiety could affect the catalytic activity of the monoaza-15-crown-5 type macrocycles derived from sugars. According to our experiments so far, the most effective enantioselective catalysts were the d-glucose- and the d-galactose-based crown ethers. To obtain more information about the effect of the carbohydrate unit, a rare monosaccharide, d-idose was incorporated into the monoaza-15-crown-5 structure. The key intermediates were methyl 4,6-O-benzylidene-α-d-idopyranoside and methyl 4,6-O-benzylidene-β-d-idopyranoside, which were synthesized from d-galactose. The efficiency of the idopyranoside-based crown compounds synthesized was investigated in asymmetric phase transfer reactions. In liquid-liquid biphasic reactions the highest enantioselectivity was 81% ee, while in solid-liquid phase systems the highest asymmetric induction was 67% ee. It was observed that the enantiodiscrimination was strongly dependent on the configuration of the anomeric center, on the side arm of the nitrogen, and on the structure of the substrate. LA - English DB - MTMT ER - TY - JOUR AU - Côrte-Real, Leonor AU - Pósa, Vivien AU - Martins, Matilde AU - Colucas, Raquel AU - May, Nóra Veronika AU - Fontrodona, Xavier AU - Romero, Isabel AU - Mendes, Filipa AU - Pinto Reis, Catarina AU - Gaspar, Maria Manuela AU - Pessoa, João Costa AU - Enyedy, Éva Anna AU - Correia, Isabel TI - Cu(II) and Zn(II) Complexes of New 8-Hydroxyquinoline Schiff Bases: Investigating Their Structure, Solution Speciation, and Anticancer Potential JF - INORGANIC CHEMISTRY J2 - INORG CHEM VL - 62 PY - 2023 IS - 29 SP - 11466 EP - 11486 PG - 21 SN - 0020-1669 DO - 10.1021/acs.inorgchem.3c01066 UR - https://m2.mtmt.hu/api/publication/34062061 ID - 34062061 N1 - Martins Matilde and Colucas Raquel contributed equally to this work. Funding Agency and Grant Number: Fundacao para a Ciencia e a Tecnologia (FCT) [UIDB/00100/2020, UIDP/00100/2020, UIDB/04138/2020, UIDP/04138/2020, UIDB/00645/2020, UIDP/00645/2020, LA/P/0056/2020, UID/Multi/04349/2019, PTDC/QUI-QIN/0586/2020]; "Lendulet" Programme (ELKH, Hungary) [LP2019-6/2019]; AGAUR (Generalitat de Catalunya) [2017-SGR-1720]; UdG (Universitat de Girona) [PONT2020/05] Funding text: This research was partially funded by Fundacao para a Ciencia e a Tecnologia (FCT) through projects UIDB/00100/2020, UIDP/00100/2020, UIDB/04138/2020, UIDP/04138/2020, UIDB/00645/2020, UIDP/00645/2020, LA/P/0056/2020, UID/Multi/04349/2019 (C2TN), and PTDC/QUI-QIN/0586/2020. The Portuguese NMR and mass spectrometry IST-UL is acknowledged for access to the equipment. The support of the "Lendulet" Programme (ELKH, LP2019-6/2019, Hungary) is also acknowledged. I.R. acknowledges AGAUR (Generalitat de Catalunya, projects 2017-SGR-1720) and UdG (Universitat de Girona, PONT2020/05). LA - English DB - MTMT ER - TY - JOUR AU - Deák, Andrea Beáta AU - Szabó, Pál Tamás AU - Bednaříková, Vendula AU - Cihlář, Jaroslav AU - Demeter, Attila AU - Remešová, Michaela AU - Colacino, Evelina AU - Čelko, Ladislav TI - The first solid-state route to luminescent Au(I)—glutathionate and its pH-controlled transformation into ultrasmall oligomeric Au10–12(SG)10–12 nanoclusters for application in cancer radiotheraphy JF - FRONTIERS IN CHEMISTRY J2 - FRONT CHEM VL - 11 PY - 2023 PG - 11 SN - 2296-2646 DO - 10.3389/fchem.2023.1178225 UR - https://m2.mtmt.hu/api/publication/34037734 ID - 34037734 AB - There is still a need for synthetic approaches that are much faster, easier to scale up, more robust and efficient for generating gold(I)–thiolates that can be easily converted into gold–thiolate nanoclusters. Mechanochemical methods can offer significantly reduced reaction times, increased yields and straightforward recovery of the product, compared to the solution-based reactions. For the first time, a new simple, rapid and efficient mechanochemical redox method in a ball-mill was developed to produce the highly luminescent, pH-responsive Au(I)–glutathionate, [Au(SG)] n . The efficient productivity of the mechanochemical redox reaction afforded orange luminescent [Au(SG)] n in isolable amounts (mg scale), usually not achieved by more conventional methods in solution. Then, ultrasmall oligomeric Au 10–12 (SG) 10–12 nanoclusters were prepared by pH-triggered dissociation of [Au(SG)] n . The pH-stimulated dissociation of the Au(I)–glutathionate complex provides a time-efficient synthesis of oligomeric Au 10–12 (SG) 10–12 nanoclusters, it