@article{MTMT:34789041,
	title = {Synthesis of Estrone Heterodimers and Evaluation of Their In Vitro Antiproliferative Activity},
	url = {https://m2.mtmt.hu/api/publication/34789041},
	author = {Bózsity-Faragó, Noémi and Nagy, Viktória and Szabó, Johanna and Pálházi, Balázs and Kele, Zoltán and Resch, Vivien Erzsébet and Paragi, Gábor and Zupkó, István and Minorics, Renáta and Mernyák, Erzsébet},
	doi = {10.3390/ijms25084274},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {25},
	unique-id = {34789041},
	issn = {1661-6596},
	abstract = {Directed structural modifications of natural products offer excellent opportunities to develop selectively acting drug candidates. Natural product hybrids represent a particular compound group. The components of hybrids constructed from different molecular entities may result in synergic action with diminished side effects. Steroidal homo- or heterodimers deserve special attention owing to their potentially high anticancer effect. Inspired by our recently described antiproliferative core-modified estrone derivatives, here, we combined them into heterodimers via Cu(I)-catalyzed azide–alkyne cycloaddition reactions. The two trans-16-azido-3-(O-benzyl)-17-hydroxy-13α-estrone derivatives were reacted with 3-O-propargyl-D-secoestrone alcohol or oxime. The antiproliferative activities of the four newly synthesized dimers were evaluated against a panel of human adherent gynecological cancer cell lines (cervical: Hela, SiHa, C33A; breast: MCF-7, T47D, MDA-MB-231, MDA-MB-361; ovarian: A2780). One heterodimer (12) exerted substantial antiproliferative activity against all investigated cell lines in the submicromolar or low micromolar range. A pronounced proapoptotic effect was observed by fluorescent double staining and flow cytometry on three cervical cell lines. Additionally, cell cycle blockade in the G2/M phase was detected, which might be a consequence of the effect of the dimer on tubulin polymerization. Computational calculations on the taxoid binding site of tubulin revealed potential binding of both steroidal building blocks, mainly with hydrophobic interactions and water bridges.},
	year = {2024},
	eissn = {1422-0067},
	orcid-numbers = {Resch, Vivien Erzsébet/0000-0003-0044-5731; Paragi, Gábor/0000-0001-5408-1748; Zupkó, István/0000-0003-3243-5300; Minorics, Renáta/0000-0001-9685-813X; Mernyák, Erzsébet/0000-0003-4494-1817}
}

@mastersthesis{MTMT:3268397,
	title = {Biológiailag aktív konjugátumok szintézise módosított ösztrán vázon},
	url = {https://m2.mtmt.hu/api/publication/3268397},
	author = {Szabó, Johanna},
	doi = {10.14232/phd.3947},
	publisher = {SZTE},
	unique-id = {3268397},
	year = {2017}
}

@article{MTMT:3201077,
	title = {Synthesis and in vitro investigation of potential antiproliferative monosaccharide-D-secoestrone bioconjugates},
	url = {https://m2.mtmt.hu/api/publication/3201077},
	author = {Bodnár, Brigitta and Mernyák, Erzsébet and Szabó, Johanna and Wölfling, János and Schneider, Gyula and Zupkó, István and Kupihár, Zoltán and Kovács, Lajos},
	doi = {10.1016/j.bmcl.2017.03.029},
	journal-iso = {BIOORG MED CHEM LETT},
	journal = {BIOORGANIC & MEDICINAL CHEMISTRY LETTERS},
	volume = {27},
	unique-id = {3201077},
	issn = {0960-894X},
	abstract = {The syntheses of monosaccharide–D-secoestrone conjugates are reported. They were prepared from 3-(prop-2-inyloxy)-D-secoestrone alcohol or oxime and monosaccharide azides via Cu(I)-catalyzed azide–alkyne cycloaddition reactions (CuAAC). The antiproliferative activities of the conjugates were investigated in vitro against a panel of human adherent cancer cell lines (HeLa, A2780 and MCF-7) by means of MTT assays. The protected D-glucose-containing D-secoestrone oxime bioconjugate (24b) proved to be the most effective with an IC50 value in the low micromolar range against A2780 cell line. © 2017 Elsevier Ltd},
	year = {2017},
	eissn = {1464-3405},
	pages = {1938-1942},
	orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817; Wölfling, János/0000-0002-3037-309X; Zupkó, István/0000-0003-3243-5300; Kupihár, Zoltán/0000-0001-5499-7617; Kovács, Lajos/0000-0002-0331-3980}
}

