@article{MTMT:34556458, title = {Comparative Solution Equilibrium Studies on Anticancer Estradiol-Based Conjugates and Their Copper Complexes}, url = {https://m2.mtmt.hu/api/publication/34556458}, author = {Enyedy, Éva Anna and Giricz, Anett and Petrasheuskaya, Tatsiana and Mészáros, János Péter and May, Nóra Veronika and Spengler, Gabriella and Kovács, Ferenc and Molnár, Barnabás and Nagyné Frank, Éva}, doi = {10.3390/inorganics12020049}, journal-iso = {INORGANICS}, journal = {INORGANICS}, volume = {12}, unique-id = {34556458}, abstract = {Steroids are often considered valuable molecular tools for the development of anticancer agents with improved pharmacological properties. Conjugation of metal chelating moieties with a lipophilic sterane backbone is a viable option to obtain novel anticancer compounds. In this work, two estradiol-based hybrid molecules (PMA-E2 and DMA-E2) with an (N,N,O) binding motif and their Cu(II) complexes were developed. The lipophilicity, solubility, and acid-base properties of the novel ligands were determined by the combined use of UV-visible spectrophotometry, pH-potentiometry, and 1H NMR spectroscopy. The solution speciation and redox activity of the Cu(II) complexes were also investigated by means of UV-visible and electron paramagnetic resonance spectroscopy. Two structurally analogous ligands (PMAP and DMAP) were also included in the studies for better interpretation of the solution chemical data obtained. Three pKa values were determined for all ligands, revealing the order of the deprotonation steps: pyridinium-NH+ or NH(CH3)2+, secondary NH2+, and OH. The dimethylamine derivatives (DMA-E2, DMAP) are found in their H2L+ forms in solution at pH 7.4, whereas the fraction of the neutral HL species is significant (34–37%) in the case of the pyridine nitrogen-containing derivatives (PMA-E2, PMAP). Both estradiol derivatives were moderately cytotoxic in human breast (MCF-7) and colon adenocarcinoma (Colo-205) cells (IC50 = 30–63 μM). They form highly stable complexes with Cu(II) ions capable of oxidizing ascorbate and glutathione. These Cu(II) complexes are somewhat more cytotoxic (IC50 = 15–45 μM) than their corresponding ligands and show a better selectivity profile.}, year = {2024}, eissn = {2304-6740}, orcid-numbers = {Enyedy, Éva Anna/0000-0002-8058-8128; Mészáros, János Péter/0000-0001-6301-5259; May, Nóra Veronika/0000-0003-4770-4681; Spengler, Gabriella/0000-0001-8085-0950; Nagyné Frank, Éva/0000-0002-1332-0551} } @mastersthesis{MTMT:33663106, title = {Ösztránvázas aza- és oxaciklusos vegyületek régiószelektív szintézise [Regioselective synthesis of aza- and oxacyclic compounds in the estrane series]}, url = {https://m2.mtmt.hu/api/publication/33663106}, author = {Molnár, Barnabás}, doi = {10.14232/phd.11500}, publisher = {Universití of Szeged}, unique-id = {33663106}, year = {2023} } @article{MTMT:33049036, title = {Efficient Access to Domain-Integrated Estradiol-Flavone Hybrids Via the Corresponding Chalcones and Their in Vitro Anticancer Potential}, url = {https://m2.mtmt.hu/api/publication/33049036}, author = {Molnár, Barnabás and Gopisetty, Mohana Krishna and Nagy, Ferenc István and Adamecz, Dóra Izabella and Kása, Zsolt and Csontné Kiricsi, Mónika and Nagyné Frank, Éva}, doi = {10.1016/j.steroids.2022.109099}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {187}, unique-id = {33049036}, issn = {0039-128X}, abstract = {Structural modification of the phenolic A-ring of estrogens at C-2 and/or C-3 significantly reduces or eliminates the hormonal effects of the compounds, thus the incorporation of other pharmacophores into these positions can provide biologically active derivatives suitable for new indications, without possessing unwanted side effects. As part of this work, A-ring integration of estradiol with chalcones and flavones was carried out in the hope of obtaining novel molecular hybrids with anticancer action. The syntheses were performed from 2-acetylestradiol-17 beta-acetate which was first reacted with various (hetero)aromatic aldehydes in a pyrrolidine-catalyzed reaction