{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T11:06:28Z","timestamp":1791111988134,"version":"4.1.0"},"reference-count":49,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2006,9,28]],"date-time":"2006-09-28T00:00:00Z","timestamp":1159401600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2006,11,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>An \u03b1\u2010galactosylceramide (<jats:italic>\u03b1<\/jats:italic>GalCer, <jats:bold>1<\/jats:bold>) and its isosteric <jats:italic>C<\/jats:italic>\u2010glycoside analogue (<jats:bold>2<\/jats:bold>) were found to possess promising immunostimulatory activity because of their ability to activate natural killer T (NKT) cells. We report the synthesis of compound <jats:bold>3<\/jats:bold>, a truncated nonisosteric <jats:italic>C<\/jats:italic>\u2010\u03b1GalCer analogue, that like <jats:bold>2<\/jats:bold> is not enzymatically labile at the glycosidic linkage, but has the anomeric carbon directly bonded to the C1 of the phytoceramide backbone. We compared the biological activity of the three ligands using an in vitro system with human dendritic cells as the antigen\u2010presenting cells and human NKT cells as the responding cells. Although <jats:bold>3<\/jats:bold> was a less potent agonist for NKT cells than <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold>, it induced cytokine production with the highest IFN\u2010\u03b3:IL\u20104 and IFN\u2010\u03b3:IL\u201013 ratios. Therefore, our data suggest that the new mimetic of \u03b1GalCer might preferentially promote Th1\u2010immune responses and serve as a potent adjuvant in the immunotherapy of cancer and infectious diseases.<\/jats:p>","DOI":"10.1002\/cbic.200600197","type":"journal-article","created":{"date-parts":[[2006,9,28]],"date-time":"2006-09-28T10:26:54Z","timestamp":1159439214000},"page":"1750-1756","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":60,"title":["Synthesis and Evaluation of an \u03b1\u2010<i>C<\/i>\u2010Galactosylceramide Analogue that Induces Th1\u2010biased Responses in Human Natural Killer T Cells"],"prefix":"10.1002","volume":"7","author":[{"given":"Xuequan","family":"Lu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liping","family":"Song","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leonid S.","family":"Metelitsa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Bittman","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,10,26]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1172\/JCI200423594"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cub.2005.05.032"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.278.5343.1626"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1084\/jem.188.8.1521"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1084\/jem.178.1.1"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1084\/jem.180.3.1097"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.7538697"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.immunol.15.1.535"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-5699(00)01735-7"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.immunol.23.021704.115742"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/nri1531"},{"key":"e_1_2_6_12_2","first-page":"1202","volume":"58","author":"Nakagawa R.","year":"1998","journal-title":"Cancer Res."},{"key":"e_1_2_6_13_2","doi-asserted-by":"crossref","first-page":"2387","DOI":"10.4049\/jimmunol.163.5.2387","volume":"163","author":"Toura I.","year":"1999","journal-title":"J. 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