TY - JOUR AU - Mészáros, Rebeka Ildikó AU - Szabó, Vivien AU - Kutus, Bence AU - Baán, Kornélia AU - Kónya, Zoltán AU - Kukovecz, Ákos AU - Sipos, Pál Miklós AU - Szabados, Márton TI - Continuous-flow hydrogenation of cinnamaldehyde over catalysts derived from modified CoAl4 layered double hydroxides incorporating Mn, Ni, Cu and Zn ions JF - APPLIED CATALYSIS A-GENERAL J2 - APPL CATAL A-GEN VL - 679 PY - 2024 PG - 14 SN - 0926-860X DO - 10.1016/j.apcata.2024.119738 UR - https://m2.mtmt.hu/api/publication/34801853 ID - 34801853 LA - English DB - MTMT ER - TY - JOUR AU - Háznagy, Márton Benedek AU - Csámpai, Antal AU - Ugrai, Imre AU - Barnabás, Molnár AU - Matti, Haukka AU - Szakonyi, Zsolt TI - Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 25 PY - 2024 IS - 8 PG - 25 SN - 1661-6596 DO - 10.3390/ijms25084325 UR - https://m2.mtmt.hu/api/publication/34791082 ID - 34791082 AB - A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (−)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (−)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues. LA - English DB - MTMT ER - TY - JOUR AU - Martos, Diána AU - Lőrinczi, Bálint AU - Szatmári, István AU - Vécsei, László AU - Tanaka, Masaru TI - The Impact of C-3 Side Chain Modifications on Kynurenic Acid: A Behavioral Analysis of Its Analogs in the Motor Domain JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 25 PY - 2024 IS - 6 PG - 25 SN - 1661-6596 DO - 10.3390/ijms25063394 UR - https://m2.mtmt.hu/api/publication/34743321 ID - 34743321 N1 - HUN-REN-SZTE Neuroscience Research Group, Hungarian Research Network, University of Szeged, Danube Neuroscience Research Laboratory, Tisza Lajos krt. 113, Szeged, H-6725, Hungary Institute of Pharmaceutical Chemistry and HUN-REN–SZTE Stereochemistry Research Group, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Department of Neurology, Albert Szent-Györgyi Medical School, University of Szeged, Semmelweis u. 6, Szeged, H-6725, Hungary Export Date: 9 April 2024 Correspondence Address: Vécsei, L.; HUN-REN-SZTE Neuroscience Research Group, Tisza Lajos krt. 113, Hungary; email: vecsei.laszlo@med.u-szeged.hu Correspondence Address: Tanaka, M.; HUN-REN-SZTE Neuroscience Research Group, Tisza Lajos krt. 113, Hungary; email: tanaka.masaru.1@med.u-szeged.hu Chemicals/CAS: kynurenic acid, 492-27-3; Kynurenic Acid; Neuroprotective Agents AB - The central nervous system (CNS) is the final frontier in drug delivery because of the blood–brain barrier (BBB), which poses significant barriers to the access of most drugs to their targets. Kynurenic acid (KYNA), a tryptophan (Trp) metabolite, plays an important role in behavioral functions, and abnormal KYNA levels have been observed in neuropsychiatric conditions. The current challenge lies in delivering KYNA to the CNS owing to its polar side chain. Recently, C-3 side chain-modified KYNA analogs have been shown to cross the BBB; however, it is unclear whether they retain the biological functions of the parent molecule. This study examined the impact of KYNA analogs, specifically, SZR-72, SZR-104, and the newly developed SZRG-21, on behavior. The analogs were administered intracerebroventricularly (i.c.v.), and their effects on the motor domain were compared with those of KYNA. Specifically, open-field (OF) and rotarod (RR) tests were employed to assess motor activity and skills. SZR-104 increased horizontal exploratory activity in the OF test at a dose of 0.04 μmol/4 μL, while SZR-72 decreased vertical activity at doses of 0.04 and 0.1 μmol/4 μL. In the RR test, however, neither KYNA nor its analogs showed any significant differences in motor skills at either dose. Side chain modification affects affective motor performance and exploratory behavior, as the results