Synthesis and biological evaluation of neoglycosphingolipids

• DOI: 10.1016/j.ejmech.2017.04.006
• Publication Date: 2017-04-05T06:46:24Z
• Authors: Shuihong Cheng; Peixing Wu; Jing Han; Yiren Wang; Yuting Cui; Zhenxing Zhang; Tatsuya Yamagata; Xuebing Li
• Keywords: Mice; Matrix Metalloproteinase 9; Cell Line, Tumor; Melanoma, Experimental; Animals; Antineoplastic Agents; 01 natural sciences; Glycosphingolipids; Up-Regulation; 0104 chemical sciences; 3. Good health

Various neoglycosphingolipids were efficiently synthesized in a one-step reaction by the coupling of free sugars with an N-alkylaminooxy-functionalized ceramide analogue. The bioactivity studies demonstrated that most of these compounds could upregulate the expression of matrix metalloproteinase-9 (MMP-9, extracellular matrix proteins associated with tumor migration) in murine melanoma B16 cells in a similar manner to the natural ganglioside monosialodihexosylganglioside (GM3), which highlights the potential use of these neoglycosphingolipids as inhibitors of tumor migration.