- RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines
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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 8
- Tashiro, Takuya,Hongo, Naomi,Nakagawa, Ryusuke,Seino, Ken-ichiro,Watarai, Hiroshi,Ishii, Yasuyuki,Taniguchi, Masaru,Mori, Kenji
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p. 8896 - 8906
(2008/12/23)
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- Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides
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α-Galactosylceramides (α-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of α-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale.
- Tsujimoto, Takashi,Ito, Yukishige
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p. 5513 - 5516
(2008/02/10)
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- Novel synthesis of α-galactosyl-ceramides and confirmation of their powerful NKT cell agonist activity
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α-Galactosyl-ceramide (1) has been identified as a powerful modulator of immunological processes through its capacity to bind CD1d molecules and specifically activate invariant natural killer (NK)-like T cells (iNKT cells). This paper describes the synthe
- Lee, Adrianne,Farrand, Kathryn J.,Dickgreber, Nina,Hayman, Colin M.,Juers, Stefan,Hermans, Ian F.,Painter, Gavin F.
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p. 2785 - 2798
(2007/10/03)
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- GLYCOLIPID DERIVATIVES, PROCESS FOR PRODUCTION OF THE SAME, INTERMEDIATES FOR SYNTHESIS THEREOF, AND PROCESS FOR PRODUCTION OF THE INTERMEDIATES
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Novel glycolipid derivatives, where the substituent of the sphingosine base part is a short carbon chain alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group and
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Page/Page column 26; 56
(2008/06/13)
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- Total synthesis of an immunosuppressive glycolipid, (2S,3S,4R)-1-O- (α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol
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(Chemical Equation Presented) A practical and efficient total synthesis of (2S,3S,4R)-1-O-(α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol, OCH 1b, a potential therapeutic candidate for Th1-mediated autoimmune diseases, is described. The synthesis
- Murata, Kenji,Toba, Tetsuya,Nakanishi, Kyoko,Takahashi, Bitoku,Yamamura, Takashi,Miyake, Sachiko,Annoura, Hirokazu
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p. 2398 - 2401
(2007/10/03)
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- Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH
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The phytosphingosine-containing α-galactosylceramides (α-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells
- Ndonye, Rachel M.,Izmirian, Douglas P.,Dunn, Matthew F.,Yu, Karl O. A.,Porcelli, Steven A.,Khurana, Archana,Kronenberg, Mitchell,Richardson, Stewart K.,Howell, Amy R.
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p. 10260 - 10270
(2007/10/03)
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- Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes
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Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive d-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and
- Fan, Gang-Ting,Pan, Yi-Shin,Lu, Kuo-Cheng,Cheng, Yu-Pei,Lin, Wan-Chen,Lin, Steven,Lin, Chun-Hung,Wong, Chi-Huey,Fang, Jim-Min,Lin, Chun-Cheng
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p. 1855 - 1862
(2007/10/03)
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- NOVEL GLYCOLIPID AND REMEDIAL AGENT FOR AUTOIMMUNE DISEASE CONTAINING THE SAME AS ACTIVE INGREDIENT
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The objective of the invention is to present an glycolipid useful in treating autoimmune diseases and a medicine thereof as active ingredient for autoimmune diseases. That is, the present invention is provide a glycolipid represented by the formula below
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- Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells
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Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of α-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An α-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of α-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in α-galactosylceramides influences cytokine release profiles. Copyright
- Goff, Randal D.,Gao, Ying,Mattner, Jochen,Zhou, Dapeng,Yin, Ning,Cantu III, Carlos,Teyton, Luc,Bendelac, Albert,Savage, Paul B.
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p. 13602 - 13603
(2007/10/03)
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