Laboratory of Medicinal Chemistry

Laboratory of Medicinal Chemistry

Ph.D. Milan Jakubek, doc. Ing.

Ph.D. Milan Jakubek, doc. Ing. — Project head

1st Faculty of Medicine of the Charles University

About us

PROJECTS:

  • Development of technology for dietary supplement preparation containing curcumin with high degree of bioavailability. (Scientific research with mcePharma, s.r.o.)
  • Oxycellulose and its chemical and non-covalent modifications: Application for systems of drug controlled release, cosmetics and wound healing preparations. (Contract research in cooperation with Synthesia, a.s.)
  • Improved growth of human skin cells on biomimetic nanofibrous matrices for active wound healing. GAČR 17-02448S
  • Study of molecular and functional mechanism of novel cytostatics (cyclic polymethinum salts) using

Group Profile (Home Institution): http://en.lf1.cuni.cz/

News

Publications

2023

Raudenská M, Petrláková K, Juriňáková T, Leischner Fialová J, Fojtů M, Jakubek M, Rösel D, Brábek J, Masařík M. Engine shutdown: migrastatic strategies and prevention of metastases. Trends Cancer. 2023 Apr;9(4):293-308. doi: 10.1016/j.trecan.2023.01.001. Epub 2023 Feb 15.

Dytrych P, Kejík Z, Hajduch J, Kaplánek R, Veselá K, Kučnirová K, Skaličková M, Venhauerová A, Hoskovec D, Martásek P, Jakubek M. Therapeutic potential and limitations of curcumin as antimetastatic agent. Biomed Pharmacother. 2023 Jul;163:114758. doi: 10.1016/j.biopha.2023.114758. (IF 7.419)

2022

Hosnedlova, B.; Kabanov, D.; Kepinska, M.; B Narayanan, V. H.; Parikesit, A. A.; Fernandez, C.; Bjoerklund, G.; Nguyen, H. V.; Farid, A.; Sochor, J.; Pholosi, A.; Baron, M.; Jakubek, M.; Kizek, R., Effect of Biosynthesized Silver Nanoparticles on Bacterial Biofilm Changes in S. aureus and E. coli. Nanomaterials 2022, 12 (13), 2183. DOI: 10.3390/nano12132183

Kunachowicz, D.; Sciskalska, M.; Jakubek, M.; Kizek, R.; Kepinska, M., Structural changes in selected human proteins induced by exposure to quantum dots, their biological relevance and possible biomedical applications. NanoImpact 2022, 26, 100405. DOI: 10.1016/j.impact.2022.100405

Antonyova, V.; Kejik, Z.; Brogyanyi, T.; Kaplanek, R.; Vesela, K.; Abramenko, N.; Ocelka, T.; Masarik, M.; Matkowski, A.; Gburek, J.; Abel, R.; Goede, A.; Preissner, R.; Novotny, P.; Jakubek, M., Non-psychotropic cannabinoids as inhibitors of TET1 protein. Bioorg. Chem. 2022, 124, 105793. DOI: 10.1016/j.bioorg.2022.105793

Zareba, N.; Wieclawik, K.; Kizek, R.; Hosnedlova, B.; Kepinska, M., The Impact of Fullerenes as Doxorubicin Nano-Transporters on Metallothionein and Superoxide Dismutase Status in MCF-10A Cells. Pharmaceutics 2022, 14 (1), 102. DOI: 10.3390/pharmaceutics14010102

Novakova, Z.; Mikesova, J.; Ondrakova, M.; Kutil, Z.; Vesela, K.; Martasek, P.; Barinka, C., Molecular characterization of a novel His333Arg variant of human protoporphyrinogen oxidase IX. Biochem. Biophys. Res. Commun. 2022, 588, 182-186. DOI: 10.1016/j.bbrc.2021.12.062

Antonyova, V.; Tatar, A.; Kaplanek, R.; Kejik, Z.; Miksatkova, L.; Martasek, P.; Dvorankova, B.; Szabo, P.; Jakubek, M. Preparation of pyrrolo[3,2-b]pyrroles with benzohydrazide substitution and their use in the treatment of cancer and neurodegenerative diseases. WO2022063352, 2022.

