Discovery of AB680: A Potent and Selective Inhibitor of CD73
Extracellular adenosine (ADO), present in high concentrations in the tumor microenvironment (TME), suppresses immune function via inhibition of T cell and NK cell activation. Intratumoral generation of ADO depends on the sequential catabolism of ATP by two ecto-nucleotidases, CD39 (ATP → AMP) and CD...
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| Veröffentlicht in: | Journal of medicinal chemistry 2020-10, Vol.63 (20), p.11448-11468 |
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| container_title | Journal of medicinal chemistry |
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| creator | Lawson, Kenneth V Kalisiak, Jaroslaw Lindsey, Erick A Newcomb, Eric T Leleti, Manmohan Reddy Debien, Laurent Rosen, Brandon R Miles, Dillon H Sharif, Ehesan U Jeffrey, Jenna L Tan, Joanne B. L Chen, Ada Zhao, Sharon Xu, Guifen Fu, Lijuan Jin, Lixia Park, Tim W Berry, Wade Moschütz, Susanne Scaletti, Emma Sträter, Norbert Walker, Nigel P Young, Stephen W Walters, Matthew J Schindler, Uli Powers, Jay P |
| description | Extracellular adenosine (ADO), present in high concentrations in the tumor microenvironment (TME), suppresses immune function via inhibition of T cell and NK cell activation. Intratumoral generation of ADO depends on the sequential catabolism of ATP by two ecto-nucleotidases, CD39 (ATP → AMP) and CD73 (AMP → ADO). Inhibition of CD73 eliminates a major pathway of ADO production in the TME and can reverse ADO-mediated immune suppression. Extensive interrogation of structure–activity relationships (SARs), structure-based drug design, and optimization of pharmacokinetic properties culminated in the discovery of AB680, a highly potent (K i = 5 pM), reversible, and selective inhibitor of CD73. AB680 is further characterized by very low clearance and long half-lives across preclinical species, resulting in a PK profile suitable for long-acting parenteral administration. AB680 is currently being evaluated in phase 1 clinical trials. Initial data show AB680 is well tolerated and exhibits a pharmacokinetic profile suitable for biweekly (Q2W) iv-administration in human. |
| doi_str_mv | 10.1021/acs.jmedchem.0c00525 |
| format | Article |
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L ; Chen, Ada ; Zhao, Sharon ; Xu, Guifen ; Fu, Lijuan ; Jin, Lixia ; Park, Tim W ; Berry, Wade ; Moschütz, Susanne ; Scaletti, Emma ; Sträter, Norbert ; Walker, Nigel P ; Young, Stephen W ; Walters, Matthew J ; Schindler, Uli ; Powers, Jay P</creator><creatorcontrib>Lawson, Kenneth V ; Kalisiak, Jaroslaw ; Lindsey, Erick A ; Newcomb, Eric T ; Leleti, Manmohan Reddy ; Debien, Laurent ; Rosen, Brandon R ; Miles, Dillon H ; Sharif, Ehesan U ; Jeffrey, Jenna L ; Tan, Joanne B. L ; Chen, Ada ; Zhao, Sharon ; Xu, Guifen ; Fu, Lijuan ; Jin, Lixia ; Park, Tim W ; Berry, Wade ; Moschütz, Susanne ; Scaletti, Emma ; Sträter, Norbert ; Walker, Nigel P ; Young, Stephen W ; Walters, Matthew J ; Schindler, Uli ; Powers, Jay P</creatorcontrib><description>Extracellular adenosine (ADO), present in high concentrations in the tumor microenvironment (TME), suppresses immune function via inhibition of T cell and NK cell activation. Intratumoral generation of ADO depends on the sequential catabolism of ATP by two ecto-nucleotidases, CD39 (ATP → AMP) and CD73 (AMP → ADO). Inhibition of CD73 eliminates a major pathway of ADO production in the TME and can reverse ADO-mediated immune suppression. Extensive interrogation of structure–activity relationships (SARs), structure-based drug design, and optimization of pharmacokinetic properties culminated in the discovery of AB680, a highly potent (K i = 5 pM), reversible, and selective inhibitor of CD73. AB680 is further characterized by very low clearance and long half-lives across preclinical species, resulting in a PK profile suitable for long-acting parenteral administration. AB680 is currently being evaluated in phase 1 clinical trials. Initial data show AB680 is well tolerated and exhibits a pharmacokinetic profile suitable for biweekly (Q2W) iv-administration in human.