Literature DB >> 19535248

Synthesis and evaluation of 3''- and 4''-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000.

Ravinder Raju1, Bernard F Castillo, Stewart K Richardson, Meena Thakur, Ryan Severins, Mitchell Kronenberg, Amy R Howell.   

Abstract

Four 3''- and 4''-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4''-fluoro analog led to the production of significant levels of IL-2.

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Year:  2009        PMID: 19535248      PMCID: PMC2710405          DOI: 10.1016/j.bmcl.2009.06.005

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  36 in total

1.  Structure-based discovery of glycolipids for CD1d-mediated NKT cell activation: tuning the adjuvant versus immunosuppression activity.

Authors:  Masakazu Fujio; Douglass Wu; Raquel Garcia-Navarro; David D Ho; Moriya Tsuji; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

Review 2.  The biology of NKT cells.

Authors:  Albert Bendelac; Paul B Savage; Luc Teyton
Journal:  Annu Rev Immunol       Date:  2007       Impact factor: 28.527

Review 3.  Immunoregulation of autoimmunity by natural killer T cells.

Authors:  Loes Linsen; Veerle Somers; Piet Stinissen
Journal:  Hum Immunol       Date:  2006-03-31       Impact factor: 2.850

Review 4.  Harnessing NKT cells for therapeutic applications.

Authors:  V Cerundolo; M Salio
Journal:  Curr Top Microbiol Immunol       Date:  2007       Impact factor: 4.291

Review 5.  The unique role of natural killer T cells in the response to microorganisms.

Authors:  Emmanuel Tupin; Yuki Kinjo; Mitchell Kronenberg
Journal:  Nat Rev Microbiol       Date:  2007-05-08       Impact factor: 60.633

6.  Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs.

Authors:  Tetsuya Toba; Kenji Murata; Kyoko Nakanishi; Bitoku Takahashi; Naohiro Takemoto; Minako Akabane; Takashi Nakatsuka; Seiichi Imajo; Takashi Yamamura; Sachiko Miyake; Hirokazu Annoura
Journal:  Bioorg Med Chem Lett       Date:  2007-03-03       Impact factor: 2.823

7.  Germline-encoded recognition of diverse glycolipids by natural killer T cells.

Authors:  James P Scott-Browne; Jennifer L Matsuda; Thierry Mallevaey; Janice White; Natalie A Borg; James McCluskey; Jamie Rossjohn; John Kappler; Philippa Marrack; Laurent Gapin
Journal:  Nat Immunol       Date:  2007-09-09       Impact factor: 25.606

Review 8.  TCR-mediated recognition of glycolipid CD1 complexes.

Authors:  B A Sullivan; M Kronenberg
Journal:  Curr Top Microbiol Immunol       Date:  2007       Impact factor: 4.291

Review 9.  CD1-restricted T cells and tumor immunity.

Authors:  J B Swann; J M C Coquet; M J Smyth; D I Godfrey
Journal:  Curr Top Microbiol Immunol       Date:  2007       Impact factor: 4.291

10.  CD1d-lipid-antigen recognition by the semi-invariant NKT T-cell receptor.

Authors:  Natalie A Borg; Kwok S Wun; Lars Kjer-Nielsen; Matthew C J Wilce; Daniel G Pellicci; Ruide Koh; Gurdyal S Besra; Mandvi Bharadwaj; Dale I Godfrey; James McCluskey; Jamie Rossjohn
Journal:  Nature       Date:  2007-06-20       Impact factor: 49.962

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  16 in total

1.  Divergent synthetic approach to 6''-modified α-GalCer analogues.

Authors:  Nora Pauwels; Sandrine Aspeslagh; Gerd Vanhoenacker; Koen Sandra; Esther D Yu; Dirk M Zajonc; Dirk Elewaut; Bruno Linclau; Serge Van Calenbergh
Journal:  Org Biomol Chem       Date:  2011-11-01       Impact factor: 3.876

2.  Vβ2 natural killer T cell antigen receptor-mediated recognition of CD1d-glycolipid antigen.

Authors:  Onisha Patel; Daniel G Pellicci; Adam P Uldrich; Lucy C Sullivan; Mugdha Bhati; Melissa McKnight; Stewart K Richardson; Amy R Howell; Thierry Mallevaey; Jingjing Zhang; Romain Bedel; Gurdyal S Besra; Andrew G Brooks; Lars Kjer-Nielsen; James McCluskey; Steven A Porcelli; Laurent Gapin; Jamie Rossjohn; Dale I Godfrey
Journal:  Proc Natl Acad Sci U S A       Date:  2011-11-07       Impact factor: 11.205

3.  A molecular basis for the exquisite CD1d-restricted antigen specificity and functional responses of natural killer T cells.

