TY - JOUR AU - Cao, Jiasong AU - Wang, Yixin AU - Wang, Shuqi AU - Shen, Yongmei AU - Li, Wen AU - Wei, Zhuo AU - Li, Shanshan AU - Lin, Qimei AU - Chang, Ying TI - Expression of Key Steroidogenic Enzymes in Human Placenta and Associated Adverse Pregnancy Outcomes JF - MATERNAL-FETAL MEDICINE J2 - MATERNAL-FETAL MEDICINE VL - 5 PY - 2023 IS - 3 SP - 163 EP - 172 PG - 10 SN - 2096-6954 DO - 10.1097/FM9.0000000000000167 UR - https://m2.mtmt.hu/api/publication/34298344 ID - 34298344 N1 - Export Date: 28 November 2023 AB - Steroid hormones, including progestagens, estrogens, androgens, corticosteroids, and their precursor cholesterol, perform essential functions in the successful establishment and maintenance of pregnancy and normal fetal development. As the core endocrine organ at the prenatal stage, the human placenta is involved in the biosynthesis, metabolism, and delivery of steroid hormones. Steroidogenic pathways are tightly regulated by placenta-intrinsic cytochrome P450 and hydroxysteroid dehydrogenase. However, the relationship between placental steroidogenic enzyme expression and adverse pregnancy outcomes is controversial. In this review, we summarize the possible upstream regulatory mechanisms of placental steroidogenic enzymes in physiologic and pathophysiologic states. We also describe the human placental barrier model and examine the potential of single-cell sequencing for evaluating the primary functions and cellular origin of steroidogenic enzymes. Finally, we examine the existing evidence for the association between placental steroidogenic enzyme dysregulation and adverse pregnancy outcomes. LA - English DB - MTMT ER - TY - JOUR AU - Ilovaisky, Alexey I. AU - Merkulova, Valentina M. AU - Chernoburova, Elena I AU - Shchetinina, Marina A. AU - Salnikova, Diana I AU - Scherbakov, Alexander M. AU - Zavarzin, Igor V AU - Terent'ev, Alexander O. TI - Secosteroidal hydrazides: Promising scaffolds for anti-breast cancer agents JF - JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY J2 - J STEROID BIOCHEM MOL BIOL VL - 214 PY - 2021 PG - 14 SN - 0960-0760 DO - 10.1016/j.jsbmb.2021.106000 UR - https://m2.mtmt.hu/api/publication/32314150 ID - 32314150 N1 - N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, 119991, Russian Federation Department of Experimental Tumor Biology, N.N. Blokhin National Medical Research Center of Oncology of the Ministry of Health of the Russian Federation, 24 Kashirskoye sh., Moscow, 115522, Russian Federation Export Date: 3 May 2022 CODEN: JSBBE Correspondence Address: Ilovaisky, A.I.; N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky prosp., Russian Federation Chemicals/CAS: lactone, 1338-03-0; Anti-Bacterial Agents; Antineoplastic Agents; Hydrazines; Lactones; Steroids AB - A convenient and selective approach to 13,17-secoestra-1,3,5(10)-trien-17-oic acid hydrazides and their N'-(het) arylmethylene derivatives was disclosed and these novel types of secosteroids were screened for cytotoxicity against hormone-dependent human breast cancer cell line MCF-7. A number of 13,17-secoestra-1,3,5(10)-trien17-oic acid [N'-(het)arylmethylene]hydrazides show significant cytotoxic effect comparable or superior to that for reference drug cisplatin. Compound 3l exhibits the highest activity with the IC50 value of about 2 mu M and is 2.8 times more active than cisplatin. Hit 13,17-secoestra-1,3,5(10)-trien-17-oic acid [N'-(het)arylmethylene] hydrazides 3d, 3l and 3q are characterized by high cytotoxicity and good selectivity towards MCF-7 breast cancer cells. The synthesized secosteroids may be considered as new promising antitumor agents. LA - English DB - MTMT ER - TY - JOUR AU - Kulmány, Ágnes Erika AU - Herman, Bianka Edina AU - Zupkó, István AU - Sinreih, Masa AU - Rižner, Tea Lanišnik AU - Savić, Marina AU - Oklješa, Aleksandar AU - Nikolić, Andrea AU - Nagy, Viktória AU - Ocsovszki, Imre AU - Szécsi, Mihály AU - Jovanović-Šanta, Suzana TI - Heterocyclic androstane and estrane D-ring modified steroids. Microwave-assisted synthesis, steroid-converting enzyme inhibition, apoptosis induction, and effects on genes encoding estrogen inactivating enzymes TS - Microwave-assisted synthesis, steroid-converting enzyme inhibition, apoptosis induction, and effects on genes encoding estrogen inactivating enzymes JF - JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY J2 - J STEROID BIOCHEM MOL BIOL VL - 214 PY - 2021 PG - 13 SN - 0960-0760 DO - 10.1016/j.jsbmb.2021.105997 UR - https://m2.mtmt.hu/api/publication/32196015 ID - 32196015 N1 - Department of Pharmacodynamics and Biopharmacy, Faculty of Pharmacy, University of Szeged, Szeged, H-6720, Hungary Department of Medicine, University of Szeged, Szeged, H-6720, Hungary Institute of Biochemistry, Faculty of Medicine, University of Ljubljana, Ljubljana, Slovenia Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Novi Sad, 21000, Serbia Department of Biochemistry, Faculty of Medicine, University of Szeged, Szeged, H-6720, Hungary Export Date: 29 March 2022 CODEN: JSBBE Correspondence Address: Jovanović-Šanta, S.; University of Novi Sad, Trg Dositeja Obradovića 3, Serbia; email: suzana.jovanovic-santa@dh.uns.ac.rs Chemicals/CAS: estradiol, 50-28-2; estrone, 53-16-7; RNA, 63231-63-0; Androstanes; Enzyme Inhibitors; Estradiol; Estranes; Estrogens; Estrone; Fatty Acids; IDS 89 Sabal serrulata extract; Phytosterols; RNA; RNA, Messenger LA - English DB - MTMT ER - TY - JOUR AU - Herman, Bianka Edina AU - Gardi, János AU - Julesz, János AU - Tömböly, Csaba AU - Szánti-Pintér, Eszter AU - Fehér, Klaudia AU - Skodáné Földes, Rita AU - Szécsi, Mihály TI - Steroidal ferrocenes as potential enzyme inhibitors of the estrogen biosynthesis JF - BIOLOGIA FUTURA J2 - BIOL FUTURA VL - 71 PY - 2020 IS - 3 SP - 249 EP - 264 PG - 16 SN - 2676-8615 DO - 10.1007/s42977-020-00023-7 UR - https://m2.mtmt.hu/api/publication/31365295 ID - 31365295 LA - English DB - MTMT ER - TY - JOUR AU - Herman, Bianka Edina AU - Kiss, Anita AU - Wölfling, János AU - Mernyák, Erzsébet AU - Szécsi, Mihály AU - Schneider, Gyula TI - Synthesis of substituted 15β-alkoxy estrone derivatives and their cofactor-dependent inhibitory effect on 17β-HSD1 JF - JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY J2 - J ENZYM INHIB MED CH VL - 34 PY - 2019 IS - 1 SP - 1271 EP - 1286 PG - 16 SN - 1475-6366 DO - 10.1080/14756366.2019.1634064 UR - https://m2.mtmt.hu/api/publication/30747981 ID - 30747981 N1 - Export Date: 6 August 2019 LA - English DB - MTMT ER - TY - THES AU - Bacsa, Ildikó TI - Ösztrán vázas vegyületek A- és D-gyűrűben történő módosítása PB - Szegedi Tudományegyetem (SZTE) PY - 2018 SP - 108 DO - 10.14232/phd.9754 UR - https://m2.mtmt.hu/api/publication/3402221 ID - 3402221 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Bacsa, Ildikó AU - Herman, Bianka Edina AU - Jójárt, Rebeka AU - Herman, Kevin Stefan AU - Wölfling, János AU - Schneider, Gyula AU - Varga, Mónika AU - Tömböly, Csaba AU - Rizner, Tea Lanisnik AU - Szécsi, Mihály AU - Mernyák, Erzsébet TI - Synthesis and structure–activity relationships of 2- and/or 4-halogenated 13β- and 13α-estrone derivatives as enzyme inhibitors of estrogen biosynthesis JF - JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY J2 - J ENZYM INHIB MED CH VL - 33 PY - 2018 IS - 1 SP - 1271 EP - 1282 PG - 12 SN - 1475-6366 DO - 10.1080/14756366.2018.1490731 UR - https://m2.mtmt.hu/api/publication/27701563 ID - 27701563 N1 - Department