TY - JOUR AU - Kadlecsik, Csaba András AU - Bognár, Gábor AU - Kenari, Fatemeh AU - Pintér, Zoltán AU - Ribeiro, Júlio César de Oliveira AU - Envall, Mário G AU - Carvalho-Silva, Valter H AU - Napolitano, Hamilton B AU - Perjési, Pál TI - (E)-2-Benzylidenecyclanones : Part XXI-Reaction of Cyclic Chalcone Analogs with Cellular Thiols: Comparison of Reactivity of (E)-2-Arylidene-1-Indanone with -1-Tetralone and -1-Benzosuberone Analogs in Thia-Michael Reactions. JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 26 PY - 2025 IS - 21 PG - 21 SN - 1661-6596 DO - 10.3390/ijms262110573 UR - https://m2.mtmt.hu/api/publication/36438388 ID - 36438388 AB - In vitro cytotoxicity of three (E)-3-(4'-X-benzylidene)-1-indanones (2a-c) displayed lower cytotoxicity towards murine P388 and L1210 leukemic cells as well as human Molt 4/C8 and CEM T-lymphocytes than the respective six- (3a-c) and seven-membered (4a-c) analogs. To study whether thiol reactivity-as a possible basis of their mechanism of action-correlates with the observed cytotoxicities, kinetics of the non-enzyme catalyzed reactions with reduced glutathione (GSH) and N-acetylcysteine (NAC) of 2a-c were investigated. Furthermore, it was also the aim of the work to compare the thiol reactivity of the open-chain chalcones (1) and their carbocyclic analogs (2-4) with different ring sizes (n = 5-7). The reactivity of the compounds and the stereochemical outcome of the reactions were evaluated using high-pressure liquid chromatography-mass spectrometry (HPLC-MS). Molecular modeling calculations were performed to rationalize the high initial rate and low conversion of the 2a indanone in comparison with those of the carbocyclic analog tetralone (3a) and benzosuberone (4a). Thiol reactivity and cancer cell cytotoxicity showed a dependence on both the ring size and the nature of aromatic substituents. LA - English DB - MTMT ER - TY - CONF AU - Bognár, Gábor AU - Rahin, Kenari AU - Zoltán, Pintér AU - Perjési, Pál ED - Kovács, Bettina ED - Glázer-Kniesz, Adrienn ED - Tislér, Ádám TI - Study on thiol reactivity of some six-membered cyclic chalcone analogs. Search for relationships between thiol reactivity and in vitro cancer cell cytotoxic effects T2 - Absztraktkötet: XII. Interdiszciplináris Doktorandusz Konferencia = Book of Abstract: XII. Interdisciplinary Doctoral Conference PB - Pécsi Tudományegyetem Doktorandusz Önkormányzat C1 - Pécs SN - 9789636262457 PY - 2024 SP - 143 EP - 143 PG - 1 UR - https://m2.mtmt.hu/api/publication/34814603 ID - 34814603 N1 - Poszter szekció LA - English DB - MTMT ER - TY - CONF AU - Zoltán, Pintér AU - Bognár, Gábor AU - Perjési, Pál TI - Study on Stereochemistry of GSH-Conjugation of Some Cyclic Chalcone Analogs, 3-(4’-X-Benzylidene)-2,3-Dihydro-1-Benzopyran-4-Ones T2 - Congressus Pharmaceuticus Hungaricus XVII. and EUFEPS Annual Meeting 2024 PB - Magyar Gyógyszerésztudományi Társaság (MGYT) C1 - Budapest PY - 2024 SP - 382 EP - 383 PG - 2 UR - https://m2.mtmt.hu/api/publication/34915245 ID - 34915245 N1 - (Poster Presentations) LA - English DB - MTMT ER - TY - CONF AU - Bognár, Gábor AU - Kenari, Fatemeh AU - Zoltán, Pintér AU - Perjési, Pál TI - Study on Thiol Reactivity of Some Six-Membered Cyclic Chalcone Analogs. Search for Relationships Between Thiol Reactivity and In Vitro Cancer Cell Cytotoxic Effects T2 - Congressus Pharmaceuticus Hungaricus XVII. and EUFEPS Annual Meeting 2024 PB - Magyar Gyógyszerésztudományi Társaság (MGYT) C1 - Budapest PY - 2024 SP - 217 EP - 217 PG - 1 UR - https://m2.mtmt.hu/api/publication/34915704 ID - 34915704 N1 - (Poster Presentations) LA - English DB - MTMT ER - TY - CONF AU - Aline, Bernardes AU - Caridad, Noda Perez AU - Bognár, Gábor AU - Zoltán, Pintér AU - Perjési, Pál TI - Study of Michael Addition Reaction Between Hydroxychalcone Derivatives and Reduced Glutathione T2 - Congressus Pharmaceuticus Hungaricus XVII. and EUFEPS Annual Meeting 2024 PB - Magyar Gyógyszerésztudományi Társaság (MGYT) C1 - Budapest PY - 2024 SP - 216 EP - 216 PG - 1 UR - https://m2.mtmt.hu/api/publication/34915719 ID - 34915719 N1 - (Poster Presentations) LA - English DB - MTMT ER - TY - JOUR AU - Bognár, Gábor AU - Kenari, Fatemeh AU - Pintér, Zoltán AU - Borges, Igor D. AU - Camargo, Ademir J. AU - Oliveira, Heibbe C. B. AU - Sanches-Neto, Flávio Olimpio AU - Carvalho-Silva, Valter H. AU - Napolitano, Hamilton B. AU - Perjési, Pál TI - (E)-2-Benzylidenecyclanones: Part XX—Reaction of Cyclic Chalcone Analogs with Cellular Thiols: Unexpected Increased Reactivity of 4-Chromanone- Compared to 1-Tetralone Analogs in Thia-Michael Reactions JF - MOLECULES J2 - MOLECULES VL - 29 PY - 2024 IS - 23 PG - 20 SN - 1431-5157 DO - 10.3390/molecules29235493 UR - https://m2.mtmt.hu/api/publication/35641336 ID - 35641336 N1 - Institute of Pharmaceutical Chemistry, University of Pécs, Pécs, H-7624, Hungary AB - In vitro relative cytotoxicity (IC50 (IIb)/IC50 (IIIb) of (E)-3-(4′-methylbenzylidene)-4-chromanone (IIIb) towards human Molt 4/C8 and CEM T-lymphocytes showed a >50-fold increase in comparison to those of the respective tetralone derivative (IIb). On the other hand, such an increase was not observed in the analogous 4-OCH3 (IIc and IIIc) derivatives. In order to study whether thiol reactivity—as a possible basis of the mechanism of action—correlates with the observed cytotoxicities, the kinetics of the non-enzyme catalyzed reactions with reduced glutathione (GSH) and N-acetylcysteine (NAC) of IIIb and IIIc were investigated. The reactivity of the compounds and the stereochemical outcome of the reactions were evaluated using high-pressure liquid chromatography-mass spectrometry (HPLC-MS). Molecular modeling calculations were performed to rationalize the unexpectedly higher thiol reactivity of the chromanones (III) compared to the carbocyclic analog tetralones (II). The results indicate the possible role of spontaneous thiol reactivity of compounds III in their recorded biological effects. LA - English DB - MTMT ER -