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Article ; Online: STING Agonist-Mediated Cytokine Secretion Is Accompanied by Monocyte Apoptosis.

Pimkova Polidarova, Marketa / Brehova, Petra / Dejmek, Milan / Birkus, Gabriel / Brazdova, Andrea

ACS infectious diseases

2022 Volume 8, Issue 3, Page(s) 463–471

Abstract: The cGAS-STING (cyclic GMP-AMP synthase-stimulator of interferon genes) pathway plays a crucial role in inducing an antiviral and antitumor immune response. We studied the effects of synthetic STING agonists on several immune populations and related ... ...

Abstract	The cGAS-STING (cyclic GMP-AMP synthase-stimulator of interferon genes) pathway plays a crucial role in inducing an antiviral and antitumor immune response. We studied the effects of synthetic STING agonists on several immune populations and related cytokine production. In comparison with the toll-like receptor 7 (TLR7) agonist, STING agonists induced secretion of a broader proinflammatory cytokine spectrum. Unlike the TLR7 agonist, the structurally diverse STING agonists partially depleted B and NK cells and completely depleted CD14+ monocytes via induction of apoptosis. The TANK-binding kinase 1 inhibitor efficiently prevented interferon alpha (IFNα) secretion and cell depletion, suggesting their possible dependence on the cGAS-STING pathway activation. Finally, IFNα, tumor necrosis factor alpha, interleukin 6, and interleukin 1 beta secretion and CD14+ monocyte apoptosis were primary responses to STING agonists, whereas IFNγ was secreted secondarily. These findings bring new insights into the cGAS-STING pathway immunomodulation that is of future therapeutic importance.
MeSH term(s)	Apoptosis ; Cytokines/metabolism ; Membrane Proteins/genetics ; Monocytes/metabolism ; Signal Transduction
Chemical Substances	Cytokines ; Membrane Proteins
Language	English
Publishing date	2022-02-08
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	2373-8227
ISSN (online)	2373-8227
DOI	10.1021/acsinfecdis.1c00554
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Article ; Online: Acidity constants and protonation sites of cyclic dinucleotides determined by capillary electrophoresis, quantum chemical calculations, and NMR spectroscopy.

Štěpánová, Sille / Andris, Erik / Gutten, Ondrej / Buděšínský, Miloš / Dejmek, Milan / Břehová, Petra / Rulíšek, Lubomír / Kašička, Václav

Electrophoresis

2023 Volume 45, Issue 7-8, Page(s) 687–705

Abstract: Cyclic dinucleotides (CDNs) are important second messengers in bacteria and eukaryotes. Detailed characterization of their physicochemical properties is a prerequisite for understanding their biological functions. Herein, we examine acid-base and ... ...

Abstract	Cyclic dinucleotides (CDNs) are important second messengers in bacteria and eukaryotes. Detailed characterization of their physicochemical properties is a prerequisite for understanding their biological functions. Herein, we examine acid-base and electromigration properties of selected CDNs employing capillary electrophoresis (CE), density functional theory (DFT), and nuclear magnetic resonance (NMR) spectroscopy to provide benchmark pK
MeSH term(s)	Electrophoresis, Capillary/methods ; Hydrogen-Ion Concentration ; Protons ; Magnetic Resonance Spectroscopy/methods ; Dinucleoside Phosphates/chemistry ; Thermodynamics ; Density Functional Theory
Chemical Substances	Protons ; Dinucleoside Phosphates
Language	English
Publishing date	2023-12-07
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	619001-7
ISSN	1522-2683 ; 0173-0835
ISSN (online)	1522-2683
ISSN	0173-0835
DOI	10.1002/elps.202300232
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Zs.A 1868: Show issues

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Article ; Online: Fluorinated cGAMP analogs, which act as STING agonists and are not cleavable by poxins: Structural basis of their function.

Klima, Martin / Dejmek, Milan / Duchoslav, Vojtech / Eisenreichova, Andrea / Sala, Michal / Chalupsky, Karel / Chalupska, Dominika / Novotná, Barbora / Birkuš, Gabriel / Nencka, Radim / Boura, Evzen

Structure (London, England : 1993)

2024 Volume 32, Issue 4, Page(s) 433–439.e4

Abstract: The cGAS-STING pathway is a crucial part of innate immunity; it serves to detect DNA in the cytoplasm and to defend against certain cancers, viruses, and bacteria. We designed and synthesized fluorinated carbocyclic cGAMP analogs, MD1203 and MD1202D (MDs) ...

