TY - JOUR AU - Vámos, Eszter AU - Kálmán, Nikoletta AU - Sturm, Eva Maria AU - Nayak, Barsha Baisakhi AU - Teppan, Julia AU - Bagóné Vántus, Viola AU - Kovács, Dominika AU - Makszin, Lilla AU - Lóránd, Tamás AU - Gallyas, Ferenc AU - Radnai, Balázs TI - Highly Selective MIF Ketonase Inhibitor KRP-6 Diminishes M1 Macrophage Polarization and Metabolic Reprogramming JF - ANTIOXIDANTS J2 - ANTIOXIDANTS-BASEL VL - 12 PY - 2023 IS - 10 PG - 23 SN - 2076-3921 DO - 10.3390/antiox12101790 UR - https://m2.mtmt.hu/api/publication/34172544 ID - 34172544 N1 - Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, 12 Szigeti Str, Pécs, 7624, Hungary Otto-Loewi Research Center for Vascular Biology, Immunology and Inflammation, Division of Pharmacology, Medical University of Graz, Neue Stiftingtalstraße 6, Graz, 8010, Austria Institute of Bioanalysis, Medical School, Szentágothai Research Center, University of Pécs, Pécs, 7622, Hungary Export Date: 15 November 2023 Correspondence Address: Radnai, B.; Department of Biochemistry and Medical Chemistry, 12 Szigeti Str, Hungary; email: balazs.radnai@aok.pte.hu AB - Macrophage polarization is highly involved in autoimmunity. M1 polarized macrophages drive inflammation and undergo metabolic reprogramming, involving downregulation of mitochondrial energy production and acceleration of glycolysis. Macrophage migration inhibitory factor (MIF), an enigmatic tautomerase (ketonase and enolase), was discovered to regulate M1 polarization. Here, we reveal that KRP-6, a potent and highly selective MIF ketonase inhibitor, reduces MIF-induced human blood eosinophil and neutrophil migration similarly to ISO-1, the most investigated tautomerase inhibitor. We equally discovered that KRP-6 prevents M1 macrophage polarization and reduces ROS production in IFN-γ-treated cells. During metabolic reprogramming, KRP-6 improved mitochondrial bioenergetics by ameliorating basal respiration, ATP production, coupling efficiency and maximal respiration in LPS+IFN-γ-treated cells. KRP-6 also reduced glycolytic flux in M1 macrophages. Moreover, the selective MIF ketonase inhibitor attenuated LPS+IFN-γ-induced downregulation of PARP-1 and PARP-2 mRNA expression. We conclude that KRP-6 represents a promising novel therapeutic compound for autoimmune diseases, which strongly involves M1 macrophage polarization. LA - English DB - MTMT ER - TY - JOUR AU - Garai, János AU - Radnai, Balázs AU - Vámos, Eszter AU - Kovács, Dominika AU - Bagóné Vántus, Viola AU - Rumbus, Zoltán AU - Pákai, Eszter AU - Garami, András AU - Gulyás, Gergely AU - Agócs, Attila AU - Krekó, Marcell AU - Zaman, K. AU - Prókai, L. AU - Őrfi, László AU - Jakus, Péter AU - Lóránd, Tamás TI - Synthesis and evaluation of a new class of MIF-inhibitors in activated macrophage cells and in experimental septic shock in mice JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY J2 - EUR J MED CHEM VL - 247 PY - 2023 PG - 11 SN - 0223-5234 DO - 10.1016/j.ejmech.2022.115050 UR - https://m2.mtmt.hu/api/publication/33546311 ID - 33546311 LA - English DB - MTMT ER - TY - JOUR AU - Lóránd, Tamás AU - Perjési, Pál TI - Heterociklusos vegyületek szintézise a Pécsi Tudományegyetem Orvosi Kémiai Intézetében JF - MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-) J2 - MAGY KÉM FOLY KÉM KÖZL VL - 128 PY - 2022 IS - 2 SP - 92 EP - 101 PG - 10 SN - 1418-9933 DO - 10.24100/MKF.2022.02.92 UR - https://m2.mtmt.hu/api/publication/33090617 ID - 33090617 LA - Hungarian DB - MTMT ER - TY - CHAP AU - Rumbus, Zoltán AU - Garai, János AU - Kéringer, Patrik AU - Radnai, Balázs AU - Lóránd, Tamás AU - Garami, András ED - Csiszár, Beáta ED - Hankó, Csilla ED - Kajos, Luca Fanni ED - Mező, Emerencia TI - The role of the macrophage migration inhibitory factor in lipopolysaccharide-induced hypothermia in mice T2 - Medical Conference for PhD Students and Experts of Clinical Sciences 2021 PB - University of Pécs, Doctoral Student Association CY - Pécs SN - 9789634296539 PY - 2021 SP - 115 EP - 115 PG - 1 UR - https://m2.mtmt.hu/api/publication/32131103 ID - 32131103 LA - English DB - MTMT ER - TY - JOUR AU - Garai, János AU - Krekó, Marcell AU - Őrfi, László AU - Jakus, Péter AU - Rumbus, Zoltán AU - Kéringer, Patrik AU - Garami, András AU - Vámos, Eszter AU - Kovács, Dominika AU - Bagóné Vántus, Viola AU - Radnai, Balázs AU - Lóránd, Tamás TI - Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice JF - JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY J2 - J ENZYM INHIB MED CH VL - 36 PY - 2021 IS - 1 SP - 1357 EP - 1369 PG - 13 SN - 1475-6366 DO - 