TY - JOUR AU - Elnaggar, Mohamed S. AU - Elissawy, Ahmed M. AU - Youssef, Fadia S. AU - Kicsák, Máté AU - Kurtán, Tibor AU - Singab, Abdel Nasser B. AU - Kalscheuer, Rainer TI - Austalide derivative from marine-derived Aspergillus sp. and evaluation of its cytotoxic and ADME/TOPKAT properties JF - RSC ADVANCES J2 - RSC ADV VL - 13 PY - 2023 IS - 24 SP - 16480 EP - 16487 PG - 8 SN - 2046-2069 DO - 10.1039/D3RA02632A UR - https://m2.mtmt.hu/api/publication/34131157 ID - 34131157 AB - In-depth chemical investigation of an ethyl acetate extract of Aspergillus sp. isolated from the soft coral Sinularia species resulted in the isolation of one new meroterpenoid, austalide Z (1), one known austalide W (2), six known prenylated indole diketopiperazine alkaloids (3–8), and phthalic acid and its ethyl derivative (9–10). The structures were established by means of 1D and 2D NMR (one- and twodimensional nuclear magnetic resonance) experiments supported by UV analysis and ESI-MS (electrospray ionization mass spectrometry). In vitro cytotoxic evaluation was performed against the Caco-2 cancer cell line using the MTT assay, which showed that the examined compounds had weak to moderate activities, with the new meroterpenoid austalide Z (1) displaying an IC50 value of 51.6 mg mL-1. ADME/TOPKAT (absorption, distribution, metabolism, excretion, and toxicity) predication performed in silico showed that most of the isolated compounds possessed reasonable pharmacokinetic, pharmacodynamic, and toxicity properties. Thus, it can be concluded that Aspergillus sp. could act as a source of drug leads for cancer prevention with promising pharmacokinetic and pharmacodynamic properties and thus could be incorporated in pharmaceutical dosage forms. LA - English DB - MTMT ER - TY - JOUR AU - Bege, Miklós AU - Bakai-Bereczki, Ilona AU - Molnár, Dénes József AU - Kicsák, Máté AU - Pénzes-Daku, Krisztina AU - Bereczky, Zsuzsanna AU - Ferenc, Györgyi AU - Kovács, Lajos AU - Herczegh, Pál AU - Borbás, Anikó TI - Synthesis and oligomerization of cysteinyl nucleosides JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 18 PY - 2020 IS - 40 SP - 8161 EP - 8178 PG - 18 SN - 1477-0520 DO - 10.1039/d0ob01890b UR - https://m2.mtmt.hu/api/publication/31616449 ID - 31616449 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office of Hungary [OTKA K 132870, K 128801, K 116228]; EU - European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00021, UNKP-19-3]; New National Excellence Program of the Ministry for Innovation and Technology Funding text: The authors gratefully acknowledge financial support for this research from the National Research, Development and Innovation Office of Hungary (OTKA K 132870, K 128801 and K 116228). The research was also supported by the EU and co-financed by the European Regional Development Fund under the projects GINOP-2.3.2-15-2016-00008 and GINOP-2.3.3-15-2016-00021. M. B. acknowledgeds support from the UNKP-19-3 New National Excellence Program of the Ministry for Innovation and Technology. Department of Pharmaceutical Chemistry, University of Debrecen, Debrecen, H-4032, Hungary Doctoral School of Pharmaceutical Sciences, University of Debrecen, Debrecen, H-4032, Hungary MTA-DE Molecular Recognition and Interaction Research Group, University of Debrecen, Debrecen, H-4032, Hungary Division of Clinical Laboratory Science, University of Debrecen, Debrecen, H-4032, Hungary Nucleic Acid Synthesis Laboratory, Biological Research Center, Szeged, H-6726, Hungary Nucleic Acids Laboratory, Department of Medicinal Chemistry, University of Szeged, Szeged, H-6720, Hungary Export Date: 3 February 2021 CODEN: OBCRA Correspondence Address: Borbás, A.; Department of Pharmaceutical