avoids high-temperature heating or the addition of harmful reducing agent (e.g., carbon monoxide). Therefore, we present herein a new and eco-friendly methodology to access oligomeric glutathione-based gold nanoclusters, already finding applications in biomedical field as efficient radiosensitizers in cancer radiotherapy. LA - English DB - MTMT ER - TY - JOUR AU - Kocsis, Dorottya AU - Varga, Petra Regina AU - Keshwan, Rusul AU - Nader, Mina AU - Lengyel, Miléna AU - Szabó, Pál Tamás AU - Antal, István AU - Kánai, Károly AU - Keglevich, György AU - Erdő, Franciska TI - Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations—An In Vitro-Ex Vivo Study JF - PHARMACEUTICS J2 - PHARMACEUTICS VL - 15 PY - 2023 IS - 5 PG - 13 SN - 1999-4923 DO - 10.3390/pharmaceutics15051464 UR - https://m2.mtmt.hu/api/publication/33810076 ID - 33810076 N1 - Faculty of Information Technology and Bionics, Pázmány Péter Catholic University, Práter u. 50a, Budapest, H-1083, Hungary Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, H-1521, Hungary Department of Pharmaceutics, Semmelweis University, Budapest, H-1092, Hungary Centre for Structural Study, Research Centre for Natural Sciences, Budapest, H-1117, Hungary Export Date: 26 July 2023 Correspondence Address: Erdő, F.; Faculty of Information Technology and Bionics, Práter u. 50a, Hungary; email: erdo.franciska@itk.ppke.hu AB - α-Aminophosphonates are organophosphorus compounds with an obvious similarity with α-amino acids. Owing to their biological and pharmacological characteristics, they have attracted the attention of many medicinal chemists. α-Aminophosphonates are known to exhibit antiviral, antitumor, antimicrobial, antioxidant and antibacterial activities, which can all be important in pathological dermatological conditions. However, their ADMET properties are not well studied. The aim of the current study was to provide preliminary information about the skin penetration of three preselected α-aminophosphonates when applying them as topical cream formulations in static and dynamic diffusion chambers. The results indicate that aminophosphonate 1a, without any substituent in the para position, shows the best release from the formulation and the highest absorption through the excised skin. However, based on our previous study, the in vitro pharmacological potency was higher in the case of para-substituted molecules 1b and 1c. The particle size and rheological studies revealed that the 2% cream of aminophosphonate 1a was the most homogenous formulation. In conclusion, the most promising molecule was 1a, but further experiments are proposed to uncover the possible transporter interactions in the skin, optimize the topical formulations and improve PK/PD profiles in case of transdermal delivery. LA - English DB - MTMT ER - TY - JOUR AU - Krstić, Gordana AU - Saidu, Muhammad Bello AU - Bombicz, Petra AU - De, Sourav AU - Ali, Hazhmat AU - Zupkó, István AU - Berkecz, Róbert AU - Gallah, Umar Shehu AU - Rédei, Dóra AU - Hohmann, Judit TI - Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus JF - JOURNAL OF NATURAL PRODUCTS J2 - J NAT PROD VL - 86 PY - 2023 IS - 4 SP - 891 EP - 896 PG - 6 SN - 0163-3864 DO - 10.1021/acs.jnatprod.2c01132 UR - https://m2.mtmt.hu/api/publication/33709446 ID - 33709446 N1 - Department of Pharmacognosy, University of Szeged, Eötvös u. 6, Szeged, 6720, Hungary Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, Belgrade, 11158, Serbia Centre for Structural Science, Research Centre for Natural Sciences, Magyar Tudósok körútja 2, Budapest, 1117, Hungary Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, 6720, Hungary Institute of Pharmaceutical Analysis, University of Szeged, Somogyi u. 4, Szeged, 6720, Hungary Bioresource Department, National Research Institute for Chemical Technology (NARICT), Zaria, 1052, Nigeria ELKH-USZ Biologically Active Natural Products Research Group, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :1 Export Date: 19 October 2023 CODEN: JNPRD Correspondence Address: Hohmann, J.; Department of Pharmacognosy, Eötvös u. 6, Hungary; email: Hohmann.judit@szte.hu Chemicals/CAS: Chromones; Monoterpenes Funding details: TKP2021-EGA-32 Funding details: Hungarian Scientific Research Fund, OTKA, K-124544 Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, K-143690 Funding details: National Research, Development and Innovation Office Funding text 1: This study was supported