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/acs.jmedchem.0c00525</identifier><identifier>PMID: 32614585</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>5'-Nucleotidase - antagonists & inhibitors ; 5'-Nucleotidase - genetics ; Animals ; Binding Sites ; CD8-Positive T-Lymphocytes - drug effects ; CD8-Positive T-Lymphocytes - metabolism ; Drug Discovery - methods ; GPI-Linked Proteins - antagonists & inhibitors ; GPI-Linked Proteins - genetics ; Haplorhini ; Humans ; Leukocytes, Mononuclear - drug effects ; Leukocytes, Mononuclear - metabolism ; Mice ; Models, Molecular ; Protein Binding ; Rats ; Small Molecule Libraries - chemical synthesis ; Small Molecule Libraries - chemistry ; Small Molecule Libraries - pharmacokinetics ; Small Molecule Libraries - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2020-10, Vol.63 (20), p.11448-11468</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-8353f24b3685e51109ca30a65acf8c4f7a867e17852fff7654d48b6f94b81e93</citedby><cites>FETCH-LOGICAL-a348t-8353f24b3685e51109ca30a65acf8c4f7a867e17852fff7654d48b6f94b81e93</cites><orcidid>0000-0001-9249-5984 ; 0000-0001-5094-6337 ; 0000-0002-2001-0500 ; 0000-0002-2605-6745 ; 0000-0002-0790-6433</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.0c00525$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jmedchem.0c00525$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32614585$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lawson, Kenneth V</creatorcontrib><creatorcontrib>Kalisiak, Jaroslaw</creatorcontrib><creatorcontrib>Lindsey, Erick A</creatorcontrib><creatorcontrib>Newcomb, Eric T</creatorcontrib><creatorcontrib>Leleti, Manmohan Reddy</creatorcontrib><creatorcontrib>Debien, Laurent</creatorcontrib><creatorcontrib>Rosen, Brandon R</creatorcontrib><creatorcontrib>Miles, Dillon H</creatorcontrib><creatorcontrib>Sharif, Ehesan U</creatorcontrib><creatorcontrib>Jeffrey, Jenna L</creatorcontrib><creatorcontrib>Tan, Joanne B. L</creatorcontrib><creatorcontrib>Chen, Ada</creatorcontrib><creatorcontrib>Zhao, Sharon</creatorcontrib><creatorcontrib>Xu, Guifen</creatorcontrib><creatorcontrib>Fu, Lijuan</creatorcontrib><creatorcontrib>Jin, Lixia</creatorcontrib><creatorcontrib>Park, Tim W</creatorcontrib><creatorcontrib>Berry, Wade</creatorcontrib><creatorcontrib>Moschütz, Susanne</creatorcontrib><creatorcontrib>Scaletti, Emma</creatorcontrib><creatorcontrib>Sträter, Norbert</creatorcontrib><creatorcontrib>Walker, Nigel P</creatorcontrib><creatorcontrib>Young, Stephen W</creatorcontrib><creatorcontrib>Walters, Matthew J</creatorcontrib><creatorcontrib>Schindler, Uli</creatorcontrib><creatorcontrib>Powers, Jay P</creatorcontrib><title>Discovery of AB680: A Potent and Selective Inhibitor of CD73</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Extracellular adenosine (ADO), present in high concentrations in the tumor microenvironment (TME), suppresses immune function via inhibition of T cell and NK cell activation. Intratumoral generation of ADO depends on the sequential catabolism of ATP by two ecto-nucleotidases, CD39 (ATP → AMP) and CD73 (AMP → ADO). Inhibition of CD73 eliminates a major pathway of ADO production in the TME and can reverse ADO-mediated immune suppression. Extensive interrogation of structure–activity relationships (SARs), structure-based drug design, and optimization of pharmacokinetic properties culminated in the discovery of AB680, a highly potent (K i = 5 pM), reversible, and selective inhibitor of CD73. AB680 is further characterized by very low clearance and long half-lives across preclinical species, resulting in a PK profile suitable for long-acting parenteral administration. AB680 is currently being evaluated in phase 1 clinical trials. Initial data show AB680 is well tolerated and exhibits a pharmacokinetic profile suitable for biweekly (Q2W) iv-administration in human.