Synthesis and biological evaluation of neoglycosphingolipids

Shuihong Cheng; Peixing Wu; Jing Han; Yiren Wang; Yuting Cui; Zhenxing Zhang; Tatsuya Yamagata; Xuebing Li

doi:10.1016/j.ejmech.2017.04.006

Synthesis and biological evaluation of neoglycosphingolipids

Eur J Med Chem. 2017 Jul 7:134:43-51. doi: 10.1016/j.ejmech.2017.04.006. Epub 2017 Apr 5.

Authors

Shuihong Cheng¹, Peixing Wu², Jing Han¹, Yiren Wang³, Yuting Cui³, Zhenxing Zhang⁴, Tatsuya Yamagata³, Xuebing Li⁵

Affiliations

¹ CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Chaoyang District, Beijing 100101, China.
² Lanzhou Institute of Animal Science and Veterinary Pharmaceutics, Chinese Academy of Agricultural Science, Lanzhou 730050, China.
³ Laboratory of Tumor Biology and Glycobiology, Shenyang Pharmaceutical University, Shenyang 110016, China.
⁴ 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.
⁵ 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.

PMID: 28399449
DOI: 10.1016/j.ejmech.2017.04.006

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.

Keywords: Anti-tumor agent; MMP-9; Neoglycosphingolipids; One-step synthesis; Stereoselective.

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Glycosphingolipids / chemical synthesis
Glycosphingolipids / chemistry*
Glycosphingolipids / pharmacology*
Matrix Metalloproteinase 9 / genetics*
Melanoma, Experimental / drug therapy*
Melanoma, Experimental / genetics
Mice
Up-Regulation / drug effects*

Substances

Antineoplastic Agents
Glycosphingolipids
Matrix Metalloproteinase 9