@article{MTMT:3097533, title = {Comparative investigation of the in vitro inhibitory potencies of 13-epimeric estrones and D-secoestrones towards 17β-hydroxysteroid dehydrogenase type 1}, url = {https://m2.mtmt.hu/api/publication/3097533}, author = {Herman, Bianka Edina and Szabó, Johanna and Bacsa, Ildikó and Wölfling, János and Schneider, Gyula and Bálint, Mónika Enikő and Hetényi, Csaba and Mernyák, Erzsébet and Szécsi, Mihály}, doi = {10.1080/14756366.2016.1204610}, journal-iso = {J ENZYM INHIB MED CH}, journal = {JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY}, volume = {31}, unique-id = {3097533}, issn = {1475-6366}, abstract = {The inhibitory effects of 13-epimeric estrones, D-secooxime and D-secoalcohol estrone compounds on human placental 17β-hydroxysteroid dehydrogenase type 1 isozyme (17β-HSD1) were investigated. The transformation of estrone to 17β-estradiol was studied by an in vitro radiosubstrate incubation method. 13α-Estrone inhibited the enzyme activity effectively with an IC50 value of 1.2 μM, which indicates that enzyme affinity is similar to that of the natural estrone substrate. The 13β derivatives and the compounds bearing a 3-hydroxy group generally exerted stronger inhibition than the 13α and 3-ether counterparts. The 3-hydroxy-13β-D-secoalcohol and the 3-hydroxy-13α-D-secooxime displayed an outstanding cofactor dependence, i.e. more efficient inhibition in the presence of NADH than NADPH. The 3-hydroxy-13β-D-secooxime has an IC50 value of 0.070 μM and is one of the most effective 17β-HSD1 inhibitors reported to date in the literature. © 2016 Informa UK Limited, trading as Taylor & Francis Group.}, keywords = {NADPH; NADH; 13α-estrone; D-secoestrone; 17β-HSD1 inhibition}, year = {2016}, eissn = {1475-6374}, pages = {61-69}, orcid-numbers = {Bacsa, Ildikó/0000-0001-8277-631X; Wölfling, János/0000-0002-3037-309X; Mernyák, Erzsébet/0000-0003-4494-1817; Szécsi, Mihály/0000-0002-4272-1362} } @article{MTMT:3017583, title = {A three-component reagent system for rapid and mild removal of O-, N- and S-trityl protecting groups}, url = {https://m2.mtmt.hu/api/publication/3017583}, author = {Kicsák, Máté and Bege, Miklós and Bakai-Bereczki, Ilona and Csávás, Magdolna and Herczeg, Mihály and Kupihár, Zoltán and Kovács, Lajos and Borbás, Anikó and Herczegh, Pál}, doi = {10.1039/C6OB00067C}, journal-iso = {ORG BIOMOL CHEM}, journal = {ORGANIC & BIOMOLECULAR CHEMISTRY}, volume = {14}, unique-id = {3017583}, issn = {1477-0520}, abstract = {A new reagent system consisting of a Lewis acid such as BF3·Et2O or Cu(OTf)2, the mild protic acid hexafluoroisopropanol and the reducing quenching agent triethylsilane was elaborated for O-, N- and S-detritylation of nucleoside, carbohydrate and amino acid derivatives. The method is compatible with acetyl, silyl, acetal and Fmoc groups.}, year = {2016}, eissn = {1477-0539}, pages = {3190-3192}, orcid-numbers = {Bakai-Bereczki, Ilona/0000-0003-4601-7257; Herczeg, Mihály/0000-0002-7938-9789; Kupihár, Zoltán/0000-0001-5499-7617; Kovács, Lajos/0000-0002-0331-3980; Borbás, Anikó/0000-0001-8462-4547} } @article{MTMT:3067612, title = {Synthesis and in Vitro Antiproliferative Evaluation of C-13 Epimers of Triazolyl-d-Secoestrone Alcohols: The First Potent 13α-D-Secoestrone Derivative}, url = {https://m2.mtmt.hu/api/publication/3067612}, author = {Szabó, Johanna and Jerkovics, N and Schneider, Gyula and Wölfling, János and Bózsity-Faragó, Noémi and Minorics, Renáta and Zupkó, István and Mernyák, Erzsébet}, doi = {10.3390/molecules21050611}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {21}, unique-id = {3067612}, issn = {1420-3049}, abstract = {The syntheses of C-13 epimeric 3-[(1-benzyl-1,2,3-triazol-4-yl)methoxy]-d-secoestrones are reported. Triazoles were prepared from 3-(prop-2-inyloxy)-d-secoalcohols and p-substituted benzyl azides