TY - JOUR AU - Csávás, Magdolna AU - Kalmár, László AU - Szoke, Petronella AU - Farkas, László Bence AU - Bécsi, Bálint AU - Kónya, Zoltán AU - Kerékgyártó, János AU - Borbás, Anikó AU - Erdődi, Ferenc AU - E Kövér, Katalin TI - A Fucosylated Lactose-Presenting Tetravalent Glycocluster Acting as a Mutual Ligand of Pseudomonas aeruginosa Lectins A (PA-IL) and B (PA-IIL)-Synthesis and Interaction Studies JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 23 PY - 2022 IS - 24 PG - 14 SN - 1661-6596 DO - 10.3390/ijms232416194 UR - https://m2.mtmt.hu/api/publication/33554482 ID - 33554482 N1 - Funding: The synthetic work was supported by the National Research and Development and Innovation Office of Hungary (K119509 to M. Cs., K129104 to F.E. and NN128368 K.E.K.) and the EU and co-financed by the European Regional Development Fund under the projects GINOP-2.3.2-15- 2016-00008, GINOP-2.3.3-15-2016-00004 and GINOP-2.3.4-15-2020-00008. AB - The Gram-negative bacterium Pseudomonas aeruginosa is an important opportunistic human pathogen associated with cystic fibrosis. P. aeruginosa produces two soluble lectins, the d-galactose-specific lectin PA-IL (LecA) and the l-fucose-specific lectin PA-IIL (LecB), among other virulence factors. These lectins play an important role in the adhesion to host cells and biofilm formation. Moreover, PA-IL is cytotoxic to respiratory cells in the primary culture. Therefore, these lectins are promising therapeutic targets. Specifically, carbohydrate-based compounds could inhibit their activity. In the present work, a 3-O-fucosyl lactose-containing tetravalent glycocluster was synthesized and utilized as a mutual ligand of galactophilic and fucophilic lectins. Pentaerythritol equipped with azido ethylene glycol-linkers was chosen as a multivalent scaffold and the glycocluster was constructed by coupling the scaffold with propargyl 3-O-fucosyl lactoside using an azide-alkyne 1,3-dipolar cycloaddition reaction. The interactions between the glycocluster and PA-IL or PA-IIL were investigated by isothermal titration microcalorimetry and saturation transfer difference NMR spectroscopy. These results may assist in the development of efficient anti-adhesion therapy for the treatment of a P. aeruginosa infection. LA - English DB - MTMT ER - TY - JOUR AU - Le, Son AU - Páll, Dávid AU - Rőth, Erzsébet AU - Tran, Tuyen AU - Debreczeni, Nóra AU - Bege, Miklós AU - Bakai-Bereczki, Ilona AU - Ostorházi, Eszter AU - Milánkovits, Márton AU - Herczegh, Pál AU - Borbás, Anikó AU - Csávás, Magdolna TI - The very first modification of pleuromutilin and lefamulin by photoinitiated radical addition reactions – Synthesis and antibacterial studies JF - PHARMACEUTICS J2 - PHARMACEUTICS VL - 13 PY - 2021 IS - 12 PG - 21 SN - 1999-4923 DO - 10.3390/pharmaceutics13122028 UR - https://m2.mtmt.hu/api/publication/32512606 ID - 32512606 N1 - Funding Agency and Grant Number: National Research and Development and Innovation Office of Hungary [K119509, K132870]; EU - European Regional Development FundEuropean Commission [GINOP-2.3.2-15-2016-00008, GINOP-2.3.4-15-2020-00008] Funding text: FundingThe synthetic work was supported by the National Research and Development and Innovation Office of Hungary (K119509, M.Cs. and K132870, A.B.) and the EU and co-financed by the European Regional Development Fund under the projects GINOP-2.3.2-15-2016-00008 and GINOP-2.3.4-15-2020-00008. LA - English DB - MTMT ER - TY - JOUR AU - Mező, Erika AU - Herczeg, Mihály AU - Demeter, Fruzsina AU - Bakai-Bereczki, Ilona AU - Csávás, Magdolna AU - Borbás, Anikó TI - Systematic Study of Regioselective Reductive Ring-Opening Reactions of 4,6-O-Halobenzylidene Acetals of Glucopyranosides JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 86 PY - 2021 IS - 18 SP - 12973 EP - 12987 PG - 15 SN - 0022-3263 DO - 10.1021/acs.joc.1c01667 UR - https://m2.mtmt.hu/api/publication/32430281 ID - 32430281 AB - Reductive openings of cyclic acetals are widely used in modern synthetic organic chemistry for the regioselective introduction of protecting groups. A systematic study was performed on the applicability and efficacy of various