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

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

doi:10.1016/j.bmcl.2009.12.103

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

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

Microbiology & Immunology

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

26 Scopus citations

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.

Original language	English (US)
Pages (from-to)	814-818
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	3
DOIs	https://doi.org/10.1016/j.bmcl.2009.12.103
State	Published - Feb 1 2010

Keywords

CD1d
Glycolipids
KRN7000
NKT cell
α-GalCer

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2009.12.103

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title = "Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry",

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.",

keywords = "CD1d, Glycolipids, KRN7000, NKT cell, α-GalCer",

author = "Park, {Jeong Ju} and Lee, {Ji Hyung} and Seo, {Kyung Chang} and Gabriel Bricard and Venkataswamy, {Manjunatha M.} and Porcelli, {Steven A.} and Chung, {Sung Kee}",

note = "Funding Information: This work was supported by the Korea Research Foundation grant funded from the Korean Government (MOEHRD: KRF-2005-070-C00078 ), and by a grant from the NIH/NIAID ( RO1 AI45889 ). ",

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AU - Park, Jeong Ju

AU - Lee, Ji Hyung

AU - Seo, Kyung Chang

AU - Bricard, Gabriel

AU - Venkataswamy, Manjunatha M.

AU - Porcelli, Steven A.

AU - Chung, Sung Kee

N1 - Funding Information: This work was supported by the Korea Research Foundation grant funded from the Korean Government (MOEHRD: KRF-2005-070-C00078 ), and by a grant from the NIH/NIAID ( RO1 AI45889 ).

PY - 2010/2/1

Y1 - 2010/2/1

N2 - 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.

AB - 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.

KW - CD1d

KW - Glycolipids

KW - KRN7000

KW - NKT cell

KW - α-GalCer

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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