Brogyanyi, T.; Kaplanek, R.; Talianova, V.; Vokurka, M.; Martasek, P.; Smetana, K.; Lacina, L.; Dvorankova, B.; Szabo, P.; Jakubek, M. Synthesis of Azulene hydrazide-hydrazones treating oncological diseases. WO2022063351, 2022.

Gál P, Brábek J, Holub M, Jakubek M, Šedo A, Lacina L, Strnadová K, Dubový P, Hornychová H, Ryška A, Smetana K Jr. Autoimmunity, cancer and COVID-19 abnormally activate wound healing pathways: critical role of inflammation. Histochem Cell Biol. 2022 Nov;158(5):415-434. doi: 10.1007/s00418-022-02140-x. (IF 2.531)

Talianová V, Kejík Z, Kaplánek R, Veselá K, Abramenko N, Lacina L, Strnadová K, Dvořánková B, Martásek P, Masařík M, Megová MH, Bušek P, Křížová J, Zdražilová L, Hansíková H, Vlčák E, Filimonenko V, Šedo A, Smetana K Jr, Jakubek M. New-Generation Heterocyclic Bis-Pentamethinium Salts as Potential Cytostatic Drugs with Dual IL-6R and Mitochondria-Targeting Activity. Pharmaceutics. 2022 Aug 17;14(8):1712. doi: 10.3390/pharmaceutics14081712.

Fialova JL, Hönigova K, Raudenska M, Miksatkova L, Zobalova R, Navratil J, Šmigová J, Moturu TR, Vicar T, Balvan J, Vesela K, Abramenko N, Kejik Z, Kaplanek R, Gumulec J, Rosel D, Martasek P, Brábek J, Jakubek M, Neuzil J, Masarik M. Pentamethinium salts suppress key metastatic processes by regulating mitochondrial function and inhibiting dihydroorotate dehydrogenase respiration. Biomed Pharmacother. 2022 Aug 30;154:113582. doi: 10.1016/j.biopha.2022.113582.

Hönigova K, Navratil J, Peltanova B, Polanska HH, Raudenska M, Masarik M. Metabolic tricks of cancer cells. Biochim Biophys Acta Rev Cancer. 2022 May;1877(3):188705. doi: 10.1016/j.bbcan.2022.188705.

2021

Kejik, Z.; Kaplanek, R.; Masarik, M.; Babula, P.; Matkowski, A.; Filipensky, P.; Vesela, K.; Gburek, J.; Sykora, D.; Martasek, P.; Jakubek, M., Iron Complexes of Flavonoids-Antioxidant Capacity and Beyond. Int. J. Mol. Sci. 2021, 22 (2), 20. DOI: 10.3390/ijms22020646

Dachev, M.; Bryndova, J.; Jakubek, M.; Moucka, Z.; Urban, M., The Effects of Conjugated Linoleic Acids on Cancer. Processes 2021, 9 (3), 17. DOI: 10.3390/pr9030454

Jakubek, M.; Masarik, M.; Briza, T.; Kaplanek, R.; Vesela, K.; Abramenko, N.; Martasek, P., PPO-Inhibiting Herbicides and Structurally Relevant Schiff Bases: Evaluation of Inhibitory Activities against Human Protoporphyrinogen Oxidase. Processes 2021, 9 (2), 16. DOI: 10.3390/pr9020383

Abramenko, N.; Kejik, Z.; Kaplanek, R.; Tatar, A.; Brogyanyi, T.; Pajkova, M.; Sykora, D.; Vesela, K.; Antonyova, V.; Dytrych, P.; Ikeda-Saito, M.; Martasek, P.; Jakubek, M., Spectroscopic study of in situ-formed metallocomplexes of proton pump inhibitors in water. Chem. Biol. Drug Des. 2021, 97 (2), 305-314. DOI: 10.1111/cbdd.13782