via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The antiproliferative activities of the products and their precursors were determined in vitro against a panel of human adherent cervical (HeLa, SiHa and C33A), breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) and ovarian (A2780) cell lines by means of MTT assays. The orientation of the angular methyl group and the substitution pattern of the benzyl group of the azide greatly influenced the cell growth-inhibitory potential of the compounds. The 13beta derivatives generally proved to be more potent than their 13alpha counterparts. Introduction of a benzyltriazolylmethyl group onto the 3-OH position seemed to be advantageous. One 13alpha compound containing an unsubstituted benzyltriazolyl function displayed outstanding antiproliferative activities against three cell lines.}, year = {2016}, eissn = {1420-3049}, orcid-numbers = {Wölfling, János/0000-0002-3037-309X; Minorics, Renáta/0000-0001-9685-813X; Zupkó, István/0000-0003-3243-5300; Mernyák, Erzsébet/0000-0003-4494-1817} } @article{MTMT:3078352, title = {Synthesis and biological evaluation of 13α-estrone derivatives as potential antiproliferative agents}, url = {https://m2.mtmt.hu/api/publication/3078352}, author = {Szabó, Johanna and Pataki, Zoltán and Wölfling, János and Schneider, Gyula and Bózsity-Faragó, Noémi and Minorics, Renáta and Zupkó, István and Mernyák, Erzsébet}, doi = {10.1016/j.steroids.2016.05.010}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {113}, unique-id = {3078352}, issn = {0039-128X}, abstract = {13 alpha-Estrone derivatives containing various substituents on C-3 and C-17 were synthesized, and evaluated by means of MU assays for in vitro antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF-7, A2780 and A431). Compounds with N-benzyltriazolylmethoxy moieties on C-3 proved to be more potent than their 3-hydroxy or 3-ether counterparts. Some triazoles exerted substantial cytostatic effects against particular tumor cell lines, with submicromolar IC50 values. (C) 2016 Elsevier Inc. All rights reserved.}, keywords = {IN-VITRO; INHIBITORS; Structural modifications; Azide–alkyne cycloaddition; Antiproliferative effect; 13α-estrone; 17-Deoxy-13α-estrone; Biochemistry & Molecular Biology}, year = {2016}, eissn = {1878-5867}, pages = {14-21}, orcid-numbers = {Wölfling, János/0000-0002-3037-309X; Minorics, Renáta/0000-0001-9685-813X; Zupkó, István/0000-0003-3243-5300; Mernyák, Erzsébet/0000-0003-4494-1817} } @article{MTMT:2939481, title = {Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides on d-secoestrone scaffolds}, url = {https://m2.mtmt.hu/api/publication/2939481}, author = {Szabó, Johanna and Bacsa, Ildikó and Wölfling, János and Schneider, Gyula and Zupkó, István and Varga, Mónika and Herman, Bianka Edina and Kalmár, László and Szécsi, Mihály and Mernyák, Erzsébet}, doi = {10.3109/14756366.2015.1050008}, journal-iso = {J ENZYM INHIB MED CH}, journal = {JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY}, volume = {31}, unique-id = {2939481}, issn = {1475-6366}, year = {2016}, eissn = {1475-6374}, pages = {574-579}, orcid-numbers = {Bacsa, Ildikó/0000-0001-8277-631X; Wölfling, János/0000-0002-3037-309X; Zupkó, István/0000-0003-3243-5300; Szécsi, Mihály/0000-0002-4272-1362; Mernyák, Erzsébet/0000-0003-4494-1817} } @article{MTMT:2994658, title = {Synthesis of A-ring halogenated 13alpha-estrone derivatives as potential 17beta-HSD1 inhibitors}, url = {https://m2.mtmt.hu/api/publication/2994658}, author = {Bacsa, Ildikó and Jójárt, Rebeka and Schneider, Gyula and Wölfling, János and Maróti, Péter and Herman, Bianka Edina and Szécsi, Mihály and Mernyák, Erzsébet}, doi = {10.1016/j.steroids.2015.10.008}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {104}, unique-id = {2994658}, issn = {0039-128X}, abstract = {13alpha-Estrone and its 3-methyl or benzyl