@article{MTMT:34722559,
	title = {Direct modulation of TRPM8 ion channels by rapamycin and analog macrolide immunosuppressants},
	url = {https://m2.mtmt.hu/api/publication/34722559},
	author = {Tóth, Balázs István and Bahar, Bazeli and Annelies, Janssens and Lisztes, Erika and Racskó, Márk and Kelemen, Balázs and Herczeg, Mihály and Nagy, Tamás Milán and E Kövér, Katalin and Argha, Mitra and Attila, Borics and Bíró, Tamás and Thomas, Voets},
	journal-iso = {ELIFE},
	journal = {ELIFE},
	unique-id = {34722559},
	issn = {2050-084X},
	year = {2024},
	eissn = {2050-084X},
	orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789}
}

@article{MTMT:34502650,
	title = {Block Synthesis and Step-Growth Polymerization of C-6-Sulfonatomethyl-Containing Sulfated Malto-Oligosaccharides and Their Biological Profiling},
	url = {https://m2.mtmt.hu/api/publication/34502650},
	author = {Herczeg, Mihály and Demeter, Fruzsina and Nagy, Tibor and Rusznyák, Ágnes and Hodek, Jan and Sipos, Éva and Lekli, István and Fenyvesi, Ferenc and Weber, Jan and Kéki, Sándor and Borbás, Anikó},
	doi = {10.3390/ijms25010677},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {25},
	unique-id = {34502650},
	issn = {1661-6596},
	abstract = {Highly sulfated malto-oligomers, similar to heparin and heparan-sulfate, have good antiviral, antimetastatic, anti-inflammatory and cell growth inhibitory effects. Due to their broad biological activities and simple structure, sulfated malto-oligomer derivatives have a great therapeutic potential, therefore, the development of efficient synthesis methods for their production is of utmost importance. In this work, preparation of α-(1→4)-linked oligoglucosides containing a sulfonatomethyl moiety at position C-6 of each glucose unit was studied by different approaches. Malto-oligomeric sulfonic acid derivatives up to dodecasaccharides were prepared by polymerization using different protecting groups, and the composition of the product mixtures was analyzed by MALDI-MS methods and size-exclusion chromatography. Synthesis of lower oligomers was also accomplished by stepwise and block synthetic methods, and then the oligosaccharide products were persulfated. The antiviral, anti-inflammatory and cell growth inhibitory activity of the fully sulfated malto-oligosaccharide sulfonic acids were determined by in vitro tests. Four tested di- and trisaccharide sulfonic acids effectively inhibited the activation of the TNF-α-mediated inflammatory pathway without showing cytotoxicity.},
	year = {2024},
	eissn = {1422-0067},
	orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Nagy, Tibor/0000-0001-8568-914X; Sipos, Éva/0009-0001-9561-2450; Borbás, Anikó/0000-0001-8462-4547}
}

@article{MTMT:34427826,
	title = {Amphiphilic Sialic Acid Derivatives as Potential Dual-Specific Inhibitors of Influenza Hemagglutinin and Neuraminidase},
	url = {https://m2.mtmt.hu/api/publication/34427826},
	author = {Lőrincz, Eszter Boglárka and Herczeg, Mihály and Houser, Josef and Rievajová, Martina and Kuki, Ákos and Malinovská, Lenka and Naesens, Lieve and Wimmerová, Michaela and Borbás, Anikó and Herczegh, Pál and Bakai-Bereczki, Ilona},
	doi = {10.3390/ijms242417268},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {24},
	unique-id = {34427826},
	issn = {1661-6596},
	abstract = {In the shadow of SARS-CoV-2, influenza seems to be an innocent virus, although new zoonotic influenza viruses evolved by mutations may lead to severe pandemics. According to WHO, there is an urgent need for better antiviral drugs. Blocking viral hemagglutinin with multivalent N-acetylneuraminic acid derivatives is a promising approach to prevent influenza infection. Moreover, dual inhibition of both hemagglutinin and neuraminidase may result in a more powerful effect. Since both viral glycoproteins can bind to neuraminic acid, we have prepared three series of amphiphilic self-assembling 2-thio-neuraminic acid derivatives constituting aggregates in aqueous medium to take advantage of their multivalent effect. One of the series was prepared by the azide-alkyne click reaction, and the other two by the thio-click reaction to yield neuraminic acid derivatives containing lipophilic tails of different sizes and an enzymatically stable thioglycosidic bond. Two of the three bis-octyl derivatives produced proved to be active against influenza viruses, while all three octyl derivatives bound to hemagglutinin and neuraminidase from H1N1 and H3N2 influenza types.},
	year = {2023},
	eissn = {1422-0067},
	orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Houser, Josef/0000-0003-4504-3891; Naesens, Lieve/0000-0001-9742-9302; Wimmerová, Michaela/0000-0002-7108-4198; Borbás, Anikó/0000-0001-8462-4547; Bakai-Bereczki, Ilona/0000-0003-4601-7257}
}

