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  1. Article: Synthesis and Biological Evaluation of Trehalose-based Bi-aryl Derivatives as C-type Lectin Ligands.

    Rasheed, Omer K / Buhl, Cassandra / Evans, Jay T / Holley, David / Ryter, Kendal T

    Tetrahedron

    2023  Volume 132

    Abstract: The identification of Mincle as the C-type lectin receptor on innate immune cells responsible for binding TDM and the realization that this receptor could be key to productive vaccines for mycobacterial infection has raised interest in the development of ...

    Abstract The identification of Mincle as the C-type lectin receptor on innate immune cells responsible for binding TDM and the realization that this receptor could be key to productive vaccines for mycobacterial infection has raised interest in the development of synthetic Mincle ligands as novel adjuvants. We recently reported on the synthesis and evaluation of Brartemicin analog UM-1024 that demonstrated Mincle agonist activity, exhibiting potent Th1/Th17 adjuvant activity that was greater than that of trehalose dibehenate (TDB). Our pursuit to understand Mincle/ligand relationships and improve the pharmacologic properties of the ligands has expanded and continues to reveal new and exciting structure activity relationships. Herein we report the synthesis of novel bi-aryl trehalose derivatives in good to excellent yields. These compounds were evaluated for their ability to engage the human Mincle receptor and tested for the induction of cytokines from human peripheral blood mononuclear cells. A preliminary structure-activity relationship (SAR) of these novel bi-aryl derivatives revealed that bi-aryl trehalose ligand
    Language English
    Publishing date 2023-01-09
    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.2022.133241
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Corrigendum: Design of Trehalose-Based Amide/Sulfonamide C-type Lectin Receptor Signaling Compounds.

    Rasheed, Omer K / Buhl, Cassandra / Evans, Jay T / Ryter, Kendal T

    ChemMedChem

    2021  Volume 17, Issue 10, Page(s) e202100376

    Language English
    Publishing date 2021-06-14
    Publishing country Germany
    Document type Published Erratum
    ZDB-ID 2218496-X
    ISSN 1860-7187 ; 1860-7179
    ISSN (online) 1860-7187
    ISSN 1860-7179
    DOI 10.1002/cmdc.202100376
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Design of Trehalose-Based Amide/Sulfonamide C-type Lectin Receptor Signaling Compounds.

    Rasheed, Omer K / Buhl, Cassandra / Evans, Jay T / Ryter, Kendal T

    ChemMedChem

    2021  Volume 16, Issue 8, Page(s) 1246–1251

    Abstract: Mincle agonists have been shown to induce inflammatory cytokine production, such as tumor necrosis factor-alpha (TNF) and promote the development of a Th1/Th17 immune response that might be crucial to development of effective vaccination against ... ...

    Abstract Mincle agonists have been shown to induce inflammatory cytokine production, such as tumor necrosis factor-alpha (TNF) and promote the development of a Th1/Th17 immune response that might be crucial to development of effective vaccination against pathogens such as Mycobacterium tuberculosis. As an expansion of our previous work, a library of 6,6'-amide and sulfonamide α,α-d-trehalose compounds with various substituents on the aromatic ring was synthesized efficiently in good to excellent yields. These compounds were evaluated for their ability to activate the human C-type lectin receptor Mincle by the induction of cytokines from human peripheral blood mononuclear cells. A preliminary structure-activity relationship (SAR) of these novel trehalose diamides and sulfonamides revealed that aryl amide-linked trehalose compounds demonstrated improved activity and relatively high potency cytokine production compared to the Mincle ligand trehalose dibehenate adjuvant (TDB) and the natural ligand trehalose dimycolate (TDM) inducing dose-dependent and human-Mincle-specific stimulation in a HEK reporter cell line.
    MeSH term(s) Adjuvants, Immunologic/chemical synthesis ; Adjuvants, Immunologic/pharmacology ; HEK293 Cells ; Humans ; Interleukin-1beta/metabolism ; Interleukin-6/metabolism ; Lectins, C-Type/agonists ; Receptors, Immunologic/agonists ; Small Molecule Libraries/chemical synthesis ; Small Molecule Libraries/pharmacology ; Sulfonamides/chemical synthesis ; Sulfonamides/pharmacology ; Trehalose/analogs & derivatives ; Trehalose/pharmacology ; Tumor Necrosis Factor-alpha/metabolism
    Chemical Substances Adjuvants, Immunologic ; CLEC4D protein, human ; IL1B protein, human ; IL6 protein, human ; Interleukin-1beta ; Interleukin-6 ; Lectins, C-Type ; Receptors, Immunologic ; Small Molecule Libraries ; Sulfonamides ; Tumor Necrosis Factor-alpha ; Trehalose (B8WCK70T7I)
    Language English
    Publishing date 2021-02-09
    Publishing country Germany
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 2218496-X
    ISSN 1860-7187 ; 1860-7179
    ISSN (online) 1860-7187
    ISSN 1860-7179
    DOI 10.1002/cmdc.202000775
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: 6,6'-Aryl trehalose analogs as potential Mincle ligands.