Abstract	The cGAS-STING pathway is a crucial part of innate immunity; it serves to detect DNA in the cytoplasm and to defend against certain cancers, viruses, and bacteria. We designed and synthesized fluorinated carbocyclic cGAMP analogs, MD1203 and MD1202D (MDs), to enhance their stability and their affinity for STING. These compounds demonstrated exceptional activity against STING. Despite their distinct chemical modifications relative to the canonical cyclic dinucleotides (CDNs), crystallographic analysis revealed a binding mode with STING that was consistent with the canonical CDNs. Importantly, MDs were resistant to cleavage by viral poxin nucleases and MDs-bound poxin adopted an unliganded-like conformation. Moreover, MDs complexed with poxin showed a conformation distinct from cGAMP bound to poxin, closely resembling their conformation when bound to STING. In conclusion, the development of MD1203 and MD1202D showcases their potential as potent STING activators with remarkable stability against poxin-mediated degradation-a crucial characteristic for future development of antivirals.
MeSH term(s)	Humans ; Nucleotides, Cyclic/chemistry ; Nucleotides, Cyclic/metabolism ; Neoplasms ; Nucleotidyltransferases/chemistry ; Immunity, Innate
Chemical Substances	cyclic guanosine monophosphate-adenosine monophosphate ; Nucleotides, Cyclic ; Nucleotidyltransferases (EC 2.7.7.-)
Language	English
Publishing date	2024-02-06
Publishing country	United States
Document type	Journal Article
ZDB-ID	1213087-4
ISSN	1878-4186 ; 0969-2126
ISSN (online)	1878-4186
ISSN	0969-2126
DOI	10.1016/j.str.2024.01.008
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Zs.A 4141: Show issues

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Article: Mercury(II) Acetate

Dejmek, Milan

Synlett

2012 Volume 23, Issue 19, Page(s) 2867–2868

Language	English
Publishing date	2012-11-07
Publisher	© Georg Thieme Verlag
Publishing place	Stuttgart ; New York
Document type	Article
ZDB-ID	2042012-2
ISSN	1437-2096 ; 0936-5214
ISSN (online)	1437-2096
ISSN	0936-5214
DOI	10.1055/s-0032-1317476
Database	Thieme publisher's database

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Article ; Online: Synthetic Stimulator of Interferon Genes (STING) Agonists Induce a Cytokine-Mediated Anti-Hepatitis B Virus Response in Nonparenchymal Liver Cells.

Pimkova Polidarova, Marketa / Vanekova, Lenka / Brehova, Petra / Dejmek, Milan / Vavrina, Zdenek / Birkus, Gabriel / Brazdova, Andrea

ACS infectious diseases

2022 Volume 9, Issue 1, Page(s) 23–32

Abstract: Chronic hepatitis B (CHB) remains a major public health problem worldwide, with limited treatment options, but inducing an antiviral response by innate immunity activation may provide a therapeutic alternative. We assessed the cytokine-mediated anti- ... ...

Abstract	Chronic hepatitis B (CHB) remains a major public health problem worldwide, with limited treatment options, but inducing an antiviral response by innate immunity activation may provide a therapeutic alternative. We assessed the cytokine-mediated anti-hepatitis B virus (HBV) potential for stimulating the cyclic GMP-AMP synthase-stimulator of interferon genes (STING) pathway using STING agonists in primary human hepatocytes (PHH) and nonparenchymal liver cells (NPCs). The natural STING agonist, 2',3'-cyclic GMP-AMP, the synthetic analogue 3',3'-c-di(2'F,2'dAMP), and its bis(pivaloyloxymethyl) prodrug had strong indirect cytokine-mediated anti-HBV effects in PHH regardless of HBV genotype. Furthermore, STING agonists induced anti-HBV cytokine secretion
MeSH term(s)	Humans ; Animals ; Mice ; Cytokines/metabolism ; Herpesvirus 1, Cercopithecine ; Hepatocytes ; Hepatitis B/drug therapy ; Interferons/metabolism
Chemical Substances	Cytokines ; Interferons (9008-11-1)
Language	English
Publishing date	2022-12-06
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	2373-8227
ISSN (online)	2373-8227
DOI	10.1021/acsinfecdis.2c00424
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Article ; Online: Structure-based design and modular synthesis of novel PI4K class II inhibitors bearing a 4-aminoquinazoline scaffold.

