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Artikel ; Online: Synthesis and structure-activity relationships of ticlopidine derivatives and analogs as inhibitors of ectonucleotidase CD39.

Bi, Chunyang / Schäkel, Laura / Mirza, Salahuddin / Sylvester, Katharina / Pelletier, Julie / Lee, Sang-Yong / Pillaiyar, Thanigaimalai / Sévigny, Jean / Müller, Christa E

Bioorganic chemistry

2023 Band 135, Seite(n) 106460

Abstract: Ticlopidine is an antithrombotic prodrug of the thienotetrahydropyridine family. For platelet inhibition it has to undergo oxidative ring-opening by cytochrome P450 enzymes. The resulting thiol reacts with a cysteine residue of the purinergic ... ...

Abstract	Ticlopidine is an antithrombotic prodrug of the thienotetrahydropyridine family. For platelet inhibition it has to undergo oxidative ring-opening by cytochrome P450 enzymes. The resulting thiol reacts with a cysteine residue of the purinergic P2Y
Mesh-Begriff(e)	Adenosine Triphosphate ; Ticlopidine ; Adenosine ; Blood Platelets ; Structure-Activity Relationship ; 5'-Nucleotidase/metabolism
Chemische Substanzen	Adenosine Triphosphate (8L70Q75FXE) ; Ticlopidine (OM90ZUW7M1) ; Adenosine (K72T3FS567) ; 5'-Nucleotidase (EC 3.1.3.5)
Sprache	Englisch
Erscheinungsdatum	2023-03-11
Erscheinungsland	United States
Dokumenttyp	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	120080-x
ISSN	1090-2120 ; 0045-2068
ISSN (online)	1090-2120
ISSN	0045-2068
DOI	10.1016/j.bioorg.2023.106460
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel ; Online: Cathepsin-Targeting SARS-CoV-2 Inhibitors: Design, Synthesis, and Biological Activity.

ACS pharmacology & translational science

2024 Band 7, Heft 2, Seite(n) 493–514

Abstract: Cathepsins (Cats) are proteases that mediate the successful entry of SARS-CoV-2 into host cells. We designed and synthesized a tailored series of 21 peptidomimetics and evaluated their inhibitory activity against human cathepsins L, B, and S. Structural ... ...

Abstract	Cathepsins (Cats) are proteases that mediate the successful entry of SARS-CoV-2 into host cells. We designed and synthesized a tailored series of 21 peptidomimetics and evaluated their inhibitory activity against human cathepsins L, B, and S. Structural diversity was realized by combinations of different C-terminal warhead functions and N-terminal capping groups, while a central Leu-Phe fragment was maintained. Several compounds were identified as promising cathepsin L and S inhibitors with
Sprache	Englisch
Erscheinungsdatum	2024-01-19
Erscheinungsland	United States
Dokumenttyp	Journal Article
ISSN	2575-9108
ISSN (online)	2575-9108
DOI	10.1021/acsptsci.3c00313
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel ; Online: Correction to "Cathepsin-Targeting SARS-CoV-2 Inhibitors: Design, Synthesis, and Biological Activity".

ACS pharmacology & translational science

2024 Band 7, Heft 4, Seite(n) 1195–1196

Abstract: This corrects the article DOI: 10.1021/acsptsci.3c00313.]. ...

Abstract	[This corrects the article DOI: 10.1021/acsptsci.3c00313.].
Sprache	Englisch
Erscheinungsdatum	2024-03-06
Erscheinungsland	United States
Dokumenttyp	Published Erratum
ISSN	2575-9108
ISSN (online)	2575-9108
DOI	10.1021/acsptsci.4c00095
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel ; Online: Heparins are potent inhibitors of ectonucleotide pyrophosphatase/phospho-diesterase-1 (NPP1) - a promising target for the immunotherapy of cancer.

Lopez, Vittoria / Schuh, H J Maximilian / Mirza, Salahuddin / Vaaßen, Victoria J / Schmidt, Michael S / Sylvester, Katharina / Idris, Riham M / Renn, Christian / Schäkel, Laura / Pelletier, Julie / Sévigny, Jean / Naggi, Annamaria / Scheffler, Björn / Lee, Sang-Yong / Bendas, Gerd / Müller, Christa E

Frontiers in immunology

2023 Band 14, Seite(n) 1173634

Abstract: Introduction: Heparins, naturally occurring glycosaminoglycans, are widely used for thrombosis prevention. Upon application as anticoagulants in cancer patients, heparins were found to possess additional antitumor activities. Ectonucleotidases have ... ...