@article{MTMT:34316518,
	title = {Mannich-type modifications of (−)-cannabidiol and (−)-cannabigerol leading to new, bioactive derivatives},
	url = {https://m2.mtmt.hu/api/publication/34316518},
	author = {Lőrincz, Eszter Boglárka and Tóth, Gergely and Spolárics, Júlia and Herczeg, Mihály and Hodek, Jan and Zupkó, István and Minorics, Renáta and Ádám, Dorottya and Oláh, Attila and Zouboulis, Christos C. and Weber, Jan and Nagy, Lajos and Ostorházi, Eszter and Bácskay, Ildikó and Borbás, Anikó and Herczegh, Pál and Bakai-Bereczki, Ilona},
	doi = {10.1038/s41598-023-45565-7},
	journal-iso = {SCI REP},
	journal = {SCIENTIFIC REPORTS},
	volume = {13},
	unique-id = {34316518},
	issn = {2045-2322},
	abstract = {(−)-Cannabidiol (CBD) and (−)-cannabigerol (CBG) are two major non-psychotropic phytocannabinoids that have many beneficial biological properties. However, due to their low water solubility and prominent first-pass metabolism, their oral bioavailability is moderate, which is unfavorable for medicinal use. Therefore, there is a great need for appropriate chemical modifications to improve their physicochemical and biological properties. In this study, Mannich-type reaction was used for the synthetic modification of CBD and CBG for the first time, and thus fifteen new cannabinoid derivatives containing one or two tertiary amino groups were prepared. Thereafter the antiviral, antiproliferative and antibacterial properties of the derivatives and their effects on certain skin cells were investigated. Some modified CBD derivatives showed remarkable antiviral activity against SARS-CoV-2 without cytotoxic effect, while synthetic modifications on CBG resulted in a significant increase in antiproliferative activity in some cases compared to the parent compound.},
	year = {2023},
	eissn = {2045-2322},
	orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Zupkó, István/0000-0003-3243-5300; Minorics, Renáta/0000-0001-9685-813X; Oláh, Attila/0000-0003-4122-5639; Ostorházi, Eszter/0000-0002-9459-7316; Borbás, Anikó/0000-0001-8462-4547; Bakai-Bereczki, Ilona/0000-0003-4601-7257}
}

@article{MTMT:33657380,
	title = {Triaza-tricyclanos – synthesis of a new class of tricyclic nucleoside analogues by stereoselective cascade cyclocondensation},
	url = {https://m2.mtmt.hu/api/publication/33657380},
	author = {Bege, Miklós and Herczeg, Mihály and Bakai-Bereczki, Ilona and Debreczeni, Nóra and Bényei, Attila Csaba and Herczegh, Pál and Borbás, Anikó},
	doi = {10.1039/D3OB00154G},
	journal-iso = {ORG BIOMOL CHEM},
	journal = {ORGANIC & BIOMOLECULAR CHEMISTRY},
	volume = {21},
	unique-id = {33657380},
	issn = {1477-0520},
	abstract = {Conformationally constrained tricyclic morpholino-nucleosides containing three new chirality centers were prepared with full stereoselectivity, through two consecutive hemiaminal-imidazolidine cascade reactions.},
	year = {2023},
	eissn = {1477-0539},
	pages = {2213-2219},
	orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Bakai-Bereczki, Ilona/0000-0003-4601-7257; Borbás, Anikó/0000-0001-8462-4547}
}

