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Technická 5
166 28 Prague 6 – Dejvice
IČO: 60461373 / VAT: CZ60461373
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Copyright: UCT Prague 2015
Information provided by the Department of Organic Chemistry. Technical support by the Computing Centre.
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All publications of our authors (since 2015): here
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| k Phonebook of the Department | |||
Professors: |
|||
|
Prof. Radek Cibulka e +420 22044 4182 d A 278c |
Head of Department | www | ResearcherID |
|
Prof. Pavel Lhoták e +420 22044 5055 d A 249 |
www | ||
|
Prof. Jaroslav Kvíčala e +420 22044 4240 d A 278d |
www | ||
|
Prof. Jiří Svoboda e +420 22044 3688 d A 278e |
www | ||
Associate Professors: |
|||
|
Assoc. Prof. Jan Budka e +420 22044 4284 d A 251 |
DOC web editor | www | |
|
Assoc. Prof. Jana Hodačová e +420 22044 4173 d A 270 |
www | ||
|
Assoc. Prof. Michal Kohout e +420 22044 5012 d A 258 |
www | ||
|
Assoc. Prof. Igor Linhart e +420 22044 4165 d A 266 |
www | ||
|
Assoc. Prof. Tomáš Tobrman e +420 22044 4245 d A 271 |
RIT | www | |
Assistant Professors: |
|||
|
Dr. Michal Himl e +420 22044 4165 d A 266 |
www | ||
|
Dr. Roman Holakovský e +420 22044 4279 d A 255 |
www | ||
|
Dr. Petr Kovaříček e +420 22044 2040 d B3 207 |
www | ||
|
Dr. Václav Kozmík e +420 22044 4118 d A 308 |
www | ||
|
Dr. Martin Krupička e +420 220 444 173 |
www | ||
|
Dr. Ondřej Kundrát e +420 22044 4280 d A 253 |
www | ResearcherID | |
|
Dr. Petra Ménová e +420 22044 3686 d A 268 |
www | ||
|
Dr. Pavla Perlíková e +420 22044 2039 d B3 206 |
www | ||
|
Dr. Markéta Rybáčková e +420 22044 4242 d A 259 |
Secretary of Department |
www | |
|
Dr. Eva Svobodová e +420 22044 4249 d A 260 |
www | ||
Technicians: |
|||
|
Květa Bártová e +420 22044 3686 d A 268 |
|||
|
Ivana Bocková, MSc. e +420 22044 4280 d A 250 |
|||
| Michaela Kadlecová
e +420 22044 4276 d A 262 b Michaela.Kadlecova@vscht.cz |
|||
|
Martina Kovandová e +420 22044 4279 d A 255 |
|||
|
Vladimír Kuneš e +420 22044 4277 d A L06 |
|||
|
Jana Netušilová e +420 22044 4164 d A 278a |
Administrative Support of Department | ||
|
Markéta Slabochová, MSc. e +420 22044 4059 d A 308 |
Economist of Department | ||
|
Helena Štenglová e +420 22044 4278 d A 257 |
|||
|
Ing. David Tetour e +420 22044 4173 d A270 |
|||
|
Marta Tokárová e +420 220 444 245 d A 271 |
|||
Essential Information for Current Students
Bachelor Students
Master Students
PhD Students
Lectures delivered by members of the Department
- Toxicology and ecology
- Organic chemistry I, II and III
- Structural analysis
- Reactivity of organic compounds
- Molecular design
- Organic synthesis I and II
- Quantum organic chemistry
- Farmacochemistry
- Organic stereochemistry
- Organometallic chemistry
- Organic chemistry of selected elements
DATA
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[obsah] => Medicinal Chemistry and Glycochemistry
We work on the borders of organic, bioorganic and medicinal chemistry. Our main interest is the synthesis of ligands for lectin receptors and their use in diagnostics and drug targeting. In addition, we synthesize ligands for the visualization of G-quadruplexes and we have just started a new project on the synthesis of agonists of muscarine receptors.
In our lab, we do mostly organic synthesis, purification of the compounds and their characterization. The preparation of nanoparticles as well as all biological testing are done by our collaborators.
In September 2021, we became an official Max Planck Partner Group. This prestigious partnership enables us to run several projects in the field of glycochemistry.
More details about the projects can be found in the Research section.
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| Group leader: | Dr. Petra Ménová |
| Technician: | Květa Bártová |
| PhD students: |
Fabricio Ramírez Cortés |
| Undergraduate students: |
Jiří Ledvinka Kateřina Jochová Vojtěch Kramný Ondřej Daněk Jan Wohlgemuth Jakub Schimmer Martin Brokeš Michal Čotek |
| Alumni: |
Morgane Moinard (FR) Vojtěch Musil Dmytro Makarov (UA) Romane Vizier (FR) Pauline Mornat (FR) |
Projects
- Synthesis of inhibitors of DC-SIGN receptor
- Preparation of nanoparticles with DC-SIGN-targeting ligands
- Synthesis of ligands for ASGPR receptor and their use in the treatment of hepatitis B
- Synthesis of ligands for G-quadruplex visualization
- Synthesis of agonists of muscarine receptor
Synthesis of inhibitors of DC-SIGN receptor
DC-SIGN is a C-type lectin receptor present on the surface of dendritic cells and macrophages. It binds to carbohydrate structures found on the surface of numerous pathogens: viruses (HIV, ebola, cytomegalovirus), bacteria (M. tuberculosis, S. pneumoniae), fungi (C. albicans), and parasites (Leishmana). The surface of these pathogens is typically rich in mannose and fucose which are natural DC-SIGN ligands. Upon binding, DC-SIGN can mediate the uptake of the pathogen into the dendritic cell and launch an immune response. Hence, DC-SIGN inhibitors could act as anti-infective agents.
