@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}
}

@article{MTMT:34131836,
	title = {Antiproliferative and Antimetastatic Properties of 16-Azidomethyl Substituted 3-O-Benzyl Estrone Analogs},
	url = {https://m2.mtmt.hu/api/publication/34131836},
	author = {Senobar Tahaei, Seyyed Ashkan and Kulmány, Ágnes Erika and Minorics, Renáta and Kiss, Anita and Szabó, Zoltán and Germán, Péter and Szebeni, Gábor and Gémes, Nikolett and Mernyák, Erzsébet and Zupkó, István},
	doi = {10.3390/ijms241813749},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {24},
	unique-id = {34131836},
	issn = {1661-6596},
	abstract = {Four diastereomers of 16-azidomethyl substituted 3-O-benzyl estradiol (1–4) and their two estrone analogs (16AABE and 16BABE) were tested for their antiproliferative properties against human gynecological cancer cell lines. The estrones were selected for additional experiments based on their outstanding cell growth-inhibiting activities. Both compounds increased hypodiploid populations of breast cancer cells, and 16AABE elicited cell cycle disturbance as evidenced by flow cytometry. The two analogs substantially increased the rate of tubulin polymerization in vitro. 16AABE and 16BABE inhibited breast cancer cells’ migration and invasive ability, as evidenced by wound healing and Boyden chamber assays. Since both estrone analogs exerted remarkable estrogenic activities, as documented by a luciferase reporter gene assay, they can be considered as promising drug candidates for hormone-independent malignancies.},
	year = {2023},
	eissn = {1422-0067},
	orcid-numbers = {Minorics, Renáta/0000-0001-9685-813X; Kiss, Anita/0000-0003-3352-0996; Szabó, Zoltán/0000-0001-8278-8038; Szebeni, Gábor/0000-0002-6998-5632; Mernyák, Erzsébet/0000-0003-4494-1817; Zupkó, István/0000-0003-3243-5300}
}

@article{MTMT:34101587,
	title = {Cytotoxic effect of 13α-estrane derivatives on breast, endometrial and ovarian cancer cell lines},
	url = {https://m2.mtmt.hu/api/publication/34101587},
	author = {Zottel, A. and Jójárt, Rebeka and Ágoston, H. and Hafner, E. and Lipušček, N. and Mernyák, Erzsébet and Rižner, T.L.},
	doi = {10.1016/j.jsbmb.2023.106350},
	journal-iso = {J STEROID BIOCHEM MOL BIOL},
	journal = {JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY},
	volume = {232},
	unique-id = {34101587},
	issn = {0960-0760},
	abstract = {Hormone-dependent cancers such as breast, uterine, and ovarian cancers account for more than 35% of all cancers in women. Worldwide, these cancers occur in more than 2.7 million women/year and account for 22% of cancer-related deaths/year. The generally accepted mechanism for the pathophysiology of estrogen-dependent cancers is estrogen receptor-mediated cell proliferation associated with an increased number of mutations. Therefore, drugs that can interfere with either local estrogen formation or estrogen action via estrogen receptors are needed. Estrane derivatives that have low or minimal estrogenic activity can affect both pathways. In this study, we investigated the effect of 36 different estrane derivatives on the proliferation of eight breast, endometrial, and ovarian cancer cell lines and the corresponding three control cell lines. Estrane derivatives 3 and 4_2Cl showed a stronger effect on the endometrial cancer cell lines KLE and Ishikawa, respectively, compared with the control cell line HIEEC, with IC50 values of 32.6 microM and 17.9 microM, respectively. Estrane derivative 4_2Cl was most active in the ovarian cancer cell line COV362 compared to the control cell line HIO80 with an IC50 value of 3.6 microM. In addition, estrane derivative 2_4I showed a strong antiproliferative effect on endometrial and ovarian cancer cell lines, while the effect on the control cell line was slight or absent. The addition of halogen at carbon 2 and/or 4 in estrane derivatives 1 and 2 increased the selectivity for endometrial cancer cells. Overall, these results suggest that single estrane derivatives are efficient cytotoxic agents for endometrial and ovarian cancer cell lines, and thus potential lead compounds for drug development. © 2023 The Authors},
	keywords = {CYTOTOXICITY; breast cancer; ENDOMETRIAL CANCER; Ovarian cancer; Estrane derivatives},
	year = {2023},
	eissn = {1879-1220},
	orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817}
}

