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Literature DB >> 20061147

Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.

Jeong-Ju Park¹, Ji Hyung Lee, Kyung-Chang Seo, Gabriel Bricard, Manjunatha M Venkataswamy, Steven A Porcelli, Sung-Kee Chung.

Abstract

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release a broad range of bioactive cytokines. In an effort to understand the structure-activity relationships, we have carried out syntheses of 26 new KRN7000 analogues incorporating aromatic residues in either or both side chains. Structural variations of the phytosphingosine moiety also include varying stereochemistry at C3 and C4, and 4-deoxy and 3,4-dideoxy versions. Their biological activities are described. Copyright (c) 2009 Elsevier Ltd. All rights reserved.

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Year: 2010 PMID： 20061147 PMCID： PMC5584937 DOI： 10.1016/j.bmcl.2009.12.103

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

36 in total

Review 1. Toward an understanding of NKT cell biology: progress and paradoxes.

Authors: Mitchell Kronenberg
Journal: Annu Rev Immunol Date: 2005 Impact factor: 28.527

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

3. Antitumor effect of alpha-galactosylceramide (KRN7000) on spontaneous hepatic metastases requires endogenous interleukin 12 in the liver.

Authors: N Fuji; Y Ueda; H Fujiwara; T Toh; T Yoshimura; H Yamagishi
Journal: Clin Cancer Res Date: 2000-08 Impact factor: 12.531

4. Synthesis and NKT cell stimulating properties of fluorophore- and biotin-appended 6"-amino-6"-deoxy-galactosylceramides.

Authors: Xiao-Ti Zhou; Claire Forestier; Randal D Goff; Chunhong Li; Luc Teyton; Albert Bendelac; Paul B Savage
Journal: Org Lett Date: 2002-04-18 Impact factor: 6.005

5. 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

6. 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

7. Invariant TCR rather than CD1d shapes the preferential activities of C-glycoside analogues against human versus murine invariant NKT cells.

Authors: Xiangming Li; Takayuki Shiratsuchi; Guangwu Chen; Paolo Dellabona; Giulia Casorati; Richard W Franck; Moriya Tsuji
Journal: J Immunol Date: 2009-09-04 Impact factor: 5.422

8. The T cell antigen receptor expressed by Valpha14i NKT cells has a unique mode of glycosphingolipid antigen recognition.

Authors: Stéphane Sidobre; Kirsten J L Hammond; Lise Bénazet-Sidobre; Sergei D Maltsev; Stewart K Richardson; Rachel M Ndonye; Amy R Howell; Teruyuki Sakai; Gurdyal S Besra; Steven A Porcelli; Mitchell Kronenberg
Journal: Proc Natl Acad Sci U S A Date: 2004-08-10 Impact factor: 11.205

Review 9. A closer look at CD1d molecules: new horizons in studying NKT cells.

Authors: Victoria S Stronge; Mariolina Salio; E Yvonne Jones; Vincenzo Cerundolo
Journal: Trends Immunol Date: 2007-09-07 Impact factor: 16.687

10. CD1-restricted NK T cells protect nonobese diabetic mice from developing diabetes.

Authors: B Wang; Y B Geng; C R Wang
Journal: J Exp Med Date: 2001-08-06 Impact factor: 14.307

9 in total

1. Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Authors: Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal: J Org Chem Date: 2011-10-04 Impact factor: 4.354

9. New Paradigm in NKT Cell Antigens: MCS-0208 (2-(Hydroxymethyl)phenylthio-phytoceramide) - an Aryl-Phytoceramide Compound with a Single Hydroxyl Group Stimulates NKT Cells.

Authors: Roser Borràs-Tudurí; Anna Alcaide; Sandrine Aspeslag; Lorena Usero; Carmen Serra; Carme Roura-Mir; Dirk Elewaut; Amadeu Llebaria
Journal: ChemMedChem Date: 2021-06-17 Impact factor: 3.466

9 in total

Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.

Review 1. Toward an understanding of NKT cell biology: progress and paradoxes.

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

3. Antitumor effect of alpha-galactosylceramide (KRN7000) on spontaneous hepatic metastases requires endogenous interleukin 12 in the liver.

4. Synthesis and NKT cell stimulating properties of fluorophore- and biotin-appended 6"-amino-6"-deoxy-galactosylceramides.

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

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

7. Invariant TCR rather than CD1d shapes the preferential activities of C-glycoside analogues against human versus murine invariant NKT cells.

8. The T cell antigen receptor expressed by Valpha14i NKT cells has a unique mode of glycosphingolipid antigen recognition.

Review 9. A closer look at CD1d molecules: new horizons in studying NKT cells.

10. CD1-restricted NK T cells protect nonobese diabetic mice from developing diabetes.

1. Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Review 2. Raising the roof: the preferential pharmacological stimulation of Th1 and th2 responses mediated by NKT cells.

3. Avidity of CD1d-ligand-receptor ternary complex contributes to T-helper 1 (Th1) polarization and anticancer efficacy.

4. Synthesis and biological activities of C-glycosides of KRN 7000 with novel ceramide residues.

5. The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.

Review 6. NKT cell networks in the regulation of tumor immunity.

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

8. Anti-protease and immunomodulatory activities of bacteria associated with Caribbean sponges.

9. New Paradigm in NKT Cell Antigens: MCS-0208 (2-(Hydroxymethyl)phenylthio-phytoceramide) - an Aryl-Phytoceramide Compound with a Single Hydroxyl Group Stimulates NKT Cells.