of Organic Chemistry, University of Szeged, Szeged, Hungary 1st Department of Medicine, University of Szeged, Szeged, Hungary Department of Microbiology, University of Szeged, University of Szeged, Szeged, Hungary Laboratory of Chemical Biology, Institute of Biochemistry, Biological Research Centre of the Hungarian Academy of Sciences, Szeged, Hungary Institute of Biochemistry, Faculty of Medicine, University of Ljubljana, Ljubljana, Slovenia Cited By :19 Export Date: 3 May 2022 CODEN: JEIMA Correspondence Address: Mernyák, E.; Department of Organic Chemistry, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Chemicals/CAS: aromatase, 9039-48-9; hydroxysteroid dehydrogenase, 9001-56-3; steryl sulfatase, 9025-62-1; estradiol 17beta dehydrogenase, 9028-61-9; estrone, 53-16-7; Aromatase; Enzyme Inhibitors; Estradiol Dehydrogenases; Estrogens; Estrone; HSD17B1 protein, human; Steryl-Sulfatase LA - English DB - MTMT ER - TY - JOUR AU - Bekic, Sofija S AU - Marinovic, Maja A AU - Petri, Edward T AU - Sakac, Marija N AU - Nikolic, Andrea R AU - Kojic, Vesna V AU - Celic, Andjelka S TI - Identification of D-seco modified steroid derivatives with affinity for estrogen receptor alpha and beta isoforms using a non-transcriptional fluorescent cell assay in yeast JF - STEROIDS J2 - STEROIDS VL - 130 PY - 2018 SP - 22 EP - 30 PG - 9 SN - 0039-128X DO - 10.1016/j.steroids.2017.12.002 UR - https://m2.mtmt.hu/api/publication/27336420 ID - 27336420 N1 - University of Novi Sad, Faculty of Sciences, Department of Chemistry, Biochemistry and Environmental Protection, Trg Dositeja Obradovića 3, Novi Sad, 21000, Serbia University of Novi Sad, Faculty of Sciences, Department of Biology and Ecology, Trg Dositeja Obradovića 2, Novi Sad, 21000, Serbia University of Novi Sad, Faculty of Medicine, Oncology Institute of Vojvodina, Put doktora Goldmana 4, Sremska Kamenica, 21204, Serbia Cited By :7 Export Date: 29 September 2021 CODEN: STEDA Correspondence Address: Ćelić, A.S.; University of Novi Sad, Trg Dositeja Obradovića 2, Serbia; email: andjelka.celic@dbe.uns.ac.rs LA - English DB - MTMT ER - TY - JOUR AU - Chatuphonprasert, W AU - Jarukamjorn, K AU - Ellinger, I TI - Physiology and pathophysiology of steroid biosynthesis, transport and metabolism in the human placenta JF - FRONTIERS IN PHARMACOLOGY J2 - FRONT PHARMACOL VL - 9 PY - 2018 IS - SEP SN - 1663-9812 DO - 10.3389/fphar.2018.01027 UR - https://m2.mtmt.hu/api/publication/27678042 ID - 27678042 N1 - Export Date: 23 February 2021 LA - English DB - MTMT ER - TY - JOUR AU - Bacsa, Ildikó AU - Dávid, Szemerédi AU - Wölfling, János AU - Schneider, Gyula AU - Lilla, Fekete AU - Mernyák, Erzsébet TI - The first Pd-catalyzed Buchwald-Hartwig aminations at C-2 or C-4 in the estrone series JF - BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY J2 - BEILSTEIN J ORG CHEM VL - 14 PY - 2018 SP - 998 EP - 1003 PG - 6 SN - 1860-5397 DO - 10.3762/bjoc.14.85 UR - https://m2.mtmt.hu/api/publication/3375836 ID - 3375836 N1 - Funding Agency and Grant Number: New National Excellence Program of the Ministry of Human Capacities [UNKP-17-4]; National Research, Development and Innovation Office-NKFIH [GINOP-2.3.2-15-2016-00038, OTKA SNN 124329] Funding text: The work of Erzsebet Mernyak in this project was supported by the UNKP-17-4 "New National Excellence Program of the Ministry of Human Capacities". This work was supported by National Research, Development and Innovation Office-NKFIH through projects GINOP-2.3.2-15-2016-00038 and OTKA SNN 124329. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Cited By :2 Export Date: 29 August 2020 CODEN: BJOCB Correspondence Address: Mernyák, E.; Department of Organic Chemistry, University of Szeged, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Funding details: Emberi Eroforrások Minisztériuma, EMMI Funding details: Hungarian Scientific Research Fund, OTKA, SNN 124329 Funding details: GINOP-2.3.2-15-2016-00038 Funding text 1: The work of Erzsébet Mernyák in this project was supported by the ÚNKP-17-4 „New National Excellence Program of the Ministry of Human Capacities”. This work was supported by National Research, Development and Innovation Office-NKFIH through projects GINOP-2.3.2-15-2016-00038 and OTKA SNN 124329. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Cited By :2 Export Date: 10 January 2021 CODEN: BJOCB Correspondence Address: Mernyák, E.; Department of Organic Chemistry, University of Szeged, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Funding details: Emberi Eroforrások Minisztériuma, EMMI Funding details: Hungarian Scientific Research Fund, OTKA, SNN 124329 Funding details: GINOP-2.3.2-15-2016-00038 Funding text 1: The work of Erzsébet Mernyák in this project was supported by the ÚNKP-17-4 „New National Excellence Program of the Ministry of Human Capacities”. This work was supported by National Research, Development and Innovation Office-NKFIH through projects GINOP-2.3.2-15-2016-00038 and OTKA SNN 124329. LA - English DB - MTMT ER - TY - JOUR AU - Jójárt, Rebeka AU - Pécsy, S. AU - Keglevich, György AU - Szécsi, Mihály AU - Laczkó-Rigó, Réka AU - Laczka, Csilla AU - Kecskeméti, Gábor AU - Mernyák, Erzsébet TI - Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors JF - BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY J2 - BEILSTEIN J ORG CHEM VL - 14 ET - 0 PY - 2018 SP - 2838 EP - 2845 PG - 8 SN - 1860-5397 DO - 10.3762/bjoc.14.262 UR - https://m2.mtmt.hu/api/publication/30331520 ID - 30331520 N1 - Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, H-1521, Hungary 1st Department of Medicine, University of Szeged, Korányi fasor 8-10, Szeged, H-6720, Hungary Membrane protein research group, Institute of Enzymology, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok körútja 2, Budapest, H-1117, Hungary Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Cited By :9 Export Date: 26 August 2021 CODEN: BJOCB Correspondence Address: Mernyák, E.; Department of Organic Chemistry, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu AB - Novel 2- or 4-phosphonated 13 alpha-estrone derivatives were synthesized via the Hirao reaction. Bromo regioisomers (2- or 4-) of 13 alpha-estrone and its 3-benzyl or 3-methyl ether were reacted with diethyl phosphite or diphenylphosphine oxide using Pd(PPh3)(4) as catalyst under microwave irradiation. The influence of the new compounds on the transport function of the organic anion transporting polypeptide OATP2B1 was investigated by measuring Cascade Blue uptake. Derivatives bearing a 3-benzyl ether function displayed substantial submicromolar OATP2B1 inhibitory activity. The inhibitory effects of the compounds on human placental steroid sulfatase (STS) and 17 beta-hydroxysteroid dehydrogenase type 1 isozyme (17 beta-HSD1) were investigated by in vitro radiosub-strate incubation methods. None of the test compounds inhibited the STS markedly. The structure-activity relationship evaluation revealed that 2-substituted 3-hydroxy derivatives are able to inhibit the 17 beta-HSD1 enzyme with submicromolar IC50 values. Dual OATP2B1 and 17 beta-HSD1 inhibitors have been identified. LA - English DB - MTMT ER - TY - JOUR AU - Bacsa, Ildikó AU - Jójárt, Rebeka AU - Wölfling, János AU - Schneider, Gyula AU - Herman, Bianka Edina AU - Szécsi, Mihály AU - Mernyák, Erzsébet TI - Synthesis of novel 13 alpha-estrone derivatives by Sonogashira coupling as potential 17 beta-HSD1 inhibitors JF - BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY J2 - BEILSTEIN J ORG CHEM VL - 13 PY - 2017 SP - 1303 EP - 1309 PG - 7 SN - 1860-5397 DO - 10.3762/bjoc.13.126 UR - https://m2.mtmt.hu/api/publication/3251236 ID - 3251236 N1 - Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary 1st Department of Medicine, University of Szeged, Korányi fasor 8–10, Szeged, H-6720, Hungary Cited By :9 Export Date: 10 January 2021 CODEN: BJOCB Correspondence Address: Mernyák, E.; Department of Organic Chemistry, University of Szeged, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Funding details: Hungarian Scientific Research Fund, OTKA, K113150 Funding details: Magyar Tudományos Akadémia, MTA Funding text 1: The work of Erzs?bet Merny?k in this project was supported by the J?nos Bolyai Research Scholarship of the Hungarian Academy of Sciences. This work was supported by the Hungarian Scientific Research Fund OTKA K113150. LA - English DB - MTMT ER - TY - JOUR AU - Bodnár, Brigitta AU - Mernyák, Erzsébet AU - Wölfling, János AU - Schneider, Gyula AU - Herman, Bianka Edina AU - Szécsi, Mihály AU - Sinka, Izabella AU - Zupkó, István AU - Kupihár, Zoltán AU - Kovács, Lajos TI - Synthesis and biological evaluation of triazolyl 13α-estrone–nucleoside bioconjugates JF - MOLECULES J2 - MOLECULES VL - 21 PY - 2016 IS - 9 PG - 16 SN - 1420-3049 DO - 10.3390/molecules21091212 UR - https://m2.mtmt.hu/api/publication/3110140 ID - 3110140 N1 - Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary 1St Department of Medicin, University of Szeged, Korányi fasor 8-10, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :6 Export Date: 30 August 2019 CODEN: MOLEF Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: hydroxysteroid dehydrogenase, 9001-56-3; 17-Hydroxysteroid Dehydrogenases; 3 (or 17)-beta-hydroxysteroid dehydrogenase; Antineoplastic Agents; Enzyme Inhibitors; Neoplasm Proteins; Nucleosides Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary 1St Department of Medicin, University of Szeged, Korányi fasor 8-10, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :6 Export Date: 11 February 2020 CODEN: MOLEF Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: hydroxysteroid dehydrogenase, 9001-56-3; 17-Hydroxysteroid Dehydrogenases; 3 (or 17)-beta-hydroxysteroid dehydrogenase; Antineoplastic Agents; Enzyme Inhibitors; Neoplasm Proteins; Nucleosides Funding Agency and Grant Number: Hungarian Scientific Research FundOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [OTKA K113150, K109293] Funding text: The authors are grateful for financial support from the Hungarian Scientific Research Fund (grants OTKA K113150 and K109293). Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary 1St Department of Medicin, University of Szeged, Korányi fasor 8-10, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :6 Export Date: 29 August 2020 CODEN: MOLEF Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: hydroxysteroid dehydrogenase, 9001-56-3; 17-Hydroxysteroid Dehydrogenases; 3 (or 17)-beta-hydroxysteroid dehydrogenase; Antineoplastic Agents; Enzyme Inhibitors; Neoplasm Proteins; Nucleosides Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary 1St Department of Medicin, University of Szeged, Korányi fasor 8-10, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Cited By :7 Export Date: 10 January 2021 CODEN: MOLEF Correspondence Address: Kupihár, Z.; Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Hungary; email: kupihar.zoltan@med.u-szeged.hu Chemicals/CAS: hydroxysteroid dehydrogenase, 9001-56-3; 17-Hydroxysteroid Dehydrogenases; 3 (or 17)-beta-hydroxysteroid dehydrogenase; Antineoplastic Agents; Enzyme Inhibitors; Neoplasm Proteins; Nucleosides LA - English DB - MTMT ER -