TY - JOUR
T1 - RCAI-61 and related 6′-modified analogs of KRN7000
T2 - Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo
AU - Tashiro, Takuya
AU - Nakagawa, Ryusuke
AU - Shigeura, Tomokuni
AU - Watarai, Hiroshi
AU - Taniguchi, Masaru
AU - Mori, Kenji
N1 - Funding Information:
We thank Mrs. S. Suzuki (née Inoue, RIKEN RCAI) for her preliminary contribution. Our thanks are due to Drs. T. Nakamura and Y. Hongo (RIKEN) for HRMS analyses. We are grateful to Drs. M. Shiozaki (RIKEN RCAI) and K. Fuhshuku (Toyama Prefectural University) for their helpful comments. This work was partly supported by Mizutani Foundation for Glycoscience and Grant-in-Aid for Young Scientists (B) (No. 20790108) to T.T. from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan.
PY - 2013/6/1
Y1 - 2013/6/1
N2 - We synthesized ten new analogs of 6′-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by α-selective galactosylation of ceramide 9 with the 6-modified d-galactopyranosyl fluorides (8a-8f) or l-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6′-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-γ even at a low concentration in mice in vivo.
AB - We synthesized ten new analogs of 6′-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by α-selective galactosylation of ceramide 9 with the 6-modified d-galactopyranosyl fluorides (8a-8f) or l-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6′-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-γ even at a low concentration in mice in vivo.
KW - CD1d
KW - Cytokine
KW - KRN7000
KW - Natural killer T cell
KW - α-Galactosyl ceramide
UR - http://www.scopus.com/inward/record.url?scp=84877839252&partnerID=8YFLogxK
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U2 - 10.1016/j.bmc.2013.03.028
DO - 10.1016/j.bmc.2013.03.028
M3 - Article
C2 - 23602521
AN - SCOPUS:84877839252
SN - 0968-0896
VL - 21
SP - 3066
EP - 3079
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 11
ER -