by the National Research, Development and Innovation Office, Hungary (NKFIH; K-143690). The authors would like to thank the financial support provided by the Ministry of Innovation and Technology of Hungary from the NKFIH Fund, project no. TKP2021-EGA-32. P.B. and S.D. are grateful to the Hungarian Scientific Research Fund (K-124544) for financial support. LA - English DB - MTMT ER - TY - JOUR AU - Kovács, Kinga Bernadett AU - Szalai, Laura AU - Szabó, Pál Tamás AU - Gém, Janka Borbála AU - Barsi, Szilvia AU - Szalai, Bence AU - Perey-Simon, Bernadett AU - Turu, Gábor AU - Tóth, András AU - Várnai, Péter AU - Hunyady, László AU - Balla, András TI - An Unexpected Enzyme in Vascular Smooth Muscle Cells: Angiotensin II Upregulates Cholesterol-25-Hydroxylase Gene Expression JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 24 PY - 2023 IS - 4 PG - 15 SN - 1661-6596 DO - 10.3390/ijms24043968 UR - https://m2.mtmt.hu/api/publication/33656921 ID - 33656921 AB - Angiotensin II (AngII) is a vasoactive peptide hormone, which, under pathological conditions, contributes to the development of cardiovascular diseases. Oxysterols, including 25-hydroxycholesterol (25-HC), the product of cholesterol-25-hydroxylase (CH25H), also have detrimental effects on vascular health by affecting vascular smooth muscle cells (VSMCs). We investigated AngII-induced gene expression changes in VSMCs to explore whether AngII stimulus and 25-HC production have a connection in the vasculature. RNA-sequencing revealed that Ch25h is significantly upregulated in response to AngII stimulus. The Ch25h mRNA levels were elevated robustly (~50-fold) 1 h after AngII (100 nM) stimulation compared to baseline levels. Using inhibitors, we specified that the AngII-induced Ch25h upregulation is type 1 angiotensin II receptor- and Gq/11 activity-dependent. Furthermore, p38 MAPK has a crucial role in the upregulation of Ch25h. We performed LC-MS/MS to identify 25-HC in the supernatant of AngII-stimulated VSMCs. In the supernatants, 25-HC concentration peaked 4 h after AngII stimulation. Our findings provide insight into the pathways mediating AngII-induced Ch25h upregulation. Our study elucidates a connection between AngII stimulus and 25-HC production in primary rat VSMCs. These results potentially lead to the identification and understanding of new mechanisms in the pathogenesis of vascular impairments. LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Buna, Levente AU - Vincze, Daniella AU - Holczbauer, Tamás AU - Mátravölgyi, Béla AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Enantioseparation of P-Stereogenic 1-Adamantyl Arylthiophosphonates and Their Stereospecific Transformation to 1-Adamantyl Aryl-H-phosphinates JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 4 PG - 14 SN - 1420-3049 DO - 10.3390/molecules28041584 UR - https://m2.mtmt.hu/api/publication/33635097 ID - 33635097 N1 - Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, Budapest, H-1111, Hungary Center for Structural Science, Chemical Crystallography Research Laboratory and Institute for Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, H-1519, Hungary Export Date: 20 March 2023 CODEN: MOLEF Correspondence Address: Varga, B.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3, Hungary; email: bencevarga@edu.bme.hu Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3, Hungary; email: bagi.peter@vbk.bme.hu AB - A focused library of 1-adamantyl arylthiophosphonates was prepared in racemic form. An enantioseparation method was developed for P-stereogenic thiophosphonates using (S)-1-phenylethylamine as the resolving agent. Under optimized conditions, three out of the five arylthiophosphonates were prepared in enantiopure form (ee > 99%). The subsequent desulfurization of optically active arylthiophosphonates gave the corresponding H-phosphinates without significant erosion of enantiomeric purity (ee = 95–98%). Hence, this reaction sequence can be considered an alternative method for the preparation of 1-adamantyl aryl-H-phopshinates. The absolute configuration of the (S)-1-adamantyl phenylphosphonothioic acid was assigned using single-crystal XRD and it allowed the confirmation that the removal of the P = S group proceeds with retention of configuration. The organocatalytic applicability of (S)-1-adamantyl phenylphosphonothioic acid was also evaluated as a P-stereogenic Brønsted acid. LA - English DB - MTMT ER -