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  1. Article: P2X7 receptor antagonists for the treatment of systemic inflammatory disorders.

    Gelin, Christine F / Bhattacharya, Anindya / Letavic, Michael A

    Progress in medicinal chemistry

    2020  Volume 59, Page(s) 63–99

    Abstract: P2X7 has continued to be a target of immense interest since it is implicated in several peripheral and central nervous system disorders that result from inflammation. This review primarily describes new P2X7 receptor antagonists that have been ... ...

    Abstract P2X7 has continued to be a target of immense interest since it is implicated in several peripheral and central nervous system disorders that result from inflammation. This review primarily describes new P2X7 receptor antagonists that have been investigated and disclosed in patent applications or primary literature since 2015. While a crystal structure of the receptor to aid in the design of novel chemical structures remains elusive, many of the chemotypes that have been disclosed contain similarities, with an amide motif present in all series that have been explored to date. Several of the recent antagonists described are brain penetrant, and two compounds are currently in clinical trials for CNS indications. Additionally, brain penetrant PET ligands have been developed that aid in measuring target engagement and these ligands can potentially be used as biomarkers.
    MeSH term(s) Humans ; Ligands ; Molecular Structure ; Mood Disorders/drug therapy ; Mood Disorders/metabolism ; Non-alcoholic Fatty Liver Disease/drug therapy ; Non-alcoholic Fatty Liver Disease/metabolism ; Purinergic P2X Receptor Antagonists/chemistry ; Purinergic P2X Receptor Antagonists/pharmacology ; Receptors, Purinergic P2X7/metabolism
    Chemical Substances Ligands ; P2RX7 protein, human ; Purinergic P2X Receptor Antagonists ; Receptors, Purinergic P2X7
    Language English
    Publishing date 2020-01-31
    Publishing country Netherlands
    Document type Journal Article ; Review
    ZDB-ID 209306-6
    ISSN 1875-7863 ; 0079-6468
    ISSN (online) 1875-7863
    ISSN 0079-6468
    DOI 10.1016/bs.pmch.2019.11.002
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  2. Article ; Online: Discovery of a Series of Substituted 1

    Gelin, Christine F / Stenne, Brice / Coate, Heather / Hiscox, Afton / Soyode-Johnson, Akinola / Wall, Jessica L / Lord, Brian / Schoellerman, Jeffrey / Coe, Kevin J / Wang, Kai / Alcázar, Jesus / Chrovian, Christa C / Dvorak, Curt A / Carruthers, Nicholas I / Koudriakova, Tatiana / Balana, Bartosz / Letavic, Michael A

    Journal of medicinal chemistry

    2023  Volume 66, Issue 4, Page(s) 2877–2892

    Abstract: Herein, we describe a series of substituted ... ...

    Abstract Herein, we describe a series of substituted 1
    MeSH term(s) Animals ; Rats ; Brain/metabolism ; Pyrimidines ; Receptors, N-Methyl-D-Aspartate/metabolism ; Structure-Activity Relationship
    Chemical Substances NR2B NMDA receptor ; Pyrimidines ; Receptors, N-Methyl-D-Aspartate
    Language English
    Publishing date 2023-02-09
    Publishing country United States
    Document type Journal Article
    ZDB-ID 218133-2
    ISSN 1520-4804 ; 0022-2623
    ISSN (online) 1520-4804
    ISSN 0022-2623
    DOI 10.1021/acs.jmedchem.2c01916
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  3. Article ; Online: Development of small molecule inhibitors of natural killer group 2D receptor (NKG2D).