Abramenko, N.; Vellieux, F.; Tesařová, P.; Kejík, Z.; Kaplánek, R.; Lacina, L.; Dvořánková, B.; Rösel, D.; Brábek, J.; Tesař, A.; Jakubek, M.; Smetana, K., Estrogen Receptor Modulators in Viral Infections Such as SARS−CoV−2: Therapeutic Consequences. Int. J. Mol. Sci. 2021, 22 (12), 6551. DOI: 10.3390/ijms22126551

Shishkanova, T. V.; Briza, T.; Rezanka, P.; Kejik, Z.; Jakubek, M., Pentamethinium Salts Nanocomposite for Electrochemical Detection of Heparin. Materials 2021, 14 (18), 5357. DOI: 10.3390/ma14185357

Fialova Leischner, J.; Raudenska, M.; Jakubek, M.; Kejik, Z.; Martasek, P.; Babula, P.; Matkowski, A.; Filipensky, P.; Masarik, M., Novel Mitochondria-targeted Drugs for Cancer Therapy. Mini-Reviews in Medicinal Chemistry 2021, 21 (7), 816-832. DOI: 10.2174/1389557520666201118153242

Jurasek, M.; Valecka, J.; Novotny, I.; Kejik, Z.; Fahnrich, J.; Maresova, A.; Tauchen, J.; Bartunek, P.; Dolensky, B.; Jakubek, M.; Drasar, P. B.; Kralova, J., Synthesis and biological evaluation of cationic TopFluor cholesterol analogues. Bioorg. Chem. 2021, 117, 105410. DOI: 10.1016/j.bioorg.2021.105410

Kejík, Z.; Kaplánek, R.; Dytrych, P.; Masařík, M.; Veselá, K.; Abramenko, N.; Hoskovec, D.; Vašáková, M.; Králová, J.; Martásek, P.; Jakubek, M., Circulating Tumour Cells (CTCs) in NSCLC: From Prognosis to Therapy Design. Pharmaceutics 2021, 13 (11). DOI: 10.3390/pharmaceutics13111879

2020

David Sýkora, Jindřich Jindřich, Vladimír Král, Milan Jakubek, Ameneh Tatar, Zdeněk Kejík, Pavel Martásek, Sergey Zakharov, Formaldehyde Reacts with Amino Acids and Peptides with a Potential Role in Acute Methanol Intoxication, Journal of Analytical Toxicology, (2020), https://doi.org/10.1093/jat/bkaa039

Krejcir, R.;  Briza, T.;  Sterba, M.;  Simoncik, O.;  Muller, P.;  Coates, P. J.;  Martasek, P.;  Vojtesek, B.; Zatloukalova, P., Anticancer pentamethinium salt is a potent photosensitizer inducing mitochondrial disintegration and apoptosis upon red light illumination. J. Photochem. Photobiol., B 2020, 209, 111939. https://doi.org/10.1016/j.jphotobiol.2020.111939

Havlik, M.; Talianova, V.; Briza, T.; Kaplanek, R.; Martasek, P.; Kralova, J.; Kral, V. Preparation of naphthalimidofurans for applications in molecular biology. WO2020114531A1, 2020.

Talianova, V.; Briza, T.; Krcova, L.; Dolensky, B.; Kralova, J.; Martasek, P.; Kral, V.; Havlik, M., Coumarin Troger's base derivatives with cyanine substitution as selective and sensitive fluorescent lysosomal probes. Bioorg. Chem. 2020, 94, 103447. DOI: 10.1016/j.bioorg.2019.103447

