Literature DB >> 23210481

Development of vizantin, a safe immunostimulant, based on the structure-activity relationship of trehalose-6,6'-dicorynomycolate.

Hirofumi Yamamoto1, Masataka Oda, Mayo Nakano, Naoyuki Watanabe, Kenta Yabiku, Masahiro Shibutani, Masahisa Inoue, Hiroshi Imagawa, Masahiro Nagahama, Seiichiro Himeno, Kojun Setsu, Jun Sakurai, Mugio Nishizawa.   

Abstract

Vizantin, 6,6'-bis-O-(3-nonyldodecanoyl)-α,α'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.

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Year:  2012        PMID: 23210481     DOI: 10.1021/jm3016443

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  9 in total

1.  MSU Crystals Enhance TDB-Mediated Inflammatory Macrophage IL-1β Secretion.

Authors:  Kanu Wahi; Kristel Kodar; Melanie J McConnell; Jacquie L Harper; Mattie S M Timmer; Bridget L Stocker
Journal:  Inflammation       Date:  2019-06       Impact factor: 4.092

2.  Aryl Trehalose Derivatives as Vaccine Adjuvants for Mycobacterium tuberculosis.

Authors:  Kendal T Ryter; George Ettenger; Omer K Rasheed; Cassandra Buhl; Robert Child; Shannon M Miller; David Holley; Alyson J Smith; Jay T Evans
Journal:  J Med Chem       Date:  2019-12-20       Impact factor: 7.446

3.  6,6'-Aryl trehalose analogs as potential Mincle ligands.

Authors:  Omer K Rasheed; George Ettenger; Cassandra Buhl; Robert Child; Shannon M Miller; Jay T Evans; Kendal T Ryter
Journal:  Bioorg Med Chem       Date:  2020-05-31       Impact factor: 3.641

4.  Design of Trehalose-Based Amide/Sulfonamide C-type Lectin Receptor Signaling Compounds.

Authors:  Omer K Rasheed; Cassandra Buhl; Jay T Evans; Kendal T Ryter
Journal:  ChemMedChem       Date:  2021-02-09       Impact factor: 3.466

5.  The natural product brartemicin is a high affinity ligand for the carbohydrate-recognition domain of the macrophage receptor mincle.

Authors:  Kristian M Jacobsen; Ulrik B Keiding; Lise L Clement; Eva S Schaffert; Neela D S Rambaruth; Mogens Johannsen; Kurt Drickamer; Thomas B Poulsen
Journal:  Medchemcomm       Date:  2015-01-07       Impact factor: 3.597

6.  Species-Specific Structural Requirements of Alpha-Branched Trehalose Diester Mincle Agonists.

Authors:  Alyson J Smith; Shannon M Miller; Cassandra Buhl; Robert Child; Margaret Whitacre; Roman Schoener; George Ettenger; David Burkhart; Kendal Ryter; Jay T Evans
Journal:  Front Immunol       Date:  2019-02-28       Impact factor: 7.561

7.  Fully synthetic Mincle-dependent self-adjuvanting cancer vaccines elicit robust humoral and T cell-dependent immune responses and protect mice from tumor development.

Authors:  Xiang Luo; Qinghai Lian; Wenwei Li; Liqing Chen; Renyu Zhang; Deying Yang; Lingqiang Gao; Xiaoxiao Qi; Zhongqiu Liu; Guochao Liao
Journal:  Chem Sci       Date:  2021-12-01       Impact factor: 9.825

Review 8.  Identification and Biological Activity of Synthetic Macrophage Inducible C-Type Lectin Ligands.

Authors:  Chriselle D Braganza; Thomas Teunissen; Mattie S M Timmer; Bridget L Stocker
Journal:  Front Immunol       Date:  2018-01-17       Impact factor: 7.561

9.  Sulfated vizantin suppresses mucin layer penetration dependent on the flagella motility of Pseudomonas aeruginosa PAO1.

Authors:  Naoki Hayashi; Yui Furue; Daichi Kai; Noriteru Yamada; Hirofumi Yamamoto; Takashi Nakano; Masataka Oda
Journal:  PLoS One       Date:  2018-11-01       Impact factor: 3.240

  9 in total

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