TY - GEN AU - Szirmai, Ádám B. AU - Barcza, Bónis AU - Tajti, Attila AU - Szalay, Péter TI - Accuracy of projected atomic virtual orbital space in embedding applications PY - 2024 UR - https://m2.mtmt.hu/api/publication/34829174 ID - 34829174 LA - English DB - MTMT ER - TY - JOUR AU - Jelenfi, Dávid Péter AU - Tajti, Attila AU - Szalay, Péter TI - Interpretation of molecular electron transport in ab initio many-electron framework incorporating zero-point nuclear motion effects JF - JOURNAL OF COMPUTATIONAL CHEMISTRY J2 - J COMPUT CHEM PY - 2024 SN - 0192-8651 DO - 10.1002/jcc.27381 UR - https://m2.mtmt.hu/api/publication/34829162 ID - 34829162 LA - English DB - MTMT ER - TY - JOUR AU - Meiszter, Enikő AU - Gazdag, Tamás AU - Mayer, Péter J. AU - Kunfi, Attila AU - Holczbauer, Tamás AU - Sulyok-Eiler, Máté AU - London, Gábor TI - Revisiting Hafner’s Azapentalenes: The Chemistry of 1,3-Bis(dimethylamino)-2-azapentalene JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM PY - 2024 PG - 11 SN - 0022-3263 DO - 10.1021/acs.joc.3c02564 UR - https://m2.mtmt.hu/api/publication/34821706 ID - 34821706 AB - Stable azaheterocyclic derivatives of pentalene have been reported by the group of Hafner in the 1970s. However, these structures remained of low interest until recently, when they started to be investigated in the context of organic light-emitting diodes’ (OLEDs’) development. Herein, we revisit the synthesis of stable azapentalene derivative 1,3-bis(dimethylamino)-2-azapentalene and further explore its properties both computationally and experimentally. Beyond the reproduction and optimization of some previously reported transformations, such as formylation and amine substitution, the available scope of reactions was expanded with azo-coupling, selective halogenations, and cross-coupling reactions. © 2024 The Authors. Published by American Chemical Society. LA - English DB - MTMT ER - TY - JOUR AU - el Battioui, Kamal AU - Chakraborty, Sohini AU - Wacha, András AU - Molnár, Dániel AU - Quemé-Peña, Mayra AU - Szigyártó, Imola Cs. AU - Szabó, Csenge Lilla AU - Bodor, Andrea AU - Horváti, Kata AU - Gyulai, Gergő AU - Bősze, Szilvia AU - Mihály, Judith AU - Jezsó, Bálint AU - Románszki, Loránd AU - Tóth, Judit AU - Varga, Zoltán AU - Mándity, István AU - Juhász, Tünde AU - Beke-Somfai, Tamás TI - In situ captured antibacterial action of membrane-incising peptide lamellae JF - NATURE COMMUNICATIONS J2 - NAT COMMUN VL - 15 PY - 2024 IS - 1 PG - 14 SN - 2041-1723 DO - 10.1038/s41467-024-47708-4 UR - https://m2.mtmt.hu/api/publication/34819821 ID - 34819821 AB - Developing unique mechanisms of action are essential to combat the growing issue of antimicrobial resistance. Supramolecular assemblies combining the improved biostability of non-natural compounds with the complex membrane-attacking mechanisms of natural peptides are promising alternatives to conventional antibiotics. However, for such compounds the direct visual insight on antibacterial action is still lacking. Here we employ a design strategy focusing on an inducible assembly mechanism and utilized electron microscopy (EM) to follow the formation of supramolecular structures of lysine-rich heterochiral β 3 -peptides, termed lamellin-2K and lamellin-3K, triggered by bacterial cell surface lipopolysaccharides. Combined molecular dynamics simulations, EM and bacterial assays confirmed that the phosphate-induced conformational change on these lamellins led to the formation of striped lamellae capable of incising the cell envelope of Gram-negative bacteria thereby exerting antibacterial activity. Our findings also provide a mechanistic link for membrane-targeting agents depicting the antibiotic mechanism derived from the in-situ formation of active supramolecules. LA - English DB - MTMT ER - TY - JOUR AU - Chen, Pengwen AU - Li, Shangwei AU - Xu, Zhining AU - Cabral, Horacio TI - Nanoassemblies of heptamethine cyanine dye-initiated poly(amino acid) enhance ROS generation for effective antitumour phototherapy. JF - Nanoscale Horizons J2 - NANOSCALE HORIZ PY - 2024 SN - 2055-6756 DO - 