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 |
Keywords
- Azetidines
- Glycosphingolipids
- KRN7000
- NKT cell
- Pyrrolidines
- α-Galactosyl ceramides
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
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Cite this
Fuhshuku, K. I., Hongo, N., Tashiro, T., Masuda, Y., Nakagawa, R., Seino, K. I., Taniguchi, M., & Mori, K. (2008). 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. Bioorganic and Medicinal Chemistry, 16(2), 950-964. https://doi.org/10.1016/j.bmc.2007.10.008