Abstract	Introduction: Heparins, naturally occurring glycosaminoglycans, are widely used for thrombosis prevention. Upon application as anticoagulants in cancer patients, heparins were found to possess additional antitumor activities. Ectonucleotidases have recently been proposed as novel targets for cancer immunotherapy. Methods and results: In the present study, we discovered that heparin and its derivatives act as potent, selective, allosteric inhibitors of the poorly investigated ectonucleotidase NPP1 (nucleotide pyrophosphatase/phosphodiesterase-1, CD203a). Structure-activity relationships indicated that NPP1 inhibition could be separated from the compounds' antithrombotic effect. Moreover, unfractionated heparin (UFH) and different low molecular weight heparins (LMWHs) inhibited extracellular adenosine production by the NPP1-expressing glioma cell line U87 at therapeutically relevant concentrations. As a consequence, heparins inhibited the ability of U87 cell supernatants to induce CD4+ T cell differentiation into immunosuppressive Treg cells. Discussion: NPP1 inhibition likely contributes to the anti-cancer effects of heparins, and their specific optimization may lead to improved therapeutics for the immunotherapy of cancer.
Mesh-Begriff(e)	Humans ; Heparin/pharmacology ; Immunotherapy ; Anticoagulants ; Heparin, Low-Molecular-Weight/pharmacology ; Heparin, Low-Molecular-Weight/therapeutic use ; Glioma
Chemische Substanzen	Heparin (9005-49-6) ; Anticoagulants ; Heparin, Low-Molecular-Weight
Sprache	Englisch
Erscheinungsdatum	2023-08-29
Erscheinungsland	Switzerland
Dokumenttyp	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2606827-8
ISSN	1664-3224 ; 1664-3224
ISSN (online)	1664-3224
ISSN	1664-3224
DOI	10.3389/fimmu.2023.1173634
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel ; Online: Protein kinase inhibitor ceritinib blocks ectonucleotidase CD39 - a promising target for cancer immunotherapy.

Schäkel, Laura / Mirza, Salahuddin / Winzer, Riekje / Lopez, Vittoria / Idris, Riham / Al-Hroub, Haneen / Pelletier, Julie / Sévigny, Jean / Tolosa, Eva / Müller, Christa E

Journal for immunotherapy of cancer

2022 Band 10, Heft 8

Abstract: Background: An important mechanism, by which cancer cells achieve immune escape, is the release of extracellular adenosine into their microenvironment. Adenosine activates adenosine A: Methods: We pursued a repurposing approach by screening a self- ... ...

Abstract	Background: An important mechanism, by which cancer cells achieve immune escape, is the release of extracellular adenosine into their microenvironment. Adenosine activates adenosine A Methods: We pursued a repurposing approach by screening a self-compiled collection of approved, mostly ATP-competitive protein kinase inhibitors, on human CD39. The best hit compound was further characterized and evaluated in various orthogonal assays and enzyme preparations, and on human immune and cancer cells. Results: The tyrosine kinase inhibitor ceritinib, a potent anticancer drug used for the treatment of anaplastic lymphoma kinase (ALK)-positive metastatic non-small cell lung cancer, was found to strongly inhibit CD39 showing selectivity versus other ectonucleotidases. The drug displays a non-competitive, allosteric mechanism of CD39 inhibition exhibiting potency in the low micromolar range, which is independent of substrate (ATP) concentration. We could show that ceritinib inhibits ATP dephosphorylation in peripheral blood mononuclear cells in a dose-dependent manner, resulting in a significant increase in ATP concentrations and preventing adenosine formation from ATP. Importantly, ceritinib (1-10 µM) substantially inhibited ATP hydrolysis in triple negative breast cancer and melanoma cells with high native expression of CD39. Conclusions: CD39 inhibition might contribute to the effects of the powerful anticancer drug ceritinib. Ceritinib is a novel CD39 inhibitor with high metabolic stability and optimized physicochemical properties; according to our knowledge, it is the first brain-permeant CD39 inhibitor. Our discovery will provide the basis (i) to develop more potent and balanced dual CD39/ALK inhibitors, and (ii) to optimize the ceritinib scaffold towards interaction with CD39 to obtain potent and selective drug-like CD39 inhibitors for future in vivo studies.
Mesh-Begriff(e)	Adenosine/metabolism ; Adenosine Triphosphate/metabolism ; Antigens, CD/metabolism ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/therapeutic use ; Apyrase/immunology ; Apyrase/metabolism ; Carcinoma, Non-Small-Cell Lung/metabolism ; Humans ; Immunotherapy ; Leukocytes, Mononuclear/metabolism ; Lung Neoplasms/metabolism ; Protein Kinase Inhibitors/pharmacology ; Pyrimidines ; Receptor Protein-Tyrosine Kinases ; Sulfones ; Tumor Microenvironment
Chemische Substanzen	Antigens, CD ; Antineoplastic Agents ; Protein Kinase Inhibitors ; Pyrimidines ; Sulfones ; Adenosine Triphosphate (8L70Q75FXE) ; Receptor Protein-Tyrosine Kinases (EC 2.7.10.1) ; Apyrase (EC 3.6.1.5) ; ENTPD1 protein, human (EC 3.6.1.5) ; ceritinib (K418KG2GET) ; Adenosine (K72T3FS567)
Sprache	Englisch
Erscheinungsdatum	2022-08-15
Erscheinungsland	England
Dokumenttyp	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2719863-7
ISSN	2051-1426 ; 2051-1426
ISSN (online)	2051-1426
ISSN	2051-1426
DOI	10.1136/jitc-2022-004660
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel: Development of Anthraquinone Derivatives as Ectonucleoside Triphosphate Diphosphohydrolase (NTPDase) Inhibitors With Selectivity for NTPDase2 and NTPDase3.

