@article{MTMT:33554482, title = {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}, url = {https://m2.mtmt.hu/api/publication/33554482}, author = {Csávás, Magdolna and Kalmár, László and Szoke, Petronella and Farkas, László Bence and Bécsi, Bálint and Kónya, Zoltán and Kerékgyártó, János and Borbás, Anikó and Erdődi, Ferenc and E Kövér, Katalin}, doi = {10.3390/ijms232416194}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {23}, unique-id = {33554482}, issn = {1661-6596}, abstract = {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.}, keywords = {lectin; Pseudomonas aeruginosa; Multivalency; saturation transfer difference NMR; fucosylated lactose}, year = {2022}, eissn = {1422-0067}, orcid-numbers = {Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:32512606, title = {The very first modification of pleuromutilin and lefamulin by photoinitiated radical addition reactions – Synthesis and antibacterial studies}, url = {https://m2.mtmt.hu/api/publication/32512606}, author = {Le, Son and Páll, Dávid and Rőth, Erzsébet and Tran, Tuyen and Debreczeni, Nóra and Bege, Miklós and Bakai-Bereczki, Ilona and Ostorházi, Eszter and Milánkovits, Márton and Herczegh, Pál and Borbás, Anikó and Csávás, Magdolna}, doi = {10.3390/pharmaceutics13122028}, journal-iso = {PHARMACEUTICS}, journal = {PHARMACEUTICS}, volume = {13}, unique-id = {32512606}, issn = {1999-4923}, year = {2021}, eissn = {1999-4923}, orcid-numbers = {Bakai-Bereczki, Ilona/0000-0003-4601-7257; Ostorházi, Eszter/0000-0002-9459-7316; Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:32430281, title = {Systematic Study of Regioselective Reductive Ring-Opening Reactions of 4,6-O-Halobenzylidene Acetals of Glucopyranosides}, url = {https://m2.mtmt.hu/api/publication/32430281}, author = {Mező, Erika and Herczeg, Mihály and Demeter, Fruzsina and Bakai-Bereczki, Ilona and Csávás, Magdolna and Borbás, Anikó}, doi = {10.1021/acs.joc.1c01667}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {86}, unique-id = {32430281}, issn = {0022-3263}, abstract = {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.}, year = {2021}, eissn = {1520-6904}, pages = {12973-12987}, orcid-numbers = {Mező, Erika/0000-0002-8329-6745; Herczeg, Mihály/0000-0002-7938-9789; Bakai-Bereczki, Ilona/0000-0003-4601-7257; Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:31845447, title = {Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa}, url = {https://m2.mtmt.hu/api/publication/31845447}, author = {Tóthné Illyés, Tünde Zita and Malinovská, Lenka and Rőth, Erzsébet and Tóth, Boglárka and Farkas, László Bence and Korsák, Marek and Wimmerová, Michaela and E Kövér, Katalin and Csávás, Magdolna}, doi = {10.3390/molecules26030542}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {26}, unique-id = {31845447}, issn = {1420-3049}, abstract = {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.}, keywords = {Pseudomonas aeruginosa; Selenoglycosides; Multivalency; galactoclusters; PA-IL lectin}, year = {2021}, eissn = {1420-3049}, orcid-numbers = {Malinovská, Lenka/0000-0002-4211-3033; Korsák, Marek/0000-0001-7357-5321; Wimmerová, Michaela/0000-0002-7108-4198; E Kövér, Katalin/0000-0001-5020-4456} } @article{MTMT:31793468, title = {Teicoplanin and vancomycin derivatives with perfluorilated alkyl groups are active against influenza and coronavirus}, url = {https://m2.mtmt.hu/api/publication/31793468}, author = {Bakai-Bereczki, Ilona and Csávás, Magdolna and Szűcs, Zsolt and Rőth, Erzsébet and Lőrincz, Eszter Boglárka and Batta, Gyula and Ostorházi, Eszter and Naesens, Lieve and Borbás, Anikó and Herczegh, Pál}, journal-iso = {ACTA PHARM HUNG}, journal = {ACTA PHARMACEUTICA HUNGARICA}, volume = {90}, unique-id = {31793468}, issn = {0001-6659}, year = {2020}, eissn = {1587-1495}, pages = {109-109}, orcid-numbers = {Bakai-Bereczki, Ilona/0000-0003-4601-7257; Batta, Gyula/0000-0002-0442-1828; Ostorházi, Eszter/0000-0002-9459-7316; Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:31419194, title = {Synthesis of Antiviral Perfluoroalkyl Derivatives of Teicoplanin and Vancomycin}, url = {https://m2.mtmt.hu/api/publication/31419194}, author = {Bakai-Bereczki, Ilona and Csávás, Magdolna and Szűcs, Zsolt and Roth, Erzsebet and Batta, Gyula and Ostorházi, Eszter and Naesens, Lieve and Borbás, Anikó and Herczegh, Pál}, doi = {10.1002/cmdc.202000260}, journal-iso = {CHEMMEDCHEM}, journal = {CHEMMEDCHEM}, volume = {15}, unique-id = {31419194}, issn = {1860-7179}, abstract = {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.}, keywords = {Influenza virus; Antiviral; CORONAVIRUS; Perfluoroalkyl; glycopeptide antibiotic}, year = {2020}, eissn = {1860-7187}, pages = {1661-1671}, orcid-numbers = {Bakai-Bereczki, Ilona/0000-0003-4601-7257; Csávás, Magdolna/0000-0002-9329-0689; Batta, Gyula/0000-0002-0442-1828; Ostorházi, Eszter/0000-0002-9459-7316; Naesens, Lieve/0000-0001-9742-9302; Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:31157343, title = {Photoinitiated Thiol‐Ene Reactions of Various 2,3‐Unsaturated O‐, C‐ S‐ and N‐Glycosides – Scope and Limitations Study}, url = {https://m2.mtmt.hu/api/publication/31157343}, author = {Kelemen, Viktor and Csávás, Magdolna and Hotzi, Judit and Herczeg, Mihály and Singh, Poonam and Rathi, Brijesh and Herczegh, Pál and Jain, Nidhi and Borbás, Anikó}, doi = {10.1002/asia.201901560}, journal-iso = {CHEM-ASIAN J}, journal = {CHEMISTRY-AN ASIAN JOURNAL}, volume = {15}, unique-id = {31157343}, issn = {1861-4728}, year = {2020}, eissn = {1861-471X}, pages = {876-891}, orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:31149647, title = {Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions}, url = {https://m2.mtmt.hu/api/publication/31149647}, author = {Csávás, Magdolna and Eszenyi, Dániel and Mező, Erika and Lázár, László and Debreczeni, Nóra and Vágvölgyiné Tóth, Marietta and Somsák, László and Borbás, Anikó}, doi = {10.3390/ijms21020573}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {21}, unique-id = {31149647}, issn = {1661-6596}, abstract = {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.}, keywords = {DIASTEREOSELECTIVE SYNTHESIS; Carbohydrate; DISACCHARIDE; Glycomimetic; thioglycoside; C-glycoside; photochemical addition; thiyl radical}, year = {2020}, eissn = {1422-0067}, orcid-numbers = {Mező, Erika/0000-0002-8329-6745; Somsák, László/0000-0002-9103-9845; Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:31129698, title = {Multivalens szénhidrátok szintézise és bakteriális lektinekkel való kölcsönhatásának vizsgálata}, url = {https://m2.mtmt.hu/api/publication/31129698}, author = {Csávás, Magdolna}, journal-iso = {MAGY KEM LAP}, journal = {MAGYAR KÉMIKUSOK LAPJA}, volume = {74}, unique-id = {31129698}, issn = {0025-0163}, year = {2019}, eissn = {1588-1199}, pages = {344-345} } @{MTMT:30942821, title = {Dataset on structure, stability and myocardial effects of a new hybrid aspirin containing nitrogen monoxide-releasing molsidomine moiety}, url = {https://m2.mtmt.hu/api/publication/30942821}, author = {Szőke, Kitti and Czompa, Attila and Lekli, István and Szabados-Fürjesi, Péter and Herczeg, Mihály and Csávás, Magdolna and Borbás, Anikó and Herczegh, Pál and Tósaki, Árpád}, doi = {10.1016/j.dib.2019.104146}, unique-id = {30942821}, abstract = {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.}, keywords = {molsidomine; ERJ-500; Hybrid aspirin}, year = {2019}, orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Borbás, Anikó/0000-0001-8462-4547} }