@article{MTMT:34616122, title = {Gradual Changes in the Aromaticity in a Series of Hydroxypyridine-Carboxylic Acid Derivatives and Their Effect on Tautomerism and Crystal Packing}, url = {https://m2.mtmt.hu/api/publication/34616122}, author = {May, Nóra Veronika and Gál, Gyula Tamás and Holczbauer, Tamás and Nagyné Bereczki, Laura and Di Marco, Valerio B. and Bombicz, Petra}, doi = {10.1021/acs.cgd.3c01118}, journal-iso = {CRYST GROWTH DES}, journal = {CRYSTAL GROWTH & DESIGN}, volume = {24}, unique-id = {34616122}, issn = {1528-7483}, abstract = {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.}, year = {2024}, eissn = {1528-7505}, pages = {1096-1109}, orcid-numbers = {May, Nóra Veronika/0000-0003-4770-4681; Bombicz, Petra/0000-0002-5509-1515} } @article{MTMT:32327556, title = {Synthesis and Characterization of Graphite Oxide Derived TiO2-Carbon Composites as Potential Electrocatalyst Supports}, url = {https://m2.mtmt.hu/api/publication/32327556}, author = {Ayyubov, Ilgar and Borbáth, Irina and Pászti, Zoltán and Sebestyén, Zoltán and Mihály, Judith and Szabó, Tamás and Nyergesné Illés, Erzsébet and Domján, Attila and Florea, Mihaela and Radu, Dana and Kuncser, Andrei and Tompos, András and Tálas, Emília}, doi = {10.1007/s11244-021-01513-1}, journal-iso = {TOP CATAL}, journal = {TOPICS IN CATALYSIS}, unique-id = {32327556}, issn = {1022-5528}, abstract = {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.}, year = {2024}, eissn = {1572-9028}, orcid-numbers = {Szabó, Tamás/0000-0001-8182-640X; Nyergesné Illés, Erzsébet/0000-0002-2901-9616; Florea, Mihaela/0000-0002-6612-6090} } @article{MTMT:34163799, title = {Effective targeting of breast cancer by the inhibition of P-glycoprotein mediated removal of toxic lipid peroxidation byproducts from drug tolerant persister cells}, url = {https://m2.mtmt.hu/api/publication/34163799}, author = {Szebényi, Kornélia and Füredi, András and Bajtai, Eszter and Sama, Sai Nagender and Csiszar, Agnes and Gombos, Balázs and Szabó, Pál Tamás and Grusch, Michael and Szakács, Gergely}, doi = {10.1016/j.drup.2023.101007}, journal-iso = {DRUG RESIST UPDATE}, journal = {DRUG RESISTANCE UPDATES}, volume = {71}, unique-id = {34163799}, issn = {1368-7646}, year = {2023}, eissn = {1532-2084}, orcid-numbers = {Szebényi, Kornélia/0000-0003-1558-8372; Füredi, András/0000-0002-7883-9901; Bajtai, Eszter/0000-0002-5352-7776; Szabó, Pál Tamás/0000-0003-2260-4641} } @article{MTMT:34133474, title = {d-Idose-Based Monoaza-15-Crown-5 Lariat Ethers: Synthesis of an Elusive d-Hexose and Application of Derived Macrocycles in Enantioselective Syntheses}, url = {https://m2.mtmt.hu/api/publication/34133474}, author = {Orbán, István and Ujj, Dóra Viktória and Mátravölgyi, Béla and Holczbauer, Tamás and Rapi, Zsolt}, doi = {10.3390/sym15091714}, journal-iso = {SYMMETRY-BASEL}, journal = {SYMMETRY (BASEL)}, volume = {15}, unique-id = {34133474}, abstract = {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.}, year = {2023}, eissn = {2073-8994}, orcid-numbers = {Ujj, Dóra Viktória/0000-0003-0724-9346; Mátravölgyi, Béla/0000-0001-8782-7972; Rapi, Zsolt/0000-0002-6035-5482} } @article{MTMT:34062061, title = {Cu(II) and Zn(II) Complexes of New 8-Hydroxyquinoline Schiff Bases: Investigating Their Structure, Solution Speciation, and Anticancer Potential}, url = {https://m2.mtmt.hu/api/publication/34062061}, author = {Côrte-Real, Leonor and Pósa, Vivien and Martins, Matilde and Colucas, Raquel and May, Nóra Veronika and Fontrodona, Xavier and Romero, Isabel and Mendes, Filipa and Pinto Reis, Catarina and Gaspar, Maria Manuela and Pessoa, João Costa and Enyedy, Éva Anna and Correia, Isabel}, doi = {10.1021/acs.inorgchem.3c01066}, journal-iso = {INORG CHEM}, journal = {INORGANIC CHEMISTRY}, volume = {62}, unique-id = {34062061}, issn = {0020-1669}, year = {2023}, eissn = {1520-510X}, pages = {11466-11486}, orcid-numbers = {Colucas, Raquel/0009-0005-6634-3123; May, Nóra Veronika/0000-0003-4770-4681; Romero, Isabel/0000-0003-4805-8394; Mendes, Filipa/0000-0003-0646-1687; Gaspar, Maria Manuela/0000-0001-6814-7226; Enyedy, Éva Anna/0000-0002-8058-8128; Correia, Isabel/0000-0001-7096-4284} } @article{MTMT:34037734, title = {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}, url = {https://m2.mtmt.hu/api/publication/34037734}, author = {Deák, Andrea Beáta and Szabó, Pál Tamás and Bednaříková, Vendula and Cihlář, Jaroslav and Demeter, Attila and Remešová, Michaela and Colacino, Evelina and Čelko, Ladislav}, doi = {10.3389/fchem.2023.1178225}, journal-iso = {FRONT CHEM}, journal = {FRONTIERS IN CHEMISTRY}, volume = {11}, unique-id = {34037734}, issn = {2296-2646}, abstract = {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.