Misehe, Mbilo / Klima, Martin / Matoušová, Marika / Chalupská, Dominika / Dejmek, Milan / Šála, Michal / Mertlíková-Kaiserová, Helena / Boura, Evzen / Nencka, Radim

Bioorganic & medicinal chemistry letters

2022 Volume 76, Page(s) 129010

Abstract: Novel 4-aminoquinazoline-6-carboxamide derivatives bearing differently substituted aryl or heteroaryl groups at position 7 in the core were rationally designed, synthesized and evaluated for biological activity in vitro as phosphatidylinositol 4-kinase ... ...

Abstract	Novel 4-aminoquinazoline-6-carboxamide derivatives bearing differently substituted aryl or heteroaryl groups at position 7 in the core were rationally designed, synthesized and evaluated for biological activity in vitro as phosphatidylinositol 4-kinase IIα (PI4K2A) inhibitors. The straightforward approach described here enabled the sequential, modular synthesis and broad functionalization of the scaffold in a mere six steps. The SAR investigation reported here is based on detailed structural analysis of the conserved binding mode of ATP and other adenine derivatives to the catalytic site of type II PI4Ks, combined with extensive docking studies. Several compounds exhibited significant activity against PI4K2A. Moreover, we solved a crystal structure of PI4K2B in complex with one of our lead ligand candidates, which validated the ligand binding site and pose predicted by our docking-based ligand model. These discoveries suggest that our structure-based approach may be further developed and employed to synthesize new inhibitors with optimized potency and selectivity for this class of PI4Ks.
MeSH term(s)	1-Phosphatidylinositol 4-Kinase/chemistry ; 1-Phosphatidylinositol 4-Kinase/metabolism ; Ligands ; Adenosine Triphosphate/metabolism ; Adenine ; Structure-Activity Relationship ; Drug Design ; Molecular Docking Simulation
Chemical Substances	4-aminoquinazoline ; 1-Phosphatidylinositol 4-Kinase (EC 2.7.1.67) ; Ligands ; Adenosine Triphosphate (8L70Q75FXE) ; Adenine (JAC85A2161)
Language	English
Publishing date	2022-09-29
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2022.129010
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Zs.A 3203: Show issues

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Article ; Online: Remdesivir triphosphate can efficiently inhibit the RNA-dependent RNA polymerase from various flaviviruses.

Konkolova, Eva / Dejmek, Milan / Hřebabecký, Hubert / Šála, Michal / Böserle, Jiří / Nencka, Radim / Boura, Evzen

Antiviral research

2020 Volume 182, Page(s) 104899

Abstract: Remdesivir was shown to inhibit RNA-dependent RNA-polymerases (RdRp) from distinct viral families such as from Filoviridae (Ebola) and Coronaviridae (SARS-CoV, SARS-CoV-2, MERS). In this study, we tested the ability of remdesivir to inhibit RdRps from ... ...

Abstract	Remdesivir was shown to inhibit RNA-dependent RNA-polymerases (RdRp) from distinct viral families such as from Filoviridae (Ebola) and Coronaviridae (SARS-CoV, SARS-CoV-2, MERS). In this study, we tested the ability of remdesivir to inhibit RdRps from the Flaviviridae family. Instead of remdesivir, we used the active species that is produced in cells from remdesivir, the appropriate triphosphate, which could be directly tested in vitro using recombinant flaviviral polymerases. Our results show that remdesivir can efficiently inhibit RdRps from viruses causing severe illnesses such as Yellow fever, West Nile fever, Japanese and Tick-borne encephalitis, Zika and Dengue. Taken together, this study demonstrates that remdesivir or its derivatives have the potential to become a broad-spectrum antiviral agent effective against many RNA viruses.
MeSH term(s)	Adenosine Triphosphate/analogs & derivatives ; Adenosine Triphosphate/chemistry ; Adenosine Triphosphate/pharmacology ; Antiviral Agents/chemistry ; Antiviral Agents/pharmacology ; Betacoronavirus/drug effects ; Betacoronavirus/enzymology ; COVID-19 ; Coronavirus Infections/drug therapy ; Coronavirus Infections/virology ; Flavivirus/drug effects ; Flavivirus/enzymology ; Humans ; Inhibitory Concentration 50 ; Pandemics ; Pneumonia, Viral/drug therapy ; Pneumonia, Viral/virology ; RNA Viruses/drug effects ; RNA Viruses/enzymology ; RNA-Dependent RNA Polymerase/antagonists & inhibitors ; RNA-Dependent RNA Polymerase/metabolism ; SARS-CoV-2
Chemical Substances	Antiviral Agents ; Adenosine Triphosphate (8L70Q75FXE) ; GS-441524 triphosphate (AEL0YED4SU) ; RNA-Dependent RNA Polymerase (EC 2.7.7.48)
Keywords	covid19
Language	English
Publishing date	2020-08-05
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	306628-9
ISSN	1872-9096 ; 0166-3542
ISSN (online)	1872-9096
ISSN	0166-3542
DOI	10.1016/j.antiviral.2020.104899
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Zs.A 1627: Show issues

