title: Synthesis and biological evaluation of neoglycosphingolipids.
abstract: 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.
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing 100101, China.
authors.forename: Shuihong
authors.initials: S
authors.lastname: Cheng
authors.affiliation: Lanzhou Institute of Animal Science and Veterinary Pharmaceutics, Chinese Academy of Agricultural Science, Lanzhou 730050, China.
authors.forename: Peixing
authors.initials: P
authors.lastname: Wu
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing 100101, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Han
authors.affiliation: Laboratory of Tumor Biology and Glycobiology, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Yiren
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Laboratory of Tumor Biology and Glycobiology, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Yuting
authors.initials: Y
authors.lastname: Cui
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing 100101, China; Savaid Medical School, University of Chinese Academy of Sciences, Huairou District, Beijing 101408, China.
authors.forename: Zhenxing
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Laboratory of Tumor Biology and Glycobiology, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Yamagata
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing 100101, China; Savaid Medical School, University of Chinese Academy of Sciences, Huairou District, Beijing 101408, China; Center for Influenza Research and Early-warning, Chinese Academy of Sciences (CASCIRE), Chaoyang District, Beijing 100101, China. Electronic address: lixb@im.ac.cn.
authors.forename: Xuebing
authors.initials: X
authors.lastname: Li
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006028:Glycosphingolipids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D020780:Matrix Metalloproteinase 9 / Q000235:genetics*; D008546:Melanoma, Experimental / Q000188:drug therapy* / Q000235:genetics; D051379:Mice; D015854:Up-Regulation / Q000187:drug effects*
chemical_list: D000970:Antineoplastic Agents; D006028:Glycosphingolipids; D020780:Matrix Metalloproteinase 9
keywords: Anti-tumor agent; MMP-9; Neoglycosphingolipids; One-step synthesis; Stereoselective