    Rasheed, Omer K / Ettenger, George / Buhl, Cassandra / Child, Robert / Miller, Shannon M / Evans, Jay T / Ryter, Kendal T

    Bioorganic & medicinal chemistry

    2020  Volume 28, Issue 14, Page(s) 115564

    Abstract: 6,6'-Aryl trehalose derivatives have been synthesized with a view towards identifying novel Th-17-inducing vaccine adjuvants based on the high affinity Mincle ligand Brartemicin. The initial structure-activity relationships of these novel trehalose-based ...

    Abstract 6,6'-Aryl trehalose derivatives have been synthesized with a view towards identifying novel Th-17-inducing vaccine adjuvants based on the high affinity Mincle ligand Brartemicin. The initial structure-activity relationships of these novel trehalose-based compounds were investigated. All compounds have been evaluated for their ability to engage the Mincle receptor and induce a potential pro-Th17 cytokine profile from human peripheral blood mononuclear cells based on IL-6 production in human peripheral blood mononuclear cells. The preliminary biological characterization of the designed analogs presented in this paper should aid in the future design and testing of more affine ligands that may foster the discovery of novel adjuvants with improved pharmacological properties.
    MeSH term(s) Dose-Response Relationship, Drug ; Humans ; Lectins, C-Type/metabolism ; Leukocytes, Mononuclear/drug effects ; Leukocytes, Mononuclear/metabolism ; Ligands ; Molecular Structure ; Receptors, Immunologic/metabolism ; Structure-Activity Relationship ; Trehalose/analogs & derivatives ; Trehalose/chemistry ; Trehalose/pharmacology
    Chemical Substances CLEC4D protein, human ; Lectins, C-Type ; Ligands ; Receptors, Immunologic ; Trehalose (B8WCK70T7I)
    Language English
    Publishing date 2020-05-31
    Publishing country England
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 1161284-8
    ISSN 1464-3391 ; 0968-0896
    ISSN (online) 1464-3391
    ISSN 0968-0896
    DOI 10.1016/j.bmc.2020.115564
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Species-Specific Structural Requirements of Alpha-Branched Trehalose Diester Mincle Agonists.

    Smith, Alyson J / Miller, Shannon M / Buhl, Cassandra / Child, Robert / Whitacre, Margaret / Schoener, Roman / Ettenger, George / Burkhart, David / Ryter, Kendal / Evans, Jay T

    Frontiers in immunology

    2019  Volume 10, Page(s) 338

    Abstract: Despite the ever present need for an ... ...

    Abstract Despite the ever present need for an effective
    MeSH term(s) Adjuvants, Immunologic ; Animals ; Cell Line ; Cord Factors/chemistry ; Cord Factors/immunology ; Cytokines/metabolism ; Humans ; Immunity, Cellular ; Lectins, C-Type ; Mice ; Molecular Structure ; Mycobacterium tuberculosis/immunology ; Structure-Activity Relationship ; Th17 Cells/immunology ; Th17 Cells/metabolism ; Trehalose/chemistry ; Trehalose/immunology
    Chemical Substances Adjuvants, Immunologic ; Cord Factors ; Cytokines ; Lectins, C-Type ; Trehalose (B8WCK70T7I)
    Language English
    Publishing date 2019-02-28
    Publishing country Switzerland
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 2606827-8
    ISSN 1664-3224 ; 1664-3224
    ISSN (online) 1664-3224
    ISSN 1664-3224
    DOI 10.3389/fimmu.2019.00338
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Aryl Trehalose Derivatives as Vaccine Adjuvants for

    Ryter, Kendal T / Ettenger, George / Rasheed, Omer K / Buhl, Cassandra / Child, Robert / Miller, Shannon M / Holley, David / Smith, Alyson J / Evans, Jay T

    Journal of medicinal chemistry

    2019  Volume 63, Issue 1, Page(s) 309–320

    Abstract: Mycobacterium ... ...