    Wang, Jocelyn / Nakafuku, Kohki M / Ziff, Jeannie / Gelin, Christine F / Gholami, Hadi / Thompson, Aaron A / Karpowich, Nathan K / Limon, Luis / Coate, Heather R / Damm-Ganamet, Kelly L / Shih, Amy Y / Grant, Joanna C / Côte, Marjorie / Mak, Puiying A / Pascual, Heather A / Rives, Marie-Laure / Edwards, James P / Venable, Jennifer D / Venkatesan, Hariharan /
    Shi, Zhicai / Allen, Samantha J / Sharma, Sujata / Kung, Pei-Pei / Shireman, Brock T

    Bioorganic & medicinal chemistry letters

    2023  Volume 96, Page(s) 129492

    Abstract: Natural killer group 2D (NKG2D) is a homodimeric activating immunoreceptor whose function is to detect and eliminate compromised cells upon binding to the NKG2D ligands (NKG2DL) major histocompatibility complex (MHC) molecules class I-related chain A ( ... ...

    Abstract Natural killer group 2D (NKG2D) is a homodimeric activating immunoreceptor whose function is to detect and eliminate compromised cells upon binding to the NKG2D ligands (NKG2DL) major histocompatibility complex (MHC) molecules class I-related chain A (MICA) and B (MICB) and UL16 binding proteins (ULBP1-6). While typically present at low levels in healthy cells and tissue, NKG2DL expression can be induced by viral infection, cellular stress or transformation. Aberrant activity along the NKG2D/NKG2DL axis has been associated with autoimmune diseases due to the increased expression of NKG2D ligands in human disease tissue, making NKG2D inhibitors an attractive target for immunomodulation. Herein we describe the discovery and optimization of small molecule PPI (protein-protein interaction) inhibitors of NKG2D/NKG2DL. Rapid SAR was guided by structure-based drug design and accomplished by iterative singleton and parallel medicinal chemistry synthesis. These efforts resulted in the identification of several potent analogs (14, 21, 30, 45) with functional activity and improved LLE.
    MeSH term(s) Humans ; NK Cell Lectin-Like Receptor Subfamily K/metabolism ; Carrier Proteins/metabolism ; Histocompatibility Antigens Class I/metabolism ; Protein Binding ; Killer Cells, Natural/metabolism ; Ligands
    Chemical Substances NK Cell Lectin-Like Receptor Subfamily K ; Carrier Proteins ; Histocompatibility Antigens Class I ; Ligands
    Language English
    Publishing date 2023-09-29
    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.2023.129492
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    Zs.A 3203: Show issues Location:
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  4. Article: Total synthesis of atrochamins F, H, I, and J through cascade reactions.

    Nicolaou, K C / Lister, Troy / Denton, Ross M / Gelin, Christine F

    Tetrahedron

    2009  Volume 64, Issue 21, Page(s) 4736–4757

    Abstract: A concise and efficient cascade-based total synthesis of artochamins F, H, I, and J is described. The potential biogenetic connection between artochamin F, or a derivative thereof, and artochamins H, I, and J, through an unusual formal [2+2] ... ...

    Abstract A concise and efficient cascade-based total synthesis of artochamins F, H, I, and J is described. The potential biogenetic connection between artochamin F, or a derivative thereof, and artochamins H, I, and J, through an unusual formal [2+2] cycloaddition process, was shown to be feasible. An alternative mechanism for this transformation is also proposed.
    Language English
    Publishing date 2009-05-20
    Publishing country England
    Document type Journal Article
    ZDB-ID 204285-x
    ISSN 1464-5416 ; 0040-4020 ; 0563-2064
    ISSN (online) 1464-5416
    ISSN 0040-4020 ; 0563-2064
    DOI 10.1016/j.tet.2008.02.108
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  5. Article ; Online: Identification of small-molecule protein-protein interaction inhibitors for NKG2D.

