title: Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments.
abstract: 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 PdCl(2)/H(2). 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.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology, Shanghai 200237, People's Republic of China.
authors.forename: Hai-Lin
authors.initials: HL
authors.lastname: Zhang
authors.forename: Xiao-Peng
authors.initials: XP
authors.lastname: He
authors.forename: Li
authors.initials: L
authors.lastname: Sheng
authors.forename: Yuan
authors.initials: Y
authors.lastname: Yao
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Xiao-Xin
authors.initials: XX
authors.lastname: Shi
authors.forename: Jia
authors.initials: J
authors.lastname: Li
authors.forename: Guo-Rong
authors.initials: GR
authors.lastname: Chen
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D057930:Click Chemistry; D004354:Drug Screening Assays, Antitumor; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D006801:Humans; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D006017:Glycolipids; D014230:Triazoles