Synytsya, A.; Poučková, P.; Zadinová, M.; Troshchynska, Y.; Štětina, J.; Synytsya, A.; Saloň, I.; Král, V., Hydrogels based on low-methoxyl amidated citrus pectin and flaxseed gum formulated with tripeptide glycyl-l-histidyl-l-lysine improve the healing of experimental cutting wounds in rats. Int. J. Biol. Macromol. 2020, 165, 3156-3168. DOI: 10.1016/j.ijbiomac.2020.09.251

Krcova, L.; Rimpelova, S.; Havlik, M.; Dolensky, B.; Vellieux, F.; Ruml, T.; Martasek, P.; Kral, V.; Briza, T., Highly selective mitochondrial probes based on fluorinated pentamethinium salts: On two-photon properties and microscopic applications. Dyes and Pigments 2020, 172, 107802. DOI: 10.1016/j.dyepig.2019.107802

Brabek, J.; Jakubek, M.; Vellieux, F.; Novotny, J.; Kolar, M.; Lacina, L.; Szabo, P.; Strnadova, K.; Rosel, D.; Dvainkova, B.; Smetana, K., Interleukin-6: Molecule in the Intersection of Cancer, Ageing and COVID-19. Int. J. Mol. Sci. 2020, 21 (21). DOI: 10.3390/ijms21217937

Antonyova, V.; Kejik, Z.; Brogyanyi, T.; Kaplanek, R.; Pajkova, M.; Talianova, V.; Hromadka, R.; Masarik, M.; Sykora, D.; Miksatkova, L.; Martasek, P.; Jakubek, M., Role of mtDNA disturbances in the pathogenesis of Alzheimer's and Parkinson's disease. DNA Repair 2020, 91-92, 102871. DOI: 10.1016/j.dnarep.2020.102871

Abramenko, N.; Kejik, Z.; Kaplanek, R.; Tatar, A.; Brogyanyi, T.; Pajkova, M.; Sykora, D.; Vesela, K.; Antonyova, V.; Dytrych, P.; Ikeda-Saito, M.; Martasek, P.; Jakubek, M., Spectroscopic study of in situ-formed metallocomplexes of proton pump inhibitors in water. Chem. Biol. Drug Des. 2020, 97 (2), 305-314. DOI: 10.1111/cbdd.13782

2019

Jakubek, M., Kejik, Z., Kaplanek, R., Antonyova, V., Hromadka, R., Sandrikova, V., Sykora, D., Martasek, P., & Kral, V. (2019). Hydrazones as novel epigenetic modulators: Correlation between TET 1 protein inhibition activity and their iron(II) binding ability. Bioorg Chem, 88, 102809. doi:10.1016/j.bioorg.2019.02.034

Briza, T., Kralova, J., Rimpelova, S., Havlik, M., Kaplanek, R., Kejik, Z., Martasek, P., Mikula, I., Dzubak, P., Hajduch, M., Ruml, T., & Kral, V. (2019). Pentamethinium salts as ligands for cancer: Sulfated polysaccharide co-receptors as possible therapeutic target. Bioorg Chem, 82, 74-85. doi:10.1016/j.bioorg.2018.02.011

Havlik, M., Talianova, V., Kaplanek, R., Briza, T., Dolensky, B., Kralova, J., Martasek, P., & Kral, V. (2019). Versatile fluorophores for bioimaging applications: pi-expanded naphthalimide derivatives with skeletal and appendage diversity. Chem Commun (Camb), 55(18), 2696-2699. doi:10.1039/c8cc09638d

Krčová, L., Krejcir, R., Zatloukalova, P., Briza, T., Coates, P.J., Sterba, M., Müller, P., Kralová, J., Martasek, P., Kral, V., Vojtesek, B. (2019) A cyclic methinium salt induces cancer cell cytotoxicity through mitophagy inhibition and energetic collapse. International Journal of Molecular Sciences, 20, 4208. doi: 10.3390/ijms20174208

Róbert Hromádka, Zdeněk Kejík, Milan Jakubek, Robert Kaplánek, Viera Šandriková, Marian Urban, Pavel Martásek, Vladimír Král: Pigments from Filamentous Ascomycetes for Combination Therapy. Curr. Med. Chem. 26 (2019) 3812-3834. doi: 10.2174/0929867325666180330091933

