@article{MTMT:34791082,
	title = {Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers},
	url = {https://m2.mtmt.hu/api/publication/34791082},
	author = {Háznagy, Márton Benedek and Csámpai, Antal and Ugrai, Imre and Barnabás, Molnár and Matti, Haukka and Szakonyi, Zsolt},
	doi = {10.3390/ijms25084325},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {25},
	unique-id = {34791082},
	issn = {1661-6596},
	abstract = {A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (−)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (−)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues.},
	year = {2024},
	eissn = {1422-0067},
	orcid-numbers = {Csámpai, Antal/0000-0003-2107-7309; Matti, Haukka/0000-0002-6744-7208; Szakonyi, Zsolt/0000-0003-2432-8409}
}

@article{MTMT:34666945,
	title = {Synthesis and Study of the Structure–Activity Relationship of Antiproliferative N-Substituted Isosteviol-Based 1,3-Aminoalcohols},
	url = {https://m2.mtmt.hu/api/publication/34666945},
	author = {Ozsvár, Dániel and Bózsity-Faragó, Noémi and Zupkó, István and Szakonyi, Zsolt},
	doi = {10.3390/ph17020262},
	journal-iso = {PHARMACEUTICALS-BASE},
	journal = {PHARMACEUTICALS},
	volume = {17},
	unique-id = {34666945},
	abstract = {Starting from isosteviol, a series of diterpenoid 1,3-aminoalcohol derivatives were prepared via stereoselective transformations. The acid-catalysed hydrolysis and rearrangement of natural stevioside produced isosteviol, which was transformed into the key intermediate methyl ester. In the next step, an 1,3-aminoalcohol library was prepared by the reductive amination of the intermediate 3-hydroxyaldehyde obtained from isosteviol in a two-step synthesis. To study the effect of the carboxylate ester function at position 4, the free carboxylic acid, benzyl ester and acryloyl ester analogues were prepared as elongated derivatives in comparison with our earlier results in this field. The antiproliferative activity of compounds against human tumour cell lines (A2780, HeLa, MCF-7 and MDA-MB-231) was investigated. In our preliminary study, the 1,3-aminoalcohol function with N-benzyl or (1H-imidazol-1-yl)-propyl substitution and benzyl ester moiety seemed essential for the reliable antiproliferative activity. The results obtained could be a good starting point to further functionalisation towards more efficient antiproliferative diterpenes.},
	year = {2024},
	eissn = {1424-8247},
	orcid-numbers = {Zupkó, István/0000-0003-3243-5300; Szakonyi, Zsolt/0000-0003-2432-8409}
}

@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:34535772,
	title = {High-performance liquid chromatographic enantioseparation of azole analogs of monoterpene lactones and amides focusing on the separation characteristics of polysaccharide-based chiral stationary phases},
	url = {https://m2.mtmt.hu/api/publication/34535772},
	author = {Németi, Gábor and Berkecz, Róbert and Le Minh, Tam and Szakonyi, Zsolt and Péter, Antal and Ilisz, István},
	doi = {10.1016/j.chroma.2024.464660},
	journal-iso = {J CHROMATOGR A},
	journal = {JOURNAL OF CHROMATOGRAPHY A},
	volume = {1717},
	unique-id = {34535772},
	issn = {0021-9673},
	year = {2024},
	eissn = {1873-3778},
	orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Berkecz, Róbert/0000-0002-9076-2177; Le Minh, Tam/0000-0002-8296-887X; Szakonyi, Zsolt/0000-0003-2432-8409; Ilisz, István/0000-0001-8282-457X}
}

@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:34353508,
	title = {Stájer Géza (1936-2015)},
	url = {https://m2.mtmt.hu/api/publication/34353508},
	author = {Szakonyi, Zsolt},
	doi = {10.24100/MKF.2023.02.46},
	journal-iso = {MAGY KÉM FOLY KÉM KÖZL},
	journal = {MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-)},
	volume = {129},
	unique-id = {34353508},
	issn = {1418-9933},
	year = {2023},
	eissn = {1418-8600},
	pages = {46-49},
	orcid-numbers = {Szakonyi, Zsolt/0000-0003-2432-8409}
}

