TY - JOUR AU - Liu, Junjie AU - Wang, Xiaoyu AU - Li, Xiaolei AU - Ni, Cheng AU - Liu, Lei AU - Bányai, István AU - Shi, Xiangyang AU - Song, Cong TI - Structural and Property Characterizations of Dual‐Responsive Core–Shell Tecto Dendrimers for Tumor Penetration and Gene Delivery Applications JF - MACROMOLECULAR RAPID COMMUNICATIONS J2 - MACROMOL RAPID COMM VL - 45 PY - 2024 IS - 17 PG - 11 SN - 1022-1336 DO - 10.1002/marc.202400251 UR - https://m2.mtmt.hu/api/publication/35261424 ID - 35261424 AB - Core–shell tecto dendrimers (CSTDs) with excellent physicochemical properties and good tumor penetration and gene transfection efficiency have been demonstrated to have the potential to replace high‐generation dendrimers in biomedical applications. However, their characterization and related biological properties of CSTDs for enhanced tumor penetration and gene delivery still lack in‐depth investigation. Herein, three types of dual‐responsive CSTDs are designed for thorough physicochemical characterization and investigation of their tumor penetration and gene delivery efficiency. Three types of CSTDs are prepared through phenylborate ester bonds of phenylboronic acid (PBA)‐decorated generation 5 (G5) poly(amidoamine) (PAMAM) dendrimers as cores and monose (galactose, glucose, or mannose)‐conjugated G3 PAMAM dendrimers as shells and thoroughly characterized via NMR and other techniques. It is shown that the produced CSTDs display strong correlation signals between the PBA and monose protons, similar hydrodynamic diameters, and dual reactive oxygen species‐ and pH‐responsivenesses. The dual‐responsive CSTDs are proven to have structure‐dependent tumor penetration property and gene delivery efficiency in terms of small interference RNA for gene silencing and plasmid DNA for gene editing, thus revealing a great potential for different biomedical applications. LA - English DB - MTMT ER - TY - JOUR AU - Czenke, Zoltán AU - Mándi, Attila AU - Király, Sándor Balázs AU - Kiss, Attila AU - Kónya-Ábrahám, Anita AU - Kurucz-Szabados, Anna AU - Cserepes, Krisztián AU - Bényei, Attila Csaba AU - Zhang, Changsheng AU - Kicsák, Máté AU - Kurtán, Tibor TI - VCD Analysis of Axial Chirality in Synthetic Stereoisomeric Biaryl-Type bis-Isochroman Heterodimers with Isolated Blocks of Central and Axial Chirality JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 25 PY - 2024 IS - 17 PG - 22 SN - 1661-6596 DO - 10.3390/ijms25179657 UR - https://m2.mtmt.hu/api/publication/35256734 ID - 35256734 AB - Optically active heterodimeric 5,5′-linked bis-isochromans, containing a stereogenic ortho-trisubstituted biaryl axis and up to four chirality centers, were synthesized stereoselectively by using a Suzuki–Miyaura biaryl coupling reaction of optically active isochroman and 1-arylpropan-2-ol derivatives, providing the first access to synthetic biaryl-type isochroman dimers. Enantiomeric pairs and stereoisomers up to seven derivatives were prepared with four different substitution patterns, which enabled us to test how OR, ECD, and VCD measurements and DFT calculations can be used to determine parallel central and axial chirality elements in three isolated blocks of chirality. In contrast to natural penicisteckins A–D and related biaryls, the ECD spectra and OR data of (aS) and (aR) atropodiastereomers did not reflect the opposite axial chirality, but they were characteristic of the central chirality. The atropodiastereomers showed consistently near-mirror-image VCD curves, allowing the determination of axial chirality with the aid of DFT calculation or by comparison of characteristic VCD transitions. LA - English DB - MTMT ER - TY - CHAP AU - Garda, Zoltán AU - Lacerda, Sara AU - Jakabné Tóth, Éva ED - Geraldes, Carlos F.G.C. TI - Mn-Based Small Complexes