Authors:  Kwok S Wun; Garth Cameron; Onisha Patel; Siew Siew Pang; Daniel G Pellicci; Lucy C Sullivan; Santosh Keshipeddy; Mary H Young; Adam P Uldrich; Meena S Thakur; Stewart K Richardson; Amy R Howell; Petr A Illarionov; Andrew G Brooks; Gurdyal S Besra; James McCluskey; Laurent Gapin; Steven A Porcelli; Dale I Godfrey; Jamie Rossjohn
Journal:  Immunity       Date:  2011-03-03       Impact factor: 31.745

4.  Human and mouse type I natural killer T cell antigen receptors exhibit different fine specificities for CD1d-antigen complex.

Authors:  Kwok S Wun; Fiona Ross; Onisha Patel; Gurdyal S Besra; Steven A Porcelli; Stewart K Richardson; Santosh Keshipeddy; Amy R Howell; Dale I Godfrey; Jamie Rossjohn
Journal:  J Biol Chem       Date:  2012-09-20       Impact factor: 5.157

5.  Amide-Linked C4″-Saccharide Modification of KRN7000 Provides Potent Stimulation of Human Invariant NKT Cells and Anti-Tumor Immunity in a Humanized Mouse Model.

Authors:  Noemi Alejandra Saavedra-Avila; Santosh Keshipeddy; Matthew J Guberman-Pfeffer; Ayax Pérez-Gallegos; Neeraj K Saini; Carolina Schäfer; Leandro J Carreño; José A Gascón; Steven A Porcelli; Amy R Howell
Journal:  ACS Chem Biol       Date:  2020-12-09       Impact factor: 5.100

Review 6.  Interplay between carbohydrate and lipid in recognition of glycolipid antigens by natural killer T cells.

Authors:  Bo Pei; Jose Luis Vela; Dirk Zajonc; Mitchell Kronenberg
Journal:  Ann N Y Acad Sci       Date:  2012-02-21       Impact factor: 5.691

7.  A single-domain bispecific antibody targeting CD1d and the NKT T-cell receptor induces a potent antitumor response.

Authors:  Roeland Lameris; Adam Shahine; Daniel G Pellicci; Adam P Uldrich; Stephanie Gras; Jérôme Le Nours; Richard W J Groen; Jana Vree; Scott J J Reddiex; Sergio M Quiñones-Parra; Stewart K Richardson; Amy R Howell; Sonja Zweegman; Dale I Godfrey; Tanja D de Gruijl; Jamie Rossjohn; Hans J van der Vliet
Journal:  Nat Cancer       Date:  2020-09-14

8.  Benzofuran sulfonates and small self-lipid antigens activate type II NKT cells via CD1d.

Authors:  Catarina F Almeida; Dylan G M Smith; Tan-Yun Cheng; Chris M Harpur; Elena Batleska; Catriona V Nguyen-Robertson; Tram Nguyen; Tamara Thelemann; Scott J J Reddiex; Shihan Li; Sidonia B G Eckle; Ildiko Van Rhijn; Jamie Rossjohn; Adam P Uldrich; D Branch Moody; Spencer J Williams; Daniel G Pellicci; Dale I Godfrey
Journal:  Proc Natl Acad Sci U S A       Date:  2021-08-24       Impact factor: 11.205

9.  The Vα14 invariant natural killer T cell TCR forces microbial glycolipids and CD1d into a conserved binding mode.

Authors:  Yali Li; Enrico Girardi; Jing Wang; Esther Dawen Yu; Gavin F Painter; Mitchell Kronenberg; Dirk M Zajonc
Journal:  J Exp Med       Date:  2010-10-04       Impact factor: 14.307

Review 10.  Recognition of CD1d-restricted antigens by natural killer T cells.

Authors:  Jamie Rossjohn; Daniel G Pellicci; Onisha Patel; Laurent Gapin; Dale I Godfrey
Journal:  Nat Rev Immunol       Date:  2012-11-16       Impact factor: 53.106

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