The primary carbohydrate binding site of DC-SIGN is rather shallow and hydrophobic and as such is not a good target for medicinal chemistry. Recent studies have shown that apart from the primary carbohydrate binding site, DC-SIGN harbours five secondary binding sites available to accommodate small drug-like molecules (Figure 1).
Figure 1. DC-SIGN receptor, primary carbohydrate binding site (yellow) and secondary binding sites I–V. Picture taken from Aretz, J. et al.: Angew. Chem. Int. Ed. 2017, 56, 7292–7296.
In this project, we synthesize substituted mannosides and fucosides which can interact with both, the primary and secondary binding site (Figure 2a). In parallel, we synthesize non-carbohydrate ligands which interact with the secondary binding sites and upon binding modulate the interaction of carbohydrates with the primary carbohydrate binding site (Figure 2b). To synthesize these compounds, we use an approach called fragment-based drug discovery.
Figure 2. Overview of the synthesized DC-SIGN ligands. a) DC-SIGN inhibitors based on D-mannose and l-fucose; b) non-carbohydrate inhibitors binding to the secondary binding sites.
Preparation of nanoparticles with DC-SIGN-targeting ligands
We use the synthesized DC-SIGN ligands to modify the surface of nanoparticles, in particular fluorescent nanodiamonds and liposomes (Figure 3). Fluorescent nanodiamonds can be used for the visualization of metastases in sentinel lymphatic nodes. Tumour-associated macrophages (TAMs) gather in the vicinity of metatases. Upon binding of the fluorescent nanodiamonds modified with DC-SIGN ligand to TAMs, the nanoparticles are internalized and their fluorescence properties enable the visualisation of the macrophages and thus indirectly of the metastases.
Liposomes modified with DC-SIGN ligands can be used for targeted delivery of therapeutic compounds to dendritic cells.
Figure 3. Nanoparticles modified with DC-SIGN ligands. a) Fluorescent nanodiamonds for the visualization of metastases; b) liposomes for targeted delivery of therapeutic compounds into dendritic cells.
Synthesis of ligands for ASGPR receptor and their use in the treatment of hepatitis B
ASGPR is a C-type lectin receptor which specifically recognizes ligands with terminal galactose or N-acetylgalactosamine. It is found almost exclusively on hepatocytes and is already clinically used for ASGPR-targeted drug delivery to the liver. Our aim is to prepare lipid nanoparticles modified with selective ASGPR ligands (Figure 4) and use these nanoparticles to transport CRISPR/Cas9 system into the liver. Several studies have already confirmed the application of CRISPR/Cas9 as a feasible approach to eradicate the hepatitis B virus DNA and thus help treat hepatitis B.
Figure 4. Lipid nanoparticles modified with ASGPR ligands.
Synthesis of ligands for G-quadruplex visualization
In collaboration with ICMUB CNRS Dijon, France, we synthesize ligands for the visualization of G-quadruplexes. Our aim is to prepare twice-as-smart fluorescent probes that act both as a smart quadruplex ligand (i.e., that assembles only in the presence of its native G-quadruplex target) and a smart fluorescent probe (i.e., the fluorescence of which is turned on only upon interaction with its target). A similar compound, N-TASQ, allowed for the very first visualization of G-quadruplexes in living human cells and since then has been used in oncology and neurology.
Figure 5. Twice-as-smart probes for the visualization of G-quadruplex. Picture taken from Laguerre, A. et al.: J. Am. Chem. Soc. 2015, 137, 8521–8525.
Synthesis of agonists of muscarine receptor
In collaboration with the group of neurochemistry from the Institute of Physiology CAS, we have just started working on the synthesis of agonists of muscarine receptors based on tetrahydropyridine. These compounds are promising agents for the treatment of neuropathies.
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- Medicinal chemistry (ENG)
- Organic chemistry: laboratory I (ENG)
- Základy farmakochemie (Fundamentals of chemistry of pharmaceuticals, CZ)
- Organická chemie A, B – seminář (Organic chemistry A, B – seminar, CZ)
- Laboratoř organické chemie I, II (Laboratory of organic chemistry I, II, CZ)
Papers
- Ménová: ASGPR a DC-SIGN: C-lektinové receptory se slibným potenciálem v medicinální chemii. Chem. Listy 2021, 115, 126–133.
Bachelor theses
Jochová Kateřina: Modified nanoparticles for DC-SIGN targeting (2021)
Ledvinka Jiří: Synthesis of mannose-based DC-SIGN antagonists (2020)
Musil Vojtěch: Synthesis of quinoxalinone-based inhibitors of DC-SIGN receptor (2020)
Wohlrábová Lucie: Chelating lipids for optical quantum nanosensors (2019)
Makarov Dmytro: Syntéza substituovaných chinolonů jako potenciálních inhibitorů DC-SIGN receptoru (2018)
Master theses
Makarov Dmytro: Synthesis of quinolone-based inhibitors of DC-SIGN receptor (2020)
Mornat Pauline: Synthesis of mannose-based DC-SIGN inhibitors bearing fluorinated arene moiety (2019)
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