000626512 001__ 626512
000626512 005__ 20250723105855.0
000626512 0247_ $$2doi$$a10.1021/acsptsci.5c00126
000626512 0247_ $$2pmid$$a40370983
000626512 0247_ $$2WOS$$aWOS:001458665100001
000626512 0247_ $$2openalex$$aopenalex:W4409141019
000626512 037__ $$aPUBDB-2025-01465
000626512 041__ $$aEnglish
000626512 082__ $$a610
000626512 1001_ $$aBi, Chunyang$$b0
000626512 245__ $$aSynthesis, Characterization, Interactions, and Immunomodulatory Function of Ectonucleotidase CD39/CD73 Inhibitor 8-Butylthioadenosine 5′-Monophosphate
000626512 260__ $$aWashington, DC$$bACS Publications$$c2025
000626512 3367_ $$2DRIVER$$aarticle
000626512 3367_ $$2DataCite$$aOutput Types/Journal article
000626512 3367_ $$0PUB:(DE-HGF)16$$2PUB:(DE-HGF)$$aJournal Article$$bjournal$$mjournal$$s1747731898_890870
000626512 3367_ $$2BibTeX$$aARTICLE
000626512 3367_ $$2ORCID$$aJOURNAL_ARTICLE
000626512 3367_ $$00$$2EndNote$$aJournal Article
000626512 500__ $$awaiting for fulltext
000626512 520__ $$aEctonucleoside triphosphate diphosphohydrolase-1 (NTPDase1, CD39) catalyzes the extracellular hydrolysis of ATP generating AMP, while ecto-5′-nucleotidase (CD73) further hydrolyzes AMP yielding immunosuppressive adenosine. 8-Butylthioadenosine 5′-monophosphate (8-BuS-AMP) was described as a CD39 inhibitor but has been poorly characterized. The standard CD39 antagonist ARL 67156 is not suitable for in vivo studies due to metabolic instability. In the present study, we optimized and upscaled the synthesis of 8-BuS-AMP and performed a comprehensive investigation of its properties. It behaves as a competitive inhibitor at human and mouse CD39, and additionally inhibits CD73. Docking studies using a homology model of human CD39 and determination of an atomic-resolution (1.06 Å) cocrystal structure with human CD73 indicated the inhibitor’s interactions within the substrate binding pockets and explained the compound’s stability toward hydrolysis. 8-BuS-AMP is metabolically highly stable in human and mouse liver microsomes. It inhibited ε-adenosine formation from ε-ATP and ε-AMP in human synovial fluid and enhanced activation and proliferation of peripheral human T lymphocytes. Thus, 8-BuS-AMP is a recommended tool compound for studying purinergic signaling in vitro and in vivo, being superior to the standard CD39 inhibitor ARL 67156. Moreover, it may serve as a lead structure to develop drugs for the immunotherapy of cancer.
000626512 536__ $$0G:(DE-HGF)POF4-6G3$$a6G3 - PETRA III (DESY) (POF4-6G3)$$cPOF4-6G3$$fPOF IV$$x0
000626512 536__ $$0G:(GEPRIS)335447717$$aDFG project G:(GEPRIS)335447717 - SFB 1328: Adeninnukleotide in Immunität und Entzündung (335447717)$$c335447717$$x1
000626512 588__ $$aDataset connected to CrossRef, Journals: bib-pubdb1.desy.de
000626512 693__ $$0EXP:(DE-H253)P-P14-20150101$$1EXP:(DE-H253)PETRAIII-20150101$$6EXP:(DE-H253)P-P14-20150101$$aPETRA III$$fPETRA Beamline P14$$x0
000626512 7001_ $$aMirza, Salahuddin$$b1
000626512 7001_ $$aBaburi, Helay$$b2
000626512 7001_ $$aSchäkel, Laura$$b3
000626512 7001_ $$aWinzer, Riekje$$b4
000626512 7001_ $$aMoschütz, Susanne$$b5
000626512 7001_ $$aKeetz, Kilian$$b6
000626512 7001_ $$aLopez, Vittoria$$b7
000626512 7001_ $$aPelletier, Julie$$b8
000626512 7001_ $$00000-0003-2922-1600$$aSévigny, Jean$$b9
000626512 7001_ $$aSchulze zur Wiesch, Julian$$b10
000626512 7001_ $$0P:(DE-HGF)0$$aClaff, Tobias$$b11
000626512 7001_ $$aTolosa, Eva$$b12
000626512 7001_ $$00000-0003-3031-3377$$aNamasivayam, Vigneshwaran$$b13
000626512 7001_ $$0P:(DE-H253)PIP1111492$$aStraeter, Norbert$$b14
000626512 7001_ $$00000-0002-0013-6624$$aMüller, Christa E.$$b15$$eCorresponding author
000626512 773__ $$0PERI:(DE-600)2934670-8$$a10.1021/acsptsci.5c00126$$gp. acsptsci.5c00126$$n5$$p1401 - 1415$$tACS pharmacology & translational science$$v8$$x2575-9108$$y2025
000626512 8564_ $$uhttps://pubs.acs.org/doi/full/10.1021/acsptsci.5c00126
000626512 8564_ $$uhttps://bib-pubdb1.desy.de/record/626512/files/bi-et-al-2025-synthesis-characterization-interactions-and-immunomodulatory-function-of-ectonucleotidase-cd39-cd73.pdf$$yRestricted
000626512 8564_ $$uhttps://bib-pubdb1.desy.de/record/626512/files/bi-et-al-2025-synthesis-characterization-interactions-and-immunomodulatory-function-of-ectonucleotidase-cd39-cd73.pdf?subformat=pdfa$$xpdfa$$yRestricted
000626512 909CO $$ooai:bib-pubdb1.desy.de:626512$$pVDB
000626512 9101_ $$0I:(DE-HGF)0$$6P:(DE-H253)PIP1111492$$aExternal Institute$$b14$$kExtern
000626512 9131_ $$0G:(DE-HGF)POF4-6G3$$1G:(DE-HGF)POF4-6G0$$2G:(DE-HGF)POF4-600$$3G:(DE-HGF)POF4$$4G:(DE-HGF)POF$$aDE-HGF$$bForschungsbereich Materie$$lGroßgeräte: Materie$$vPETRA III (DESY)$$x0
000626512 9141_ $$y2025
000626512 915__ $$0StatID:(DE-HGF)0100$$2StatID$$aJCR$$bACS PHARMACOL TRANSL : 2022$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)0200$$2StatID$$aDBCoverage$$bSCOPUS$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)0300$$2StatID$$aDBCoverage$$bMedline$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)0199$$2StatID$$aDBCoverage$$bClarivate Analytics Master Journal List$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)0112$$2StatID$$aWoS$$bEmerging Sources Citation Index$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)0150$$2StatID$$aDBCoverage$$bWeb of Science Core Collection$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)1050$$2StatID$$aDBCoverage$$bBIOSIS Previews$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)1190$$2StatID$$aDBCoverage$$bBiological Abstracts$$d2024-12-10
000626512 915__ $$0StatID:(DE-HGF)9905$$2StatID$$aIF >= 5$$bACS PHARMACOL TRANSL : 2022$$d2024-12-10
000626512 9201_ $$0I:(DE-H253)EMBL-User-20120814$$kEMBL-User$$lEMBL-User$$x0
000626512 980__ $$ajournal
000626512 980__ $$aVDB
000626512 980__ $$aI:(DE-H253)EMBL-User-20120814
000626512 980__ $$aUNRESTRICTED