Baqi, Younis / Rashed, Mahmoud / Schäkel, Laura / Malik, Enas M / Pelletier, Julie / Sévigny, Jean / Fiene, Amelie / Müller, Christa E

Frontiers in pharmacology

2020 Band 11, Seite(n) 1282

Abstract: Ectonucleoside triphosphate diphosphohydrolases (NTPDases) catalyze the hydrolysis of nucleoside tri- and di-phosphates to mono-phosphates. The products are subsequently hydrolyzed by ecto-5'-nucleotidase (ecto-5'-NT) to nucleosides. NTPDase inhibitors ... ...

Abstract	Ectonucleoside triphosphate diphosphohydrolases (NTPDases) catalyze the hydrolysis of nucleoside tri- and di-phosphates to mono-phosphates. The products are subsequently hydrolyzed by ecto-5'-nucleotidase (ecto-5'-NT) to nucleosides. NTPDase inhibitors have potential as novel drugs, e.g., for the treatment of inflammation, neurodegenerative diseases, and cancer. In this context, a series of anthraquinone derivatives structurally related to the anthraquinone dye reactive blue-2 (RB-2) was synthesized and evaluated as inhibitors of human NTPDases utilizing a malachite green assay. We identified several potent and selective inhibitors of human NTPDase2 and -3. Among the most potent NTPDase2 inhibitors were 1-amino-4-(9-phenanthrylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (20, PSB-16131, IC
Sprache	Englisch
Erscheinungsdatum	2020-08-27
Erscheinungsland	Switzerland
Dokumenttyp	Journal Article
ZDB-ID	2587355-6
ISSN	1663-9812
ISSN	1663-9812
DOI	10.3389/fphar.2020.01282
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel: Sulfated Polysaccharides from Macroalgae Are Potent Dual Inhibitors of Human ATP-Hydrolyzing Ectonucleotidases NPP1 and CD39

Lopez, Vittoria / Schäkel, Laura / Schuh, H. J. Maximilian / Schmidt, Michael S. / Mirza, Salahuddin / Renn, Christian / Pelletier, Julie / Lee, Sang-Yong / Sévigny, Jean / Alban, Susanne / Bendas, Gerd / Müller, Christa E.

Marine drugs. 2021 Jan. 22, v. 19, no. 2

2021

Abstract: Extracellular ATP mediates proinflammatory and antiproliferative effects via activation of P2 nucleotide receptors. In contrast, its metabolite, the nucleoside adenosine, is strongly immunosuppressive and enhances tumor proliferation and metastasis. The ... ...