}, year = {2023}, eissn = {2296-2646}, orcid-numbers = {Szabó, Pál Tamás/0000-0003-2260-4641} } @article{MTMT:33810076, title = {Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations—An In Vitro-Ex Vivo Study}, url = {https://m2.mtmt.hu/api/publication/33810076}, author = {Kocsis, Dorottya and Varga, Petra Regina and Keshwan, Rusul and Nader, Mina and Lengyel, Miléna and Szabó, Pál Tamás and Antal, István and Kánai, Károly and Keglevich, György and Erdő, Franciska}, doi = {10.3390/pharmaceutics15051464}, journal-iso = {PHARMACEUTICS}, journal = {PHARMACEUTICS}, volume = {15}, unique-id = {33810076}, issn = {1999-4923}, abstract = {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.}, year = {2023}, eissn = {1999-4923}, orcid-numbers = {Kocsis, Dorottya/0000-0001-7908-3248; Lengyel, Miléna/0000-0001-8865-054X; Szabó, Pál Tamás/0000-0003-2260-4641; Antal, István/0000-0002-5434-201X; Keglevich, György/0000-0002-5366-472X; Erdő, Franciska/0000-0001-6265-3777} } @article{MTMT:33709446, title = {Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus}, url = {https://m2.mtmt.hu/api/publication/33709446}, author = {Krstić, Gordana and Saidu, Muhammad Bello and Bombicz, Petra and De, Sourav and Ali, Hazhmat and Zupkó, István and Berkecz, Róbert and Gallah, Umar Shehu and Rédei, Dóra and Hohmann, Judit}, doi = {10.1021/acs.jnatprod.2c01132}, journal-iso = {J NAT PROD}, journal = {JOURNAL OF NATURAL PRODUCTS}, volume = {86}, unique-id = {33709446}, issn = {0163-3864}, year = {2023}, eissn = {1520-6025}, pages = {891-896}, orcid-numbers = {Krstić, Gordana/0000-0001-6945-6178; Bombicz, Petra/0000-0002-5509-1515; De, Sourav/0000-0003-3014-8084; Zupkó, István/0000-0003-3243-5300; Berkecz, Róbert/0000-0002-9076-2177; Rédei, Dóra/0000-0002-5013-247X; Hohmann, Judit/0000-0002-2887-6392} } @article{MTMT:33656921, title = {An Unexpected Enzyme in Vascular Smooth Muscle Cells: Angiotensin II Upregulates Cholesterol-25-Hydroxylase Gene Expression}, url = {https://m2.mtmt.hu/api/publication/33656921}, author = {Kovács, Kinga Bernadett and Szalai, Laura and Szabó, Pál Tamás and Gém, Janka Borbála and Barsi, Szilvia and Szalai, Bence and Perey-Simon, Bernadett and Turu, Gábor and Tóth, András and Várnai, Péter and Hunyady, László and Balla, András}, doi = {10.3390/ijms24043968}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {24}, unique-id = {33656921}, issn = {1661-6596}, abstract = {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.}, year = {2023}, eissn = {1422-0067}, orcid-numbers = {Kovács, Kinga Bernadett/0000-0003-0912-3843; Szabó, Pál Tamás/0000-0003-2260-4641; Barsi, Szilvia/0000-0002-8779-2383; Szalai, Bence/0000-0002-9320-5704; Turu, Gábor/0000-0002-4421-3812; Tóth, András/0000-0003-2746-9370; Várnai, Péter/0000-0002-7777-806X; Hunyady, László/0000-0002-8438-7251; Balla, András/0000-0002-6450-2793} } @article{MTMT:33635097, title = {Enantioseparation of P-Stereogenic 1-Adamantyl Arylthiophosphonates and Their Stereospecific Transformation to 1-Adamantyl Aryl-H-phosphinates}, url = {https://m2.mtmt.hu/api/publication/33635097}, author = {Varga, Bence and Buna, Levente and Vincze, Daniella and Holczbauer, Tamás and Mátravölgyi, Béla and Fogassy, Elemér and Keglevich, György and Bagi, Péter}, doi = {10.3390/molecules28041584}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {28}, unique-id = {33635097}, issn = {1420-3049}, abstract = {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.}, year = {2023}, eissn = {1420-3049}, orcid-numbers = {Mátravölgyi, Béla/0000-0001-8782-7972; Bagi, Péter/0000-0002-9043-6435} }