    Thompson, Aaron A / Harbut, Michael B / Kung, Pei-Pei / Karpowich, Nathan K / Branson, Jeffrey D / Grant, Joanna C / Hagan, Deborah / Pascual, Heather A / Bai, Guoyun / Zavareh, Reza Beheshti / Coate, Heather R / Collins, Bernard C / Côte, Marjorie / Gelin, Christine F / Damm-Ganamet, Kelly L / Gholami, Hadi / Huff, Adam R / Limon, Luis / Lumb, Kevin J /
    Mak, Puiying A / Nakafuku, Kohki M / Price, Edmund V / Shih, Amy Y / Tootoonchi, Mandana / Vellore, Nadeem A / Wang, Jocelyn / Wei, Na / Ziff, Jeannie / Berger, Scott B / Edwards, James P / Gardet, Agnès / Sun, Siquan / Towne, Jennifer E / Venable, Jennifer D / Shi, Zhicai / Venkatesan, Hariharan / Rives, Marie-Laure / Sharma, Sujata / Shireman, Brock T / Allen, Samantha J

    Proceedings of the National Academy of Sciences of the United States of America

    2023  Volume 120, Issue 18, Page(s) e2216342120

    Abstract: NKG2D (natural-killer group 2, member D) is a homodimeric transmembrane receptor that plays an important role in NK, ... ...

    Abstract NKG2D (natural-killer group 2, member D) is a homodimeric transmembrane receptor that plays an important role in NK, γδ
    MeSH term(s) Killer Cells, Natural ; NK Cell Lectin-Like Receptor Subfamily K ; Ligands ; CD8-Positive T-Lymphocytes ; Protein Binding
    Chemical Substances NK Cell Lectin-Like Receptor Subfamily K ; Ligands
    Language English
    Publishing date 2023-04-25
    Publishing country United States
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 209104-5
    ISSN 1091-6490 ; 0027-8424
    ISSN (online) 1091-6490
    ISSN 0027-8424
    DOI 10.1073/pnas.2216342120
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    Zs.A 1148: Show issues Location:
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  6. Article: Cascade reactions involving formal [2+2] thermal cycloadditions: total synthesis of artochamins F, H, I, and J.

    Nicolaou, K C / Lister, Troy / Denton, Ross M / Gelin, Christine F

    Angewandte Chemie (International ed. in English)

    2007  Volume 46, Issue 39, Page(s) 7501–7505

    MeSH term(s) Benzopyrans/chemical synthesis ; Benzopyrans/chemistry ; Catechols/chemical synthesis ; Catechols/chemistry ; Microwaves ; Models, Molecular ; Molecular Structure ; Organic Chemicals/chemical synthesis ; Organic Chemicals/chemistry ; Polycyclic Compounds/chemical synthesis ; Polycyclic Compounds/chemistry ; Stilbenes/chemical synthesis ; Stilbenes/chemistry ; Temperature
    Chemical Substances Benzopyrans ; Catechols ; Organic Chemicals ; Polycyclic Compounds ; Stilbenes ; artochamin F ; artochamin H ; artochamin I ; artochamin J
    Language English
    Publishing date 2007
    Publishing country Germany
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.200702363
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  7. Article ; Online: Synthesis of the QRSTU domain of maitotoxin and its 85-epi- and 86-epi-diastereoisomers.

    Nicolaou, K C / Gelin, Christine F / Seo, Jae Hong / Huang, Zhihong / Umezawa, Taiki

    Journal of the American Chemical Society

    2010  Volume 132, Issue 28, Page(s) 9900–9907

    Abstract: A devised synthetic strategy toward the QRSTU ring system 4 of the marine-derived biotoxin maitotoxin (1) delivered, in addition to 4, its diastereoisomers 85-epi-QRSTU and 86-epi-QRSTU ring systems 5 and 6. The convergent route to these maitotoxin ... ...