Milan Jakubek, Zdeněk Kejíka, Robert Kaplánek, Róbert Hromádka, Viera Šandriková, David Sýkora, Veronika Antonyová, Marian Urban, Petr Dytrych, Ivan Mikula, Pavel Martásek, Vladimír Král: Strategy for improved therapeutic efficiency of curcumin in the treatment of gastric cancer. Biomed. Pharmacother. 118 (2019) 109278. doi: 10.1016/j.biopha.2019.109278

2018

Kejik, Z., Jakubek, M., Kaplanek, R., Kralova, J., Mikula, I., Martasek, P., & Kral, V. (2018). Epigenetic bagents in combined anticancer therapy. Future Med Chem, 10(9), 1113-1130. doi:10.4155/fmc-2017-0203

2017

Kejik, Z., Kaplanek, R., Havlik, M., Briza, T., Jakubek, M., Kralova, J., Mikula, I., Martasek, P., & Kral, V. (2017). Optical probes and sensors as perspective tools in epigenetics. Bioorg Med Chem, 25(8), 2295-2306. doi:10.1016/j.bmc.2017.01.011

2016

Brezaniova, I., Hruby, M., Kralova, J., Kral, V., Cernochova, Z., Cernoch, P., Slouf, M., Kredatusova, J., & Stepanek, P. (2016). Temoporfin-loaded 1-tetradecanol-based thermoresponsive solid lipid nanoparticles for photodynamic therapy. J Control Release, 241, 34-44. doi:10.1016/j.jconrel.2016.09.009

2015

Briza, T., Kralova, J., Dolensky, B., Rimpelova, S., Kejik, Z., Ruml, T., Hajduch, M., Dzubak, P., Mikula, I., Martasek, P., Pouckova, P., & Kral, V. (2015). Striking antitumor activity of a methinium system with incorporated quinoxaline unit obtained by spontaneous cyclization. Chembiochem, 16(4), 555-558. doi:10.1002/cbic.201402662

Kaplanek, R., Jakubek, M., Rak, J., Kejik, Z., Havlik, M., Dolensky, B., Frydrych, I., Hajduch, M., Kolar, M., Bogdanova, K., Kralova, J., Dzubak, P., & Kral, V. (2015). Caffeine-hydrazones as anticancer agents with pronounced selectivity toward T-lymphoblastic leukaemia cells. Bioorg Chem, 60, 19-29. doi:10.1016/j.bioorg.2015.03.003

Kaplanek, R., Havlik, M., Dolensky, B., Rak, J., Dzubak, P., Konecny, P., Hajduch, M., Kralova, J., & Kral, V. (2015). Synthesis and biological activity evaluation of hydrazone derivatives based on a Troger's base skeleton. Bioorg Med Chem, 23(7), 1651-1659. doi:10.1016/j.bmc.2015.01.029

Team

Ing. et. Ing. Božena Hosnedlová, Ph.D. Ing. et. Ing. Božena Hosnedlová, Ph.D.

Ing. et. Ing.
Božena Hosnedlová, Ph.D.

Research Fellow

bozena.hosnedlova@lf1.cuni.cz
+420325873025
Ing. Miroslav Louma Ing. Miroslav Louma

Ing.
Miroslav Louma

Technical and economic support

miroslav.louma@lf1.cuni.cz
+420325873025
Bc. Vojtěch Albert Borek Bc. Vojtěch Albert Borek

Bc.
Vojtěch Albert Borek

Technical and economic support

vojtech.borek@lf1.cuni.cz
+420325873025
Fréderic Vellieux Fréderic Vellieux

Fréderic Vellieux

Managing Scientist of the Centre of Molecular Structure

frederic.vellieux@lf1.cuni.cz
+420325873012

Teaching

Offered topics

thesis author thesis name thesis type