Molecular Diversity

, Volume 15, Issue 4, pp 889–900 | Cite as

Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments

  • Hai-Lin Zhang
  • Xiao-Peng He
  • Li Sheng
  • Yuan Yao
  • Wei Zhang
  • Xiao-Xin Shi
  • Jia Li
  • Guo-Rong Chen
Full-Length Paper


Series of novel 6-triazole-linked galacto- or glucolipids were efficiently synthesized from O-benzylated sugar azides and various lipid alkynes via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (click chemistry) followed by hydrogenolysis with PdCl2/H2. Subsequent MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay toward a panel of human cancer cell lines revealed that these triazologlycolipids possess low-to-modest toxicity on A549 (lung), MCF-7 (breast), HeLa (cervix), and HepG2 (liver). Furthermore, both the carbon chain length at the lipid end and the epimeric identity of the glycosyl moiety were determined to impact their corresponding bioactivity.


Glycolipid Click reaction Triazole Cytotoxicity MTT assay 


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Supplementary material

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Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  • Hai-Lin Zhang
    • 1
  • Xiao-Peng He
    • 1
    • 3
  • Li Sheng
    • 2
  • Yuan Yao
    • 1
  • Wei Zhang
    • 2
  • Xiao-Xin Shi
    • 1
  • Jia Li
    • 2
  • Guo-Rong Chen
    • 1
  1. 1.Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of PharmacyEast China University of Science and TechnologyShanghaiPeople’s Republic of China
  2. 2.National Center for Drug Screening, State Key Laboratory of Drug ResearchShanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of SciencesShanghaiPeople’s Republic of China
  3. 3.PPSM, ENS CachanCNRSCACHANFrance

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