hydride donor and protic or Lewis acid reagent combinations in the reductive ring opening of glucosidic 4,6-halobenzylidene acetals bearing an ortho-, meta-, and para-chloro- or -bromo substituent on the benzene ring. Most of the reagent combinations tested cleaved the 4,6-O-halobenzylidene acetal rings at O4 or O6 efficiently and with the expected regioselectivity. The LiAlH4-AlCl3 and the BH3 center dot THF-TMSOTf combinations produced the 4-O-halobenzyl ether/6-OH products with complete regioselectivity and high yields. The use of Me3N center dot BH3-AlCl3 reagent system in toluene was also effective in cleaving the acetal ring at O6 but was accompanied by Al-chelation-assisted debenzylation side reactions. The NaCNBH3-HCl and the Et3SiH-BF3 center dot Et2O combinations were highly effective in yielding the 6-halobenzyl ether/4-OH derivatives. Et3SiH, in combination with TfOH, produced the 6-O-ether/4-OH products in rapid reactions but also triggered silylation and reductive halobenzylation as secondary transformations. Reductive opening of the 1,3-dioxane ring of pyranosidic 4,6-O-halobenzylidene acetals by the proper reagent combination was found to be an efficient method for the regioselective introduction of versatile halobenzyl protecting groups onto the pyranose ring. LA - English DB - MTMT ER - TY - JOUR AU - Tóthné Illyés, Tünde Zita AU - Malinovská, Lenka AU - Rőth, Erzsébet AU - Tóth, Boglárka AU - Farkas, László Bence AU - Korsák, Marek AU - Wimmerová, Michaela AU - E Kövér, Katalin AU - Csávás, Magdolna TI - Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa JF - MOLECULES J2 - MOLECULES VL - 26 PY - 2021 IS - 3 PG - 11 SN - 1420-3049 DO - 10.3390/molecules26030542 UR - https://m2.mtmt.hu/api/publication/31845447 ID - 31845447 N1 - Funding Agency and Grant Number: National Research and Development and Innovation Office of Hungary [K119509, K128368]; European Regional Development FundEuropean Commission [GINOP-2.3.2-15-2016-00008]; Janos Bolyai Fellowship of the Hungarian Academy of Sciences; Czech Science FoundationGrant Agency of the Czech Republic [18-18964S]; CIISB research infrastructure - MEYS CR [LM2018127] Funding text: The synthetic work was supported by the National Research and Development and Innovation Office of Hungary (K119509, M.C., K128368, K.E.K.) and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008. The project was supported by the Janos Bolyai Fellowship (M.C.) of the Hungarian Academy of Sciences. The project was further supported by the Czech Science Foundation (18-18964S). We acknowledge the Biomolecular Interactions and Crystallization Core Facility of CEITEC MU supported by the CIISB research infrastructure (LM2018127 funded by MEYS CR) for their support with obtaining the scientific data presented in this paper. AB - Synthesis of tetravalent thio- and selenogalactopyranoside-containing glycoclusters using azide-alkyne click strategy is presented. Prepared compounds are potential ligands of Pseudomonas aeruginosa lectin PA-IL. P. aeruginosa is an opportunistic human pathogen associated with cystic fibrosis, and PA-IL is one of its virulence factors. The interactions of PA-IL and tetravalent glycoconjugates were investigated using hemagglutination inhibition assay and compared with mono- and divalent galactosides (propargyl 1-thio- and 1-seleno-β-d-galactopyranoside, digalactosyl diselenide and digalactosyl disulfide). The lectin-carbohydrate interactions were also studied by saturation transfer difference NMR technique. Both thio- and seleno-tetravalent glycoconjugates were able to inhibit PA-IL significantly better than simple d-galactose or their intermediate compounds from the synthesis. LA - English DB - MTMT ER - TY - JOUR AU - Bakai-Bereczki, Ilona AU - Csávás, Magdolna AU - Szűcs, Zsolt AU - Rőth, Erzsébet AU - Lőrincz, Eszter Boglárka AU - Batta, Gyula AU - Ostorházi, Eszter AU - Naesens, Lieve AU - Borbás, Anikó AU - Herczegh, Pál TI - Teicoplanin and vancomycin derivatives with perfluorilated alkyl groups are active against influenza and coronavirus JF - ACTA PHARMACEUTICA HUNGARICA J2 - ACTA PHARM HUNG VL - 90 PY - 2020 IS - 2-3 