@article{MTMT:34577084, title = {Stereoselective synthesis and antiproliferative activity of allo-gibberic acid-based 1,3-aminoalcohols regioisomers}, url = {https://m2.mtmt.hu/api/publication/34577084}, author = {Khdar, Zein Alabdeen and Le Minh, Tam and Schelz, Zsuzsanna and Zupkó, István and Szakonyi, Zsolt}, doi = {10.1039/D3MD00665D}, journal-iso = {RSC MED CHEM}, journal = {RSC MEDICINAL CHEMISTRY}, volume = {15}, unique-id = {34577084}, abstract = {A new library of allo -gibberic acid-based aminoalcohol regioisomers was synthesised stereoselectively starting from commercially available gibberellic acid, which yields allo -gibberic acid under mild acidic conditions. The successful formation of hydroxymethyl...}, year = {2024}, eissn = {2632-8682}, pages = {874-887}, orcid-numbers = {Le Minh, Tam/0000-0002-8296-887X; Schelz, Zsuzsanna/0000-0002-8519-4830; Zupkó, István/0000-0003-3243-5300; Szakonyi, Zsolt/0000-0003-2432-8409} } @article{MTMT:34499406, title = {CuAAC-Based Synthesis, Copper-Catalyzed Aldehyde-Forming Hydrolytic Fission and Antiproliferative Evaluation of Novel Ferrocenoylamino-Substituted Triazole-Tethered Quinine–Chalcone Hybrids}, url = {https://m2.mtmt.hu/api/publication/34499406}, author = {Dembo, António and Ferenczi, Etelka and Jernei, Tamás and Bor, Andrea and Schelz, Zsuzsanna and Zupkó, István and Varga, Szilárd and Csámpai, Antal}, doi = {10.3390/molecules29020375}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {29}, unique-id = {34499406}, issn = {1420-3049}, abstract = {A series of novel triazole-tethered ferrocenoylamino-substituted cinchona–chalcone hybrids along with two representative benzoylamino-substituted reference compounds were prepared by three methods of CuAAC chemistry. In line with the limited success or complete failure of attempted conversions with low catalyst loadings, by means of DFT modeling studies, we demonstrated that a substantial part of the Cu(I) ions can be chelated and thus trapped in the aroylamino-substituted cinchona fragment and all of the accessible coordinating sites of the chalcone residues. Accordingly, increased amounts of catalysts were used to achieve acceptable yields; however, the cycloadditions with para-azidochalcones were accompanied by partial or complete aldehyde-forming hydrolytic fission of the enone C=C bond in a substituent-, solvent- and copper load-dependent manner. The experienced hydrolytic stability of the hybrids obtained by cycloadditions with ortho-azidochalcones was interpreted in terms of relative energetics, DFT reactivity indices and MO analysis of simplified models of two isomer copper–enone complexes. The novel hybrids were evaluated on HeLa, MDA-MB-231 and A2780 cell lines and showed substantial activity at low-to-submicromolar concentrations. An organometallic model carrying 3,4,5-trimethoxyphenyl residue in the enone part with a para-disubstituted benzene ring in the central skeletal region was identified as the most potent antiproliferative lead, characterized by submicromolar IC50 values measured on the three investigated cells. The biological assays also disclosed that this ferrocenoylamino-containing lead compound displays a ca. two- to five-fold more substantial antiproliferative effect than its benzoylamino-substituted counterpart.