Literature DB >> 24900444

Heteroaromatic Moieties in the Sphingosine Backbone of α-Galactosylceramides for Noncovalent Interactions with CD1d.

Yongju Kim1, Jonghoon Kim1, Keunhee Oh2, Dong-Sup Lee2, Seung Bum Park3.   

Abstract

A series of α-GalCer analogues containing heterocyclic and aromatic moieties in the sphingosine backbone were synthesized to improve the selectivity in the Th1/Th2 cytokine profile via noncovalent interaction with three aromatic residues at the binding pocket of CD1d. In vitro and in vivo biological evaluations revealed the treatment of α-GalCer analogue (6) induced the selective stimulation of natural killer T cells to facilitate the secretion of Th2 cytokines.

Entities:  

Keywords:  CD1d; cytokine secretion; noncovalent interaction; selectivity; α-Galactosylceramide

Year:  2012        PMID： 24900444      PMCID： PMC4025800          DOI： 10.1021/ml200278u

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  25 in total

1.  Crystal structure of mouse CD1d bound to the self ligand phosphatidylcholine: a molecular basis for NKT cell activation.

Authors:  Barbara Giabbai; Stèphane Sidobre; M D Max Crispin; Yovan Sanchez-Ruìz; Angela Bachi; Mitchell Kronenberg; Ian A Wilson; Massimo Degano
Journal:  J Immunol       Date:  2005-07-15       Impact factor: 5.422

2.  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 3.  Raising the NKT cell family.

Authors:  Dale I Godfrey; Sanda Stankovic; Alan G Baxter
Journal:  Nat Immunol       Date:  2010-02-07       Impact factor: 25.606

4.  Modulation of CD1d-restricted NKT cell responses by using N-acyl variants of alpha-galactosylceramides.

Authors:  Karl O A Yu; Jin S Im; Alberto Molano; Yves Dutronc; Petr A Illarionov; Claire Forestier; Nagatoshi Fujiwara; Isa Arias; Sachiko Miyake; Takashi Yamamura; Young-Tae Chang; Gurdyal S Besra; Steven A Porcelli
Journal:  Proc Natl Acad Sci U S A       Date:  2005-02-18       Impact factor: 11.205

5.  A phase I study of the natural killer T-cell ligand alpha-galactosylceramide (KRN7000) in patients with solid tumors.

Authors:  Giuseppe Giaccone; Cornelis J A Punt; Yoshitaka Ando; Rita Ruijter; Nobusuke Nishi; Marlies Peters; B Mary E von Blomberg; Rik J Scheper; Hans J J van der Vliet; Alfons J M van den Eertwegh; Marja Roelvink; Jos Beijnen; Heinz Zwierzina; Herbert M Pinedo
Journal:  Clin Cancer Res       Date:  2002-12       Impact factor: 12.531

6.  The crystal structure of human CD1d with and without alpha-galactosylceramide.

Authors:  Michael Koch; Victoria S Stronge; Dawn Shepherd; Stephan D Gadola; Bini Mathew; Gerd Ritter; Alan R Fersht; Gurdyal S Besra; Richard R Schmidt; E Yvonne Jones; Vincenzo Cerundolo
Journal:  Nat Immunol       Date:  2005-07-10       Impact factor: 25.606

7.  A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells.

Authors:  K Miyamoto; S Miyake; T Yamamura
Journal:  Nature       Date:  2001-10-04       Impact factor: 49.962

8.  Efficient synthesis of alpha-galactosyl ceramide analogues using glycosyl iodide donors.

Authors:  Wenjun Du; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

9.  Differential recognition of CD1d-alpha-galactosyl ceramide by the V beta 8.2 and V beta 7 semi-invariant NKT T cell receptors.

Authors:  Daniel G Pellicci; Onisha Patel; Lars Kjer-Nielsen; Siew Siew Pang; Lucy C Sullivan; Konstantinos Kyparissoudis; Andrew G Brooks; Hugh H Reid; Stephanie Gras; Isabelle S Lucet; Ruide Koh; Mark J Smyth; Thierry Mallevaey; Jennifer L Matsuda; Laurent Gapin; James McCluskey; Dale I Godfrey; Jamie Rossjohn
Journal:  Immunity       Date:  2009-07-17       Impact factor: 31.745

10.  The length of lipids bound to human CD1d molecules modulates the affinity of NKT cell TCR and the threshold of NKT cell activation.

Authors:  Corinna McCarthy; Dawn Shepherd; Sebastian Fleire; Victoria S Stronge; Michael Koch; Petr A Illarionov; Giovanna Bossi; Mariolina Salio; Galit Denkberg; Faye Reddington; Andrea Tarlton; B Gopal Reddy; Richard R Schmidt; Yoram Reiter; Gillian M Griffiths; P Anton van der Merwe; Gurdyal S Besra; E Yvonne Jones; Facundo D Batista; Vincenzo Cerundolo
Journal:  J Exp Med       Date:  2007-05-07       Impact factor: 14.307
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  4 in total

1.  Synthesis and Biological Activities of 5-Thio-α-GalCers.

Authors:  Jingjing Bi; Jing Wang; Kai Zhou; Yuancheng Wang; Min Fang; Yuguo Du
Journal:  ACS Med Chem Lett       Date:  2015-02-11       Impact factor: 4.345

2.  Development of α-GalCer Analogues with an α-Fluorocarbonyl Moiety as Th2-Selective Ligands of CD1d.

Authors:  Hyunsoo Kim; Heebum Song; Jun-Gyu Park; Dong-Sup Lee; Seung Bum Park
Journal:  ACS Med Chem Lett       Date:  2019-04-24       Impact factor: 4.345

3.  Galactosylsphingamides: new α-GalCer analogues to probe the F'-pocket of CD1d.

Authors:  Joren Guillaume; Jing Wang; Jonas Janssens; Soumya G Remesh; Martijn D P Risseeuw; Tine Decruy; Mathy Froeyen; Dirk Elewaut; Dirk M Zajonc; Serge Van Calenbergh
Journal:  Sci Rep       Date:  2017-06-27       Impact factor: 4.379

4.  Anti-inflammatory effects of α-galactosylceramide analogs in activated microglia: involvement of the p38 MAPK signaling pathway.

Authors:  Yeon-Hui Jeong; Yongju Kim; Heebum Song; Young Sun Chung; Seung Bum Park; Hee-Sun Kim
Journal:  PLoS One       Date:  2014-02-11       Impact factor: 3.240
  4 in total

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