Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH

G Velmourougane; R Raju; G Bricard; JS Im; Gurdyal Besra; SA Porcelli; AR Howell

doi:10.1016/j.bmcl.2009.05.042

Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH

G Velmourougane, R Raju, G Bricard, JS Im, Gurdyal Besra, SA Porcelli, AR Howell

Biosciences

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15 Citations (Scopus)

Abstract

An alpha-galactosyl ceramide (alpha-GalCer) 2 was synthesized and evaluated for its ability to stimulate iNKTcell proliferation and elicit T-helper cytokines, IL-4 and IFN gamma. Compound 2 combines the acyl chain of the potent, Th2 biasing alpha-GalCer 1 with a sphingoid base of the same length as that found in OCH, which also exhibits Th2 skewing, Such complementation may enhance cytokine bias, which is thought to be important for therapeutic applications of iNKT cell stimulation. Two related alpha-GalCers, 3 and 4, with saturated acyl chains were prepared for comparison. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3386-3388
Number of pages	3
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	19
Issue number	13
DOIs	https://doi.org/10.1016/j.bmcl.2009.05.042
Publication status	Published - 1 Jul 2009

Keywords

iNKT cell stimulation
Glycolipids
Alpha-galactosyl ceramides
CD1d

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10.1016/j.bmcl.2009.05.042

Modulation of Immune Responses by aGalCer Analogues Through Differential Activation of CD1d-restricted NKT Cells
Besra, D. & Lammas, T.
Medical Research Council
1/06/05 → 30/11/09
Project: Research Councils

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title = "Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH",

abstract = "An alpha-galactosyl ceramide (alpha-GalCer) 2 was synthesized and evaluated for its ability to stimulate iNKTcell proliferation and elicit T-helper cytokines, IL-4 and IFN gamma. Compound 2 combines the acyl chain of the potent, Th2 biasing alpha-GalCer 1 with a sphingoid base of the same length as that found in OCH, which also exhibits Th2 skewing, Such complementation may enhance cytokine bias, which is thought to be important for therapeutic applications of iNKT cell stimulation. Two related alpha-GalCers, 3 and 4, with saturated acyl chains were prepared for comparison. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "iNKT cell stimulation, Glycolipids, Alpha-galactosyl ceramides, CD1d",

author = "G Velmourougane and R Raju and G Bricard and JS Im and Gurdyal Besra and SA Porcelli and AR Howell",

year = "2009",

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doi = "10.1016/j.bmcl.2009.05.042",

language = "English",

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journal = "Bioorganic & Medicinal Chemistry Letters",

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T1 - Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH

AU - Velmourougane, G

AU - Raju, R

AU - Bricard, G

AU - Im, JS

AU - Besra, Gurdyal

AU - Porcelli, SA

AU - Howell, AR

PY - 2009/7/1

Y1 - 2009/7/1

N2 - An alpha-galactosyl ceramide (alpha-GalCer) 2 was synthesized and evaluated for its ability to stimulate iNKTcell proliferation and elicit T-helper cytokines, IL-4 and IFN gamma. Compound 2 combines the acyl chain of the potent, Th2 biasing alpha-GalCer 1 with a sphingoid base of the same length as that found in OCH, which also exhibits Th2 skewing, Such complementation may enhance cytokine bias, which is thought to be important for therapeutic applications of iNKT cell stimulation. Two related alpha-GalCers, 3 and 4, with saturated acyl chains were prepared for comparison. (C) 2009 Elsevier Ltd. All rights reserved.

AB - An alpha-galactosyl ceramide (alpha-GalCer) 2 was synthesized and evaluated for its ability to stimulate iNKTcell proliferation and elicit T-helper cytokines, IL-4 and IFN gamma. Compound 2 combines the acyl chain of the potent, Th2 biasing alpha-GalCer 1 with a sphingoid base of the same length as that found in OCH, which also exhibits Th2 skewing, Such complementation may enhance cytokine bias, which is thought to be important for therapeutic applications of iNKT cell stimulation. Two related alpha-GalCers, 3 and 4, with saturated acyl chains were prepared for comparison. (C) 2009 Elsevier Ltd. All rights reserved.

KW - iNKT cell stimulation

KW - Glycolipids

KW - Alpha-galactosyl ceramides

KW - CD1d

U2 - 10.1016/j.bmcl.2009.05.042

DO - 10.1016/j.bmcl.2009.05.042

M3 - Article

C2 - 19481452

VL - 19

SP - 3386

EP - 3388

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 13

ER -

Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH

Abstract

Keywords

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Modulation of Immune Responses by aGalCer Analogues Through Differential Activation of CD1d-restricted NKT Cells

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