}, year = {2024}, eissn = {1420-3049}, orcid-numbers = {Schelz, Zsuzsanna/0000-0002-8519-4830; Zupkó, István/0000-0003-3243-5300; Varga, Szilárd/0000-0001-9611-5168; Csámpai, Antal/0000-0003-2107-7309} } @article{MTMT:34475300, title = {New 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline Derivatives: Synthesis and Biological Evaluation as Novel Anticancer Agents by Targeting G-Quadruplex}, url = {https://m2.mtmt.hu/api/publication/34475300}, author = {Guillon, Jean and Le Borgne, Marc and Milano, Vittoria and Guédin-Beaurepaire, Aurore and Moreau, Stéphane and Pinaud, Noël and Ronga, Luisa and Savrimoutou, Solène and Albenque-Rubio, Sandra and Marchivie, Mathieu and Kalout, Haouraa and Walker, Charley and Chevallier, Louise and Buré, Corinne and Largy, Eric and Gabelica, Valérie and Mergny, Jean-Louis and Baylot, Virginie and Ferrer, Jacky and Idrissi, Yamina and Chevret, Edith and Cappellen, David and Desplat, Vanessa and Schelz, Zsuzsanna and Zupkó, István}, doi = {10.3390/ph17010030}, journal-iso = {PHARMACEUTICALS-BASE}, journal = {PHARMACEUTICALS}, volume = {17}, unique-id = {34475300}, abstract = {The syntheses of novel 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazolines 12 and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinolines 13 are reported here in six steps starting from various halogeno-quinazoline-2,4-(1H,3H)-diones or substituted anilines. The antiproliferative activities of the products were determined in vitro against a panel of breast (MCF-7 and MDA-MB-231), human adherent cervical (HeLa and SiHa), and ovarian (A2780) cell lines. Disubstituted 6- and 7-phenyl-bis(3-dimethylaminopropyl)aminomethylphenyl-quinazolines 12b, 12f, and 12i displayed the most interesting antiproliferative activities against six human cancer cell lines. In the series of quinoline derivatives, 6-phenyl-bis(3-dimethylaminopropyl)aminomethylphenylquinoline 13a proved to be the most active. G-quadruplexes (G4) stacked non-canonical nucleic acid structures found in specific G-rich DNA, or RNA sequences in the human genome are considered as potential targets for the development of anticancer agents. Then, as small aza-organic heterocyclic derivatives are well known to target and stabilize G4 structures, their ability to bind G4 structures have been determined through FRET melting, circular dichroism, and native mass spectrometry assays. Finally, telomerase inhibition ability has been also assessed using the MCF-7 cell line.}, year = {2024}, eissn = {1424-8247}, orcid-numbers = {Guillon, Jean/0000-0001-8577-3894; Le Borgne, Marc/0000-0003-1398-075X; Pinaud, Noël/0000-0001-7646-5312; Mergny, Jean-Louis/0000-0003-3043-8401; Chevret, Edith/0000-0002-9724-8437; Schelz, Zsuzsanna/0000-0002-8519-4830; Zupkó, István/0000-0003-3243-5300} } @article{MTMT:34432666, title = {Az immunszuppresszió helye a gyógyszeres terápiában}, url = {https://m2.mtmt.hu/api/publication/34432666}, author = {Schelz, Zsuzsanna}, journal-iso = {GYÓGYSZERÉSZET}, journal = {GYÓGYSZERÉSZET}, volume = {67}, unique-id = {34432666}, issn = {0017-6036}, year = {2023}, pages = {259-262}, orcid-numbers = {Schelz, Zsuzsanna/0000-0002-8519-4830} } @article{MTMT:34417276, title = {Stereoselective Synthesis and Antiproliferative Activity of Steviol-Based Diterpene 1,3-Aminoalcohol Regioisomers}, url = {https://m2.mtmt.hu/api/publication/34417276}, author = {Bai, Dorottya and Schelz, Zsuzsanna and Boncz, Mária Fanni and Zupkó, István and Szakonyi, Zsolt}, doi = {10.3390/molecules28247962}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {28}, unique-id = {34417276}, issn = {1420-3049}, abstract = {A series of novel diterpene-type 1,3-aminoalcohols and their regioisomers have been synthesised from natural stevioside in a stereoselective manner. The key intermediate β-keto alcohol was prepared using Wagner–Meerwein rearrangement of the epoxide derived from steviol methyl ester. The primary aminoalcohol was formed via Raney-nickel-catalysed hydrogenation of an oxime, and a versatile library of aminoalcohols was synthesised using a Schiff base with the primary amines. The aminoalcohol regioisomers were prepared from the mesylate of the β-keto alcohols. The corresponding primary aminoalcohol was formed via the palladium-catalysed hydrogenation of hydroxyl-azide, and click reactions of the latter were also carried out. The new compounds were characterised using 1D- and 2D-NMR techniques and HRMS measurements. The in vitro investigations showed high inhibition of cell growth in human cancer cell lines (HeLa, SiHa, A2780, MCF-7 and MDA-MB-231) in the case of naphthalic N-substituted derivatives. The antiproliferative effects were assayed using the MTT method.