Chemistry, Hungary; email: borbas.aniko@pharm.unideb.hu Funding details: European Commission, EC Funding details: National Research, Development and Innovation Office Funding details: Hungarian Scientific Research Fund, OTKA, K 128801, K 116228, K 132870 Funding details: Ministry for Innovation and Technology Funding details: European Regional Development Fund, FEDER, GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00021 Funding text 1: The authors gratefully acknowledge financial support for this research from the National Research, Development and Innovation Office of Hungary (OTKA K 132870, K 128801 and K 116228). The research was also supported by the EU and cofinanced by the European Regional Development Fund under the projects GINOP-2.3.2-15-2016-00008 and GINOP-2.3.3-15-2016-00021. M. B. acknowledgeds support from the ÚNKP-19-3 New National Excellence Program of the Ministry for Innovation and Technology. AB - Nucleoside and nucleic acid analogues are known to possess a considerable therapeutic potential. In this work, by coupling cysteine to nucleosides, we successfully synthesized compounds that may not only have interesting biological properties in their monomeric form, but can be used beyond that, for oligomerization, in order to produce new types of synthetic nucleic acids. We elaborated different strategies for the synthesis of cysteinyl nucleosides as monomers of cysteinyl nucleic acids using nucleophilic substitution or thiol–ene coupling as a synthetic tool, and utilised on two complementary nucleosides, uridine and adenosine. Dipeptidyl dinucleosides and pentameric cysteinyl uridine were prepared from the monomeric building blocks, which are the first members of a new class of peptide nucleic acids containing the entire ribofuranosyl nucleoside units bound to the peptide backbone. LA - English DB - MTMT ER - TY - JOUR AU - Bege, Miklós AU - Kiss, Alexandra AU - Kicsák, Máté AU - Bakai-Bereczki, Ilona AU - Baksa, Viktória AU - Király, Gábor AU - Szemán-Nagy, Gábor AU - Máthéné Szigeti, Zsuzsa AU - Herczegh, Pál AU - Borbás, Anikó TI - Synthesis and Cytostatic Effect of 3’-deoxy-3’-C-Sulfanylmethyl Nucleoside Derivatives with d-xylo Configuration JF - MOLECULES J2 - MOLECULES VL - 24 PY - 2019 IS - 11 PG - 23 SN - 1420-3049 DO - 10.3390/molecules24112173 UR - https://m2.mtmt.hu/api/publication/30710099 ID - 30710099 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office of Hungary [TET_15_IN-1-2016-0071, K128801]; Debrecen Venture Catapult Program [EFOP-3.6.1-16-2016-00022, EFOP-3.6.3-VEKOP-16-2017-00009]; New National Excellence Program of the Ministry of Human Capacities [UNKP-18-3]; EUEuropean Union (EU); European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00021, GINOP-2.3.3-15-2016-00004] Funding text: This research was funded by: the National Research, Development and Innovation Office of Hungary (TET_15_IN-1-2016-0071 and K128801), the "Debrecen Venture Catapult Program" (EFOP-3.6.1-16-2016-00022 and EFOP-3.6.3-VEKOP-16-2017-00009) and the UNKP-18-3 New National Excellence Program of the Ministry of Human Capacities. The research was also supported by the EU and co-financed by the European Regional Development Fund under the projects GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00021 and GINOP-2.3.3-15-2016-00004. Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem Tér 1, Debrecen, 4032, Hungary Department of Biotechnology and Microbiology, University of Debrecen, Egyetem Tér 1, Debrecen, 4032, Hungary Cited By :1 Export Date: 17 December 2019 CODEN: MOLEF Correspondence Address: Borbás, A.; Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem Tér 1, Hungary; email: borbas.aniko@pharm.unideb.hu Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem Tér 1, Debrecen, 4032, Hungary Department of Biotechnology and Microbiology, University of Debrecen, Egyetem Tér 1, Debrecen, 4032, Hungary Cited By :6 Export Date: 3 February 2021 CODEN: MOLEF Correspondence Address: Borbás, A.; Department of Pharmaceutical Chemistry, Egyetem Tér 1, Hungary; email: borbas.aniko@pharm.unideb.hu Funding details: EFOP-3.6.3-VEKOP-16-2017-00009, EFOP-3.6.1-16-2016-00022 Funding details: European Commission, EC Funding details: National Research, Development and Innovation Office, TÉT_15_IN-1-2016-0071, K128801 Funding details: Emberi Eroforrások Minisztériuma, EMMI Funding details: European Regional Development Fund, FEDER, GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00004, GINOP-2.3.3-15-2016-00021 Funding text 1: Funding: This research was funded by: the National Research, Development and Innovation Office of Hungary (TÉT_15_IN-1-2016-0071 and K128801), the “Debrecen Venture Catapult Program” (EFOP-3.6.1-16-2016-00022 and EFOP-3.6.3-VEKOP-16-2017-00009) and the ÚNKP-18-3 New National Excellence Program of the Ministry of Human Capacities. The research was also supported by the EU and co-financed by the European Regional Development Fund under the projects GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00021 and GINOP-2.3.3-15-2016-00004. AB - A small library of 3’-deoxy-C3’-substituted xylofuranosyl-pyrimidine nucleoside analogues were prepared by photoinduced thiol-ene addition of various thiols, including normal and branched alkyl-, 2-hydroxyethyl, benzyl-, and sugar thiols, to 3’-exomethylene derivatives of 2’,5’-di-O-tert-butyldimethylsilyl-protected ribothymidine and uridine. The bioactivity of these derivatives was studied on tumorous SCC (mouse squamous carcinoma cell) and immortalized control HaCaT (human keratinocyte) cell lines. Several alkyl-substituted analogues elicited promising cytostatic activity in low micromolar concentrations with a slight selectivity toward tumor cells. Near-infrared live-cell imaging revealed SCC tumor cell-specific mitotic blockade via genotoxicity of analogue 10, bearing an n-butyl side chain. This analogue essentially affects the chromatin structure of SCC tumor cells, inducing a condensed nuclear material and micronuclei as also supported by fluorescent microscopy. The results highlight that thiol-ene chemistry represents an efficient strategy to discover novel nucleoside analogues with non-natural sugar structures as anticancer agents. LA - English DB - MTMT ER - TY - GEN AU - Bege, Miklós AU - Kicsák, Máté AU - Kiss, Alexandra AU - Nagy, Zsolt László AU - Keresztesi, Petra AU - Borbás, Anikó TI - Furanózgyűrűn módosított nukleozidszármazékok szintézise és citotoxicitási vizsgálata tumoros és nem tumoros sejtvonalakon ET - 0 PY - 2019 UR - https://m2.mtmt.hu/api/publication/30623119 ID - 30623119 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Szűcs, Zsolt AU - Ostorházi, Eszter AU - Kicsák, Máté AU - Nagy, Lajos AU - Borbás, Anikó AU - Herczegh, Pál TI - New semisynthetic teicoplanin derivatives have comparable in vitro activity to that of oritavancin against clinical isolates of VRE JF - JOURNAL OF ANTIBIOTICS J2 - J ANTIBIOT VL - 72 PY - 2019 IS - 7 SP - 524 EP - 534 PG - 11 SN - 0021-8820 DO - 10.1038/s41429-019-0164-1 UR - https://m2.mtmt.hu/api/publication/30605418 ID - 30605418 N1 - Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, Debrecen, H-4032, Hungary Department of Medical Microbiology, Semmelweis University, Nagyvárad tér 4, Budapest, H-1089, Hungary Department of Applied Chemistry, University of Debrecen, Egyetem tér 1, Debrecen, H-4032, Hungary Cited By :5 Export Date: 28 November 2021 CODEN: