Literature DB >> 16876422

Phosphatidylinositol mannosides: synthesis and adjuvant properties of phosphatidylinositol di- and tetramannosides.

Gary D Ainge1, Natalie A Parlane, Michel Denis, Colin M Hayman, David S Larsen, Gavin F Painter.   

Abstract

Phosphatidylinositol mannosides (PIMs) isolated from mycobacteria have been identified as an important class of glycolipids with significant immune modulating properties. We present here the syntheses of phosphatidylinositol dimannoside (PIM2, 1) and phosphatidylinositol tetramannoside (PIM4, 2) and evaluate their adjuvant properties in a transgenic mouse model. The key step in the synthetic methodology for the synthesis of 2 relies on the selective glycosylation of diol 3 with mannosyl donor 11. Both synthetic PIMs were effective at enhancing IFN-gamma when given as adjuvants with a model antigen, with PIM2 being the more active. These data suggest that in this assay the PIM core structure is responsible for the observed biological activity.

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Year:  2006        PMID: 16876422     DOI: 10.1016/j.bmc.2006.07.003

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  13 in total

1.  Synthesis and Toll-like receptor 4 (TLR4) activity of phosphatidylinositol dimannoside analogues.

Authors:  Gary D Ainge; William John Martin; Benjamin J Compton; Colin M Hayman; David S Larsen; Sung-Il Yoon; Ian A Wilson; Jacquie L Harper; Gavin F Painter
Journal:  J Med Chem       Date:  2011-10-05       Impact factor: 7.446

2.  Mycobacterial phosphatidylinositol mannosides negatively regulate host Toll-like receptor 4, MyD88-dependent proinflammatory cytokines, and TRIF-dependent co-stimulatory molecule expression.

Authors:  Emilie Doz; Stéphanie Rose; Nathalie Court; Sophie Front; Virginie Vasseur; Sabine Charron; Martine Gilleron; Germain Puzo; Isabelle Fremaux; Yves Delneste; François Erard; Bernhard Ryffel; Olivier R Martin; Valerie F J Quesniaux
Journal:  J Biol Chem       Date:  2009-06-26       Impact factor: 5.157

3.  Synthesis of the C-glycoside of α-(D)-mannose-(1 → 6)-(D)-myo-inositol.

Authors:  Sunej Hans; Ahmad Altiti; David R Mootoo
Journal:  Org Biomol Chem       Date:  2013-09-25       Impact factor: 3.876

4.  Soluble CD36 ectodomain binds negatively charged diacylglycerol ligands and acts as a co-receptor for TLR2.

Authors:  Maximiliano J Jimenez-Dalmaroni; Nengming Xiao; Adam L Corper; Petra Verdino; Gary D Ainge; Dave S Larsen; Gavin F Painter; Pauline M Rudd; Raymond A Dwek; Kasper Hoebe; Bruce Beutler; Ian A Wilson
Journal:  PLoS One       Date:  2009-10-22       Impact factor: 3.240

5.  Enhanced protection against bovine tuberculosis after coadministration of Mycobacterium bovis BCG with a Mycobacterial protein vaccine-adjuvant combination but not after coadministration of adjuvant alone.

Authors:  D Neil Wedlock; Michel Denis; Gavin F Painter; Gary D Ainge; H Martin Vordermeier; R Glyn Hewinson; Bryce M Buddle
Journal:  Clin Vaccine Immunol       Date:  2008-03-12

6.  Role of phosphatidylinositol mannosides in the interaction between mycobacteria and DC-SIGN.

Authors:  Nicole N Driessen; Roy Ummels; Janneke J Maaskant; Sudagar S Gurcha; Gurdyal S Besra; Gary D Ainge; David S Larsen; Gavin F Painter; Christina M J E Vandenbroucke-Grauls; Jeroen Geurtsen; Ben J Appelmelk
Journal:  Infect Immun       Date:  2009-08-03       Impact factor: 3.441

7.  Soluble human TLR2 ectodomain binds diacylglycerol from microbial lipopeptides and glycolipids.

Authors:  Maximiliano J Jiménez-Dalmaroni; Catherine M Radcliffe; David J Harvey; Mark R Wormald; Petra Verdino; Gary D Ainge; David S Larsen; Gavin F Painter; Richard Ulevitch; Bruce Beutler; Pauline M Rudd; Raymond A Dwek; Ian A Wilson
Journal:  Innate Immun       Date:  2014-03-03       Impact factor: 2.680

8.  Synthesis of a tristearoyl lipomannan via preactivation-based iterative one-pot glycosylation.

Authors:  Jian Gao; Zhongwu Guo
Journal:  J Org Chem       Date:  2013-12-03       Impact factor: 4.354

Review 9.  Chemical Synthesis of Cell Wall Constituents of Mycobacterium tuberculosis.

Authors:  Mira Holzheimer; Jeffrey Buter; Adriaan J Minnaard
Journal:  Chem Rev       Date:  2021-06-30       Impact factor: 60.622

10.  Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity.

Authors:  Pratap S Patil; Ting-Jen Rachel Cheng; Medel Manuel L Zulueta; Shih-Ting Yang; Larry S Lico; Shang-Cheng Hung
Journal:  Nat Commun       Date:  2015-06-03       Impact factor: 14.919

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