@article{MTMT:33635459,
	title = {First Synthesis of DBU-Conjugated Cationic Carbohydrate Derivatives and Investigation of Their Antibacterial and Antifungal Activity},
	url = {https://m2.mtmt.hu/api/publication/33635459},
	author = {Demeter, Fruzsina and Török, Patrik and Kiss, Alexandra and Kovásznai-Oláh, Richárd and Máthéné Szigeti, Zsuzsa and Baksa, Viktória and Kovács, Fruzsina and Balla , Noémi and Fenyvesi, Ferenc and Váradi, Judit and Borbás, Anikó and Herczeg, Mihály},
	doi = {10.3390/ijms24043550},
	journal-iso = {INT J MOL SCI},
	journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES},
	volume = {24},
	unique-id = {33635459},
	issn = {1661-6596},
	abstract = {The emergence of drug-resistant bacteria and fungi represents a serious health problem worldwide. It has long been known that cationic compounds can inhibit the growth of bacteria and fungi by disrupting the cell membrane. The advantage of using such cationic compounds is that the microorganisms would not become resistant to cationic agents, since this type of adaptation would mean significantly altering the structure of their cell walls. We designed novel, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)-derived amidinium salts of carbohydrates, which may be suitable for disturbing the cell walls of bacteria and fungi due to their quaternary ammonium moiety. A series of saccharide-DBU conjugates were prepared from 6-iodo derivatives of d-glucose, d-mannose, d-altrose and d-allose by nucleophilic substitution reactions. We optimized the synthesis of a d-glucose derivative, and studied the protecting group free synthesis of the glucose-DBU conjugates. The effect of the obtained quaternary amidinium salts against Escherichia coli and Staphylococcus aureus bacterial strains and Candida albicans yeast was investigated, and the impact of the used protecting groups and the sugar configuration on the antimicrobial activity was analyzed. Some of the novel sugar quaternary ammonium compounds with lipophilic aromatic groups (benzyl and 2-napthylmethyl) showed particularly good antifungal and antibacterial activity.},
	year = {2023},
	eissn = {1422-0067},
	orcid-numbers = {Borbás, Anikó/0000-0001-8462-4547; Herczeg, Mihály/0000-0002-7938-9789}
}

@article{MTMT:33574039,
	title = {Synthesis of the Three Most Expensive l-Hexose Thioglycosides from d-Glucose},
	url = {https://m2.mtmt.hu/api/publication/33574039},
	author = {Demeter, Fruzsina and Bényei, Attila Csaba and Borbás, Anikó and Herczeg, Mihály},
	doi = {10.1055/s-0042-1751394},
	journal-iso = {SYNTHESIS-STUTTGART},
	journal = {SYNTHESIS-STUTTGART},
	volume = {55},
	unique-id = {33574039},
	issn = {0039-7881},
	abstract = {The biologically important l-hexoses, which are less widespread than d-hexoses, cannot be obtained from natural sources or can only be extracted very costly. Due to the complexity of their synthesis, their commercially available derivatives (which are sold mostly in free form) are also very expensive, which is further exacerbated by the current rapid rise in prices. In the present work, starting from the cheapest d-hexose, d-glucose, using inexpensive and readily available chemicals, a reaction pathway was developed in which the three most expensive l-hexoses (l-idose, l-altrose, and l-talose) were successfully prepared in orthogonally protected thioglycoside form, ready for glycosylation. The l-ido and l-talo derivatives were synthesized by C-5 epimerization of the corresponding 5,6-unsaturated thioglycosides. From the l-ido derivatives, the orthogonally protected thioglycosides of l-altrose were then prepared by C-4 epimerization. Different approaches to the preparation of the key intermediates, 5,6-unsaturated thioglycoside derivatives, were systematically investigated in the presence of various protecting groups (ether and ester) and using commercially available reagents.},
	year = {2023},
	eissn = {1437-210X},
	pages = {1087-1111},
	orcid-numbers = {Borbás, Anikó/0000-0001-8462-4547; Herczeg, Mihály/0000-0002-7938-9789}
}