@article{MTMT:34034428,
	title = {Investigation of Anticancer Properties of Monoterpene-Aminopyrimidine Hybrids on A2780 Ovarian Cancer Cells},
	url = {https://m2.mtmt.hu/api/publication/34034428},
	author = {Nagy, Viktória and Mounir, Raji and Szebeni, Gábor and Szakonyi, Zsolt and Gémes, Nikolett and Minorics, Renáta and Germán, Péter and Zupkó, István},
	doi = {10.3390/ijms241310581},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {24},
	unique-id = {34034428},
	issn = {1661-6596},
	abstract = {The present study aimed to characterize the antiproliferative and antimetastatic properties of two recently synthesized monoterpene-aminopyrimidine hybrids (1 and 2) on A2780 ovary cancer cells. Both agents exerted a more pronounced cell growth inhibitory action than the reference agent cisplatin, as determined by the MTT assay. Tumor selectivity was assessed using non-cancerous fibroblast cells. Hybrids 1 and 2 induced changes in cell morphology and membrane integrity in A2780 cells, as evidenced by Hoechst 33258–propidium iodide fluorescent staining. Cell cycle analysis by flow cytometry revealed substantial changes in the distribution of A2780 ovarian cancer cells, with an increased rate in the subG1 and G2/M phases, at the expense of the G1 cell population. Moreover, the tested molecules accelerated tubulin polymerization in a cell-free in vitro system. The antimetastatic properties of both tested compounds were investigated by wound healing and Boyden chamber assays after 24 and 48 h of incubation. Treatment with 1 and 2 resulted in time- and concentration-dependent inhibition of migration and invasion of A2780 cancer cells. These results support that the tested agents may be worth of further investigation as promising anticancer drug candidates.},
	year = {2023},
	eissn = {1422-0067},
	orcid-numbers = {Szebeni, Gábor/0000-0002-6998-5632; Szakonyi, Zsolt/0000-0003-2432-8409; Minorics, Renáta/0000-0001-9685-813X; Zupkó, István/0000-0003-3243-5300}
}

@CONFERENCE{MTMT:33693549,
	title = {NICOTINIC ACID CATABOLISM IN ASPERGILLUS NIDULANS: AN EXAMPLE OF CONVERGENT EVOLUTION},
	url = {https://m2.mtmt.hu/api/publication/33693549},
	author = {Kozma-Bognárné Hamari, Zsuzsanna and Eszter, Bokor and Ámon, Judit and Varga, Mónika and Szekeres, András and Hegedüs, Zsófia and Tamás, Jakusch and Szakonyi, Zsolt and Flipphi, Michel Johannes Anthonie and Vágvölgyi, Csaba and Gácser, Attila and Claudio, Scazzocchio},
	booktitle = {16th European Conference on Fungal Genetics: Programme & Abstracts},
	unique-id = {33693549},
	abstract = {Nicotinic acid (niacin) is a precursor of NAD and NADP and thus an essential metabolite. Its degradation has been previously described only in bacteria.
		We describe, for the first time, a complete eukaryotic pathway of nico- tinic acid (NA) catabolism. The genes are organised in three co-regu- lated gene clusters, which encode eight enzymes, two transporters and the pathway specific transcription factor. The pathway is conserved; and its variable organisation in the Pezizomycotina illustrates cluster evolution and horizontal gene transfer.
		Reverse genetics was coupled with state-of-the-art chemical charac- terisation of each intermediate. The first step, the conversion of NA to 6-hydroxynicotinic acid (6-NA) is common to prokaryotic and eukary- otic pathways, even if catalysed by independently evolved enzymes. While two downstream metabolites, 2,5-dihydroxypyridine and 2,3,6-tri- hydroxypyridine, are common to various prokaryotic routes, other steps and metabolites are unprecedented: 3-hydroxypiperidine-2,6-dione and 5,6-dihydroxypiperidine-2-one intermediate metabolites have not been identified previously in any organism, the latter being a completely nov- el chemical compound. Furthermore, the hydrolytic N-C ring opening results in α-hydroxyglutaramate, a compound not detected in analo- gous prokaryotic pathways. Remarkably, the physiological inducer of the whole pathway is a near-terminal intermediate metabolite: 5,6-di- hydroxypiperidine-2-one.
		While most steps are cytosolic, two steps take place in the peroxi- somes. 6-NA monooxygenase (HxnX) enters peroxisomes through a canonical PTS-1 signal, while HxnW, a polyol dehydrogenase, is co-transported by piggybacking HxnX.
		The genomic organisation and phylogeny of the pathway cognate genes and proteins, showed that this catabolic pathway is of fungal (Ascomycota) origin and thus it exemplifies convergent evolution of catabolic pathways between fungi and bacteria, where at least four different pathways occur.},
	year = {2023},
	pages = {767-768},
	orcid-numbers = {Kozma-Bognárné Hamari, Zsuzsanna/0000-0001-6374-5083; Ámon, Judit/0000-0002-3234-6167; Szekeres, András/0000-0003-1651-4623; Szakonyi, Zsolt/0000-0003-2432-8409; Vágvölgyi, Csaba/0000-0003-0009-7773}
}