10.1080/14756366.2021.1916010 UR - https://m2.mtmt.hu/api/publication/32095838 ID - 32095838 LA - English DB - MTMT ER - TY - CHAP AU - Lóránd, Tamás AU - Kulcsár, Győző AU - Petra, Horváth AU - Perjési, Pál ED - Perjési, Pál TI - ULTRA-VIOLET AND INFRARED SPECTROSCOPY OF CHALCONES AND CYCLIC CHALCONE ANALOGS. EFFECT OF THE RING SIZE AND THE SUBSTITUENTS T2 - Chalcones and their synthetic analogs PB - Nova Science Publishers CY - New York, New York SN - 9781536187946 T3 - Chemistry Research and Applications PY - 2020 SP - 57 EP - 92 PG - 36 UR - https://m2.mtmt.hu/api/publication/31839932 ID - 31839932 N1 - Export Date: 7 May 2024 LA - English DB - MTMT ER - TY - JOUR AU - Linzembold, Ildikó Erzsébet AU - Czett, Dalma AU - Böddi, Katalin AU - Kurtán, Tibor AU - Király, Sándor Balázs AU - Gulyás, Gergely AU - Takátsy, Anikó AU - Lóránd, Tamás AU - Deli, József AU - Agócs, Attila AU - Nagy, Veronika TI - Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates JF - MOLECULES J2 - MOLECULES VL - 25 PY - 2020 IS - 3 PG - 21 SN - 1420-3049 DO - 10.3390/molecules25030636 UR - https://m2.mtmt.hu/api/publication/31155279 ID - 31155279 AB - Flavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydrophobic carotenoids with hydrophilic flavonoids, such as daidzein and chrysin, was achieved, resulting in new amphipathic structures. 7-Azidohexyl ethers of daidzein and chrysin were prepared in five steps, and their azide-alkyne [4 + 2] cycloaddition with pentynoates of 80-apo-β-carotenol, zeaxanthin, and capsanthin afforded carotenoid–flavonoid conjugates. The trolox-equivalent antioxidant capacity against ABTS•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however, were found to exhibit a synergistic enhancement in antioxidant capacities. ECD (electronic circular dichroism) and UV-vis analysis of zeaxanthin–flavonoid conjugates revealed that they form different optically active J-aggregates in acetone/water and tetrahydrofuran/water mixtures depending on the solvent ratio and type of the applied aprotic polar solvent, while the capsanthin derivatives showed no self-assembly. The zeaxanthin bis-triazole conjugates with daidzein and with chrysin, differing only in the position of a phenolic hydroxyl group, showed significantly different aggregation profile upon the addition of water. LA - English DB - MTMT ER - TY - JOUR AU - Berzaghi, R. AU - Agócs, Attila AU - Gulyás, Gergely AU - Kocsis, Béla AU - Ribas, J.C. AU - Lóránd, Tamás TI - Novel cell wall antifungals reveal a special synergistic activity in pbr1 mutants resistant to the glucan synthesis antifungals papulacandins and echinocandins JF - FRONTIERS IN MICROBIOLOGY J2 - FRONT MICROBIOL VL - 10 PY - 2019 PG - 12 SN - 1664-302X DO - 10.3389/fmicb.2019.01692 UR - https://m2.mtmt.hu/api/publication/30758489 ID - 30758489 LA - English DB - MTMT ER - TY - JOUR AU - Lutz, Z AU - Orban, K AU - Bóna, Ágnes AU - Márk, László AU - Maász, Gábor AU - Prókai, László AU - Seress, László AU - Lóránd, Tamás TI - Mannich Ketones as Possible Antimycobacterial Agents. JF - ARCHIV DER PHARMAZIE J2 - ARCH PHARM VL - 350 PY - 2017 IS - 9 PG - 9 SN - 0365-6233 DO - 10.1002/ardp.201700102 UR - https://m2.mtmt.hu/api/publication/3252956 ID - 3252956 AB - Twenty-three known unsaturated and fused Mannich ketones and their reduced derivatives (amino alcohols) were selected for an antituberculotic study. They were screened against several mycobacterial strains including Mycobacterium tuberculosis, M. xenopi, and M. gordonae, and minimum inhibitory concentration values were also determined using the standard antituberculotic drug isoniazid (INH) as a reference. Structure-activity relationships were also studied. The mode of action of the test compounds was investigated using transmission electron microscopy, high-performance liquid chromatography, and matrix-assisted desorption/ionization mass spectrometry. Several test substances proved to be as potent as INH, but their antimycobacterial spectra were broader than that of INH. Our findings suggest that their mode of action is probably through the inhibition of mycobacterial cell wall biosynthesis. LA - English DB - MTMT ER - TY - JOUR AU - Agócs, Attila AU - Bokor, Éva AU - Takátsy, Anikó AU - Lóránd, Tamás AU - Deli, József AU - Somsák, László AU - Nagy, Veronika TI - Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction JF - TETRAHEDRON J2 - TETRAHEDRON VL - 73 PY - 2017 IS - 5 SP - 519 EP - 526 PG - 8 SN - 0040-4020 DO - 10.1016/j.tet.2016.12.035 UR - https://m2.mtmt.hu/api/publication/3157933 ID - 3157933 LA - English DB - MTMT ER -