    Abstract A devised synthetic strategy toward the QRSTU ring system 4 of the marine-derived biotoxin maitotoxin (1) delivered, in addition to 4, its diastereoisomers 85-epi-QRSTU and 86-epi-QRSTU ring systems 5 and 6. The convergent route to these maitotoxin fragments involved coupling of UT and Q building blocks 9 (obtained from 2-deoxy-D-ribose) and 10 (obtained from D-ribose) followed by ring-closing metathesis to afford enol ether 8, whose elaboration to the targeted QRSTU ring system 4 required its conversion to hydroxy ketone 7. The latter compound (7) was transformed to the final product through a hydroxy dithioketal cyclization, followed by oxidation/methylation of the resulting O,S-mixed ketal to install the last of the five methyl groups contained within the target molecule (4). (13)C NMR spectroscopic analysis of synthesized fragments 4, 5, and 6 and comparisons with maitotoxin provided strong support for the originally assigned structure of the QRSTU domain of the natural product.
    MeSH term(s) Cyclization ; Magnetic Resonance Spectroscopy ; Marine Toxins/chemical synthesis ; Marine Toxins/chemistry ; Oxocins/chemical synthesis ; Oxocins/chemistry ; Stereoisomerism
    Chemical Substances Marine Toxins ; Oxocins ; maitotoxin (9P59GES78D)
    Language English
    Publishing date 2010-07-27
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/ja103708j
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  8. Article: Cascade Reactions Involving Formal [2+2] Thermal Cycloadditions: Total Synthesis of Artochamins F, H, I, and J

    Nicolaou, K.C / Lister, Troy / Denton, Ross M / Gelin, Christine F

    Angewandte Chemie. 2007 Oct. 01, v. 46, no. 39

    2007  

    Language English
    Dates of publication 2007-1001
    Size p. 7501-7505.
    Publishing place Wiley-VCH Verlag
    Document type Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.200702363
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  9. Article ; Online: A Dipolar Cycloaddition Reaction To Access 6-Methyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridines Enables the Discovery Synthesis and Preclinical Profiling of a P2X7 Antagonist Clinical Candidate.

    Chrovian, Christa C / Soyode-Johnson, Akinola / Peterson, Alexander A / Gelin, Christine F / Deng, Xiaohu / Dvorak, Curt A / Carruthers, Nicholas I / Lord, Brian / Fraser, Ian / Aluisio, Leah / Coe, Kevin J / Scott, Brian / Koudriakova, Tatiana / Schoetens, Freddy / Sepassi, Kia / Gallacher, David J / Bhattacharya, Anindya / Letavic, Michael A

    Journal of medicinal chemistry

    2017  Volume 61, Issue 1, Page(s) 207–223

    Abstract: A single pot dipolar cycloaddition reaction/Cope elimination sequence was developed to access novel 1,4,6,7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridine P2X7 antagonists that contain a synthetically challenging chiral center. The structure-activity ... ...

    Abstract A single pot dipolar cycloaddition reaction/Cope elimination sequence was developed to access novel 1,4,6,7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridine P2X7 antagonists that contain a synthetically challenging chiral center. The structure-activity relationships of the new compounds are described. Two of these compounds, (S)-(2-fluoro-3-(trifluoromethyl)phenyl)(1-(5-fluoropyrimidin-2-yl)-6-methyl-1,4,6,7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridin-5-yl)methanone (compound 29) and (S)-(3-fluoro-2-(trifluoromethyl)pyridin-4-yl)(1-(5-fluoropyrimidin-2-yl)-6-methyl-1,4,6,7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridin-5-yl)methanone (compound 35), were found to have robust P2X7 receptor occupancy at low doses in rat with ED
    MeSH term(s) Animals ; Cycloaddition Reaction ; Dogs ; Drug Design ; Humans ; Male ; Mice ; Models, Molecular ; Molecular Conformation ; Purinergic P2X Receptor Antagonists/chemical synthesis ; Purinergic P2X Receptor Antagonists/chemistry ; Purinergic P2X Receptor Antagonists/pharmacokinetics ; Purinergic P2X Receptor Antagonists/pharmacology ; Pyridines/chemical synthesis ; Pyridines/chemistry ; Pyridines/pharmacokinetics ; Pyridines/pharmacology ; Rats ; Receptors, Purinergic P2X7/metabolism ; Stereoisomerism ; Tissue Distribution
    Chemical Substances Purinergic P2X Receptor Antagonists ; Pyridines ; Receptors, Purinergic P2X7
    Language English
    Publishing date 2017-12-20
    Publishing country United States
    Document type Journal Article
    ZDB-ID 218133-2
    ISSN 1520-4804 ; 0022-2623
    ISSN (online) 1520-4804
    ISSN 0022-2623
    DOI 10.1021/acs.jmedchem.7b01279
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    Zs.B 151: Show issues Location:
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  10. Article ; Online: Identification of a novel small molecule HIF-1alpha translation inhibitor.

