TY - JOUR AU - Szepesi Kovács, Dénes AU - Pásztor, Bettina AU - Ábrányi-Balogh, Péter AU - Petri, László AU - Imre, Tímea AU - Simon, József AU - Tátrai, Enikő AU - Várady, György AU - Tóvári, József AU - Szijj, Peter A AU - Keserű, György Miklós TI - Site-Selective Antibody Conjugation with Dibromopyrazines JF - BIOCONJUGATE CHEMISTRY J2 - BIOCONJUGATE CHEM VL - 35 PY - 2024 IS - 9 SP - 1373 EP - 1379 PG - 7 SN - 1043-1802 DO - 10.1021/acs.bioconjchem.4c00296 UR - https://m2.mtmt.hu/api/publication/35176724 ID - 35176724 N1 - Funding Agency and Grant Number: Pharma Lab [2018-1.3.1-VKE-2018-00032, RRF-2.3.1-21-2022-00015, TKP2021-EGA-44]; National Tumor Biology Laboratory [NLP-17]; National Office of Research, Innovation and Technology [PD124598, PD143427]; Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences; New National Excellence Program of the Ministry for Culture and Innovation from the source of the National Research, Development and Innovation Fund [UNKP-23-4] Funding text: This work was supported by the 2018-1.3.1-VKE-2018-00032, Pharma Lab RRF-2.3.1-21-2022-00015, TKP2021-EGA-44, National Tumor Biology Laboratory (NLP-17), PD124598, and PD143427 grants of the National Office of Research, Innovation and Technology. P.A.-B. is grateful for the support of the Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences. L.P. was supported by the UNKP-23-4 New National Excellence Program of the Ministry for Culture and Innovation from the source of the National Research, Development and Innovation Fund. The authors acknowledge the fruitful discussions with Prof. Vijay Chudasama (Department of Chemistry, University College London, London, U.K.). AB - In recent years, antibody conjugates have evolved as state-of-the-art options for diagnostic and therapeutic applications. During site-selective antibody conjugation, incomplete rebridging of antibody chains limits the homogeneity of conjugates and calls for the development of new rebridging agents. Herein, we report a dibromopyrazine derivative optimized to reach highly homogeneous conjugates rapidly and with high conversion on rebridging of trastuzumab, even providing a feasible route for antibody modification in acidic conditions. Furthermore, coupling a fluorescent dye and a cytotoxic drug resulted in effective antibody conjugates with excellent serum stability and in vitro selectivity, demonstrating the utility of the dibromopyrazine rebridging agent to produce on-demand future antibody conjugates for diagnostic or therapeutic applications. LA - English DB - MTMT ER - TY - JOUR AU - Kovács, Ervin AU - Szepesi Kovács, Dénes AU - Mucsi, Zoltán TI - Láthatóvá tenni a ráksejteket. Új festék a mikroszkópos tumordiagnosztikábanLáthatóvá tenni a ráksejteket/ Új festék a mikroszkópos tumordiagnosztikában JF - TERMÉSZET VILÁGA J2 - TERMÉSZET VILÁGA VL - 154 PY - 2023 IS - 6 SP - 259 EP - 263 PG - 5 SN - 0040-3717 UR - https://m2.mtmt.hu/api/publication/34016504 ID - 34016504 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Szepesi Kovács, Dénes AU - Chiovini, Balázs AU - Müller, Dalma AU - Tóth, Estilla Zsófia AU - Fülöp, Anna AU - Ábrányi-Balogh, Péter AU - Wittner, Lucia AU - Várady, György AU - Farkas, Ödön AU - Turczel, Gábor AU - Katona, Gergely AU - Győrffy, Balázs AU - Keserű, György Miklós AU - Mucsi, Zoltán AU - Rózsa J., Balázs AU - Kovács, Ervin TI - Synthesis and Application of Two-Photon Active Fluorescent Rhodol