Heteroaromatic moieties in the sphingosine backbone of α- Galactosylceramides for noncovalent interactions with CD1d

Yongju Kim; Jonghoon Kim; Keunhee Oh; Dong Sup Lee; Seung Bum Park

doi:10.1021/ml200278u

Heteroaromatic moieties in the sphingosine backbone of α- Galactosylceramides for noncovalent interactions with CD1d

Yongju Kim, Jonghoon Kim, Keunhee Oh, Dong Sup Lee, Seung Bum Park

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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.

Original language	English
Pages (from-to)	151-154
Number of pages	4
Journal	ACS Medicinal Chemistry Letters
Volume	3
Issue number	2
DOIs	https://doi.org/10.1021/ml200278u
Publication status	Published - 2012 Feb 9
Externally published	Yes

Keywords

CD1d
cytokine secretion
noncovalent interaction
selectivity
α-Galactosylceramide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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AU - Kim, Yongju

AU - Kim, Jonghoon

AU - Oh, Keunhee

AU - Lee, Dong Sup

AU - Park, Seung Bum

PY - 2012/2/9

Y1 - 2012/2/9

N2 - 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.

AB - 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.

KW - CD1d

KW - cytokine secretion

KW - noncovalent interaction

KW - selectivity

KW - α-Galactosylceramide

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Heteroaromatic moieties in the sphingosine backbone of α- Galactosylceramides for noncovalent interactions with CD1d

Abstract

Keywords

ASJC Scopus subject areas

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