    Narita, Takuhito / Yin, Shaoman / Gelin, Christine F / Moreno, Carlos S / Yepes, Manuel / Nicolaou, K C / Van Meir, Erwin G

    Clinical cancer research : an official journal of the American Association for Cancer Research

    2009  Volume 15, Issue 19, Page(s) 6128–6136

    Abstract: Purpose: Hypoxia inducible factor-1 (HIF-1), the central mediator of the cellular response to low oxygen, functions as a transcription factor for a broad range of genes that provide adaptive responses to oxygen deprivation. HIF-1 is overexpressed in ... ...

    Abstract Purpose: Hypoxia inducible factor-1 (HIF-1), the central mediator of the cellular response to low oxygen, functions as a transcription factor for a broad range of genes that provide adaptive responses to oxygen deprivation. HIF-1 is overexpressed in cancer and has become an important therapeutic target in solid tumors. In this study, a novel HIF-1alpha inhibitor was identified and its molecular mechanism was investigated.
    Experimental design: Using a HIF-responsive reporter cell-based assay, a 10,000-member natural product-like chemical compound library was screened to identify novel HIF-1 inhibitors. This led us to discover KC7F2, a lead compound with a central structure of cystamine. The effects of KC7F2 on HIF-1 transcription, translation, and protein degradation processes were analyzed.
    Results: KC7F2 markedly inhibited HIF-mediated transcription in cells derived from different tumor types, including glioma, breast, and prostate cancers, and exhibited enhanced cytotoxicity under hypoxia. KC7F2 prevented the activation of HIF-target genes such as carbonic anhydrase IX, matrix metalloproteinase 2 (MMP2), endothelin 1, and enolase 1. An investigation into the mechanism of action of KC7F2 showed that it worked through the down-regulation of HIF-1alpha protein synthesis, an effect accompanied by the suppression of the phosphorylation of eukaryotic translation initiation factor 4E binding protein 1 and p70 S6 kinase, key regulators of HIF-1alpha protein synthesis.
    Conclusion: These results show that KC7F2 is a potent HIF-1 pathway inhibitor and its potential as a cancer therapy agent warrants further study.
    MeSH term(s) Animals ; Antineoplastic Agents/isolation & purification ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/therapeutic use ; Cell Hypoxia/drug effects ; Cell Hypoxia/physiology ; Cell Proliferation/drug effects ; Cells, Cultured ; Disulfides/isolation & purification ; Disulfides/pharmacology ; Disulfides/therapeutic use ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor/methods ; Humans ; Hypoxia-Inducible Factor 1, alpha Subunit/antagonists & inhibitors ; Hypoxia-Inducible Factor 1, alpha Subunit/metabolism ; Mice ; Models, Biological ; Neoplasms/drug therapy ; Neoplasms/pathology ; Oxygen/pharmacology ; Protein Biosynthesis/drug effects ; Protein Processing, Post-Translational/drug effects ; Small Molecule Libraries/analysis ; Sulfonamides/isolation & purification ; Sulfonamides/pharmacology ; Sulfonamides/therapeutic use
    Chemical Substances Antineoplastic Agents ; Disulfides ; HIF1A protein, human ; Hypoxia-Inducible Factor 1, alpha Subunit ; KC7F2 compound ; Small Molecule Libraries ; Sulfonamides ; Oxygen (S88TT14065)
    Language English
    Publishing date 2009-09-29
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 1225457-5
    ISSN 1557-3265 ; 1078-0432
    ISSN (online) 1557-3265
    ISSN 1078-0432
    DOI 10.1158/1078-0432.CCR-08-3180
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