ether were halogenated in ring A with N-bromo- or N-iodosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin as electrophile triggers. The chemo- and regioselectivities of the reactions depended greatly on the nature of the substituent on C-3. Bromination of the ethers led to 2- and 4-regioisomers. Bis-halogenation occurred only in the case of the phenolic derivative. Iodination and bromination resulted in similar products, except that the 3-benzyl ether could not be iodinated under the applied conditions. The potential inhibitory action of the new halogenated 13alpha-estrones on human 17beta-hydroxysteroid dehydrogenase 1 activity was investigated via in vitro radiosubstrate incubation. Some compounds proved to be effective inhibitors, with IC50 values in the submicromolar range.}, year = {2015}, eissn = {1878-5867}, pages = {230-236}, orcid-numbers = {Bacsa, Ildikó/0000-0001-8277-631X; Wölfling, János/0000-0002-3037-309X; Szécsi, Mihály/0000-0002-4272-1362; Mernyák, Erzsébet/0000-0003-4494-1817} } @article{MTMT:2878758, title = {Synthesis of trans-16-triazolyl-13α-methyl-17-estradiol diastereomers and the effects of structural modifications on their in vitro antiproliferative activities}, url = {https://m2.mtmt.hu/api/publication/2878758}, author = {Mernyák, Erzsébet and Kovács, Ida Jusztina and Minorics, Renáta and Sere, Péter and Czégány, Dóra and Sinka, Izabella and Wölfling, János and Schneider, Gyula and Újfaludi, Zsuzsanna and Boros, Imre Miklós and Ocsovszki, Imre and Varga, Mónika and Zupkó, István}, doi = {10.1016/j.jsbmb.2015.04.001}, journal-iso = {J STEROID BIOCHEM MOL BIOL}, journal = {JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY}, volume = {150}, unique-id = {2878758}, issn = {0960-0760}, abstract = {Abstract Novel 16-triazoles in the 13α-estrone series were synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition of the two diastereomeric (on C-16 and on C-17) 16-azido-13α-estra-1,3,5(10)-trien-17-ol 3-benzyl ethers with substituted phenylacetylenes. The new heterocyclic derivatives were evaluated in vitro by means of MTT assays for antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF-7, A431, A2780, T47D, MDA-MB-231 and MDA-MB-361). The inversion of the configurations at C-16 and C-17 selectively affected the growth-inhibitory properties of the tested compounds. The 16β,17α isomers generally proved to be potent on all cell lines, with IC50 values comparable to those of the reference agent cisplatin. Change of the substitution pattern of the phenyl group of the acetylene led to great differences in antiproliferative properties. Exclusively the p-phenyl-substituted triazoles exerted high cytostatic effects. One of the most potent compounds activated caspase-3 and caspase-9 without influencing caspase-8, confirming the induction of apoptosis via the intrinsic pathway.}, keywords = {APOPTOSIS; Azide–alkyne cycloaddition; Antiproliferative effect; Cell cycle blockade; 13α-estradiol}, year = {2015}, eissn = {1879-1220}, pages = {123-134}, orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817; Minorics, Renáta/0000-0001-9685-813X; Wölfling, János/0000-0002-3037-309X; Újfaludi, Zsuzsanna/0000-0003-4738-0963; Boros, Imre Miklós/0000-0001-8504-9687; Ocsovszki, Imre/0000-0003-1290-996X; Zupkó, István/0000-0003-3243-5300} } @article{MTMT:1818336, title = {A facile ″click″ approach to novel 15beta-triazolyl-5alpha-androstane derivatives, and an evaluation of their antiproliferative activities in vitro}, url = {https://m2.mtmt.hu/api/publication/1818336}, author = {Kádár, Zalán and Molnár, Judit and Schneider, Gyula and Zupkó, István and Nagyné Frank, Éva}, doi = {10.1016/j.bmc.2012.01.008}, journal-iso = {BIOORGAN MED CHEM}, journal = {BIOORGANIC & MEDICINAL CHEMISTRY}, volume = {20}, unique-id = {1818336}, issn = {0968-0896}, year = {2012}, eissn = {1464-3391}, pages = {1396-1402}, orcid-numbers = {Zupkó, István/0000-0003-3243-5300; Nagyné Frank, Éva/0000-0002-1332-0551} } @article{MTMT:1983613, title = {Antiproliferative effect of normal and 13-epi-d-homoestrone and their 3-methyl ethers on human reproductive cancer cell lines}, url = {https://m2.mtmt.hu/api/publication/1983613}, author = {Minorics, Renáta and Bózsity-Faragó, Noémi and Wölfling, János and Mernyák, Erzsébet and Schneider, Gyula and Márki, Árpád and Falkay, György and Ocsovszki, Imre and Zupkó, István}, doi = {10.1016/j.jsbmb.2012.04.009}, journal-iso = {J STEROID BIOCHEM MOL BIOL}, journal = {JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY}, volume = {132}, unique-id = {1983613}, issn = {0960-0760}, abstract = {The possibility of the therapeutic use of estrogens emerged following the recognition that certain estradiol analogs, and particularly metabolites (e.g. the A-ring metabolite 2-hydroxyestrone, etc.) inhibit the differentiation of diverse tumor cell lines. Until recently, despite the investigation of numerous synthetic d-ring-substituted estrone derivatives, no analysis had been published on the effects of d-ring expansion of estrone on its tumor-suppressing activity. The aim of the present study was to characterize the antiproliferative effects of normal and 13-epi-d-homoestrone and their 3-methyl ethers (1-4) on human reproductive cancer cell lines. The antitumor activities of the two epimer pairs on HeLa, MCF-7 and Ishikawa cells were determined. Normal d-homoestrone exerted the greatest cytostatic effect on HeLa cells (IC(50)=5.5muM) and was subjected to further investigations to elucidate its mechanism of action on apoptosis induction. Morphological changes detected by Hoechst 33258-propidium iodide double staining, the cell cycle arrest at phase G2/M and the subsequent increase in the proportion of the subG1 fraction determined by flow cytometric analysis and the significant increase in the activity of caspase-3 confirmed the induction of apoptosis in HeLa cells treated with d-homoestrone. d-Homoestrone was also tested on a non-cancerous human lung fibroblast cell line (MRC-5) to determine its selective toxicity. The concentration in which it inhibited cell proliferation by 50% was at least six times higher for the fibroblast cells than for cervical cancer cells. No significant in vivo estrogenic activity was observed as concerns the uterus weight of gonadectomized rats after a 7-day treatment with normal d-homoestrone. These results led to the conclusion that normal d-homoestrone is a novel antitumor compound with a similar activity on HeLa cells as that of the reference agent cisplatin, but its selectivity toward non-cancerous cells is significantly higher than that of cisplatin. It may be considered to be a basic lead molecule for the preclinical development of potential anticancer agents.}, year = {2012}, eissn = {1879-1220}, pages = {168-175}, orcid-numbers = {Minorics, Renáta/0000-0001-9685-813X; Wölfling, János/0000-0002-3037-309X; Mernyák, Erzsébet/0000-0003-4494-1817; Márki, Árpád/0000-0002-6056-8891; Ocsovszki, Imre/0000-0003-1290-996X; Zupkó, István/0000-0003-3243-5300} } @article{MTMT:1005881, title = {Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers}, url = {https://m2.mtmt.hu/api/publication/1005881}, author = {Wölfling, János and Mernyák, Erzsébet and Nagyné Frank, Éva and Falkay, György and Márki, Árpád and Minorics, Renáta and Schneider, Gyula}, doi = {10.1016/S0039-128X(02)00181-2}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {68}, unique-id = {1005881}, issn = {0039-128X}, year = {2003}, eissn = {1878-5867}, pages = {277-288}, orcid-numbers = {Wölfling, János/0000-0002-3037-309X; Mernyák, Erzsébet/0000-0003-4494-1817; Nagyné Frank, Éva/0000-0002-1332-0551; Márki, Árpád/0000-0002-6056-8891; Minorics, Renáta/0000-0001-9685-813X} }