</description><subject>5'-Nucleotidase - antagonists & inhibitors</subject><subject>5'-Nucleotidase - genetics</subject><subject>Animals</subject><subject>Binding Sites</subject><subject>CD8-Positive T-Lymphocytes - drug effects</subject><subject>CD8-Positive T-Lymphocytes - metabolism</subject><subject>Drug Discovery - methods</subject><subject>GPI-Linked Proteins - antagonists & inhibitors</subject><subject>GPI-Linked Proteins - genetics</subject><subject>Haplorhini</subject><subject>Humans</subject><subject>Leukocytes, Mononuclear - drug effects</subject><subject>Leukocytes, Mononuclear - metabolism</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Protein Binding</subject><subject>Rats</subject><subject>Small Molecule Libraries - chemical synthesis</subject><subject>Small Molecule Libraries - chemistry</subject><subject>Small Molecule Libraries - pharmacokinetics</subject><subject>Small Molecule Libraries - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM1Kw0AUhQdRbKy-gci8QOqd30zETWz9KRQU7D5MJjM0pUnKTFro25ua1qWru7jnO3A-hO4JTAhQ8qhNmKxrW5qVrSdgAAQVFygigkLMFfBLFAFQGlNJ2QjdhLAGAEYou0YjRiXhQokIPc-qYNq99QfcOpy9SAVPOMNfbWebDuumxN92Y01X7S2eN6uqqLrWH6PTWcJu0ZXTm2DvTneMlm-vy-lHvPh8n0-zRawZV12smGCO8oJJJawgBFKjGWgptHHKcJdoJRNLEiWocy6RgpdcFdKlvFDEpmyM-FBrfBuCty7f-qrW_pATyI8u8t5FfnaRn1z02MOAbXdF__uDzuP7AAyBX7zd-aYf8X_nD32iaxY</recordid><startdate>20201022</startdate><enddate>20201022</enddate><creator>Lawson, Kenneth V</creator><creator>Kalisiak, Jaroslaw</creator><creator>Lindsey, Erick A</creator><creator>Newcomb, Eric T</creator><creator>Leleti, Manmohan Reddy</creator><creator>Debien, Laurent</creator><creator>Rosen, Brandon R</creator><creator>Miles, Dillon H</creator><creator>Sharif, Ehesan U</creator><creator>Jeffrey, Jenna L</creator><creator>Tan, Joanne B. 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L</au><au>Chen, Ada</au><au>Zhao, Sharon</au><au>Xu, Guifen</au><au>Fu, Lijuan</au><au>Jin, Lixia</au><au>Park, Tim W</au><au>Berry, Wade</au><au>Moschütz, Susanne</au><au>Scaletti, Emma</au><au>Sträter, Norbert</au><au>Walker, Nigel P</au><au>Young, Stephen W</au><au>Walters, Matthew J</au><au>Schindler, Uli</au><au>Powers, Jay P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of AB680: A Potent and Selective Inhibitor of CD73</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2020-10-22</date><risdate>2020</risdate><volume>63</volume><issue>20</issue><spage>11448</spage><epage>11468</epage><pages>11448-11468</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>Extracellular adenosine (ADO), present in high concentrations in the tumor microenvironment (TME), suppresses immune function via inhibition of T cell and NK cell activation. Intratumoral generation of ADO depends on the sequential catabolism of ATP by two ecto-nucleotidases, CD39 (ATP → AMP) and CD73 (AMP → ADO). Inhibition of CD73 eliminates a major pathway of ADO production in the TME and can reverse ADO-mediated immune suppression. Extensive interrogation of structure–activity relationships (SARs), structure-based drug design, and optimization of pharmacokinetic properties culminated in the discovery of AB680, a highly potent (K i = 5 pM), reversible, and selective inhibitor of CD73. AB680 is further characterized by very low clearance and long half-lives across preclinical species, resulting in a PK profile suitable for long-acting parenteral administration. AB680 is currently being evaluated in phase 1 clinical trials. Initial data show AB680 is well tolerated and exhibits a pharmacokinetic profile suitable for biweekly (Q2W) iv-administration in human.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>32614585</pmid><doi>10.1021/acs.jmedchem.0c00525</doi><tpages>21</tpages><orcidid>https://orcid.org/0000-0001-9249-5984</orcidid><orcidid>https://orcid.org/0000-0001-5094-6337</orcidid><orcidid>https://orcid.org/0000-0002-2001-0500</orcidid><orcidid>https://orcid.org/0000-0002-2605-6745</orcidid><orcidid>https://orcid.org/0000-0002-0790-6433</orcidid></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2020-10, Vol.63 (20), p.11448-11468 |
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| source | MEDLINE; ACS Publications |
| subjects | 5'-Nucleotidase - antagonists & inhibitors 5'-Nucleotidase - genetics Animals Binding Sites CD8-Positive T-Lymphocytes - drug effects CD8-Positive T-Lymphocytes - metabolism Drug Discovery - methods GPI-Linked Proteins - antagonists & inhibitors GPI-Linked Proteins - genetics Haplorhini Humans Leukocytes, Mononuclear - drug effects Leukocytes, Mononuclear - metabolism Mice Models, Molecular Protein Binding Rats Small Molecule Libraries - chemical synthesis Small Molecule Libraries - chemistry Small Molecule Libraries - pharmacokinetics Small Molecule Libraries - pharmacology Structure-Activity Relationship |
| title | Discovery of AB680: A Potent and Selective Inhibitor of CD73 |
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