TY - JOUR AU - Bózsity-Faragó, Noémi AU - Nagy, Viktória AU - Szabó, Johanna AU - Pálházi, Balázs AU - Kele, Zoltán AU - Resch, Vivien Erzsébet AU - Paragi, Gábor AU - Zupkó, István AU - Minorics, Renáta AU - Mernyák, Erzsébet TI - Synthesis of Estrone Heterodimers and Evaluation of Their In Vitro Antiproliferative Activity JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 25 PY - 2024 IS - 8 PG - 15 SN - 1661-6596 DO - 10.3390/ijms25084274 UR - https://m2.mtmt.hu/api/publication/34789041 ID - 34789041 AB - 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. LA - English DB - MTMT ER - TY - THES AU - Szabó, Johanna TI - Biológiailag aktív konjugátumok szintézise módosított ösztrán vázon PB - Szegedi Tudományegyetem (SZTE) PY - 2017 SP - 119 DO - 10.14232/phd.3947 UR - https://m2.mtmt.hu/api/publication/3268397 ID - 3268397 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Bodnár, Brigitta AU - Mernyák, Erzsébet AU - Szabó, Johanna AU - Wölfling, János AU - Schneider, Gyula AU - Zupkó, István AU - Kupihár, Zoltán AU - Kovács, Lajos TI - Synthesis and in vitro investigation of potential antiproliferative monosaccharide-D-secoestrone bioconjugates JF - BIOORGANIC & MEDICINAL CHEMISTRY LETTERS J2 - BIOORG MED CHEM LETT VL - 27 PY - 2017 IS - 9 SP - 1938 EP - 1942 PG - 5 SN - 0960-894X DO - 10.1016/j.bmcl.2017.03.029 UR - https://m2.mtmt.hu/api/publication/3201077 ID - 3201077 N1 - Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :3 Export Date: 11 February 2020 CODEN: BMCLE Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; estrone, 53-16-7; glucose, 50-99-7, 84778-64-3; Alkynes; Antineoplastic Agents; Azides; D-secoestrone; Estrone; Glucose; Glycoconjugates; Monosaccharides; Oximes Funding details: Hungarian Scientific Research Fund Funding details: K109293, K113150 Funding details: European Social Fund, ESF, A/2-11/1-2012-0001 Funding details: A-11/1/KONV-2012-0047, T?MOP-4.2.2 Funding text 1: The authors thank the Hungarian Scientific Research Fund ? Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (T?MOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund ? Belgium and Hungary (T?MOP-4.2.4.A/2-11/1-2012-0001 ?National Excellence Program?). Funding Agency and Grant Number: Hungarian Scientific Research Fund HungaryOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [OTKA K113150, K109293]; New Hungary Development Plan [TAMOP-4.2.2.A-11/1/KONV-2012-0047]; European UnionEuropean Union (EU); State of Hungary; European Social Fund - Belgium and Hungary [TAMOP-4.2.4.A/2-11/1-2012-0001] Funding text: The authors thank the Hungarian Scientific Research Fund Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (TAMOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund - Belgium and Hungary (TAMOP-4.2.4.A/2-11/1-2012-0001 'National Excellence Program'). Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :3 Export Date: 29 August 2020 CODEN: BMCLE Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; estrone, 53-16-7; glucose, 50-99-7, 84778-64-3; Alkynes; Antineoplastic Agents; Azides; D-secoestrone; Estrone; Glucose; Glycoconjugates; Monosaccharides; Oximes Funding details: European Social Fund, ESF, T?MOP-4.2.4, A/2-11/1-2012-0001 Funding details: Hungarian Scientific Research Fund, OTKA Funding details: European Commission, EC Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding details: -2012-0047 Funding text 1: The authors thank the Hungarian Scientific Research Fund ? Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (T?MOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund ? Belgium and Hungary (T?MOP-4.2.4.A/2-11/1-2012-0001 ?National Excellence Program?). Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :4 Export Date: 10 January 2021 CODEN: BMCLE Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; estrone, 53-16-7; glucose, 50-99-7, 84778-64-3; Alkynes; Antineoplastic Agents; Azides; D-secoestrone; Estrone; Glucose; Glycoconjugates; Monosaccharides; Oximes Funding details: European Social Fund, ESF, T?MOP-4.2.4, A/2-11/1-2012-0001 Funding details: Hungarian Scientific Research Fund, OTKA Funding details: European Commission, EC Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding details: -2012-0047 Funding text 1: The authors thank the Hungarian Scientific Research Fund ? Hungary (OTKA K113150 and K109293), the New Hungary Development Plan (T?MOP-4.2.2.A-11/1/KONV-2012-0047) for financial support. This research was also supported by the European Union and the State of Hungary, co-financed by the European Social Fund ? Belgium and Hungary (T?MOP-4.2.4.A/2-11/1-2012-0001 ?National Excellence Program?). AB - 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 LA - English DB - MTMT ER - TY - JOUR AU - Bózsity-Faragó, Noémi AU - Minorics, Renáta AU - Szabó, Johanna AU - Mernyák, Erzsébet AU - Schneider, Gyula AU - Wölfling, János AU - Wang, Hui-Chun AU - Wu, Chin-Chung AU - Ocsovszki, Imre AU - Zupkó, István TI - Mechanism of antiproliferative action of a new D-secoestrone-triazole derivative in cervical cancer cells and its effect on cancer cell motility JF - JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY J2 - J STEROID BIOCHEM MOL BIOL VL - 165 ET - 0 PY - 2017 SP - 247 EP - 257 PG - 11 SN - 0960-0760 DO - 10.1016/j.jsbmb.2016.06.013 UR - https://m2.mtmt.hu/api/publication/3097024 ID - 3097024 AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Herman, Bianka Edina AU - Szabó, Johanna AU - Bacsa, Ildikó AU - Wölfling, János AU - Schneider, Gyula AU - Bálint, Mónika Enikő AU - Hetényi, Csaba AU - Mernyák, Erzsébet AU - Szécsi, Mihály TI - Comparative investigation of the in vitro inhibitory potencies of 13-epimeric estrones and D-secoestrones towards 17β-hydroxysteroid dehydrogenase type 1 JF - JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY J2 - J ENZYM INHIB MED CH VL - 31 PY - 2016 IS - Suppl. 3 SP - 61 EP - 69 PG - 9 SN - 1475-6366 DO - 10.1080/14756366.2016.1204610 UR - https://m2.mtmt.hu/api/publication/3097533 ID - 3097533 N1 - MTA-ELTE Molecular Biophysics Research Group, Hungarian Academy of Sciences, Budapest, Hungary AB - 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. LA - English DB - MTMT ER - TY - CONF AU - Herman, Bianka Edina AU - Szabó, Johanna AU - Bacsa, Ildikó AU - Wölfling, János AU - Schneider, Gyula AU - Mernyák, Erzsébet AU - Szécsi, Mihály AU - Gardi, János AU - Valkusz, Zsuzsanna TI - A 17β-HSD1 enzimaktivitás in vitro vizsgálata 13α-ösztron származékokkal. A Magyar Endokrinológiai és Anyagcsere Társaság XXVI. Jubileumi Kongresszusa TS - A Magyar Endokrinológiai és Anyagcsere Társaság XXVI. Jubileumi Kongresszusa T2 - A Magyar Endokrinológiai és Anyagcsere Társaság XXVI. Jubileumi Kongresszusa PB - Medicina Könyvkiadó C1 - Budapest PY - 2016 SP - 159 EP - 159 PG - 1 UR - https://m2.mtmt.hu/api/publication/3081947 ID - 3081947 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Szabó, Johanna AU - Pataki, Zoltán AU - Wölfling, János AU - Schneider, Gyula AU - Bózsity-Faragó, Noémi AU - Minorics, Renáta AU - Zupkó, István AU - Mernyák, Erzsébet TI - Synthesis and biological evaluation of 13α-estrone derivatives as potential antiproliferative agents JF - STEROIDS J2 - STEROIDS VL - 113 PY - 2016 SP - 14 EP - 21 PG - 8 SN - 0039-128X DO - 10.1016/j.steroids.2016.05.010 UR - https://m2.mtmt.hu/api/publication/3078352 ID - 3078352 N1 - Funding Agency and Grant Number: Hungarian Scientific Research FundOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [OTKA K113150, K109293]; Richter Gedeon Plc.; European UnionEuropean Union (EU); State of Hungary; European Social FundEuropean Social Fund (ESF) [TAMOP 4.2.4. A/2-11-1-2012-0001] Funding text: The authors are grateful for financial support from the Hungarian Scientific Research Fund (OTKA K113150 and K109293) and Richter Gedeon Plc. This research was supported by the European Union and the State of Hungary, co-financed by the European Social Fund in the framework of TAMOP 4.2.4. A/2-11-1-2012-0001 'National Excellence Program'. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :14 Export Date: 29 August 2020 CODEN: STEDA Correspondence Address: Zupkó, I.; Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Hungary; email: zupko@pharm.u-szeged.hu Chemicals/CAS: estrone, 53-16-7; Antineoplastic Agents; Estrone Funding details: European Social Fund, ESF Funding details: European Commission, EC Funding details: Hungarian Scientific Research Fund, OTKA Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding text 1: The authors are grateful for financial support from the Hungarian Scientific Research Fund ( OTKA K113150 and K109293 ) and Richter Gedeon Plc . This research was supported by the European Union and the State of Hungary, co-financed by the European Social Fund in the framework of TÁMOP 4.2.4. A/2-11-1-2012-0001 ‘National Excellence Program’. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :16 Export Date: 10 January 2021 CODEN: STEDA Correspondence Address: Zupkó, I.; Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Hungary; email: zupko@pharm.u-szeged.hu Chemicals/CAS: estrone, 53-16-7; Antineoplastic Agents; Estrone Funding details: European Social Fund, ESF Funding details: European Commission, EC Funding details: Hungarian Scientific Research Fund, OTKA Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding text 1: The authors are grateful for financial support from the Hungarian Scientific Research Fund ( OTKA K113150 and K109293 ) and Richter Gedeon Plc . This research was supported by the European Union and the State of Hungary, co-financed by the European Social Fund in the framework of TÁMOP 4.2.4. A/2-11-1-2012-0001 ‘National Excellence Program’. AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Szabó, Johanna AU - Jerkovics, N AU - Schneider, Gyula AU - Wölfling, János AU - Bózsity-Faragó, Noémi AU - Minorics, Renáta AU - Zupkó, István AU - Mernyák, Erzsébet TI - Synthesis and in Vitro Antiproliferative Evaluation of C-13 Epimers of Triazolyl-d-Secoestrone Alcohols: The First Potent 13α-D-Secoestrone Derivative JF - MOLECULES J2 - MOLECULES VL - 21 PY - 2016 IS - 5 PG - 13 SN - 1420-3049 DO - 10.3390/molecules21050611 UR - https://m2.mtmt.hu/api/publication/3067612 ID - 3067612 N1 - Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :14 Export Date: 11 February 2020 CODEN: MOLEF Correspondence Address: Mernyák, E.; Department of Organic Chemistry, University of Szeged, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; Alcohols; Alkynes; Azides; Triazoles Funding details: K109293, K113150 Funding details: Magyar Tudományos Akadémia, MTA Funding details: Hungarian Scientific Research Fund Funding details: Richter Gedeon Talentum Alapítvány Funding text 1: The authors are grateful for financial support from the Hungarian Scientific Research Fund (OTKA K113150 and K109293). The work of No?mi B?zsity and Ren?ta Minorics was supported by a PhD Fellowship of the Talentum Fund of Richter Gedeon Plc. (Budapest) and a J?nos Bolyai Research Scholarship of the Hungarian Academy of Sciences, respectively. Funding Agency and Grant Number: Hungarian Scientific Research FundOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [OTKA K113150, K109293]; Talentum Fund of Richter Gedeon Plc. (Budapest); Janos Bolyai Research Scholarship of the Hungarian Academy of SciencesHungarian Academy of Sciences Funding text: The authors are grateful for financial support from the Hungarian Scientific Research Fund (OTKA K113150 and K109293). The work of Noemi Bozsity and Renata Minorics was supported by a PhD Fellowship of the Talentum Fund of Richter Gedeon Plc. (Budapest) and a Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences, respectively. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :17 Export Date: 29 August 2020 CODEN: MOLEF Correspondence Address: Mernyák, E.; Department of Organic Chemistry, University of Szeged, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; Alcohols; Alkynes; Azides; Triazoles Funding details: Hungarian Scientific Research Fund, OTKA Funding details: Magyar Tudományos Akadémia, MTA Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding details: Richter Gedeon Talentum AlapÃtvány Funding text 1: The authors are grateful for financial support from the Hungarian Scientific Research Fund (OTKA K113150 and K109293). The work of No?mi B?zsity and Ren?ta Minorics was supported by a PhD Fellowship of the Talentum Fund of Richter Gedeon Plc. (Budapest) and a J?nos Bolyai Research Scholarship of the Hungarian Academy of Sciences, respectively. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :19 Export Date: 10 January 2021 CODEN: MOLEF Correspondence Address: Mernyák, E.; Department of Organic Chemistry, University of Szeged, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Chemicals/CAS: azide, 12596-60-0, 14343-69-2; Alcohols; Alkynes; Azides; Triazoles Funding details: Magyar Tudományos Akadémia, MTA Funding details: Hungarian Scientific Research Fund, OTKA Funding details: Hungarian Scientific Research Fund, OTKA, K109293, K113150 Funding details: Richter Gedeon Talentum Alapítvány Funding text 1: The authors are grateful for financial support from the Hungarian Scientific Research Fund (OTKA K113150 and K109293). The work of No?mi B?zsity and Ren?ta Minorics was supported by a PhD Fellowship of the Talentum Fund of Richter Gedeon Plc. (Budapest) and a J?nos Bolyai Research Scholarship of the Hungarian Academy of Sciences, respectively. AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Szabó, Johanna AU - Bacsa, Ildikó AU - Wölfling, János AU - Schneider, Gyula AU - Zupkó, István AU - Varga, Mónika AU - Herman, Bianka Edina AU - Kalmár, László AU - Szécsi, Mihály AU - Mernyák, Erzsébet TI - Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides on d-secoestrone scaffolds JF - JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY J2 - J ENZYM INHIB MED CH VL - 31 PY - 2016 IS - 4 SP - 574 EP - 579 PG - 6 SN - 1475-6366 DO - 10.3109/14756366.2015.1050008 UR - https://m2.mtmt.hu/api/publication/2939481 ID - 2939481 N1 - Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, Hungary Cereal Research Non-Profit Ltd., Szeged, Hungary 1st Department of Medicine, University of Szeged, Szeged, Hungary Department of Obstetrics and Gynecology, University of Szeged, Szeged, Hungary Cited By :14 Export Date: 23 February 2021 CODEN: JEIMA Correspondence Address: Mernyák, E.; Department of Organic Chemistry, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Chemicals/CAS: amide, 17655-31-1; cisplatin, 15663-27-1, 26035-31-4, 96081-74-2; estradiol 17beta dehydrogenase, 9028-61-9; estrone, 53-16-7; Antineoplastic Agents; Benzyl Compounds; D-secoestrone; Enzyme Inhibitors; Estradiol Dehydrogenases; Estrone; HSD17B1 protein, human; N-((1-benzyl-1,2,3-triazol-4-yl)methyl)carboxamide; Triazoles LA - English DB - MTMT ER - TY - GEN AU - Szabó, Johanna AU - Jerkovics, N AU - Herman, Bianka Edina AU - Schneider, Gyula AU - Wölfling, János AU - Minorics, Renáta AU - Bózsity-Faragó, Noémi AU - Zupkó, I AU - Szécsi, Mihály AU - Mernyák, Erzsébet TI - Preparation and antiproliferative screening of heterocycle-fused D-secoalcohols in the 13α- and 13β-estrone series PY - 2015 UR - https://m2.mtmt.hu/api/publication/3026644 ID - 3026644 LA - English DB - MTMT ER -