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.
authors.affiliation: Department of Chemistry, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea.
authors.forename: Jeong-Ju
authors.initials: JJ
authors.lastname: Park
authors.forename: Ji Hyung
authors.initials: JH
authors.lastname: Lee
authors.forename: Kyung-Chang
authors.initials: KC
authors.lastname: Seo
authors.forename: Gabriel
authors.initials: G
authors.lastname: Bricard
authors.forename: Manjunatha M
authors.initials: MM
authors.lastname: Venkataswamy
authors.forename: Steven A
authors.initials: SA
authors.lastname: Porcelli
authors.forename: Sung-Kee
authors.initials: SK
authors.lastname: Chung
mesh_terms: D004305:Dose-Response Relationship, Drug; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000494:pharmacology; D018793:Interleukin-13 / Q000096:biosynthesis; D013237:Stereoisomerism
chemical_list: D005699:Galactosylceramides; D006841:Hydrocarbons, Aromatic; D018793:Interleukin-13; C103873:KRN 7000