as MRI Contrast Agents T2 - Lanthanide and Other Transition Metal Ion Complexes and Nanoparticles in Magnetic Resonance Imaging PB - CRC Press CY - Boca Raton, Florida SN - 9781003374688 T3 - Metal Ions in Life Sciences, ISSN 1559-0836 ; 27. PY - 2024 SP - 151 EP - 180 PG - 30 DO - 10.1201/9781003374688-5 UR - https://m2.mtmt.hu/api/publication/35191235 ID - 35191235 LA - English DB - MTMT ER - TY - JOUR AU - Garda, Zoltán AU - Szeremeta, Frédéric AU - Quin, Océane AU - Molnár, Enikő AU - Váradi, Balázs AU - Clémençon, Rudy AU - Même, Sandra AU - Pichon, Chantal AU - Tircsó, Gyula AU - Jakabné Tóth, Éva TI - Small, Fluorinated Mn2+ Chelate as an Efficient 1H and 19F MRI Probe. JF - ANGEWANDTE CHEMIE-INTERNATIONAL EDITION J2 - ANGEW CHEM INT EDIT PY - 2024 SP - e202410998 PG - 8 SN - 1433-7851 DO - 10.1002/anie.202410998 UR - https://m2.mtmt.hu/api/publication/35161067 ID - 35161067 N1 - Accepted AB - We explore the potential of fluorine-containing small Mn2+ chelates as alternatives to perfluorinated nanoparticles, widely used as 19F MRI probes. In MnL1, the cyclohexanediamine skeleton and two piperidine rings, involving each a metal-coordinating amide group and an appended CF3 moiety, provide high rigidity to the complex. This allows for good control of the Mn-F distance (rMnF = 8.2±0.2 Å determined from 19F relaxation data), as well as for high kinetic inertness (a dissociation half-life of 1285 h is estimated for physiological conditions). The paramagnetic Mn2+ leads to a ~150-fold acceleration of the longitudinal 19F relaxation, with moderate line-broadening effect, resulting in T2/T1 ratios of 0.8 (9.4 T). Owing to its inner sphere water molecule, MnL1 is a good 1H relaxation agent as well (r1 = 5.36 mM-1s-1 at 298K, 20MHz). MnL1 could be readily visualized in 19F MRI by using fast acquisition techniques, both in phantom images and living mice following intramuscular injection, with remarkable signal-to-noise ratios and short acquisition times. While applications in targeted imaging or cell therapy monitoring require further optimisation of the molecular structure, these results argue for the potential of such small, monohydrated and fluorinated Mn2+ complexes for combined 19F and 1H MRI detection. LA - English DB - MTMT ER - TY - GEN AU - Lente, Gábor TI - Mind a négy magyar versenyző érmet nyert a kémiai diákolimpián PY - 2024 UR - https://m2.mtmt.hu/api/publication/35153631 ID - 35153631 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Sándor, Balázs AU - Hőgyéné Grenács, Ágnes Judit AU - Nagy, Lajos AU - Hollóczki, Oldamur AU - Várnagy, Katalin TI - Complex Formation and Hydrolytic Processes of Protected Peptides Containing the –SXH– Motif in the Presence of Nickel(II) Ion JF - CHEMBIOCHEM J2 - CHEMBIOCHEM VL - & PY - 2024 SN - 1439-4227 DO - 10.1002/cbic.202400475 UR - https://m2.mtmt.hu/api/publication/35134053 ID - 35134053 AB - Interactions between metal ions and proteins are considered reversible, such as the coordination of a metal ion to a protein or enzyme, but irreversible processes like the oxidative reactions, aggregation or hydrolytic processes may occur. In the presence of Ni(II)‐ions selective hydrolysis of the peptides containing the –SXH– or –TXH– motif was observed. Since the side chain of histidine serves as the metal ion binding site for many native proteins, and very often histidine is present in a –SXH– or –TXH– sequence, to study the complex formation and hydrolytic processes in presence of nickel(II) ion four peptides were synthesised: Ac‐SKHM‐NH2, A3SSH‐NH2, A4SSH‐NH2, AAAeKSH‐NH2. The Ni(II)‐induced hydrolysis of Ac‐SKHM‐NH2 peptide occurs rapidly in alkaline medium already at room temperature. In two peptides containing –SSH– sequence on the C‐termini, the N‐terminal part is the