@article{MTMT:3097024,
	title = {Mechanism of antiproliferative action of a new D-secoestrone-triazole derivative in cervical cancer cells and its effect on cancer cell motility},
	url = {https://m2.mtmt.hu/api/publication/3097024},
	author = {Bózsity-Faragó, Noémi and Minorics, Renáta and Szabó, Johanna and Mernyák, Erzsébet and Schneider, Gyula and Wölfling, János and Wang, Hui-Chun and Wu, Chin-Chung and Ocsovszki, Imre and Zupkó, István},
	doi = {10.1016/j.jsbmb.2016.06.013},
	journal-iso = {J STEROID BIOCHEM MOL BIOL},
	journal = {JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY},
	volume = {165},
	unique-id = {3097024},
	issn = {0960-0760},
	abstract = {Abstract Cervical cancer is the fourth most frequently diagnosed tumor and the fourth leading cause of cancer death in females worldwide. Cervical cancer is predominantly related with human papilloma virus (HPV) infection, with the most oncogenic types being HPV-18 and -16. Our previous studies demonstrated that some D-secoestrone derivatives exert pronounced antiproliferative activity. The aim of the current investigation was to characterize the mechanism of action of D-secoestrone-triazole (D-SET) on three cervical cancer cell lines with different pathological backgrounds. The growth-inhibitory effects of D-SET were determined by a standard MTT assay. We have found that D-SET exerts a pronounced growth-inhibitory effect on HPV 18-positive HeLa and HPV-negative C-33 A cells, but it has no substantial inhibitory activity on HPV 16-positive SiHa or on intact fibroblast MRC-5 cell lines. After 24 h incubation, cells showed the morphological and biochemical signs of apoptosis determined by fluorescent double staining, flow cytometry and caspase-3 activity assay. Besides the elevation of the ratio of cells in the subG1 phase, flow cytometric analysis revealed a cell cycle arrest at G2/M in both HeLa and C-33 A cell lines. To distinguish the G2/M cell population immunocytochemical flow cytometric analysis was performed on HeLa cells. The results show that D-SET significantly increases the ratio of phosphorylated histone H3, indicating cell accumulation in the M phase. Additionally, D-SET significantly increased the maximum rate of microtube formation measured by an in vitro tubulin polymerization assay. Besides its direct antiproliferative activity, the antimigratory property of D-SET has been investigated. Our results demonstrate that D-SET significantly inhibits the migration and invasion of HeLa cells after 24 h incubation. These results suggests that D-SET is a potent antiproliferative agent against HPV 16+ and HPV-negative cervical cancer cell lines, with an efficacious motility-inhibiting activity against HPV 16+ cells. Accordingly D-SET can be regarded as a potential drug candidate with a promising new mechanism of action among the antiproliferative steroids, potentially allowing for the design of novel anticancer agents.},
	keywords = {APOPTOSIS; Tubulin polymerization; Antiproliferative effect; G2/M phase arrest; cell migration and invasion; D-secoestrone-triazole},
	year = {2017},
	eissn = {1879-1220},
	pages = {247-257},
	orcid-numbers = {Minorics, Renáta/0000-0001-9685-813X; Mernyák, Erzsébet/0000-0003-4494-1817; Wölfling, János/0000-0002-3037-309X; Ocsovszki, Imre/0000-0003-1290-996X; Zupkó, István/0000-0003-3243-5300}
}

@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}
}

@CONFERENCE{MTMT:3081947,
	title = {A 17β-HSD1 enzimaktivitás in vitro vizsgálata 13α-ösztron származékokkal. A Magyar Endokrinológiai és Anyagcsere Társaság XXVI. Jubileumi Kongresszusa},
	url = {https://m2.mtmt.hu/api/publication/3081947},
	author = {Herman, Bianka Edina and Szabó, Johanna and Bacsa, Ildikó and Wölfling, János and Schneider, Gyula and Mernyák, Erzsébet and Szécsi, Mihály and Gardi, János and Valkusz, Zsuzsanna},
	booktitle = {A Magyar Endokrinológiai és Anyagcsere Társaság XXVI. Jubileumi Kongresszusa},
	unique-id = {3081947},
	year = {2016},
	pages = {159-159},
	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; Valkusz, Zsuzsanna/0000-0003-1928-6160}
}

@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: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: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}
}

@misc{MTMT:3026644,
	title = {Preparation and antiproliferative screening of heterocycle-fused D-secoalcohols in the 13α- and 13β-estrone series},
	url = {https://m2.mtmt.hu/api/publication/3026644},
	author = {Szabó, Johanna and Jerkovics, N and Herman, Bianka Edina and Schneider, Gyula and Wölfling, János and Minorics, Renáta and Bózsity-Faragó, Noémi and Zupkó, I and Szécsi, Mihály and Mernyák, Erzsébet},
	unique-id = {3026644},
	year = {2015},
	orcid-numbers = {Wölfling, János/0000-0002-3037-309X; Minorics, Renáta/0000-0001-9685-813X; Szécsi, Mihály/0000-0002-4272-1362; Mernyák, Erzsébet/0000-0003-4494-1817}
}