Dyes for Antibody Conjugation and In Vitro Cell Imaging JF - ACS OMEGA J2 - ACS OMEGA VL - 8 PY - 2023 IS - 25 SP - 22836 EP - 22843 PG - 8 SN - 2470-1343 DO - 10.1021/acsomega.3c01796 UR - https://m2.mtmt.hu/api/publication/34015800 ID - 34015800 N1 - Funding Agency and Grant Number: National Office of Science, Innovation and Technology (NKFIH) [2018-1.3.1-VKE-2018-00032, KFI-18-2018-00097, TKP2021-EGA-42, 2020-1.1.5-GYORSITOSAV-2021-00004, TKP2021-NVA-14]; New National Excellence Program of the Ministry for Innovation and Technology [NKFIH PD124598, BO/799/21/7]; Janos Bolyai Research Scholarship [UNKP-22-ME3] Funding text: The research was supported by the 2018-1.3.1-VKE-2018-00032, KFI-18-2018-00097, TKP2021-EGA-42, 2020-1.1.5-GYORSITOSAV-2021-00004, and TKP2021-NVA-14 grants of the National Office of Science, Innovation and Technology (NKFIH). We are grateful for the support of NKFIH PD124598 and UNKP-19-3-I-BME-408 New National Excellence Program of the Ministry for Innovation and Technology and Janos Bolyai Research Scholarship (BO/799/21/7, UNKP-22-ME3). The authors acknowledge the supportive work of Krisztina Nemeth. We are grateful for the possibility to use ELKH Cloud, which helped us achieve the results published in this paper. LA - English DB - MTMT ER - TY - JOUR AU - Szepesi Kovács, Dénes AU - Kontra, Bence AU - Chiovini, Balázs AU - Müller, Dalma AU - Tóth, Estilla Zsófia AU - Ábrányi-Balogh, Péter AU - Wittner, Lucia AU - Várady, György AU - Turczel, Gábor AU - Farkas, Ödön AU - Owen, Michael Christopher AU - Katona, Gergely AU - Győrffy, Balázs AU - Keserű, György Miklós AU - Mucsi, Zoltán AU - Rózsa J., Balázs AU - Kovács, Ervin TI - Effective Synthesis, Development and Application of a Highly Fluorescent Cyanine Dye for Antibody Conjugation and Microscopy Imaging JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 21 PY - 2023 IS - 44 SP - 8829 EP - 8836 PG - 8 SN - 1477-0520 DO - 10.1039/D3OB01471A UR - https://m2.mtmt.hu/api/publication/34205650 ID - 34205650 N1 - Funding Agency and Grant Number: National Office of Science, Innovation and Technology (NKFIH) [2018-1.3.1-VKE-2018-00032, KFI-18-2018-00097, TKP2021-EGA-42, TKP2021-NVA-15, 2020-1.1.5-GYORSITOSAV-2021-00004, 2020-2.1.1-ED-2021-00190, 2020-2.1.1-ED-2022-00208, TKP2021-NVA-14]; Janos Bolyai Research Scholarship [BO/799/21/7, UNKP-22-ME3] Funding text: This research was supported by the 2018-1.3.1-VKE-2018-00032, KFI-18-2018-00097, TKP2021-EGA-42, TKP2021-NVA-15, 2020-1.1.5-GYORSITOSAV-2021-00004, 2020-2.1.1-ED-2021-00190, 2020-2.1.1-ED-2022-00208 and TKP2021-NVA-14 grants of the National Office of Science, Innovation and Technology (NKFIH). We are grateful for the support from the Janos Bolyai Research Scholarship (BO/799/21/7, UNKP-22-ME3). The authors acknowledge the supportive work of Krisztina Nemeth. On behalf of the Development and mechanistic study of DNA dyes (PI: Dr Ervin Kovacs, ELKH Research Centre for Natural Sciences) project we are grateful for the possibility to use ELKH Cloud,53 which helped us achieve the results published in this paper. AB - An asymmetric cyanine-type fluorescent dye was designed and synthesized via a versatile, multi-step process, aiming to conjugate with an Her2+ receptor specific antibody by an azide-alkyne click reaction. The aromaticity and the excitation and relaxation energetics of the fluorophore were characterized by computational methods. The synthesized