@article{MTMT:33332835,
	title = {Synthesis of a Heparinoid Pentasaccharide Containing L-Guluronic Acid Instead of L-Iduronic Acid with Preserved Anticoagulant Activity},
	url = {https://m2.mtmt.hu/api/publication/33332835},
	author = {Herczeg, Mihály and Demeter, Fruzsina and Lisztes, Erika and Racskó, Márk and Tóth, Balázs István and Timári, István and Bereczky, Zsuzsanna and E Kövér, Katalin and Borbás, Anikó},
	doi = {10.1021/acs.joc.2c01928},
	journal-iso = {J ORG CHEM},
	journal = {JOURNAL OF ORGANIC CHEMISTRY},
	volume = {87},
	unique-id = {33332835},
	issn = {0022-3263},
	abstract = {L-Iduronic acid is a key constituent of heparin and heparan sulfate polysaccharides due to its unique conformational plasticity, which facilitates the binding of polysaccharides to proteins. At the same time, this is the synthetically most challenging unit of heparinoid oligosaccharides; therefore, there is a high demand for its replacement with a more easily accessible sugar unit. In the case of idraparinux, an excellent anticoagulant heparinoid pentasaccharide, we demonstrated that L-iduronic acid can be replaced by an easier-to-produce L-sugar while maintaining its essential biological activity. From the inexpensive D-mannose, through a highly functionalized phenylthio mannoside, the L-gulose donor was prepared by C-5 epimerization in 10 steps with excellent yield. This unit was incorporated into the pentasaccharide by alpha-selective glycosylation and oxidized to L-guluronic acid. The complete synthesis required only 36 steps, with 21 steps for the longest linear route. The guluronate containing pentasaccharide inhibited coagulation factor Xa by 50% relative to the parent compound, representing an excellent anticoagulant activity. To the best of our knowledge, this is the first biologically active heparinoid anticoagulant which contains a different sugar unit instead of L-iduronic acid.},
	year = {2022},
	eissn = {1520-6904},
	pages = {15830-15836},
	orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Bereczky, Zsuzsanna/0000-0002-1483-3703; Borbás, Anikó/0000-0001-8462-4547}
}

@article{MTMT:32859682,
	title = {Synthesis of Four Orthogonally Protected Rare l-Hexose Thioglycosides from d-Mannose by C-5 and C-4 Epimerization},
	url = {https://m2.mtmt.hu/api/publication/32859682},
	author = {Demeter, Fruzsina and Bakai-Bereczki, Ilona and Borbás, Anikó and Herczeg, Mihály},
	doi = {10.3390/molecules27113422},
	journal-iso = {MOLECULES},
	journal = {MOLECULES},
	volume = {27},
	unique-id = {32859682},
	issn = {1420-3049},
	abstract = {l-Hexoses are important components of biologically relevant compounds and precursors of some therapeuticals. However, they typically cannot be obtained from natural sources and due to the complexity of their synthesis, their commercially available derivatives are also very expensive. Starting from one of the cheapest d-hexoses, d-mannose, using inexpensive and readily available chemicals, we developed a reaction pathway to obtain two orthogonally protected l-hexose thioglycoside derivatives, l-gulose and l-galactose, through the corresponding 5,6-unsaturated thioglycosides by C-5 epimerization. From these derivatives, the orthogonally protected thioglycosides of further two l-hexoses (l-allose and l-glucose) were synthesized by C-4 epimerization. The preparation of the key intermediates, the 5,6-unsaturated derivatives, was systematically studied using various protecting groups. By the method developed, we are able to produce highly functionalized l-gulose derivatives in 9 steps (total yields: 21-23%) and l-galactose derivatives in 12 steps (total yields: 6-8%) starting from d-mannose.},
	year = {2022},
	eissn = {1420-3049},
	orcid-numbers = {Bakai-Bereczki, Ilona/0000-0003-4601-7257; Borbás, Anikó/0000-0001-8462-4547; Herczeg, Mihály/0000-0002-7938-9789}
}

@{MTMT:32465340,
	title = {Protecting Group Manipulations in Carbohydrate Synthesis},
	url = {https://m2.mtmt.hu/api/publication/32465340},
	author = {Magdolna, Csávás and Herczeg, Mihály and István, Bajza and Borbás, Anikó},
	booktitle = {Comprehensive Glycoscience},
	doi = {10.1016/B978-0-12-819475-1.00087-0},
	unique-id = {32465340},
	year = {2021},
	pages = {464-524},
	orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Borbás, Anikó/0000-0001-8462-4547}
}