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Article ; Online: Vinylphosphonate-based cyclic dinucleotides enhance STING-mediated cancer immunotherapy.

Dejmek, Milan / Brazdova, Andrea / Otava, Tomáš / Polidarova, Marketa Pimkova / Klíma, Martin / Smola, Miroslav / Vavrina, Zdenek / Buděšínský, Miloš / Dračínský, Martin / Liboska, Radek / Boura, Evzen / Birkuš, Gabriel / Nencka, Radim

European journal of medicinal chemistry

2023 Volume 259, Page(s) 115685

Abstract: Cyclic dinucleotides (CDNs) trigger the cyclic GMP-AMP synthase-stimulator of interferon genes (cGAS-STING) pathway, which plays a key role in cytosolic DNA sensing and thus in immunomodulation against infections, cell damage and cancer. However, cancer ... ...

Abstract	Cyclic dinucleotides (CDNs) trigger the cyclic GMP-AMP synthase-stimulator of interferon genes (cGAS-STING) pathway, which plays a key role in cytosolic DNA sensing and thus in immunomodulation against infections, cell damage and cancer. However, cancer immunotherapy trials with CDNs have shown immune activation, but not complete tumor regression. Nevertheless, we designed a novel class of CDNs containing vinylphosphonate based on a STING-affinity screening assay. In vitro, acyloxymethyl phosphate/phosphonate prodrugs of these vinylphosphonate CDNs were up to 1000-fold more potent than the clinical candidate ADU-S100. In vivo, the lead prodrug induced tumor-specific T cell priming and facilitated tumor regression in the 4T1 syngeneic mouse model of breast cancer. Moreover, we solved the crystal structure of this ligand bound to the STING protein. Therefore, our findings not only validate the therapeutic potential of vinylphosphonate CDNs but also open up opportunities for drug development in cancer immunotherapy bridging innate and adaptive immunity.
MeSH term(s)	Animals ; Mice ; Nucleotides, Cyclic/pharmacology ; Nucleotides, Cyclic/metabolism ; DNA ; Neoplasms/drug therapy ; Immunotherapy ; Immunity, Innate
Chemical Substances	Nucleotides, Cyclic ; ADU-S100 (FMW9ZVF53N) ; DNA (9007-49-2)
Language	English
Publishing date	2023-07-26
Publishing country	France
Document type	Journal Article
ZDB-ID	188597-2
ISSN	1768-3254 ; 0009-4374 ; 0223-5234
ISSN (online)	1768-3254
ISSN	0009-4374 ; 0223-5234
DOI	10.1016/j.ejmech.2023.115685
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Article ; Online: Exploring positions 6 and 7 of a quinazoline-based scaffold leads to changes in selectivity and potency towards RIPK2/3 kinases.

Misehe, Mbilo / Matoušová, Marika / Dvořáková, Alexandra / Hercík, Kamil / Škach, Kryštof / Chalupská, Dominika / Dejmek, Milan / Šála, Michal / Hájek, Miroslav / Boura, Evzen / Mertlíková-Kaiserová, Helena / Nencka, Radim

European journal of medicinal chemistry

2023 Volume 260, Page(s) 115717

Abstract: Receptor-interacting protein kinases 2 and 3 (RIPK2 and RIPK3) are considered attractive therapeutic enzyme targets for the treatment of a multitude of inflammatory diseases and cancers. In this study, we developed three interrelated series of novel ... ...