@article{MTMT:34067941,
	title = {Synthesis and in vitro photodynamic activity of aza-BODIPY-based photosensitizers},
	url = {https://m2.mtmt.hu/api/publication/34067941},
	author = {Hlogyik, Tamás and Laczkó-Rigó, Réka and Bakos, Éva and Poór, Miklós and Kele, Zoltán and Laczka, Csilla and Mernyák, Erzsébet},
	doi = {10.1039/d3ob00699a},
	journal-iso = {ORG BIOMOL CHEM},
	journal = {ORGANIC & BIOMOLECULAR CHEMISTRY},
	volume = {21},
	unique-id = {34067941},
	issn = {1477-0520},
	abstract = {Aza-BODIPY dyes have recently come to attention owing to their excellent chemical and photophysical properties. In particular, their absorption and emission maxima can efficiently be shifted to the red or even to the NIR spectral region. On this basis, aza-BODIPY derivatives are widely investigated as fluorescent probes or phototherapeutic agents. Here we report the synthesis of a set of novel aza-BODIPY derivatives as potential photosensitizers for use in photodynamic therapy. Triazolyl derivatives were obtained via Cu(I)-catalyzed azide-alkyne cycloaddition as the key step. In vitro photodynamic activities of the newly synthesized compounds were evaluated on the A431 human epidermoid carcinoma cell line. Structural differences influenced the light-induced toxicity of the test compounds markedly. Compared to the initial tetraphenyl aza-BODIPY derivative, the compound bearing two hydrophilic triethylene glycol side chains showed substantial, more than 250-fold, photodynamic activity with no dark toxicity. Our newly synthesized aza-BODIPY derivative, acting in the nanomolar range, might serve as a promising candidate for the design of more active and selective photosensitizers.},
	year = {2023},
	eissn = {1477-0539},
	pages = {6018-6027},
	orcid-numbers = {Kele, Zoltán/0000-0002-4401-0302; Mernyák, Erzsébet/0000-0003-4494-1817}
}

@article{MTMT:33727646,
	title = {Investigation of the Antineoplastic Effects of 2-(4-Chlorophenyl)-13α-Estrone Sulfamate against the HPV16-Positive Human Invasive Cervical Carcinoma Cell Line SiHa},
	url = {https://m2.mtmt.hu/api/publication/33727646},
	author = {Ali, Hazhmat and Traj, Péter and Szebeni, Gábor and Gémes, Nikolett and Resch, Vivien Erzsébet and Paragi, Gábor and Mernyák, Erzsébet and Minorics, Renáta and Zupkó, István},
	doi = {10.3390/ijms24076625},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {24},
	unique-id = {33727646},
	issn = {1661-6596},
	abstract = {Cervical carcinoma is one of the most frequent malignant gynecological cancers in women of reproductive age. Because of the poor tolerability of currently available chemotherapeutic agents, efforts have been focused on developing innovative molecules, including steroids, that exert antineoplastic effects with a better safety profile. In addition to their endocrine properties, certain estrogens exhibit additional biological activities, such as antiangiogenic and anticancer effects. Based on previous studies, the antineoplastic properties of 13α-estrone sulfamate derivatives (13AES1-3) were investigated, and the mechanism of action for the most promising compound 13AES3 was explored. Based on their effects on the viability of different human adherent gynecological cancer cells, the SiHa cervical cell line was used for mechanistic experiments. The most active analog 13AES3 was shown to exert considerable proapoptotic effects, as evidenced by a colorimetric caspase-3 assay and fluorescent double staining. It also elicited antimigratory and anti-invasive effects in a concentration-dependent manner, as evidenced by wound healing and Boyden chamber assays, respectively. Regarding their mechanism of action, 13AES derivatives were shown to inhibit tubulin polymerization, and computer simulations provided a possible explanation for the importance of the presence of the chlorophenyl ring on the estrane skeleton. 13AES3 is considered to be the first 13α-estrone derivative with a significant antineoplastic potency against SiHa cancer cells. Therefore, it might serve as a valuable lead molecule for the design of anticancer agents targeting cervical carcinomas.},
	keywords = {APOPTOSIS; Antiproliferative; anti-invasive; 13α-estrone and cervical carcinoma; tubulin-microtubule system},
	year = {2023},
	eissn = {1422-0067},
	orcid-numbers = {Szebeni, Gábor/0000-0002-6998-5632; Resch, Vivien Erzsébet/0000-0003-0044-5731; Paragi, Gábor/0000-0001-5408-1748; Mernyák, Erzsébet/0000-0003-4494-1817; Minorics, Renáta/0000-0001-9685-813X; Zupkó, István/0000-0003-3243-5300}
}

