TY - CHAP AU - Várnagy, Erzsébet AU - Tóth, Gergő AU - Hosztafi, Sándor AU - Fejős, Ida AU - Malanga, Milo AU - Béni, Szabolcs TI - Ciklodextrin-segített kapilláris elektroforézis: benzil-izokinolin alkaloidok enantiomer-elválasztása T2 - Biotechnológus Napok 2024 CY - Budapest SN - 9786150200880 PY - 2024 SP - 22 UR - https://m2.mtmt.hu/api/publication/34831171 ID - 34831171 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Ötvös, Ferenc AU - Szűcs, Edina AU - Urai, Ákos AU - Köteles, István AU - Szabó, Pál Tamás AU - Varga, Zsuzsanna Katalin AU - Gombos, Dávid AU - Hosztafi, Sándor AU - Benyhe, Sándor TI - Synthesis and biochemical evaluation of 17-N-beta-aminoalkyl-4,5α-epoxynormorphinans JF - SCIENTIFIC REPORTS J2 - SCI REP VL - 13 PY - 2023 IS - 1 PG - 16 SN - 2045-2322 DO - 10.1038/s41598-023-46317-3 UR - https://m2.mtmt.hu/api/publication/34407138 ID - 34407138 N1 - Export Date: 25 February 2024 AB - Opiate alkaloids and their synthetic derivatives are still widely used in pain management, drug addiction, and abuse. To avoid serious side effects, compounds with properly designed pharmacological profiles at the opioid receptor subtypes are long needed. Here a series of 17- N -substituted derivatives of normorphine and noroxymorphone analogues with five- and six-membered ring substituents have been synthesized for structure–activity study. Some compounds showed nanomolar affinity to MOR, DOR and KOR in in vitro competition binding experiments with selective agonists [ 3 H]DAMGO, [ 3 H]Ile 5,6 -deltorphin II and [ 3 H]HS665, respectively. Pharmacological characterization of the compounds in G-protein signaling was determined by [ 35 S]GTPγS binding assays. The normorphine analogues showed higher affinity to KOR compared to MOR and DOR, while most of the noroxymorphone derivatives did not bind to KOR. The presence of 14-OH substituent resulted in a shift in the pharmacological profiles in the agonist > partial agonist > antagonist direction compared to the parent compounds. A molecular docking-based in silico method was also applied to estimate the pharmacological profile of the compounds. Docking energies and the patterns of the interacting receptor atoms, obtained with experimentally determined active and inactive states of MOR, were used to explain the observed pharmacological features of the compounds. LA - English DB - MTMT ER - TY - CONF AU - Tűz, Boglárka AU - Noszál, Béla AU - Hosztafi, Sándor AU - Mazák, Károly TI - β-cyclodextrin complex formation and protonation equilibria of morphine and other opioid compounds of therapeutic interest T2 - EUROCD 2023 7th European Cyclodextrin Conference PY - 2023 UR - https://m2.mtmt.hu/api/publication/34163635 ID - 34163635 LA - English DB - MTMT ER - TY - JOUR AU - Marton, Janos AU - Fekete, Anikó AU - Cumming, Paul AU - Hosztafi, Sándor AU - Mikecz, Pál AU - Henriksen, Gjermund TI - Diels-Alder Adducts of Morphinan-6,8-Dienes and Their Transformations JF - MOLECULES J2 - MOLECULES VL - 27 PY - 2022 IS - 9 PG - 111 SN - 1420-3049 DO - 10.3390/molecules27092863 UR - https://m2.mtmt.hu/api/publication/32856172 ID - 32856172 N1 - ABX Advanced Biochemical Compounds Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, Radeberg, D-01454, Germany Department of Medical Imaging, Division of Nuclear Medicine and Translational Imaging, Faculty of Medicine, University of Debrecen, Nagyerdei krt. 98, Debrecen, H-4032, Hungary Department of Nuclear Medicine, Bern University Hospital, Freiburgstraße 18, Bern, 3010, Switzerland School of Psychology and Counselling, Queensland University of Technology, Brisbane, QLD 4059, Australia Institute of Pharmaceutical Chemistry, Semmelweis Medical University, Högyes Endre utca 9, Budapest, H-1092, Hungary Norwegian Medical Cyclotron Centre Ltd., Sognsvannsveien 20, Oslo, N-0372, Norway Institute of Basic Medical Sciences, University of Oslo, Oslo, N-0317, Norway Institute of Physics, University of Oslo, Sem Sælands vei 24, Oslo, N-0371, Norway Export Date: 2 June 2022 CODEN: MOLEF Correspondence Address: Marton, J.; ABX Advanced Biochemical Compounds Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, Germany; email: marton@abx.de Correspondence Address: Henriksen, G.; Norwegian Medical Cyclotron Centre Ltd., Sognsvannsveien 20, Norway; email: gjermund.henriksen@syklotronsenteret.no AB - 6,14-ethenomorphinans are semisynthetic