@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}
}

@{MTMT:33643161,
	title = {Pharmacological investigation of a newly synthesized monoterpene-based 2,4-diaminopyrimidine type derivatives lines in vitro},
	url = {https://m2.mtmt.hu/api/publication/33643161},
	author = {Nagy, Viktória and Mounir, Raji and Szakonyi, Zsolt and Gábor, J. Szebeni and Zupkó, István},
	booktitle = {Natural vs. Artificial Networks: The Usefulness of the Concept in Health, Life, and Technical Sciences},
	unique-id = {33643161},
	abstract = {According to estimates from the World Health Organization (WHO),
		cancer ranks as one of the major health burdens and a leading cause of
		mortality globally. Gynecologic cancers (breast, uterus, cervix, and
		ovaries) are found among the 10 most frequently diagnosed cancer types.
		Natural products including terpenes are one of the most investigated group
		of compounds in lead-finding studies. Several studies have revealed that
		monoterpenes may prevent the carcinogenesis process and exert growthinhibiting
		action against cancer cells.
		To determine the antiproliferative activity of a newly synthesized set
		of monoterpene-based 2,4-diaminopyrimidine type derivatives against
		gynecological cancer cell lines. The mechanism of the most effective
		analogues was additionally tested to describe their mechanism of action.
		The growth-inhibitory effects of the tested compounds were
		determined by MTT assay on a cell line panel (Hela, Siha, MDA-MB-231,
		and MCF-7, A2780, and NIH/3T3 fibroblast to characterize the cancer
		selectivity). To identify the changes in the cell cycle phase distribution of
		the treated cells, cell cycle analysis was performed. To distinguish
		apoptotic and necrotic cells by their nuclear morphology and membrane
		integrity, fluorescent staining was applied.
		Two out of 20 monoterpene derivatives exhibited promising
		antiproliferative action with IC50 values below 10 μM. These analogues
		elicited substantial changes in the cell cycle distribution of A2780 ovarian cancer cells with increased number of cells in SubG1 and G2/M phases on
		the expense of G1 population. The proapoptotic potential of these agents
		were confirmed by propidium-Hoechst 33258 staining.
		Our results suggest that the new monoterpene compounds may be
		regarded as promising candidates in the development of new anticancer
		agents, against ovarian cancer cell lines.},
	year = {2022},
	pages = {85-86},
	orcid-numbers = {Szakonyi, Zsolt/0000-0003-2432-8409; Zupkó, István/0000-0003-3243-5300}
}