Laboratory of Medicinal Chemistry

Laboratory of Medicinal Chemistry

Ing. Milan Jakubek, Ph.D.

Ing. Milan Jakubek, Ph.D. — 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

Events

Publications

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.

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. 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
+420325873028
Prof. Ing. René Kizek, Dr.Sc. Prof. Ing. René Kizek, Dr.Sc.

Prof. Ing.
René Kizek, Dr.Sc.

Research Fellow

rene.kizek@lf1.cuni.cz
+420325873025
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

Teaching

Offered topics

thesis author thesis name thesis type