Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.
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.
Park
Jeong-Ju
JJ
Department of Chemistry, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea.
Lee
Ji Hyung
JH
Seo
Kyung-Chang
KC
Bricard
Gabriel
G
Venkataswamy
Manjunatha M
MM
Porcelli
Steven A
SA
Chung
Sung-Kee
SK
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
D005699:Galactosylceramides; D006841:Hydrocarbons, Aromatic; D018793:Interleukin-13; C103873:KRN 7000