Abstract	Receptor-interacting protein kinases 2 and 3 (RIPK2 and RIPK3) are considered attractive therapeutic enzyme targets for the treatment of a multitude of inflammatory diseases and cancers. In this study, we developed three interrelated series of novel quinazoline-based derivatives to investigate the effects of extensive modifications of positions 6 and 7 of the central core on the inhibitory activity and the selectivity against these RIPKs. The design of the derivatives was inspired by analyses of available literary knowledge on both RIPK2 and RIPK3 in complex with known quinazoline or quinoline inhibitors. Enzymatic investigations for bioactivity of the prepared molecules against purified RIPKs (RIPK1-4) shed light on multiple potent and selective RIPK2 and dual RIPK2/3 inhibitors. Furthermore, evaluations in living cells against the RIPK2-NOD1/2-mediated signaling pathways, identified as the potential primary targets, demonstrated nanomolar inhibition for a majority of the compounds. In addition, we have demonstrated overall good stability of various lead inhibitors in both human and mouse microsomes and plasma. Several of these compounds also were evaluated for selectivity across 58 human kinases other than RIPKs, exhibiting outstanding specificity profiles. We have thus clearly demonstrated that tuning appropriate substitutions at positions 6 and 7 of the developed quinazoline derivatives may lead to interesting potency and specificities against RIPK2 and RIPK3. This knowledge might therefore be employed for the targeted preparation of new, highly potent and selective tools against these RIPKs, which could be of utility in biological and clinical research.
MeSH term(s)	Humans ; Animals ; Mice ; Microsomes ; Quinazolines/pharmacology ; Receptor-Interacting Protein Serine-Threonine Kinase 2
Chemical Substances	Quinazolines ; RIPK2 protein, human (EC 2.7.11.1) ; Receptor-Interacting Protein Serine-Threonine Kinase 2 (EC 2.7.11.1)
Language	English
Publishing date	2023-08-09
Publishing country	France
Document type	Journal Article
ZDB-ID	188597-2
ISSN	1768-3254 ; 0009-4374 ; 0223-5234
ISSN (online)	1768-3254
ISSN	0009-4374 ; 0223-5234
DOI	10.1016/j.ejmech.2023.115717
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Article ; Online: Non-Nucleotide RNA-Dependent RNA Polymerase Inhibitor That Blocks SARS-CoV-2 Replication.

Dejmek, Milan / Konkoľová, Eva / Eyer, Luděk / Straková, Petra / Svoboda, Pavel / Šála, Michal / Krejčová, Kateřina / Růžek, Daniel / Boura, Evzen / Nencka, Radim

Viruses

2021 Volume 13, Issue 8

Abstract: SARS-CoV-2 has caused an extensive pandemic of COVID-19 all around the world. Key viral enzymes are suitable molecular targets for the development of new antivirals against SARS-CoV-2 which could represent potential treatments of the corresponding ... ...

Abstract	SARS-CoV-2 has caused an extensive pandemic of COVID-19 all around the world. Key viral enzymes are suitable molecular targets for the development of new antivirals against SARS-CoV-2 which could represent potential treatments of the corresponding disease. With respect to its essential role in the replication of viral RNA, RNA-dependent RNA polymerase (RdRp) is one of the prime targets. HeE1-2Tyr and related derivatives were originally discovered as inhibitors of the RdRp of flaviviruses. Here, we present that these pyridobenzothiazole derivatives also significantly inhibit SARS-CoV-2 RdRp, as demonstrated using both polymerase- and cell-based antiviral assays.
MeSH term(s)	Adenosine Monophosphate/analogs & derivatives ; Adenosine Monophosphate/pharmacology ; Alanine/analogs & derivatives ; Alanine/pharmacology ; Animals ; Antiviral Agents/pharmacology ; Benzothiazoles/pharmacology ; Cell Line ; Cell Survival/drug effects ; Coronavirus RNA-Dependent RNA Polymerase/antagonists & inhibitors ; Dose-Response Relationship, Drug ; Enzyme Inhibitors/pharmacology ; Humans ; Microbial Sensitivity Tests ; Pyridones/pharmacology ; SARS-CoV-2/drug effects ; SARS-CoV-2/enzymology ; SARS-CoV-2/physiology ; Virus Replication/drug effects
Chemical Substances	Antiviral Agents ; Benzothiazoles ; Enzyme Inhibitors ; HeE1-2Tyr ; Pyridones ; remdesivir (3QKI37EEHE) ; Adenosine Monophosphate (415SHH325A) ; Coronavirus RNA-Dependent RNA Polymerase (EC 2.7.7.48) ; NSP12 protein, SARS-CoV-2 (EC 2.7.7.48) ; Alanine (OF5P57N2ZX)
Language	English
Publishing date	2021-08-11
Publishing country	Switzerland
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2516098-9
ISSN	1999-4915 ; 1999-4915
ISSN (online)	1999-4915
ISSN	1999-4915
DOI	10.3390/v13081585
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