    Abstract Mycobacterium tuberculosis
    MeSH term(s) Adjuvants, Immunologic/chemical synthesis ; Adjuvants, Immunologic/metabolism ; Adjuvants, Immunologic/therapeutic use ; Animals ; Binding Sites ; Cattle ; Cell Line ; Female ; Humans ; Lectins, C-Type/agonists ; Lectins, C-Type/metabolism ; Mice, Inbred BALB C ; Molecular Docking Simulation ; Molecular Structure ; Mycobacterium tuberculosis/drug effects ; Receptors, Immunologic/agonists ; Receptors, Immunologic/metabolism ; Structure-Activity Relationship ; Trehalose/analogs & derivatives ; Trehalose/chemical synthesis ; Trehalose/metabolism ; Trehalose/therapeutic use ; Tuberculosis/therapy ; Tuberculosis Vaccines/therapeutic use
    Chemical Substances Adjuvants, Immunologic ; CLEC4D protein, human ; Lectins, C-Type ; Receptors, Immunologic ; Tuberculosis Vaccines ; brartemicin ; Trehalose (B8WCK70T7I)
    Language English
    Publishing date 2019-12-20
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 218133-2
    ISSN 1520-4804 ; 0022-2623
    ISSN (online) 1520-4804
    ISSN 0022-2623
    DOI 10.1021/acs.jmedchem.9b01598
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: Global changes in gene expression by human polymorphonuclear leukocytes during receptor-mediated phagocytosis: cell fate is regulated at the level of gene expression.

    Kobayashi, Scott D / Voyich, Jovanka M / Buhl, Cassandra L / Stahl, Robert M / DeLeo, Frank R

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

    2002  Volume 99, Issue 10, Page(s) 6901–6906

    Abstract: Phagocytes are a critical component of the innate immune response in humans and eliminate invading microorganisms through a process known as phagocytosis. Two distinct receptor-linked phagocytic pathways, one with Ab receptors (FcRs; FcR, Fc receptor) ... ...

    Abstract Phagocytes are a critical component of the innate immune response in humans and eliminate invading microorganisms through a process known as phagocytosis. Two distinct receptor-linked phagocytic pathways, one with Ab receptors (FcRs; FcR, Fc receptor) and the other complement receptors (CRs), mediate binding and ingestion of pathogens by human polymorphonuclear leukocytes (PMNs). Although progress has been made toward defining complex signal transduction processes that underlie phagocytosis in each pathway, very little is known about gene regulation during or after phagocytosis. Therefore, we used human oligonucleotide microarrays to identify changes in expression of 12,561 genes accompanying FcR- and CR-mediated phagocytosis. Eighty-four percent of 279 differentially expressed genes were induced or repressed 90 min after ingestion of Ab- and/or complement-opsonized particles. Unexpectedly, more than 30 of these genes encoded proteins involved in at least three distinct apoptotic pathways. Ninety-four differentially expressed cell fate-related genes were identified between 180 and 360 min after phagocytosis and most were induced or repressed by PMNs activated through both receptors simultaneously. By using flow cytometry, we found that FcR- and CR-mediated phagocytosis each promoted programmed cell death in human PMNs; however, phagocytosis mediated by the combination of FcRs and CRs induced apoptosis earlier than that by either receptor alone. Our results reveal distinct patterns of receptor-mediated gene expression that define complex inducible apoptotic pathways in activated PMNs. Most significantly, we discovered that programmed cell death is regulated at the level of gene expression. Thus, we hypothesize that gene regulation in PMNs facilitates resolution of inflammatory responses.
    MeSH term(s) Apoptosis ; Cell Differentiation ; Gene Expression ; Gene Expression Profiling ; Humans ; Neutrophils/cytology ; Neutrophils/metabolism ; Phagocytosis/genetics ; Phagocytosis/physiology ; Polymerase Chain Reaction/methods ; Receptors, Complement/metabolism ; Receptors, Fc/metabolism
    Chemical Substances Receptors, Complement ; Receptors, Fc
    Language English
    Publishing date 2002-05-14
    Publishing country United States
    Document type Journal Article
    ZDB-ID 209104-5
    ISSN 1091-6490 ; 0027-8424
    ISSN (online) 1091-6490
    ISSN 0027-8424
    DOI 10.1073/pnas.092148299
    Database MEDical Literature Analysis and Retrieval System OnLINE

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