dye exhibited excellent fluorescence properties for confocal microscopy, offering efficient applicability in in vitro imaging due to its merits such as a high molar absorption coefficient (36 816 M-1 cm-1), excellent brightness, optimal wavelength (627 nm), larger Stokes shift (26 nm) and appropriate photostability compared to cyanines. The conjugated cyanine-trastuzumab was constructed via an effective, metal-free, strain-promoted azide-alkyne click reaction leading to a regulated number of dyes being conjugated. This novel cyanine-labelled antibody was successfully applied for in vitro confocal imaging and flow cytometry of Her2+ tumor cells. An azido cyanine dye was synthesized and characterized by computational and experimental techniques and applied in tumor cell imaging. LA - English DB - MTMT ER - TY - JOUR AU - Szepesi Kovács, Dénes AU - Hajdu, Imre AU - Mészáros, Gergely AU - Wittner, Lucia AU - Meszéna, Domokos AU - Tóth, Estilla Zsófia AU - Hegedűs, Zita AU - Randelovic, Ivan AU - Tóvári, József AU - Szabó, Tímea AU - Szilágyi, Bence AU - Milen, Mátyás AU - Keserű, György Miklós AU - Ábrányi-Balogh, Péter TI - Synthesis and characterization of new fluorescent boro-β-carboline dyes JF - RSC ADVANCES J2 - RSC ADV VL - 11 PY - 2021 IS - 21 SP - 12802 EP - 12807 PG - 6 SN - 2046-2069 DO - 10.1039/D1RA02132J UR - https://m2.mtmt.hu/api/publication/31951354 ID - 31951354 N1 - Research Centre for Natural Sciences, Medicinal Chemistry Research Group, Budapest, POB 286, Hungary Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, 1521, Hungary Research Centre for Natural Sciences, Comparative Psychophysiology Research Group, Budapest, POB 286, Hungary Faculty of Information Technology and Bionics, Pázmány Péter Catholic University, Budapest, POB 278, Hungary János Szentágothai Doctoral School of Neurosciences, Semmelweis University, Budapest, 1085, Hungary National Institute of Oncology, Department of Experimental Pharmacology, POB 21, Budapest, 1525, Hungary Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, POB 100, Budapest, 1475, Hungary Export Date: 30 August 2021 CODEN: RSCAC Correspondence Address: Keserű, G.M.; Research Centre for Natural Sciences, POB 286, Hungary; email: keseru.gyorgy@ttk.hu LA - English DB - MTMT ER - TY - JOUR AU - Szepesi Kovács, Dénes AU - Keserű, György Miklós AU - Ábrányi-Balogh, Péter TI - Application of Boroisoquinoline Fluorophores as Chemodosimeters for Fluoride Ion and Pd (0) JF - MATERIALS J2 - MATERIALS VL - 13 PY - 2020 IS - 1 SP - 199 SN - 1996-1944 DO - 10.3390/ma13010199 UR - https://m2.mtmt.hu/api/publication/31038453 ID - 31038453 LA - English DB - MTMT ER - TY - JOUR AU - Szepesi Kovács, Dénes AU - Kormos, Attila AU - Demeter, Orsolya AU - Dancsó, András AU - Keserű, György Miklós AU - Milen, Mátyás AU - Ábrányi-Balogh, Péter TI - Synthesis and fluorescent properties of boroisoquinolines, a new family of fluorophores JF - RSC ADVANCES J2 - RSC ADV VL - 8 PY - 2018 IS - 67 SP - 38598 EP - 38605 PG - 8 SN - 2046-2069 DO - 10.1039/c8ra08241c UR - https://m2.mtmt.hu/api/publication/30340445 ID - 30340445 N1 - Export Date: 7 December 2018 Funding Agency and Grant Number: Hungarian Academy of Sciences; Hungarian Science Foundation [OTKA PD124598] Funding text: P. A.-B. is grateful for the postdoctoral fellowship of the Hungarian Academy of Sciences and the Hungarian Science Foundation (OTKA PD124598). LA - English DB - MTMT ER -