JANTA Correspondence Address: Herczegh, P.; Department of Pharmaceutical Chemistry, Egyetem tér 1, Hungary; email: herczeghp@gmail.com Chemicals/CAS: oritavancin, 171099-57-3, 192564-14-0; teicoplanin, 61036-62-2, 61036-64-4; vancomycin, 1404-90-6, 1404-93-9; Anti-Bacterial Agents; Lipoglycopeptides; oritavancin; Teicoplanin AB - Ten analogues of a teicoplanin pseudoaglycon derivative have been synthesized with the aim of optimizing the in vitro activity of the compound against VanA type vancomycin resistant enterococci (VRE) isolated from hospitalized patients. Teicoplanin, vancomycin, and oritavancin were used as reference antibiotics for the antibacterial evaluations. One of the new derivatives exhibited far superior activity than the original compound. The in vitro MICs measured were comparable to that of oritavancin against the investigated VRE strains. LA - English DB - MTMT ER - TY - THES AU - Kicsák, Máté TI - Új heterotriciklust tartalmazó nukleozid analógok szintézise PY - 2018 UR - https://m2.mtmt.hu/api/publication/3381624 ID - 3381624 N1 - Tudományág: gyógyszerészeti tudományok Témavezető: Herczegh Pál Beadás éve: 2018 A védés időpontja: 2018-05-08 13:00 A fokozat odaítélésének dátuma: 2018-05-16 Debreceni Egyetem, Gyógyszerészeti Tudományok Doktori Iskola Debrecen, Magyarország LA - Hungarian DB - MTMT ER - TY - JOUR AU - Kicsák, Máté AU - Mándi, Attila AU - Szabolcs, Varga AU - Herczeg, Mihály AU - Batta, Gyula AU - Bényei, Attila Csaba AU - Borbás, Anikó AU - Herczegh, Pál TI - Tricyclanos: conformationally constrained nucleoside analogues with a new heterotricycle obtained from a D-ribofuranose unit JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 16 PY - 2018 IS - 3 SP - 393 EP - 401 PG - 9 SN - 1477-0520 DO - 10.1039/c7ob02296d UR - https://m2.mtmt.hu/api/publication/3294083 ID - 3294083 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office [OTKA K 109208, 105459, NKFI PD 121020, ANN 110821]; EUEuropean Union (EU); European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008, TAMOP-4.2.2.B-15/1/KONV-2015-0001, TAMOP-4.2.1.C-14/1/KONV-2015-0004] Funding text: The authors gratefully acknowledge financial support from the National Research, Development and Innovation Office (OTKA K 109208 and 105459, NKFI PD 121020 and ANN 110821). The research was also supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008 as well as in the framework of TAMOP-4.2.2.B-15/1/KONV-2015-0001 and TAMOP-4.2.1.C-14/1/KONV-2015-0004. CPU time was granted by the Governmental Information-Technology Development Agency (KIFU). The authors thank Dr Dyanne Cruickshank (Rigaku Oxford Diffraction) for collecting X-ray data and Erzsebet Roth for excellent technical assistance. LA - English DB - MTMT ER - TY - JOUR AU - Bege, Miklós AU - Bakai-Bereczki, Ilona AU - Herczeg, Mihály AU - Kicsák, Máté AU - Eszenyi, Dániel AU - Herczegh, Pál AU - Borbás, Anikó TI - Low-temperature, photoinduced thiol-ene click reaction: a mild and efficient method for the synthesis of sugar-modified nucleosides JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 15 PY - 2017 IS - 43 SP - 9226 EP - 9233 PG - 8 SN - 1477-0520 DO - 10.1039/c7ob02184d UR - https://m2.mtmt.hu/api/publication/3290295 ID - 3290295 N1 - Megjegyzés-27087234 Megjegyzés-27015481 OA No Megjegyzés-27015483 OA No Megjegyzés-27015484 OA No Megjegyzés-27015480 OA No Funding Agency and Grant Number: National Research, Development and Innovation Office of Hungary [OTKA K 109208, TET_15_IN-1-2016-0071]; EUEuropean Union (EU); European Regional Development FundEuropean Union (EU) [GINOP-2.3.2-15-2016-00008] Funding text: The authors gratefully acknowledge financial support for this research from the National