RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines.
RCAI-84, 91, and 105-108 (1-6), the analogs of KRN7000 (A) with a ureido or a thioureido linkage instead of a carboxamido bond, were synthesized to examine their immunostimulatory activity against mouse lymphocytes. According to their bioassay, the ureido analog of KRN7000 [RCAI-105 (1)] and its 6'-O-methylated derivative [RCAI-106 (4)] induced a large amount of IFN-γ in mice in vivo. The hexadecyl ureido analog [RCAI-84 (2)] was comparable to KRN7000 in its bioactivity. The octylureido [RCAI-107 (3)], 5-phenylpentylureido [RCAI-108 (5)], and thioureido [RCAI-91 (6)] analogs were almost inactive.
Glycosphingolipid Synthesis Group, Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN, Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan.
Takuya
T
Tashiro
Tomokuni
T
Shigeura
Hiroshi
H
Watarai
Masaru
M
Taniguchi
Kenji
K
Mori
D000818:Animals; D016207:Cytokines / Q000378:metabolism*; D005699:Galactosylceramides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007371:Interferon-gamma / Q000378:metabolism; D018664:Interleukin-12 / Q000378:metabolism; D015847:Interleukin-4 / Q000378:metabolism; D008214:Lymphocytes / Q000187:drug effects / Q000276:immunology / Q000378:metabolism*; D051379:Mice; D008810:Mice, Inbred C57BL; D018417:Th1 Cells / Q000187:drug effects / Q000276:immunology / Q000378:metabolism*
D016207:Cytokines; D005699:Galactosylceramides; D018664:Interleukin-12; D015847:Interleukin-4; D007371:Interferon-gamma; C103873:KRN 7000