10.1039/d3nh00584d UR - https://m2.mtmt.hu/api/publication/34816178 ID - 34816178 AB - Phototherapy shows great potential for pinpoint tumour treatment. Heptamethine cyanine dyes like IR783 have high potential as agents for antitumour phototherapy due to their inherent tumour targeting ability, though their effectiveness in vivo is unsatisfactory for clinical translation. To overcome this limitation, we present an innovative strategy involving IR783-based polymeric nanoassemblies that improve the dye's performance as an antitumoural photosensitizer. In the formulation, IR783 is modified with cysteamine and used to initiate the ring-opening polymerization (ROP) of the N-carboxyanhydride of benzyl-L-aspartate (BLA), resulting in IR783-installed poly(BLA). Compared to free IR783, the IR783 dye in the polymer adopts a twisted molecular conformation and tuned electron orbital distribution, remarkably enhancing its optical properties. In aqueous environments, the polymers spontaneously assemble into nanostructures with 60 nm diameter, showcasing surface-exposed IR783 dyes that function as ligands for cancer cell and mitochondria targeting. Moreover, the nanoassemblies stabilized the dyes and enhanced the generation of reactive oxygen species (ROS) upon laser irradiation. Thus, in murine tumor models, a single injection of the nanoassemblies with laser irradiation significantly inhibits tumour growth with no detectable off-target toxicity. These findings highlight the potential for improving the performance of heptamethine cyanine dyes in antitumor phototherapy through nano-enabled strategies. LA - English DB - MTMT ER - TY - JOUR AU - Szaniszló, Szebasztián AU - Csámpai, Antal AU - Horváth, Dániel AU - Tomecz, Richárd AU - Farkas, Viktor AU - Perczel, András TI - Unveiling the Oxazolidine Character of Pseudoproline Derivatives by Automated Flow Peptide Chemistry JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 25 PY - 2024 IS - 8 SP - 4150 SN - 1661-6596 DO - 10.3390/ijms25084150 UR - https://m2.mtmt.hu/api/publication/34781847 ID - 34781847 AB - Pseudoproline derivatives such as Thr(ΨPro)-OH are commonly used in peptide synthesis to reduce the likelihood of peptide aggregation and to prevent aspartimide (Asi) formation during the synthesis process. In this study, we investigate notable by-products such as aspartimide formation and an imine derivative of the Thr(ΨPro) moiety observed in flow peptide chemistry synthesis. To gain insight into the formation of these unexpected by-products, we design a series of experiments. Furthermore, we demonstrate the oxazolidine character of the pseudoproline moiety and provide plausible mechanisms for the two-way ring opening of oxazolidine leading to these by-products. In addition, we present evidence that Asi formation appears to be catalyzed by the presence of the pseudoproline moiety. These observed side reactions are attributed to elevated temperature and pressure; therefore, caution is advised when using ΨPro derivatives under such harsh conditions. In addition, we propose a solution whereby thermodynamically controlled Asi formation can be kinetically prevented. LA - English DB - MTMT ER - TY - JOUR AU - Tarchoun, Karima AU - Soltész, Dóra AU - Farkas, Viktor AU - Lee, Ho-Jin AU - Szabó, Ildikó AU - Bánóczi, Zoltán TI - Influence of Aza-Glycine Substitution on the Internalization of Penetratin JF - PHARMACEUTICS J2 - PHARMACEUTICS VL - 16 PY - 2024 IS - 4 SP - 477 SN - 1999-4923 DO - 10.3390/pharmaceutics16040477 UR - https://m2.mtmt.hu/api/publication/34765015 ID - 34765015 AB - The cell-penetrating peptide (CPP) penetratin has gained much attention over many years due to its potential role as a transporter for a broad range of cargo into cells. The modification of penetratin has been extensively investigated too. Aza-peptides are peptide analogs in which one or more of the amino residues are replaced by a semicarbazide. This substitution results in conformational restrictions and modifications in hydrogen bonding properties, which affect the structure and may lead to enhanced activity and