@inproceedings{MTMT:34831171, title = {Ciklodextrin-segített kapilláris elektroforézis: benzil-izokinolin alkaloidok enantiomer-elválasztása}, url = {https://m2.mtmt.hu/api/publication/34831171}, author = {Várnagy, Erzsébet and Tóth, Gergő and Hosztafi, Sándor and Fejős, Ida and Malanga, Milo and Béni, Szabolcs}, booktitle = {Biotechnológus Napok 2024}, unique-id = {34831171}, year = {2024}, pages = {22}, orcid-numbers = {Várnagy, Erzsébet/0009-0004-8348-4545; Tóth, Gergő/0000-0001-5341-319X; Hosztafi, Sándor/0000-0003-3793-4651; Fejős, Ida/0000-0002-3458-0854; Béni, Szabolcs/0000-0001-7056-6825} } @article{MTMT:34407138, title = {Synthesis and biochemical evaluation of 17-N-beta-aminoalkyl-4,5α-epoxynormorphinans}, url = {https://m2.mtmt.hu/api/publication/34407138}, author = {Ötvös, Ferenc and Szűcs, Edina and Urai, Ákos and Köteles, István and Szabó, Pál Tamás and Varga, Zsuzsanna Katalin and Gombos, Dávid and Hosztafi, Sándor and Benyhe, Sándor}, doi = {10.1038/s41598-023-46317-3}, journal-iso = {SCI REP}, journal = {SCIENTIFIC REPORTS}, volume = {13}, unique-id = {34407138}, issn = {2045-2322}, abstract = {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.}, year = {2023}, eissn = {2045-2322}, orcid-numbers = {Urai, Ákos/0000-0002-7168-3916; Szabó, Pál Tamás/0000-0003-2260-4641; Hosztafi, Sándor/0000-0003-3793-4651} } @CONFERENCE{MTMT:34163635, title = {β-cyclodextrin complex formation and protonation equilibria of morphine and other opioid compounds of therapeutic interest}, url = {https://m2.mtmt.hu/api/publication/34163635}, author = {Tűz, Boglárka and Noszál, Béla and Hosztafi, Sándor and Mazák, Károly}, booktitle = {EUROCD 2023 7th European Cyclodextrin Conference}, unique-id = {34163635}, year = {2023}, orcid-numbers = {Noszál, Béla/0000-0003-3898-3084; Hosztafi, Sándor/0000-0003-3793-4651; Mazák, Károly/0000-0002-9682-4826} } @article{MTMT:32856172, title = {Diels-Alder Adducts of Morphinan-6,8-Dienes and Their Transformations}, url = {https://m2.mtmt.hu/api/publication/32856172}, author = {Marton, Janos and Fekete, Anikó and Cumming, Paul and Hosztafi, Sándor and Mikecz, Pál and Henriksen, Gjermund}, doi = {10.3390/molecules27092863}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {27}, unique-id = {32856172}, issn = {1420-3049}, abstract = {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.}, keywords = {DIELS-ALDER REACTION; radiolabeling; morphine alkaloids; POSITRON-EMISSION-TOMOGRAPHY; opioid receptors; MORPHINE-THEBAINE GROUP; O-demethylation; Biochemistry & Molecular Biology; rational drug design; methyl vinyl ketone; NUCLEOPHILIC-SUBSTITUTION REACTIONS; Kappa-opioid receptor; morphinan-6; 8-dienes; Grignard addition; ACID-CATALYZED REARRANGEMENTS; C-11 LABELED DIPRENORPHINE; RING CONSTRAINED ANALOGS}, year = {2022}, eissn = {1420-3049}, orcid-numbers = {Cumming, Paul/0000-0002-0257-9621; Hosztafi, Sándor/0000-0003-3793-4651} } @article{MTMT:32630183, title = {β-cyclodextrin complex formation and protonation equilibria of morphine and other opioid compounds of therapeutic interest}, url = {https://m2.mtmt.hu/api/publication/32630183}, author = {Tűz, Boglárka and Noszál, Béla and Hosztafi, Sándor and Mazák, Károly}, doi = {10.1016/j.ejps.2022.106120}, journal-iso = {EUR J PHARM SCI}, journal = {EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES}, volume = {171}, unique-id = {32630183}, issn = {0928-0987}, keywords = {BETA-CYCLODEXTRIN; MORPHINE; stability constant; ROESY; inclusion complex; H-1 NMR-titration}, year = {2022}, eissn = {1879-0720}, orcid-numbers = {Noszál, Béla/0000-0003-3898-3084; Hosztafi, Sándor/0000-0003-3793-4651; Mazák, Károly/0000-0002-9682-4826} } @article{MTMT:32033868, title = {Synthesis of 3‐O‐Carboxyalkyl Morphine Derivatives and Characterization of Their Acid‐Base Properties}, url = {https://m2.mtmt.hu/api/publication/32033868}, author = {Köteles, István and Mazák, Károly and Tóth, Gergő and Horváth, Péter and Kiss, Eszter and Tűz, Boglárka