Abstract
Conformationally restricted analogues of KRN7000, an α-d-galactosyl ceramide, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells to produce cytokines. RCAI-8, 9, 51, and 52 are the analogues with a pyrrolidine ring, and RCAI-18, 19, 49, and 50 are those with an azetidine ring. RCAI-18 was shown to be a potent inducer of cytokine production by mouse NKT cells, while RCAI-51 was a moderately active inducer.
| Original language | English |
|---|---|
| Pages (from-to) | 950-964 |
| Number of pages | 15 |
| Journal | Bioorganic and Medicinal Chemistry |
| Volume | 16 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2008 Jan 15 |
| Externally published | Yes |
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Keywords
- α-Galactosyl ceramides
- Azetidines
- Glycosphingolipids
- KRN7000
- NKT cell
- Pyrrolidines
ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry
- Drug Discovery
- Pharmaceutical Science
Cite this
RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring : Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines. / Fuhshuku, Ken ichi; Hongo, Naomi; Tashiro, Takuya; Masuda, Yui; Nakagawa, Ryusuke; Seino, Ken ichiro; Taniguchi, Masaru; Mori, Kenji.
In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 2, 15.01.2008, p. 950-964.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring
T2 - Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines
AU - Fuhshuku, Ken ichi
AU - Hongo, Naomi
AU - Tashiro, Takuya
AU - Masuda, Yui
AU - Nakagawa, Ryusuke
AU - Seino, Ken ichiro
AU - Taniguchi, Masaru
AU - Mori, Kenji
PY - 2008/1/15
Y1 - 2008/1/15
N2 - Conformationally restricted analogues of KRN7000, an α-d-galactosyl ceramide, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells to produce cytokines. RCAI-8, 9, 51, and 52 are the analogues with a pyrrolidine ring, and RCAI-18, 19, 49, and 50 are those with an azetidine ring. RCAI-18 was shown to be a potent inducer of cytokine production by mouse NKT cells, while RCAI-51 was a moderately active inducer.
AB - Conformationally restricted analogues of KRN7000, an α-d-galactosyl ceramide, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells to produce cytokines. RCAI-8, 9, 51, and 52 are the analogues with a pyrrolidine ring, and RCAI-18, 19, 49, and 50 are those with an azetidine ring. RCAI-18 was shown to be a potent inducer of cytokine production by mouse NKT cells, while RCAI-51 was a moderately active inducer.
KW - α-Galactosyl ceramides
KW - Azetidines
KW - Glycosphingolipids
KW - KRN7000
KW - NKT cell
KW - Pyrrolidines
UR - http://www.scopus.com/inward/record.url?scp=38549147057&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=38549147057&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2007.10.008
DO - 10.1016/j.bmc.2007.10.008
M3 - Article
C2 - 17950609
AN - SCOPUS:38549147057
VL - 16
SP - 950
EP - 964
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 2
ER -