major binding site for the nickel(II) ion, but the formation of dinuclear complexes was also observed. In the [Ni2LH–6]2– complex of hexapeptide, the coordination sphere of the metal ions is saturated with deprotonated Ser‐O–, which does not result in hydrolysis of the peptide. For A4SSH‐NH2, both Ni(II) ions fulfill the conditions for hydrolysis, which was confirmed by HPLC analyses at pH ~ 8.2 and 25 °C. LA - English DB - MTMT ER - TY - JOUR AU - Papp, Vanda AU - Janovics, Róbert AU - Kéri, Mónika TI - NMR characterization of the permeability and structure of Boda Claystone Formation (BCF) BCF - reservoir rock by NMR JF - SCIENTIA ET SECURITAS J2 - SCI SEC VL - 4 PY - 2024 IS - 4 SP - 285 EP - 293 PG - 9 SN - 2732-2688 DO - 10.1556/112.2023.00187 UR - https://m2.mtmt.hu/api/publication/34922285 ID - 34922285 N1 - Kötetszámozás: Volume 4 (2023.), Issue 4 (4. füzet) AB - High-level radioactive waste can be safely disposed of in deep geological repositories, for which a possible geological environment in Hungary is the Boda Claystone Formation. In the repository site selection, the geochemical investigation of the host rock is necessary including the structural characterization. In this study, the porosity (p%~1.5% and 5.84%) and the T2cutoff value (0.12 ms and 0.10 ms) of two siliciclastic rocks was determined by desktop low-field NMR, the value of which differed from the 3 ms accepted for clay-bound water and the 33 ms for movable water in clastic reservoirs. Based on the T2cutoff, the producible porosity was found to be high, however, based on the T2 distributions, the bound-water types dominate the composition of the water phase of the rock. LA - English DB - MTMT ER - TY - JOUR AU - Dunkel, Petra AU - Bogdán, Dóra AU - Deme, Ruth AU - Zimber, Ádám AU - Ballayová, Veronika AU - Csizmadia, Eszter AU - Kontra, Bence AU - Kalydi, Eszter AU - Bényei, Attila Csaba AU - Mátyus, Péter AU - Mucsi, Zoltán TI - C(sp 3 )–H cyclizations of 2-(2-vinyl)phenoxy- tert -anilines JF - RSC ADVANCES J2 - RSC ADV VL - 14 PY - 2024 IS - 24 SP - 16784 EP - 16800 PG - 17 SN - 2046-2069 DO - 10.1039/D3RA08974F UR - https://m2.mtmt.hu/api/publication/34873088 ID - 34873088 N1 - Department of Organic Chemistry, Semmelweis University, Hőgyes Endre utca 7, Budapest, H-1092, Hungary Department of Chemical Drugs, Masaryk University, Palackého 1946/1, Brno, 612, Czech Republic Department of Biological Chemistry, Brain Vision Center, Liliom utca 43-45, Budapest, H-1094, Hungary Institute of Physical Chemistry, University of Debrecen, Egyetem tér 1, Debrecen, H-4010, Hungary University of Veterinary Medicine, István utca 2, Budapest, H-1078, Hungary Department of Chemistry, Femtonics Ltd, Tűzoltó utca 59, Budapest, H-1094, Hungary Institute of Chemistry, University of Miskolc, Egyetem út 1, Miskolc, H-3515, Hungary Export Date: 04 June 2024; Cited By: 0; Correspondence Address: P. Dunkel; Department of Organic Chemistry, Semmelweis University, Budapest, Hőgyes Endre utca 7, H-1092, Hungary; email: dunkel.petra@semmelweis.hu; Z. Mucsi; Department of Biological Chemistry, Brain Vision Center, Budapest, Liliom utca 43-45, H-1094, Hungary; email: zmucsi@femtonics.eu; CODEN: RSCAC AB - Cyclizations of 2-(2-vinyl)phenoxy- tert -anilines under thermal conditions yield oxazonine or octahydro-dipyrroloquinoline products. The transformations can be considered as further extensions of [1, n ]-H transfer and cyclization of tertiary anilines. LA - English DB - MTMT ER - TY - JOUR AU - Bunda, Szilvia AU - Kálmán-Szabó, Ibolya AU - Lihi, Norbert AU - Képes, Zita AU - Szikra, Dezső AU - Péliné Szabó, Judit AU - Timári, István AU - Szücs, Dániel AU - May, Nóra Veronika AU - Papp, Gábor Csaba AU - Trencsényi, György AU - Kálmán, Ferenc Krisztián TI - Diagnosis of Melanoma