Research, Development and Innovation Office of Hungary (OTKA K 109208 and TET_15_IN-1-2016-0071). The research was also supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008. Cited By :12 Export Date: 3 February 2021 CODEN: OBCRA Correspondence Address: Borbás, A.; Department of Pharmaceutical Chemistry, Egyetem tér 1, Hungary; email: borbas.aniko@pharm.unideb.hu Funding details: European Commission, EC Funding details: Hungarian Scientific Research Fund, OTKA, TÉT_15_IN-1-2016-0071, K 109208 Funding details: European Regional Development Fund, FEDER, GINOP-2.3.2-15-2016-00008 Funding text 1: The authors gratefully acknowledge financial support for this research from the National Research, Development and Innovation Office of Hungary (OTKA K 109208 and TÉT_15_IN-1-2016-0071). The research was also supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008. LA - English DB - MTMT ER - TY - JOUR AU - Kicsák, Máté AU - Bege, Miklós AU - Bakai-Bereczki, Ilona AU - Csávás, Magdolna AU - Herczeg, Mihály AU - Kupihár, Zoltán AU - Kovács, Lajos AU - Borbás, Anikó AU - Herczegh, Pál TI - A three-component reagent system for rapid and mild removal of O-, N- and S-trityl protecting groups JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 14 PY - 2016 IS - 12 SP - 3190 EP - 3192 PG - 3 SN - 1477-0520 DO - 10.1039/C6OB00067C UR - https://m2.mtmt.hu/api/publication/3017583 ID - 3017583 N1 - Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, Debrecen, H-4032, Hungary Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Cited By :11 Export Date: 3 February 2021 CODEN: OBCRA Correspondence Address: Borbás, A.; Department of Pharmaceutical Chemistry, Egyetem tér 1, Hungary; email: borbas.aniko@pharm.unideb.hu AB - A new reagent system consisting of a Lewis acid such as BF3·Et2O or Cu(OTf)2, the mild protic acid hexafluoroisopropanol and the reducing quenching agent triethylsilane was elaborated for O-, N- and S-detritylation of nucleoside, carbohydrate and amino acid derivatives. The method is compatible with acetyl, silyl, acetal and Fmoc groups. LA - English DB - MTMT ER - TY - JOUR AU - Herczeg, Mihály AU - Csávás, Magdolna AU - Bakai-Bereczki, Ilona AU - Mező, Erika AU - Eszenyi, Dániel AU - Kicsák, Máté AU - Hadházi, Ádám AU - Tollas, Szilvia AU - Varga, Eszter AU - Szilágyi, Eszter AU - Molnár, J Dénes AU - Bege, Miklós AU - Pénzes, András AU - Herczegh, Pál AU - Borbás, Anikó TI - Gyógyhatású szénhidrátok - a véralvadásgátlástól a géncsendesítésig JF - MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-) J2 - MAGY KÉM FOLY KÉM KÖZL VL - 121 PY - 2015 IS - 1 SP - 13 EP - 21 PG - 9 SN - 1418-9933 UR - https://m2.mtmt.hu/api/publication/2922308 ID - 2922308 AB - Synthesis of carbohydrate mimetics for potential pharmaceutical applications is one of our main research topics in the Department of Pharmaceutical Chemistry at the University of Debrecen. As therapeutical application of glycosides is hampered by their in vivo instability and their low binding affinity towards proteins, we focus on the design and synthesis of unnatural derivatives with an increased stability and with better binding properties. In this article, we summarized our recent results in the following topics: i) synthesis and biological evaluation of heparinoid pentasaccharide sulfonic acids; ii) preparation of thio-linked glycosides by photoinduced free radical hydrothiolation of endocyclic double bond of sugars and application of the thiol addition method in the synthesis of self-assembling multivalent thiomannobioside ligands of mannose-binding lectins; iii) synthesis of a cysteinyl uridine pentapeptide, the first member of a novel type of peptide nucleic acids. LA - Hungarian DB - MTMT ER -