TY - JOUR
T1 - RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage
T2 - Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines
AU - Tashiro, Takuya
AU - Hongo, Naomi
AU - Nakagawa, Ryusuke
AU - Seino, Ken ichiro
AU - Watarai, Hiroshi
AU - Ishii, Yasuyuki
AU - Taniguchi, Masaru
AU - Mori, Kenji
N1 - Funding Information:
We are grateful to Mr. H. Kamijuku (St. Marianna University School of Medicine) and Ms. Y. Nagata (RIKEN) for their preliminary contribution in bioassay. We thank Ms. K. Utsunomiya and Mr. H. Tawaragi for their technical support of this work. We also thank Mr. K. Sakai and Dr. M. Iida (both at Seikagaku Kogyo Co.) for their helpful comments. T.T. thanks Professor T. Nakata (Science University of Tokyo) for his encouragement. This work was partly supported by Grant-in Aid for Young Scientists (B) (No. 20790108) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan.
PY - 2008/10/1
Y1 - 2008/10/1
N2 - RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 (1) with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production.
AB - RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 (1) with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production.
KW - Cytokines
KW - NKT cell
KW - OCH
KW - Sulfonamide
KW - α-Galactosylceramides
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U2 - 10.1016/j.bmc.2008.08.060
DO - 10.1016/j.bmc.2008.08.060
M3 - Article
C2 - 18790646
AN - SCOPUS:52949098710
SN - 0968-0896
VL - 16
SP - 8896
EP - 8906
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 19
ER -