selectivity of the modified peptide. In this work, the Trp residues of penetratin were substituted by aza-glycine or glycine residues to examine the effect of these modifications on the cellular uptake and the internalization mechanism. The substitution of Trp48 or Trp48,56 dramatically reduced the internalization, showing the importance of Trp48 in cellular uptake. Interestingly, while aza-glycine in the position of Trp56 increased the cellular uptake, Gly reduced it. The two Trp-modified derivatives showed altered internalization pathways, too. Based on our knowledge, this is the first study about the effect of aza-amino acid substitution on the cell entry of CPPs. Our results suggest that aza-amino acid insertion is a useful modification to change the internalization of a CPP. LA - English DB - MTMT ER - TY - JOUR AU - Béres, Kende Attila AU - Dürvanger, Zsolt AU - Homonnay, Zoltán AU - Nagyné Bereczki, Laura AU - Barta Holló, Berta AU - Farkas, Attila AU - Petruševski, Vladimir M. AU - Kótai, László TI - Insight into the Structure and Redox Chemistry of [Carbonatotetraamminecobalt(III)] Permanganate and Its Monohydrate as Co-Mn-Oxide Catalyst Precursors of the Fischer-Tropsch Synthesis JF - INORGANICS J2 - INORGANICS VL - 12 PY - 2024 IS - 4 SP - 94 SN - 2304-6740 DO - 10.3390/inorganics12040094 UR - https://m2.mtmt.hu/api/publication/34753165 ID - 34753165 AB - [Carbonatotetraamminecobalt(III)] permanganate monohydrate was synthesized first in the metathesis reaction of [Co(NH3)4CO3]NO3 and NaMnO4 in aqueous solution. Its thermal dehydration at 100 °C resulted in phase-pure [Co(NH3)4CO3]MnO4 (compound 1). Compounds 1 and 2 (i.e., the hydrated form) were studied with IR, far-IR, and low-temperature Raman spectroscopies, and their vibrational modes were assigned. The lattice parameters were determined by powder X-ray diffraction (PXRD) and single crystal X-ray diffraction (SXRD) methods for the triclinic and orthorhombic compounds 1 and 2, respectively. The detailed structure of compound 2 was determined, and the role of hydrogen bonds in the structural motifs was clarified. UV studies on compounds 1 and 2 showed the distortion of the octahedral geometry of the complex cation during dehydration because of the partial loss of the hydrogen bonds between the crystal water and the ligands of the complex cation. The thermal decomposition consists of a solid phase quasi-intramolecular redox reaction between the ammonia ligands and permanganate anions with the formation of ammonia oxidation products (H2O, NO, N2O, and CO2). The solid phase reaction product is amorphous cobalt manganese oxide containing ammonium, carbonate (and nitrate) anions. The temperature-controlled thermal decomposition of compound 2 in toluene at 110 °C showed that one of the decomposition intermediates is ammonium nitrate. The decomposition intermediates are transformed into Co1.5Mn1.5O4 spinel with MnCo2O4 structure upon further heating. Solid compound 2 gave the spinel at 500 °C both in an inert and air atmosphere, whereas the sample pre-treated in toluene at 110 °C without and with the removal of ammonium nitrate by aqueous washing, gave the spinel already at 300 and 400 °C, respectively. The molten NH4NO3 is a medium to start spinel crystallization, but its decomposition stops further crystal growth of the spinel phase. By this procedure, the particle size of the spinel product as low as ~4.0 nm could be achieved for the treatments at 300 and 400 °C, and it increased only to 5.7 nm at 500 °C. The nano-sized mixed cobalt manganese oxides are potential candidates as Fischer-Tropsch catalysts. LA - English DB - MTMT ER - TY - JOUR AU - Csomos, Attila AU - Madarász, Miklós AU - Turczel, Gábor AU - Cseri, Levente AU - Katona, Gergely AU - Rózsa J., Balázs AU - Kovács, Ervin AU - Mucsi, Zoltán TI - A Molecular Hybrid of the GFP Chromophore and 2,2′-Bipyridine: An Accessible Sensor for Zn2+ Detection with Fluorescence Microscopy JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 25 PY - 2024 IS - 6 PG - 14 SN - 1661-6596 DO - 10.3390/ijms25063504 UR - https://m2.mtmt.hu/api/publication/34748236 ID - 34748236 N1 - Department of Chemistry, Femtonics Ltd, Tűzoltó utca 59, Budapest, H-1094, Hungary Hevesy György PhD School of Chemistry, Eötvös Loránd University, Pázmány Péter sétány 1/A, Budapest, H-1117, Hungary BrainVisionCenter, Liliom utca 43, Budapest, H-1094, Hungary NMR Research Laboratory, HUN-REN Research Centre for Natural Sciences, Magyar Tudósok körútja 2, Budapest, H-1117, Hungary Department of Organic Chemistry & Technology, Budapest University of Technology & Economics, 3. Muegyetem rakpart, Budapest, H-1111, Hungary Two-Photon Measurement Technology Research Group, Pázmány Péter Catholic University, Práter utca 50/a, Budapest, H-1083, Hungary Laboratory of 3D Functional Network and Dendritic Imaging, Institute of Experimental Medicine, Szigony utca 43, Budapest, H-1083, Hungary Polymer Chemistry and Physics Research Group, HUN-REN Research Centre for Natural Sciences, Magyar Tudósok körútja 2, Budapest, H-1117, Hungary Faculty of Materials and Chemical Sciences, University of Miskolc, Miskolc, H-3515, Hungary Export Date: 12 April 2024 Correspondence Address: Rózsa, B.; BrainVisionCenter, Liliom utca 43, Hungary; email: rozsabal@koki.hu Correspondence Address: Kovács, E.; Two-Photon Measurement Technology Research Group, Práter utca 50/a, Hungary; email: kovacs.ervin@ttk.hu AB - The few commercially available chemosensors and published probes for in vitro Zn2+ detection in two-photon microscopy are compromised by their flawed spectroscopic properties, causing issues in selectivity or challenging multistep syntheses. Herein, we present the development of an effective small molecular GFP chromophore-based fluorescent chemosensor with a 2,2′-bipyridine chelator moiety (GFZnP BIPY) for Zn2+ detection that has straightforward synthesis and uncompromised properties. Detailed experimental characterizations of the free and the zinc-bound compounds within the physiologically relevant pH range are presented. Excellent photophysical characteristics are reported, including a 53-fold fluorescence enhancement with excitation and emission maxima at 422 nm and 492 nm, respectively. A high two-photon cross section of 3.0 GM at 840 nm as well as excellent metal ion selectivity are reported. In vitro experiments on HEK 293 cell culture were carried out using two-photon microscopy to demonstrate the applicability of the novel sensor for zinc bioimaging. LA - English DB - MTMT ER - TY - CONF AU - Schlosser, Gitta (Vácziné) AU - Molnár, Adrienn AU - Papp, Dávid AU - Gellén, Gabriella AU - Virág, Dávid AU - Ludányi, Krisztina AU - Dalmadi Kiss, Borbála AU - Arko, Matevž AU - Iglič, Aleš AU - Svete Nemec, Alenka AU - Erjavec, Vladimira AU - Kralj-Iglič, Veronika TI - Omics Mass Spectrometry Analysis of Canine Plasma T2 - Proceedings of 10th Socratic Lectures PB - University of Lubljana Press C1 - Ljubljana SN - 9789612972660 PY - 2024 SP - 67 EP - 72 PG - 6 DO - 10.55295/PSL.2024.I11 UR - https://m2.mtmt.hu/api/publication/34743412 ID - 34743412 AB - Abstract: Blood derived products, such as autologous plasma, have high clinical importance and are applied in numerous therapeutic fields. The preparation of autologous plasma from the patient's own blood is easy to perform by centrifugation, however, the prep-aration procedure can significantly affect the blood cells, platelets and vesicles in the sample. Therefore, it is of utmost importance to understand the impact of sample pro-cessing on the chemical composition of plasma preparations as well as on their biolog-ical activity. Here, we present a mass spectrometry-based plasma profiling method in which three compound groups: lipids, proteins and glycoproteins are analysed in a single workflow. Analysis of the chemical composition of plasma samples prepared by different centrifugation protocols revealed differences in the lipid and glycoprotein profiles, demonstrating the importance of standardized protocols for the preparation of plasma products. Keywords: Plasma; Lipids; Proteins; Glycoproteins; Mass Spectrometry, Ion Mobility LA - English DB - MTMT ER -