show for the first time. In this study, we showed that KYNA analogs alter emotional components such as motor-associated curiosity and emotions. Consequently, drug design necessitates the development of precise strategies to traverse the BBB while paying close attention to modifications in their effects on behavior. LA - English DB - MTMT ER - TY - JOUR AU - Hu, Hao-Chun AU - Yu, Szu-Yin AU - Tsi, Yi-Hong AU - Hsieh, Pei-Wen AU - Wang, Hui-Chun AU - Chen, Yan-Ning AU - Chuang, Ya-Ting AU - Lee, Min-Yu AU - Chang, Hsueh-Wei AU - Hu, Hao-Chun AU - Wu, Yang-Chang AU - Chang, Fang-Rong AU - Szatmári, István AU - Fülöp, Ferenc TI - Synthesis of bioactive evodiamine and rutaecarpine analogues under a ball milling condition JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 22 PY - 2024 IS - 13 SP - 2620 EP - 2629 PG - 10 SN - 1477-0520 DO - 10.1039/D4OB00056K UR - https://m2.mtmt.hu/api/publication/34721105 ID - 34721105 AB - Mechanochemical reactions achieved by processes such as milling and grinding offer a promising alternative to traditional solution-based chemistry. This approach not only eliminates the need for large quantities of solvents,... LA - English 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 - Gombár, Gyöngyi AU - Ungor, Ditta Anita AU - Szatmári, István AU - Juhász, Ádám AU - Csapó, Edit TI - Tryptophanhydroxamic Acid-Stabilized Ultrasmall Gold Nanoclusters: Tuning the Selectivity for Metal Ion Sensing JF - NANOMATERIALS J2 - NANOMATERIALS-BASEL VL - 14 PY - 2024 IS - 5 PG - 15 SN - 2079-4991 DO - 10.3390/nano14050434 UR - https://m2.mtmt.hu/api/publication/34689790 ID - 34689790 AB - Sub-nanometer-sized gold nanoclusters (Au NCs) were prepared via the spontaneous reduction of [AuCl4]−- ions with a hydroxamate derivative of L-tryptophan (Trp) natural amino acid (TrpHA). The prepared TrpHA-Au NCs possess intense blue emission (λem = 470 nm; λex = 380 nm) with a 2.13% absolute quantum yield and 1.47 ns average lifetime. The Trp-stabilized noble metal NCs are excellent metal ion sensors for Fe3+, but in this work, we highlighted that the incorporation of the hydroxamate functional group with an excellent metal ion binding capability can tune the selectivity and sensitivity of these NCs, which is a promising way to design novel strategies for the detection of other metal ions as well. Moreover, their simultaneous identification can also be realized. By decreasing the sensitivity of our nano-sensor for Fe3+ (limit of detection (LOD) ~11 µM), it was clearly demonstrated that the selectivity for Cu2+-ions can be significantly increased (LOD = 3.16 µM) in an acidic (pH = 3–4) condition. The surface-bounded TrpHA molecules can coordinate the Cu2+ confirmed by thermodynamic data, which strongly generates the linking of the NCs via the Cu2+ ions in acidic pH, and a parallel fluorescence quenching occurs. In the case of Fe3+, the degree of quenching strongly depends on the metal ion concentration, and it only occurs when the NCs are not able to bind more Fe3+ (~10 µM) on the surface, causing the NCs’ aggregation. LA - English DB - MTMT ER - TY - JOUR AU - Ozsvár, Dániel AU - Bózsity-Faragó, Noémi AU - Zupkó, István AU - Szakonyi, Zsolt TI - Synthesis and Study of the Structure–Activity Relationship of Antiproliferative N-Substituted Isosteviol-Based 1,3-Aminoalcohols JF - PHARMACEUTICALS J2 - PHARMACEUTICALS-BASE VL - 17 PY - 2024 IS - 2 PG - 18 SN - 1424-8247 DO - 10.3390/ph17020262 UR - https://m2.mtmt.hu/api/publication/34666945 ID - 34666945 AB - Starting from isosteviol, a series of diterpenoid 1,3-aminoalcohol derivatives were prepared via stereoselective transformations. The acid-catalysed hydrolysis and rearrangement of natural stevioside produced isosteviol, which was