and Hosztafi, Sándor}, doi = {10.1002/cbdv.202100135}, journal-iso = {CHEM BIODIVERS}, journal = {CHEMISTRY & BIODIVERSITY}, volume = {18}, unique-id = {32033868}, issn = {1612-1872}, year = {2021}, eissn = {1612-1880}, orcid-numbers = {Köteles, István/0000-0002-1678-233X; Mazák, Károly/0000-0002-9682-4826; Tóth, Gergő/0000-0001-5341-319X; Horváth, Péter/0000-0001-7149-4173; Kiss, Eszter/0000-0001-7953-9348; Hosztafi, Sándor/0000-0003-3793-4651} } @article{MTMT:31565342, title = {Synthesis of Potential Haptens with Morphine Skeleton and Determination of Protonation Constants}, url = {https://m2.mtmt.hu/api/publication/31565342}, author = {Köteles, István and Mazák, Károly and Tóth, Gergő and Tűz, Boglárka and Hosztafi, Sándor}, doi = {10.3390/molecules25174009}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {25}, unique-id = {31565342}, issn = {1420-3049}, year = {2020}, eissn = {1420-3049}, orcid-numbers = {Köteles, István/0000-0002-1678-233X; Mazák, Károly/0000-0002-9682-4826; Tóth, Gergő/0000-0001-5341-319X; Hosztafi, Sándor/0000-0003-3793-4651} } @article{MTMT:31365974, title = {N-Phenethyl Substitution in 14-Methoxy-N-methylmorphinan-6-ones Turns Selective µ Opioid Receptor Ligands into Dual µ/δ Opioid Receptor Agonists}, url = {https://m2.mtmt.hu/api/publication/31365974}, author = {Dumitrascuta, Maria and Bermudez, Marcel and Ben Haddou, Tanila and Guerrieri, Elena and Schläfer, Lea and Ritsch, Andreas and Hosztafi, Sándor and Lantero, Aquilino and Kreutz, Christoph and Massotte, Dominique and Schmidhammer, Helmut and Wolber, Gerhard and Spetea, Mariana}, doi = {10.1038/s41598-020-62530-w}, journal-iso = {SCI REP}, journal = {SCIENTIFIC REPORTS}, volume = {10}, unique-id = {31365974}, issn = {2045-2322}, year = {2020}, eissn = {2045-2322}, orcid-numbers = {Hosztafi, Sándor/0000-0003-3793-4651} } @article{MTMT:31267477, title = {Comparisons of in Vivo and in Vitro Opioid Effects of Newly Synthesized 14-Methoxycodeine-6-O-sulfate and Codeine-6-O-sulfate}, url = {https://m2.mtmt.hu/api/publication/31267477}, author = {Zádor, Ferenc and Mohammadzadeh, Amir and Balogh, Mihály and Zádori, Zoltán Sándor and Király, Kornél P and Barsi, Szilvia and Galambos, Anna Rita and László, Szilvia Bianka and Hutka, Barbara and Váradi, András and Hosztafi, Sándor and Riba, Pál and Benyhe, Sándor and Fürst, Zsuzsanna and Al-Khrasani, Mahmoud}, doi = {10.3390/molecules25061370}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {25}, unique-id = {31267477}, issn = {1420-3049}, year = {2020}, eissn = {1420-3049}, orcid-numbers = {Mohammadzadeh, Amir/0000-0001-6747-1913; Balogh, Mihály/0000-0003-3296-0316; Zádori, Zoltán Sándor/0000-0001-7312-618X; Király, Kornél P/0000-0002-7252-0422; Barsi, Szilvia/0000-0002-8779-2383; László, Szilvia Bianka/0000-0001-9755-8972; Hutka, Barbara/0000-0002-7692-2744; Hosztafi, Sándor/0000-0003-3793-4651; Riba, Pál/0000-0002-7886-4816; Fürst, Zsuzsanna/0000-0002-2760-1274; Al-Khrasani, Mahmoud/0000-0001-8488-3266} } @article{MTMT:31187730, title = {Synthesis, biochemical, pharmacological characterization and in silico profile modelling of highly potent opioid orvinol and thevinol derivatives}, url = {https://m2.mtmt.hu/api/publication/31187730}, author = {Szűcs, Edina and Marton, János and Szabó, Zoltán and Hosztafi, Sándor and Kékesi, Gabriella and Tuboly, Gábor and Bánki, László and Horváth, Gyöngyi and Szabó, Pál Tamás and Tömböly, Csaba and Varga, Katalin Zsuzsanna and Benyhe, Sándor and Ötvös, Ferenc}, doi = {10.1016/j.ejmech.2020.112145}, journal-iso = {EUR J MED CHEM}, journal = {EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY}, volume = {191}, unique-id = {31187730}, issn = {0223-5234}, year = {2020}, eissn = {1768-3254}, orcid-numbers = {Hosztafi, Sándor/0000-0003-3793-4651; Kékesi, Gabriella/0000-0002-0185-2155; Horváth, Gyöngyi/0000-0002-6025-4577; Szabó, Pál Tamás/0000-0003-2260-4641; Tömböly, Csaba/0000-0002-2609-2498; Benyhe, Sándor/0000-0002-2235-5334} }