opiate derivatives containing an ethylene bridge between positions 6 and 14 in ring-C of the morphine skeleton that imparts a rigid molecular structure. These compounds represent an important family of opioid receptor ligands in which the 6,14-etheno bridged structural motif originates from a [4 + 2] cycloaddition of morphinan-6,8-dienes with dienophiles. Certain 6,14-ethenomorphinans having extremely high affinity for opioid receptors are often non-selective for opioid receptor subtypes, but this view is now undergoing some revision. The agonist 20R-etorphine and 20R-dihydroetorphine are several thousand times more potent analgesics than morphine, whereas diprenorphine is a high-affinity non-selective antagonist. The partial agonist buprenorphine is used as an analgesic in the management of post-operative pain or in substitution therapy for opiate addiction, sometimes in combination with the non-selective antagonist naloxone. In the context of the current opioid crisis, we communicated a summary of several decades of work toward generating opioid analgesics with lesser side effects or abuse potential. Our summary placed a focus on Diels-Alder reactions of morphinan-6,8-dienes and subsequent transformations of the cycloadducts. We also summarized the pharmacological aspects of radiolabeled 6,14-ethenomorphinans used in molecular imaging of opioid receptors. LA - English DB - MTMT ER - TY - JOUR AU - Tűz, Boglárka AU - Noszál, Béla AU - Hosztafi, Sándor AU - Mazák, Károly TI - β-cyclodextrin complex formation and protonation equilibria of morphine and other opioid compounds of therapeutic interest JF - EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES J2 - EUR J PHARM SCI VL - 171 PY - 2022 PG - 11 SN - 0928-0987 DO - 10.1016/j.ejps.2022.106120 UR - https://m2.mtmt.hu/api/publication/32630183 ID - 32630183 N1 - Export Date: 27 May 2022 CODEN: EPSCE LA - English DB - MTMT ER - TY - JOUR AU - Köteles, István AU - Mazák, Károly AU - Tóth, Gergő AU - Horváth, Péter AU - Kiss, Eszter AU - Tűz, Boglárka AU - Hosztafi, Sándor TI - Synthesis of 3‐O‐Carboxyalkyl Morphine Derivatives and Characterization of Their Acid‐Base Properties JF - CHEMISTRY & BIODIVERSITY J2 - CHEM BIODIVERS VL - 18 PY - 2021 IS - 7 PG - 10 SN - 1612-1872 DO - 10.1002/cbdv.202100135 UR - https://m2.mtmt.hu/api/publication/32033868 ID - 32033868 N1 - Cited By :1 Export Date: 20 February 2022 CODEN: CBHIA Correspondence Address: Köteles, I.; Department of Pharmaceutical Chemistry, Hőgyes Endre u. 9., Hungary; email: koteles.istvan@pharma.semmelweis-univ.hu LA - English DB - MTMT ER - TY - JOUR AU - Köteles, István AU - Mazák, Károly AU - Tóth, Gergő AU - Tűz, Boglárka AU - Hosztafi, Sándor TI - Synthesis of Potential Haptens with Morphine Skeleton and Determination of Protonation Constants JF - MOLECULES J2 - MOLECULES VL - 25 PY - 2020 IS - 17 PG - 32 SN - 1420-3049 DO - 10.3390/molecules25174009 UR - https://m2.mtmt.hu/api/publication/31565342 ID - 31565342 N1 - Funding Agency and Grant Number: Hungarian Academy of SciencesHungarian Academy of Sciences; Ministry for Innovation and Technology [UNKP-19-4-SE-28]; National Research, Development and Innovation Office, Hungary [NKFIH KH-130401, VEKOP-2.3.3-15-2017-00020]; ELTE Institutional Excellence Program of the Hungarian Ministry of Human Capacities [1783-3/2018/FEKUTSRAT] Funding text: This work was supported by the Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences (G. Toth). The financial support from Bolyai + New National Excellence Program (grant number: UNKP-19-4-SE-28) of the Ministry for Innovation and Technology is highly appreciated (G. Toth). This research was supported by the National Research, Development and Innovation Office, Hungary (NKFIH KH-130401, VEKOP-2.3.3-15-2017-00020), the ELTE Institutional Excellence Program (1783-3/2018/FEKUTSRAT) of the Hungarian Ministry of Human Capacities. Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre u. 9., Budapest, H-1092, Hungary Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Pázmány Péter sétány 1/C, Budapest, H-1117, Hungary Export Date: 18 February 2021 CODEN: MOLEF Correspondence Address: Köteles, I.; Department of Pharmaceutical Chemistry, Hogyes Endre u. 9., Hungary; email: koteles.istvan@pharma.semmelweis-univ.hu Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre u. 9., Budapest, H-1092, Hungary Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Pázmány Péter sétány 1/C, Budapest, H-1117, Hungary Cited By :1 Export Date: 15 August 2021 CODEN: MOLEF Correspondence Address: Köteles, I.; Department of Pharmaceutical Chemistry, Hogyes Endre u. 9., Hungary; email: koteles.istvan@pharma.semmelweis-univ.hu LA - English DB - MTMT ER - TY - JOUR AU - Dumitrascuta, Maria AU - Bermudez, Marcel AU - Ben Haddou, Tanila AU - Guerrieri, Elena AU - Schläfer, Lea AU - Ritsch, Andreas AU - Hosztafi, Sándor AU - Lantero, Aquilino AU - Kreutz, Christoph AU - Massotte, Dominique AU - Schmidhammer, Helmut AU - Wolber, Gerhard AU - Spetea, Mariana TI - N-Phenethyl Substitution in 14-Methoxy-N-methylmorphinan-6-ones Turns Selective µ Opioid Receptor Ligands into Dual µ/δ Opioid Receptor Agonists JF - SCIENTIFIC REPORTS J2 - SCI REP VL - 10 PY - 2020 IS - 1 PG - 12 SN - 2045-2322 DO - 10.1038/s41598-020-62530-w UR - https://m2.mtmt.hu/api/publication/31365974 ID - 31365974 N1 - Funding Agency and Grant Number: Tyrolean Research Fund [UNI-0404/1596]; Forderungsbeitrage Aktion D. Swarovski KG 2014; Bilateral Cooperation Program Austria-France "Amadee" [FR 12/2016]; Austrian Science FundAustrian Science Fund (FWF) [FWF: TRP19-B18, I 2463-B21]; German Research FoundationGerman Research Foundation (DFG) [DFG: 407626949]; University of Innsbruck Funding text: This work was supported by the Tyrolean Research Fund (UNI-0404/1596), the Forderungsbeitrage Aktion D. Swarovski KG 2014, the Bilateral Cooperation Program Austria-France "Amadee" (FR 12/2016), the Austrian Science Fund (FWF: TRP19-B18 and I 2463-B21) and the German Research Foundation (DFG: 407626949). Tanila Ben Haddou was supported by the University of Innsbruck PhD stipend program. LA - English DB - MTMT ER - TY - JOUR AU - Zádor, Ferenc AU - Mohammadzadeh, Amir AU - Balogh, Mihály AU - Zádori, Zoltán Sándor AU - Király, Kornél P AU - Barsi, Szilvia AU - Galambos, Anna Rita AU - László, Szilvia Bianka AU - Hutka, Barbara AU - Váradi, András AU - Hosztafi, Sándor AU - Riba, Pál AU - Benyhe, Sándor AU - Fürst, Zsuzsanna AU - Al-Khrasani, Mahmoud TI - Comparisons of in Vivo and in Vitro Opioid Effects of Newly Synthesized 14-Methoxycodeine-6-O-sulfate and Codeine-6-O-sulfate JF - MOLECULES J2 - MOLECULES VL - 25 PY - 2020 IS - 6 PG - 22 SN - 1420-3049 DO - 10.3390/molecules25061370 UR - https://m2.mtmt.hu/api/publication/31267477 ID - 31267477 N1 - Cited By :8 Export Date: 22 February 2022 CODEN: MOLEF LA - English DB - MTMT ER - TY - JOUR AU - Szűcs, Edina AU - Marton, János AU - Szabó, Zoltán AU - Hosztafi, Sándor AU - Kékesi, Gabriella AU - Tuboly, Gábor AU - Bánki, László AU - Horváth, Gyöngyi AU - Szabó, Pál Tamás AU - Tömböly, Csaba AU - Varga, Katalin Zsuzsanna AU - Benyhe, Sándor AU - Ötvös, Ferenc TI - Synthesis, biochemical, pharmacological characterization and in silico profile modelling of highly potent opioid orvinol and thevinol derivatives JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY J2 - EUR J MED CHEM VL - 191 PY - 2020 PG - 15 SN - 0223-5234 DO - 10.1016/j.ejmech.2020.112145 UR - https://m2.mtmt.hu/api/publication/31187730 ID - 31187730 N1 - Institute of Biochemistry, Biological Research Center, Temesvári krt. 62, Szeged, H-6726, Hungary Doctoral School of Theoretical Medicine, Faculty of Medicine, University of Szeged, Dóm tér 10, Szeged, H-6720, Hungary ABX Advanced Biochemical Compounds, Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, Radeberg, D-01454, Germany Royal Institute of Technology (KTH), School of Engineering Sciences in Chemistry, Biotechnology and Health, Department of Chemistry, Organic Chemistry, Stockholm, S-100 44, Sweden Institute of Pharmaceutical Chemistry, Semmelweis Medical University, Hőgyes Endre utca 9, Budapest, H-1092, Hungary Department of Physiology, Faculty of Medicine, University of Szeged, Dóm tér 10, Szeged, H-6720, Hungary Department of Neurology, Faculty of Medicine, University of Szeged, Semmelweis u 6, Szeged, H-6725, Hungary Department of Traumatology, Faculty of Medicine, University of Szeged, Semmelweis u 6, Szeged, H-6725, Hungary Research Centre for Natural Sciences, MS Metabolomics Research Laboratory, Magyar tudósok krt. 2, Budapest, H-1117, Hungary Export Date: 27 May 2021 CODEN: EJMCA Correspondence Address: Ötvös, F.; Institute of Biochemistry, Hungary; email: otvos@brc.hu LA - English DB - MTMT ER -