@article{MTMT:36438388, title = {(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.}, url = {https://m2.mtmt.hu/api/publication/36438388}, author = {Kadlecsik, Csaba András and Bognár, Gábor and Kenari, Fatemeh and Pintér, Zoltán and Ribeiro, Júlio César de Oliveira and Envall, Mário G and Carvalho-Silva, Valter H and Napolitano, Hamilton B and Perjési, Pál}, doi = {10.3390/ijms262110573}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {26}, unique-id = {36438388}, issn = {1661-6596}, abstract = {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.}, keywords = {GLUTATHIONE; DFT calculations; N-acetylcysteine; CHALCONE; Anticancer activity; Thia-Michael addition; Molecular electrostatic; benzylidenebenzosuberones; benzylideneindanones; benzylidenetetralones}, year = {2025}, eissn = {1422-0067}, orcid-numbers = {Kadlecsik, Csaba András/0009-0005-8238-6430; Perjési, Pál/0000-0002-1057-9664} } @CONFERENCE{MTMT:34814603, title = {Study on thiol reactivity of some six-membered cyclic chalcone analogs. Search for relationships between thiol reactivity and in vitro cancer cell cytotoxic effects}, url = {https://m2.mtmt.hu/api/publication/34814603}, author = {Bognár, Gábor and Rahin, Kenari and Zoltán, Pintér and Perjési, Pál}, booktitle = {Absztraktkötet: XII. Interdiszciplináris Doktorandusz Konferencia = Book of Abstract: XII. Interdisciplinary Doctoral Conference}, unique-id = {34814603}, year = {2024}, pages = {143-143}, orcid-numbers = {Perjési, Pál/0000-0002-1057-9664} } @CONFERENCE{MTMT:34915245, title = {Study on Stereochemistry of GSH-Conjugation of Some Cyclic Chalcone Analogs, 3-(4’-X-Benzylidene)-2,3-Dihydro-1-Benzopyran-4-Ones}, url = {https://m2.mtmt.hu/api/publication/34915245}, author = {Zoltán, Pintér and Bognár, Gábor and Perjési, Pál}, booktitle = {Congressus Pharmaceuticus Hungaricus XVII. and EUFEPS Annual Meeting 2024}, unique-id = {34915245}, year = {2024}, pages = {382-383}, orcid-numbers = {Perjési, Pál/0000-0002-1057-9664} } @CONFERENCE{MTMT:34915704, title = {Study on Thiol Reactivity of Some Six-Membered Cyclic Chalcone Analogs. Search for Relationships Between Thiol Reactivity and In Vitro Cancer Cell Cytotoxic Effects}, url = {https://m2.mtmt.hu/api/publication/34915704}, author = {Bognár, Gábor and Kenari, Fatemeh and Zoltán, Pintér and Perjési, Pál}, booktitle = {Congressus Pharmaceuticus Hungaricus XVII. and EUFEPS Annual Meeting 2024}, unique-id = {34915704}, year = {2024}, pages = {217-217}, orcid-numbers = {Perjési, Pál/0000-0002-1057-9664} } @CONFERENCE{MTMT:34915719, title = {Study of Michael Addition Reaction Between Hydroxychalcone Derivatives and Reduced Glutathione}, url = {https://m2.mtmt.hu/api/publication/34915719}, author = {Aline, Bernardes and Caridad, Noda Perez and Bognár, Gábor and Zoltán, Pintér and Perjési, Pál}, booktitle = {Congressus Pharmaceuticus Hungaricus XVII. and EUFEPS Annual Meeting 2024}, unique-id = {34915719}, year = {2024}, pages = {216-216}, orcid-numbers = {Perjési, Pál/0000-0002-1057-9664} } @article{MTMT:35641336, title = {(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}, url = {https://m2.mtmt.hu/api/publication/35641336}, author = {Bognár, Gábor and Kenari, Fatemeh and Pintér, Zoltán and Borges, Igor D. and Camargo, Ademir J. and Oliveira, Heibbe C. B. and Sanches-Neto, Flávio Olimpio and Carvalho-Silva, Valter H. and Napolitano, Hamilton B. and Perjési, Pál}, doi = {10.3390/molecules29235493}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {29}, unique-id = {35641336}, issn = {1431-5157}, abstract = {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.}, year = {2024}, eissn = {1420-3049}, orcid-numbers = {Oliveira, Heibbe C. B./0000-0002-6937-9982; Sanches-Neto, Flávio Olimpio/0000-0002-0664-171X; Carvalho-Silva, Valter H./0000-0002-7411-0099; Napolitano, Hamilton B./0000-0002-6047-9995; Perjési, Pál/0000-0002-1057-9664} }