}, year = {2023}, eissn = {1420-3049}, orcid-numbers = {Schelz, Zsuzsanna/0000-0002-8519-4830; Boncz, Mária Fanni/0009-0008-7938-484X; Zupkó, István/0000-0003-3243-5300; Szakonyi, Zsolt/0000-0003-2432-8409} } @article{MTMT:34165889, title = {Repositioning of HMG-CoA Reductase Inhibitors as Adjuvants in the Modulation of Efflux Pump-Mediated Bacterial and Tumor Resistance}, url = {https://m2.mtmt.hu/api/publication/34165889}, author = {Schelz, Zsuzsanna and Abdallah, Hiba Faroug Muddather and Zupkó, István}, doi = {10.3390/antibiotics12091468}, journal-iso = {ANTIBIOTICS-BASEL}, journal = {ANTIBIOTICS}, volume = {12}, unique-id = {34165889}, abstract = {Efflux pump (EP)-mediated multidrug resistance (MDR) seems ubiquitous in bacterial infections and neoplastic diseases. The diversity and lack of specificity of these efflux mechanisms raise a great obstacle in developing drugs that modulate efflux pumps. Since developing novel chemotherapeutic drugs requires large investments, drug repurposing offers a new approach that can provide alternatives as adjuvants in treating resistant microbial infections and progressive cancerous diseases. Hydroxy-methyl-glutaryl coenzyme-A (HMG-CoA) reductase inhibitors, also known as statins, are promising agents in this respect. Originally, statins were used in the therapy of dyslipidemia and for the prevention of cardiovascular diseases; however, extensive research has recently been performed to elucidate the functions of statins in bacterial infections and cancers. The mevalonate pathway is essential in the posttranslational modification of proteins related to vital eukaryotic cell functions. In this article, a comparative review is given about the possible role of HMG-CoA reductase inhibitors in managing diseases of bacterial and neoplastic origin. Molecular research and clinical studies have proven the justification of statins in this field. Further well-designed clinical trials are urged to clarify the significance of the contribution of statins to the lower risk of disease progression in bacterial infections and cancerous diseases.}, keywords = {Statins; Mevalonate pathway; drug repositioning; HMG-COA REDUCTASE INHIBITORS; Reversal of multidrug resistance; efflux-mediated multidrug resistance; isoprenoid synthesis}, year = {2023}, eissn = {2079-6382}, orcid-numbers = {Schelz, Zsuzsanna/0000-0002-8519-4830; Zupkó, István/0000-0003-3243-5300} } @CONFERENCE{MTMT:33941008, title = {Chemical composition and antiproliferative properties of Peganum harmala}, url = {https://m2.mtmt.hu/api/publication/33941008}, author = {Nasibova, Tohfa and Hohmann, Judit and Schelz, Zsuzsanna and Zupkó, István and Horváth, Attila and Barta, Anita and Abdallah, Hiba Faroug Muddather}, booktitle = {4th Symposium of Young Researchers on Pharmacognosy}, doi = {10.14232/syrmpnpr.2023.9}, unique-id = {33941008}, year = {2023}, pages = {15-15}, orcid-numbers = {Hohmann, Judit/0000-0002-2887-6392; Schelz, Zsuzsanna/0000-0002-8519-4830; Zupkó, István/0000-0003-3243-5300; Abdallah, Hiba Faroug Muddather/0000-0001-8472-330X} } @{MTMT:33939840, title = {In vitro Antiproliferative and Antimetastatic Proprieties of Peganum harmala}, url = {https://m2.mtmt.hu/api/publication/33939840}, author = {Abdallah, Hiba Faroug Muddather and Schelz, Zsuzsanna and Nasibova, Tohfa and Hohmann, Judit and Zupkó, István}, booktitle = {XXVI. Tavaszi Szél Konferencia 2023 : Absztrakt kötet}, unique-id = {33939840}, year = {2023}, pages = {345-345}, orcid-numbers = {Schelz, Zsuzsanna/0000-0002-8519-4830; Hohmann, Judit/0000-0002-2887-6392; Zupkó, István/0000-0003-3243-5300} } @article{MTMT:33708328, title = {Isolation and NMR Scaling Factors for the Structure Determination of Lobatolide H, a Flexible Sesquiterpene from Neurolaena lobata}, url = {https://m2.mtmt.hu/api/publication/33708328}, author = {Kovács, Tibor and Lajter, Ildikó and Kúsz, Norbert and Schelz, Zsuzsanna and Bózsity-Faragó, Noémi and Borbás, Anikó and Zupkó, István and Krupitza, Georg and Frisch, Richard and Hohmann, Judit and Vasas, Andrea and Mándi, Attila}, doi = {10.3390/ijms24065841}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {24}, unique-id = {33708328}, issn = {1661-6596}, abstract = {A new flexible germacranolide (1, lobatolide H) was isolated from the aerial parts of Neurolaena lobata. The structure elucidation was performed by classical NMR experiments and DFT NMR calculations. Altogether, 80 theoretical level combinations with existing 13C NMR scaling factors were tested, and the best performing ones were applied on 1. 1H and 13C NMR scaling factors were also developed for two combinations utilizing known exomethylene containing derivatives, and the results were complemented by homonuclear coupling constant (JHH) and TDDFT-ECD calculations to elucidate the stereochemistry of 1. Lobatolide H possessed remarkable antiproliferative activity against human cervical tumor cell lines with different HPV status (SiHa and C33A), induced cell cycle disturbance and exhibited a substantial antimigratory effect in SiHa cells.}, keywords = {STEREOCHEMISTRY; ANTIPROLIFERATIVE ACTIVITY; natural product; DFT calculations; ECD calculations; antimigratory effect; NMR shift parameter development}, year = {2023}, eissn = {1422-0067}, orcid-numbers = {Kúsz, Norbert/0000-0002-9973-6442; Schelz, Zsuzsanna/0000-0002-8519-4830; Borbás, Anikó/0000-0001-8462-4547; Zupkó, István/0000-0003-3243-5300; Hohmann, Judit/0000-0002-2887-6392; Vasas, Andrea/0000-0002-1818-7702} } @article{MTMT:33547781, title = {Stereoselective Synthesis and Antiproliferative Activities of Tetrafunctional Diterpene Steviol Derivatives}, url = {https://m2.mtmt.hu/api/publication/33547781}, author = {Bai, Dorottya and Schelz, Zsuzsanna and Erdős, Dóra and Kis, Anna K. and Nagy, Viktória and Zupkó, István and Balogh, György Tibor and Szakonyi, Zsolt}, doi = {10.3390/ijms24021121}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {24}, unique-id = {33547781}, issn = {1661-6596}, abstract = {A new family of diterpene-type aminotriol derivatives has been synthesised from stevioside in a stereoselective manner. The key intermediate spiro-epoxide was prepared through the methyl ester of the allilyc diol derived from steviol. The oxirane ring was opened with primary and secondary amines, providing a versatile library of aminotriols. The corresponding primary aminotriol was formed by palladium-catalysed hydrogenation, and an N,O-heterocyclic compound was synthesised in a regioselective reaction. All new compounds were characterised by 1D- and 2D-NMR techniques and HRMS measurements. In our in vitro investigations, we found that the aromatic N-substituted derivatives exhibited high inhibition of cell growth on human cancer cell lines (HeLa, SiHa, A2780, MCF-7 and MDA-MB-231). The antiproliferative activities were assayed by the MTT method. Furthermore, the introduction of an additional hydroxy group slightly increased the biological activity. The drug-likeness of the compounds was assessed by in silico and experimental physicochemical characterisations, completed by kinetic aqueous solubility and in vitro intestinal-specific parallel artificial membrane permeability assay (PAMPA-GI) measurements.}, year = {2023}, eissn = {1422-0067}, orcid-numbers = {Schelz, Zsuzsanna/0000-0002-8519-4830; Kis, Anna K./0000-0002-3743-0958; Zupkó, István/0000-0003-3243-5300; Balogh, György Tibor/0000-0003-3347-1880; Szakonyi, Zsolt/0000-0003-2432-8409} }