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

Research output: Contribution to journalArticle

25 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)814-818
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number3
DOIs
StatePublished - Feb 1 2010

Fingerprint

Stereochemistry
Bioactivity
phytosphingosine
Natural Killer T-Cells
Structure-Activity Relationship
Cytokines
Ligands
KRN 7000
Proteins

Keywords

  • CD1d
  • Glycolipids
  • KRN7000
  • NKT cell
  • α-GalCer

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Medicine(all)

Cite this

Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry. / Park, Jeong Ju; Lee, Ji Hyung; Seo, Kyung Chang; Bricard, Gabriel; Venkataswamy, Manjunatha M.; Porcelli, Steven A.; Chung, Sung Kee.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 20, No. 3, 01.02.2010, p. 814-818.

Research output: Contribution to journalArticle

Park, Jeong Ju ; Lee, Ji Hyung ; Seo, Kyung Chang ; Bricard, Gabriel ; Venkataswamy, Manjunatha M. ; Porcelli, Steven A. ; Chung, Sung Kee. / Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry. In: Bioorganic and Medicinal Chemistry Letters. 2010 ; Vol. 20, No. 3. pp. 814-818.
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