Abstract	Extracellular ATP mediates proinflammatory and antiproliferative effects via activation of P2 nucleotide receptors. In contrast, its metabolite, the nucleoside adenosine, is strongly immunosuppressive and enhances tumor proliferation and metastasis. The conversion of ATP to adenosine is catalyzed by ectonucleotidases, which are expressed on immune cells and typically upregulated on tumor cells. In the present study, we identified sulfopolysaccharides from brown and red sea algae to act as potent dual inhibitors of the main ATP-hydrolyzing ectoenzymes, ectonucleotide pyrophosphatase/phosphodiesterase-1 (NPP1) and ecto-nucleoside triphosphate diphosphohydrolase-1 (NTPDase1, CD39), showing nano- to picomolar potency and displaying a non-competitive mechanism of inhibition. We showed that one of the sulfopolysaccharides tested as a representative example reduced adenosine formation at the surface of the human glioblastoma cell line U87 in a concentration-dependent manner. These natural products represent the most potent inhibitors of extracellular ATP hydrolysis known to date and have potential as novel therapeutics for the immunotherapy of cancer.
Schlagwörter	adenosine ; glioblastoma ; humans ; hydrolysis ; immunosuppression ; immunotherapy ; macroalgae ; metabolites ; metastasis ; polysaccharides ; Red Sea
Sprache	Englisch
Erscheinungsverlauf	2021-0122
Erscheinungsort	Multidisciplinary Digital Publishing Institute
Dokumenttyp	Artikel
ZDB-ID	2175190-0
ISSN	1660-3397
ISSN	1660-3397
DOI	10.3390/md19020051
Datenquelle	NAL Katalog (AGRICOLA)

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Artikel ; Online: Sulfated Polysaccharides from Macroalgae Are Potent Dual Inhibitors of Human ATP-Hydrolyzing Ectonucleotidases NPP1 and CD39.

Lopez, Vittoria / Schäkel, Laura / Schuh, H J Maximilian / Schmidt, Michael S / Mirza, Salahuddin / Renn, Christian / Pelletier, Julie / Lee, Sang-Yong / Sévigny, Jean / Alban, Susanne / Bendas, Gerd / Müller, Christa E

Marine drugs

2021 Band 19, Heft 2

Abstract	Extracellular ATP mediates proinflammatory and antiproliferative effects via activation of P2 nucleotide receptors. In contrast, its metabolite, the nucleoside adenosine, is strongly immunosuppressive and enhances tumor proliferation and metastasis. The conversion of ATP to adenosine is catalyzed by ectonucleotidases, which are expressed on immune cells and typically upregulated on tumor cells. In the present study, we identified sulfopolysaccharides from brown and red sea algae to act as potent dual inhibitors of the main ATP-hydrolyzing ectoenzymes, ectonucleotide pyrophosphatase/phosphodiesterase-1 (NPP1) and ecto-nucleoside triphosphate diphosphohydrolase-1 (NTPDase1, CD39), showing nano- to picomolar potency and displaying a non-competitive mechanism of inhibition. We showed that one of the sulfopolysaccharides tested as a representative example reduced adenosine formation at the surface of the human glioblastoma cell line U87 in a concentration-dependent manner. These natural products represent the most potent inhibitors of extracellular ATP hydrolysis known to date and have potential as novel therapeutics for the immunotherapy of cancer.
Mesh-Begriff(e)	Adenosine Triphosphate/antagonists & inhibitors ; Adenosine Triphosphate/metabolism ; Apyrase/antagonists & inhibitors ; Apyrase/metabolism ; Cell Line, Tumor ; Dose-Response Relationship, Drug ; Humans ; Hydrolysis/drug effects ; Phosphoric Diester Hydrolases/metabolism ; Polysaccharides/chemistry ; Polysaccharides/isolation & purification ; Polysaccharides/physiology ; Pyrophosphatases/antagonists & inhibitors ; Pyrophosphatases/metabolism ; Seaweed/chemistry ; Seaweed/isolation & purification ; Sulfuric Acid Esters/chemistry ; Sulfuric Acid Esters/isolation & purification ; Sulfuric Acid Esters/pharmacology
Chemische Substanzen	Polysaccharides ; Sulfuric Acid Esters ; Adenosine Triphosphate (8L70Q75FXE) ; Phosphoric Diester Hydrolases (EC 3.1.4.-) ; ectonucleotide pyrophosphatase phosphodiesterase 1 (EC 3.1.4.1) ; Pyrophosphatases (EC 3.6.1.-) ; Apyrase (EC 3.6.1.5) ; ENTPD1 protein, human (EC 3.6.1.5)
Sprache	Englisch
Erscheinungsdatum	2021-01-22
Erscheinungsland	Switzerland
Dokumenttyp	Journal Article
ZDB-ID	2175190-0
ISSN	1660-3397 ; 1660-3397
ISSN (online)	1660-3397
ISSN	1660-3397
DOI	10.3390/md19020051
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel ; Online: 2-Substituted thienotetrahydropyridine derivatives: Allosteric ectonucleotidase inhibitors.

