886034-76-0Relevant academic research and scientific papers
Synthesis and biological evaluation of α-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3)
Xia, Chengfeng,Yao, Qingjia,Schuemann, Jens,Rossy, Emmanuel,Chen, Wenlan,Zhu, Lizhi,Zhang, Wenpeng,De Libero, Gennaro,Wang, Peng George
, p. 2195 - 2199 (2007/10/03)
Glycoceramides can activate NKT cells by binding with CD1d to produce IFN-γ, IL-4, and other cytokines. An efficient synthetic pathway for α-galactosylceramide (KRN7000) was established by coupling a protected galactose donor to a properly protected ceramide. During the investigation, it was discovered that when the ceramide was protected with benzyl groups, only β-galactosylceramide was produced from the glycosylation reaction. In contrast, the ceramide with benzoyl protecting groups produced α-galactosylceramide. Isoglobotrihexosylceramide (iGb3) was prepared by glycosylation of Galα1-3Galβ1-4Glc donor with 2-azido-sphingosine in high yield. Biological assays on the synthetic KRN7000 and iGb3 were performed using human and murine iNKT cell clones or hybridomas.
Structure-activity relationship of α-galactosylceramides against b16- bearing mice
Morita,Motoki,Akimoto,Natori,Sakai,Sawa,Yamaji,Koezuka,Kobayashi,Fukushima
, p. 2176 - 2187 (2007/10/02)
Agelasphin-9b, (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-16-methyl-2-[N- ((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(α- D-galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.