@article{MTMT:33663109,
	title = {Synthesis of hydrocortisone esters targeting androgen and glucocorticoid receptors in prostate cancer in vitro},
	url = {https://m2.mtmt.hu/api/publication/33663109},
	author = {Peřina, Miroslav and Kiss, Anita and Mernyák, Erzsébet and Mada, Lukáš and Schneider, Gyula and Jorda, Radek},
	doi = {10.1016/j.jsbmb.2023.106269},
	journal-iso = {J STEROID BIOCHEM MOL BIOL},
	journal = {JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY},
	volume = {229},
	unique-id = {33663109},
	issn = {0960-0760},
	year = {2023},
	eissn = {1879-1220},
	orcid-numbers = {Kiss, Anita/0000-0003-3352-0996; Mernyák, Erzsébet/0000-0003-4494-1817}
}

@article{MTMT:33594496,
	title = {Synthesis and Antiproliferative Activity of Steroidal Diaryl Ethers},
	url = {https://m2.mtmt.hu/api/publication/33594496},
	author = {Kovács, Édua and Ali, Hazhmat and Minorics, Renáta and Traj, Péter and Resch, Vivien Erzsébet and Paragi, Gábor and Bruszel, Bella and Zupkó, István and Mernyák, Erzsébet},
	doi = {10.3390/molecules28031196},
	journal-iso = {MOLECULES},
	journal = {MOLECULES},
	volume = {28},
	unique-id = {33594496},
	issn = {1420-3049},
	abstract = {Novel 13α-estrone derivatives have been synthesized via direct arylation of the phenolic hydroxy function. Chan–Lam couplings of arylboronic acids with 13α-estrone as a nucleophilic partner were carried out under copper catalysis. The antiproliferative activities of the newly synthesized diaryl ethers against a panel of human cancer cell lines (A2780, MCF-7, MDA-MB 231, HeLa, SiHa) were investigated by means of MTT assays. The quinoline derivative displayed substantial antiproliferative activity against MCF-7 and HeLa cell lines with low micromolar IC50 values. Disturbance of tubulin polymerization has been confirmed by microplate-based photometric assay. Computational calculations reveal significant interactions of the quinoline derivative with the taxoid binding site of tubulin.},
	year = {2023},
	eissn = {1420-3049},
	orcid-numbers = {Minorics, Renáta/0000-0001-9685-813X; Resch, Vivien Erzsébet/0000-0003-0044-5731; Paragi, Gábor/0000-0001-5408-1748; Zupkó, István/0000-0003-3243-5300; Mernyák, Erzsébet/0000-0003-4494-1817}
}

@{MTMT:33338885,
	title = {In Vitro Evaluation of Antiproliferative and Antimetastatic Activity of the Newly Synthesized 2-(4-Chlorophenyl)-13α-Estrone Sulfamate},
	url = {https://m2.mtmt.hu/api/publication/33338885},
	author = {Ali, Hazhmat and Mernyák, Erzsébet and Traj, Péter and Gábor, J. Szebeni and Minorics, Renáta and Zupkó, István},
	booktitle = {Natural vs. Artificial Networks: The Usefulness of the Concept in Health, Life, and Technical Sciences},
	unique-id = {33338885},
	year = {2022},
	pages = {81-82},
	orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817; Minorics, Renáta/0000-0001-9685-813X; Zupkó, István/0000-0003-3243-5300}
}

@{MTMT:33272208,
	title = {BODIPY-típusú fluorofórok szintézise},
	url = {https://m2.mtmt.hu/api/publication/33272208},
	author = {Tamási, Zita and Mernyák, Erzsébet},
	booktitle = {Vegyészkonferencia 2022},
	unique-id = {33272208},
	year = {2022},
	pages = {107-108},
	orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817}
}

@{MTMT:33272206,
	title = {Biomolekulák konjugálására alkalmas aza-BODIPY-típusú fluorofórok szintézise},
	url = {https://m2.mtmt.hu/api/publication/33272206},
	author = {Hlogyik, Tamás and Mernyák, Erzsébet},
	booktitle = {Vegyészkonferencia 2022},
	unique-id = {33272206},
	year = {2022},
	pages = {84-85},
	orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817}
}