Schäkel, Laura / Mirza, Salahuddin / Pietsch, Markus / Lee, Sang-Yong / Keuler, Tim / Sylvester, Katharina / Pelletier, Julie / Sévigny, Jean / Pillaiyar, Thanigaimalai / Namasivayam, Vigneshwaran / Gütschow, Michael / Müller, Christa E

Archiv der Pharmazie

2021 Band 354, Heft 12, Seite(n) e2100300

Abstract: The antithrombotic prodrugs ticlopidine and clopidogrel are thienotetrahydro-pyridine derivatives that are metabolized in the liver to produce thiols that irreversibly block adenosine diphosphate (ADP)-activated ... ...

Abstract	The antithrombotic prodrugs ticlopidine and clopidogrel are thienotetrahydro-pyridine derivatives that are metabolized in the liver to produce thiols that irreversibly block adenosine diphosphate (ADP)-activated P2Y
Mesh-Begriff(e)	5'-Nucleotidase/antagonists & inhibitors ; Allosteric Regulation/drug effects ; Apyrase/antagonists & inhibitors ; Enzyme Inhibitors/chemical synthesis ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; GPI-Linked Proteins/antagonists & inhibitors ; Humans ; Structure-Activity Relationship ; Thienopyridines/chemical synthesis ; Thienopyridines/chemistry ; Thienopyridines/pharmacology ; Ticlopidine/pharmacology
Chemische Substanzen	Enzyme Inhibitors ; GPI-Linked Proteins ; Thienopyridines ; 5'-Nucleotidase (EC 3.1.3.5) ; NT5E protein, human (EC 3.1.3.5) ; Apyrase (EC 3.6.1.5) ; ENTPD1 protein, human (EC 3.6.1.5) ; Ticlopidine (OM90ZUW7M1)
Sprache	Englisch
Erscheinungsdatum	2021-10-26
Erscheinungsland	Germany
Dokumenttyp	Comparative Study ; Journal Article
ZDB-ID	6381-2
ISSN	1521-4184 ; 0365-6233 ; 1437-1014
ISSN (online)	1521-4184
ISSN	0365-6233 ; 1437-1014
DOI	10.1002/ardp.202100300
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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Artikel: Nucleotide Analog ARL67156 as a Lead Structure for the Development of CD39 and Dual CD39/CD73 Ectonucleotidase Inhibitors.

Schäkel, Laura / Schmies, Constanze C / Idris, Riham M / Luo, Xihuan / Lee, Sang-Yong / Lopez, Vittoria / Mirza, Salahuddin / Vu, The Hung / Pelletier, Julie / Sévigny, Jean / Namasivayam, Vigneshwaran / Müller, Christa E

Frontiers in pharmacology

2020 Band 11, Seite(n) 1294

Abstract: Nucleoside triphosphate diphosphohydrolase1 (NTPDase1, CD39) inhibitors have potential as novel drugs for the (immuno)therapy of cancer. They increase the extracellular concentration of immunostimulatory ATP and reduce the formation of AMP, which can be ... ...

Abstract	Nucleoside triphosphate diphosphohydrolase1 (NTPDase1, CD39) inhibitors have potential as novel drugs for the (immuno)therapy of cancer. They increase the extracellular concentration of immunostimulatory ATP and reduce the formation of AMP, which can be further hydrolyzed by ecto-5'-nucleotidase (CD73) to immunosuppressive, cancer-promoting adenosine. In the present study, we synthesized analogs and derivatives of the standard CD39 inhibitor ARL67156, a nucleotide analog which displays a competitive mechanism of inhibition. Structure-activity relationships were analyzed at the human enzyme with respect to substituents in the
Sprache	Englisch
Erscheinungsdatum	2020-09-08
Erscheinungsland	Switzerland
Dokumenttyp	Journal Article
ZDB-ID	2587355-6
ISSN	1663-9812
ISSN	1663-9812
DOI	10.3389/fphar.2020.01294
Datenquelle	MEDical Literature Analysis and Retrieval System OnLINE

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