in DMSO. The chalcones thus obtained were then subjected to oxidative cyclization with I2 in DMSO to afford estradiol-flavone hybrids in good yields. All newly synthesized derivatives were tested in vitro for cytotoxicity on human malignant cell lines of diverse origins as well as on a non-cancerous cell line, and the results demonstrated that estradiol-flavone hybrids containing a structure-integrated flavone moiety were the most active and cancer cell-selective agents. The minimal inhibitory concentration values (IC50) were calculated for selected compounds (3c, 3d and 3e) and their apoptosis inducing capacity was verified by RT-qPCR (real-time quantitative poly-merase chain reaction). The results suggest an important structure-activity relationship regarding estradiol-flavone hybrids that could form a promising synthetic platform and rationale for future drug developments.}, year = {2022}, eissn = {1878-5867}, orcid-numbers = {Gopisetty, Mohana Krishna/0000-0002-4310-3478; Adamecz, Dóra Izabella/0000-0002-1883-9600; Kása, Zsolt/0000-0003-4352-7761; Csontné Kiricsi, Mónika/0000-0002-8416-2052; Nagyné Frank, Éva/0000-0002-1332-0551} } @article{MTMT:32619224, title = {Regioselective synthesis, physicochemical properties and anticancer activity of 2-aminomethylated estrone derivatives}, url = {https://m2.mtmt.hu/api/publication/32619224}, author = {Molnár, Barnabás and Njangiru, Isaac Kinyua and Mótyán, Gergő and Leits, Péter and Zupkó, István and Minorics, Renáta and Balogh, György Tibor and Nagyné Frank, Éva}, doi = {10.1016/j.jsbmb.2022.106064}, journal-iso = {J STEROID BIOCHEM MOL BIOL}, journal = {JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY}, volume = {219}, unique-id = {32619224}, issn = {0960-0760}, year = {2022}, eissn = {1879-1220}, orcid-numbers = {Mótyán, Gergő/0000-0002-0741-106X; Zupkó, István/0000-0003-3243-5300; Minorics, Renáta/0000-0001-9685-813X; Balogh, György Tibor/0000-0003-3347-1880; Nagyné Frank, Éva/0000-0002-1332-0551} } @article{MTMT:31571893, title = {Multistep Synthesis and In Vitro Anticancer Evaluation of 2-Pyrazolyl-Estradiol Derivatives, Pyrazolocoumarin-Estradiol Hybrids and Analogous Compounds}, url = {https://m2.mtmt.hu/api/publication/31571893}, author = {Molnár, Barnabás and Gopisetty, Mohana Krishna and Adamecz, Dóra Izabella and Csontné Kiricsi, Mónika and Nagyné Frank, Éva}, doi = {10.3390/molecules25184039}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {25}, unique-id = {31571893}, issn = {1420-3049}, year = {2020}, eissn = {1420-3049}, orcid-numbers = {Gopisetty, Mohana Krishna/0000-0002-4310-3478; Adamecz, Dóra Izabella/0000-0002-1883-9600; Csontné Kiricsi, Mónika/0000-0002-8416-2052; Nagyné Frank, Éva/0000-0002-1332-0551} } @article{MTMT:30423715, title = {Microwave-Assisted Stereoselective Heterocyclization to Novel Ring D-fused Arylpyrazolines in the Estrone Series}, url = {https://m2.mtmt.hu/api/publication/30423715}, author = {Mótyán, Gergő and Molnár, Barnabás and Wölfling, János and Nagyné Frank, Éva}, doi = {10.3390/molecules24030569}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {24}, unique-id = {30423715}, issn = {1420-3049}, year = {2019}, eissn = {1420-3049}, orcid-numbers = {Mótyán, Gergő/0000-0002-0741-106X; Wölfling, János/0000-0002-3037-309X; Nagyné Frank, Éva/0000-0002-1332-0551} } @article{MTMT:3372993, title = {Synthesis of novel 17-triazolyl-androst-5-en-3-ol epimers via Cu(I)-catalyzed azide-alkyne cycloaddition and their inhibitory effect on 17α-hydroxylase/C17,20-lyase}, url = {https://m2.mtmt.hu/api/publication/3372993}, author = {Kiss, Anita and Herman, Bianka Edina and Görbe, Tamás and Mernyák, Erzsébet and Molnár, Barnabás and Wölfling, János and Szécsi, Mihály and Schneider, Gyula}, doi = {10.1016/j.steroids.2018.03.006}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {135}, unique-id = {3372993}, issn = {0039-128X}, year = {2018}, eissn = {1878-5867}, pages = {79-91}, orcid-numbers = {Kiss, Anita/0000-0003-3352-0996; Mernyák, Erzsébet/0000-0003-4494-1817; Wölfling, János/0000-0002-3037-309X; Szécsi, Mihály/0000-0002-4272-1362} }