SP - 109 EP - 109 PG - 1 SN - 0001-6659 UR - https://m2.mtmt.hu/api/publication/31793468 ID - 31793468 LA - English DB - MTMT ER - TY - JOUR AU - Bakai-Bereczki, Ilona AU - Csávás, Magdolna AU - Szűcs, Zsolt AU - Roth, Erzsebet AU - Batta, Gyula AU - Ostorházi, Eszter AU - Naesens, Lieve AU - Borbás, Anikó AU - Herczegh, Pál TI - Synthesis of Antiviral Perfluoroalkyl Derivatives of Teicoplanin and Vancomycin JF - CHEMMEDCHEM J2 - CHEMMEDCHEM VL - 15 PY - 2020 IS - 17 SP - 1661 EP - 1671 PG - 11 SN - 1860-7179 DO - 10.1002/cmdc.202000260 UR - https://m2.mtmt.hu/api/publication/31419194 ID - 31419194 AB - The limited scope of antiviral drugs and increasing problem of antiviral drug resistance represent a global health threat. Glycopeptide antibiotics and their lipophilic derivatives have emerged as relevant inhibitors of diverse viruses. Herein, we describe a new strategy for the synthesis of dual hydrophobic and lipophobic derivatives of glycopeptides to produce selective antiviral agents without membrane-disrupting activity. Perfluorobutyl and perfluorooctyl moieties were attached through linkers of different length to azido derivatives of vancomycin aglycone and teicoplanin pseudoaglycone, and the new derivatives were evaluated against a diverse panel of viruses. The teicoplanin derivatives displayed strong anti-influenza virus activity at nontoxic concentrations. Some of the perfluoroalkylated glycopeptides were also active against a few other viruses such as herpes simplex virus or coronavirus. These data encourage further exploration of glycopeptide analogues for broad antiviral application. LA - English DB - MTMT ER - TY - JOUR AU - Kelemen, Viktor AU - Csávás, Magdolna AU - Hotzi, Judit AU - Herczeg, Mihály AU - Singh, Poonam AU - Rathi, Brijesh AU - Herczegh, Pál AU - Jain, Nidhi AU - Borbás, Anikó TI - Photoinitiated Thiol‐Ene Reactions of Various 2,3‐Unsaturated O‐, C‐ S‐ and N‐Glycosides – Scope and Limitations Study JF - CHEMISTRY-AN ASIAN JOURNAL J2 - CHEM-ASIAN J VL - 15 PY - 2020 IS - 6 SP - 876 EP - 891 PG - 16 SN - 1861-4728 DO - 10.1002/asia.201901560 UR - https://m2.mtmt.hu/api/publication/31157343 ID - 31157343 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office of Hungary [TET_15_IN-1-2016-0071, K109208, K119509]; Premium Postdoctoral Program of HAS [PPD 461038]; Gedeon Richter's Talentum Foundation (Budapest, Gyomri ut); Debrecen Venture Catapult Program [EFOP-3.6.1-16-2016-00022, EFOP-3.6.3-VEKOP-16-2017-00009]; Janos Bolyai Fellowship of the Hungarian Academy of Sciences; New National Excellence Program of the Ministry for Innovation and Technology [UNKP-19-3]; European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00021, GINOP-2.3.3-15-2016-00004]; EUEuropean Union (EU) Funding text: This research was funded by: the National Research, Development and Innovation Office of Hungary (TET_15_IN-1-2016-0071, K109208 and K119509), the Premium Postdoctoral Program of HAS (PPD 461038), Gedeon Richter's Talentum Foundation (1103 Budapest, Gyomri ut 19-21.), the "Debrecen Venture Catapult Program" (EFOP-3.6.1-16-2016-00022 and EFOP-3.6.3-VEKOP-16-2017-00009, Janos Bolyai Fellowship of the Hungarian Academy of Sciences (M. Csavas) and the UNKP-19-3 New National Excellence Program of the Ministry for Innovation and Technology. The research was also supported by the EU and co-financed by the European Regional Development Fund under the projects GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00021 and GINOP-2.3.3-15-2016-00004. The authors gratefully acknowledge Tobias Sturzer and Attila Benyei for performing the X-ray spectroscopy experiments. LA - English DB - MTMT ER - TY - JOUR AU - Csávás, Magdolna AU - Eszenyi, Dániel AU - Mező, Erika AU - Lázár, László AU - Debreczeni, Nóra AU - Vágvölgyiné Tóth, Marietta AU - Somsák, László AU - Borbás, Anikó TI - Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 21 PY - 2020 IS - 2 PG - 27 SN - 1661-6596 DO - 10.3390/ijms21020573 UR - https://m2.mtmt.hu/api/publication/31149647 ID - 31149647 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office of Hungary [K119509, K132870, FK 128766]; EUEuropean Union (EU); European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00004, GINOP-2.3.3-15-2016-00021]; Hungarian Academy of SciencesHungarian Academy of Sciences; New National Excellence Program of the Ministry for Innovation and Technology [UNKP-19-4]; Debrecen Venture Catapult Program [EFOP-3.6.1-16-2016-00022] Funding text: This research was funded by the National Research, Development and Innovation Office of Hungary under the projects K119509 (M.C.), K132870 (A.B.) and FK 128766 (M.T.). The project was also supported by the EU and co-financed by the European Regional Development Fund under the projects GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00004 and GINOP-2.3.3-15-2016-00021. "Developing Pharmaceutical Technology R&D Infrastructure on the University of Debrecen" project. The publication was supported by the Janos Bolyai Fellowship (M.C. and L.L.) of the Hungarian Academy of Sciences and the UNKP-19-4 New National Excellence Program of the Ministry for Innovation and Technology (M.C.). The author acknowledges the support from EFOP-3.6.1-16-2016-00022 "Debrecen Venture Catapult Program" (N.D.). AB - Oligosaccharides and glycoconjugates are abundant in all living organisms, taking part in a multitude of biological processes. The application of natural O-glycosides in biological studies and drug development is limited by their sensitivity to enzymatic hydrolysis. This issue made it necessary to design hydrolytically stable carbohydrate mimetics, where sulfur, carbon, or longer interglycosidic connections comprising two or three atoms replace the glycosidic oxygen. However, the formation of the interglycosidic linkages between the sugar residues in high diastereoslectivity poses a major challenge. Here, we report on stereoselective synthesis of carbon-sulfur-bridged disaccharide mimetics by the free radical addition of carbohydrate thiols onto the exo-cyclic double bond of unsaturated sugars. A systematic study on UV-light initiated radical mediated hydrothiolation reactions of enoses bearing an exocyclic double bond at C1, C2, C3, C4, C5, and C6 positions of the pyranosyl ring with various sugar thiols was performed. The effect of temperature and structural variations of the alkenes and thiols on the efficacy and stereoselectivity of the reactions was systematically studied and optimized. The reactions proceeded with high efficacy and, in most cases, with complete diastereoselectivity producing a broad array of disaccharide mimetics coupling through an equatorially oriented methylensulfide bridge. LA - English DB - MTMT ER - TY - JOUR AU - Csávás, Magdolna TI - Multivalens szénhidrátok szintézise és bakteriális lektinekkel való kölcsönhatásának vizsgálata JF - MAGYAR KÉMIKUSOK LAPJA J2 - MAGY KEM LAP VL - 74 PY - 2019 IS - 11 SP - 344 EP - 345 PG - 2 SN - 0025-0163 UR - https://m2.mtmt.hu/api/publication/31129698 ID - 31129698 LA - Hungarian DB - MTMT ER - TY - DATA AU - Szőke, Kitti AU - Czompa, Attila AU - Lekli, István AU - Szabados-Fürjesi, Péter AU - Herczeg, Mihály AU - Csávás, Magdolna AU - Borbás, Anikó AU - Herczegh, Pál AU - Tósaki, Árpád TI - Dataset on structure, stability and myocardial effects of a new hybrid aspirin containing nitrogen monoxide-releasing molsidomine moiety PY - 2019 DO - 10.1016/j.dib.2019.104146 UR - https://m2.mtmt.hu/api/publication/30942821 ID - 30942821 AB - Herein H-1 and C-13 NMR spectra of ERJ-500, a new hybrid aspirin derivative, covalently conjugated to nitrogen monoxide donor linsidomine are presented as well as NMR spectra of its synthetic intermediate compounds. HPLC-MS measurements data are also included, demonstrating the stability of the linsidomine-aspirin hybrid in oxidation reactions. This data article also concerns miscellaneous myocardial parameters of isolated rat hearts as a complementation of the tables shown in the paper entitled "A new, vasoactive hybrid aspirin containing nitrogen monoxide-releasing molsidomine moiety" Szoke et al., 2019. Column tables represent data of aorta flow, aortic pressure, derivated aortic pressure and cardiac output. (c) 2019 The Authors. Published by Elsevier Inc. LA - English DB - MTMT ER -