with 61Cu-Labeled PET Tracer JF - JOURNAL OF MEDICINAL CHEMISTRY J2 - J MED CHEM VL - 67, PY - 2024 IS - 11 SP - 9342 EP - 9354 PG - 13 SN - 0022-2623 DO - 10.1021/acs.jmedchem.4c00479 UR - https://m2.mtmt.hu/api/publication/34861986 ID - 34861986 N1 - Funding Agency and Grant Number: Magyar Tudom?nyos Akad?mia [FK-134551]; Hungarian National Research, Development and Innovation Office [UNKP-23-5, UNKP-23-4-II]; New National Excellence Program; National Research, Development and Innovation Fund; Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences; Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund; University of Debrecen Scientific Research Bridging Fund Funding text: The research was funded by the Hungarian National Research, Development and Innovation Office (FK-134551) project, the New National Excellence Program UNKP-23-5, and the UNKP-23-4-II New National Excellence Program of The Ministry for Culture and Innovation from the source of the National Research, Development and Innovation Fund (K.Z.). F.K.K. and N.L. acknowledge the financial support of the Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences. The authors are indebted to KIFU for awarding access to the resources based in Hungary. The research was supported by the KDP-2021 program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund (G.T. and I.K.-S.). This work is also supported by the University of Debrecen Scientific Research Bridging Fund (DETKA). AB - Until the recent years, substances containing radioactive Cu-61 were strongly considered as potential positron-emitting radiopharmaceuticals for use in positron emission tomography (PET) applications; however, due to their suitably long half-life, and generator-independent and cost-effective production, they seem to be economically viable for human imaging. Since malignant melanoma (MM) is a major public health problem, its early diagnosis is a crucial contributor to long-term survival, which can be achieved using radiolabeled alpha-melanocyte-stimulating hormone analog NAPamide derivatives. Here, we report on the physicochemical features of a new CB-15aneN(5)-based Cu(II) complex ([Cu(KFTGdiac)](-)) and the ex vivo and in vivo characterization of its NAPamide conjugate. The rigid chelate possesses prompt complex formation and suitable inertness (t(1/2) = 18.4 min in 5.0 M HCl at 50 degrees C), as well as excellent features in the diagnosis of B16-F10 melanoma tumors (T/M(SUVs) (in vivo): 12.7, %ID/g: 6.6 +/- 0.3, T/M (ex vivo): 22). LA - English DB - MTMT ER - TY - JOUR AU - Kajtár, Mihály AU - Király, Sándor Balázs AU - Bényei, Attila Csaba AU - Kiss, Attila AU - Kónya-Ábrahám, Anita AU - Zhang, Ning AU - Horváth, Lilla AU - Bősze, Szilvia AU - Li, Dehai AU - Kotschy, András AU - Paczal, Attila AU - Kurtán, Tibor TI - Competing Domino Knoevenagel-Cyclization Sequences with N -Arylcinnamylamines JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 89 PY - 2024 IS - 10 SP - 6937 EP - 6950 PG - 14 SN - 0022-3263 DO - 10.1021/acs.joc.4c00299 UR - https://m2.mtmt.hu/api/publication/34846781 ID - 34846781 AB - Domino Knoevenagel-cyclization reactions of Narylcinnamylamines were carried out with active methylene reagents, which took place with five competing cyclization mechanisms: intramolecular hetero Diels-Alder reaction, stepwise polar [2 + 2] cycloaddition, styryl or aza-Diels-Alder reactions followed by rearomatization, and [1,5]-hydride shift-6-endo cyclization. In the stepwise aza-Diels-Alder reaction, the Nvinylpyridinium moiety acted as an azadiene, producing a condensed heterocycle with tetrahydroquinolizinium and tetrahydroquiniline subunits. Antiproliferative activity with low micromolar IC50 values was identified for some of the novel scaffolds. LA - English DB - MTMT ER -