transformed into the key intermediate methyl ester. In the next step, an 1,3-aminoalcohol library was prepared by the reductive amination of the intermediate 3-hydroxyaldehyde obtained from isosteviol in a two-step synthesis. To study the effect of the carboxylate ester function at position 4, the free carboxylic acid, benzyl ester and acryloyl ester analogues were prepared as elongated derivatives in comparison with our earlier results in this field. The antiproliferative activity of compounds against human tumour cell lines (A2780, HeLa, MCF-7 and MDA-MB-231) was investigated. In our preliminary study, the 1,3-aminoalcohol function with N-benzyl or (1H-imidazol-1-yl)-propyl substitution and benzyl ester moiety seemed essential for the reliable antiproliferative activity. The results obtained could be a good starting point to further functionalisation towards more efficient antiproliferative diterpenes. LA - English DB - MTMT ER - TY - JOUR AU - Khdar, Zein Alabdeen AU - Le Minh, Tam AU - Schelz, Zsuzsanna AU - Zupkó, István AU - Szakonyi, Zsolt TI - Stereoselective synthesis and antiproliferative activity of allo-gibberic acid-based 1,3-aminoalcohols regioisomers JF - RSC MEDICINAL CHEMISTRY J2 - RSC MED CHEM VL - 15 PY - 2024 IS - 3 SP - 874 EP - 887 PG - 14 SN - 2632-8682 DO - 10.1039/D3MD00665D UR - https://m2.mtmt.hu/api/publication/34577084 ID - 34577084 AB - A new library of allo -gibberic acid-based aminoalcohol regioisomers was synthesised stereoselectively starting from commercially available gibberellic acid, which yields allo -gibberic acid under mild acidic conditions. The successful formation of hydroxymethyl... LA - English DB - MTMT ER - TY - JOUR AU - Németi, Gábor AU - Berkecz, Róbert AU - Le Minh, Tam AU - Szakonyi, Zsolt AU - Péter, Antal AU - Ilisz, István TI - High-performance liquid chromatographic enantioseparation of azole analogs of monoterpene lactones and amides focusing on the separation characteristics of polysaccharide-based chiral stationary phases JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1717 PY - 2024 PG - 9 SN - 0021-9673 DO - 10.1016/j.chroma.2024.464660 UR - https://m2.mtmt.hu/api/publication/34535772 ID - 34535772 N1 - Institute of Pharmaceutical Analysis, Interdisciplinary Excellence Centre, University of Szeged, Somogyi u. 4, Szeged, H-6720, Hungary Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Export Date: 5 February 2024 CODEN: JCRAE Correspondence Address: Ilisz, I.; Institute of Pharmaceutical Analysis, Somogyi u. 4, Hungary; email: ilisz.istvan@szte.hu Funding details: 6752 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding details: Innovációs és Technológiai Minisztérium Funding details: National Research, Development and Innovation Office, K137607, TKP2021-EGA-32 Funding text 1: This work was supported by the National Research, Development and Innovation Office-NKFIA through project K137607. Project no. TKP2021-EGA-32 has been implemented with the support provided by the Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund, financed under the TKP2021-EGA funding scheme. This work was supported by the ÚNKP-21-4 New National Excellence Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund. The publication was funded by the University of Szeged Open Access Fund (No. 6752). LA - English DB - MTMT ER - TY - JOUR AU - Szőllősi, György AU - Resch, Vivien Erzsébet AU - Kolcsár, Vanessza Judit TI - Asymmetric transfer hydrogenation of 2,3-diphenylpropenoic acids over heterogeneous palladium catalysts modified by cinchona alkaloids JF - JOURNAL OF CATALYSIS J2 - J CATAL VL - 429 PY - 2024 PG - 12 SN - 0021-9517 DO - 10.1016/j.jcat.2024.115290 UR - https://m2.mtmt.hu/api/publication/34502096 ID - 34502096 LA - English DB - MTMT ER -