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学科主题: 药学
题名:
Rapid probing of sialylated glycoproteins in vitro and in vivo via metabolic oligosaccharide engineering of a minimal cyclopropene reporter
作者: Xiong, De-Cai1,2; Zhu, Jingjing1,2,3; Han, Ming-Jie1,2; Luo, Hui-Xin1,2; Wang, Cong1,2; Yu, Yang1,2; Ye, Yuqian1,2; Tai, Guihua3; Ye, Xin-Shan1,2
刊名: ORGANIC & BIOMOLECULAR CHEMISTRY
发表日期: 2015
DOI: 10.1039/c5ob00069f
卷: 13, 期:13, 页:3911-3917
收录类别: SCI ; IC
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: SIALIC ACIDS ; CLICK CHEMISTRY ; BIOORTHOGONAL REACTIONS ; CHEMICAL GLYCOBIOLOGY ; PHOTOCLICK-CHEMISTRY ; LIVING ANIMALS ; CROSS-LINKING ; CELL-SURFACES ; LIVE CELLS ; GLYCANS
英文摘要:

ManNAc analogues are important chemical tools for probing sialylation dynamically via metabolic oligosaccharide engineering (MOE). The size of N-acyl and the nature of the chemical handle are two determinants of metabolic incorporation efficiency. We demonstrated a minimal, stable, bioorthogonal, and reactive N-Cp (N-(cycloprop-2-ene-1-ylcarbonyl)) group and the imaging of sialylated glycans using Ac(4)ManNCp in vitro and in vivo. The results revealed that the Cp group can efficiently be incorporated into the cellular sialic acid and detected rapidly by the reaction with FITC-Tz in different cells. The metabolic incorporation efficiency of non-cytotoxic Ac(4)ManNCp is not only superior to Ac(4)ManNMCp, but also superior to the widely-used Ac(4)ManNAz in some cell lines. Moreover, when Ac(4)ManNCp was administered to mice, a rapid and intense labelling of splenocytes as well as glycoproteins of sera and organs was observed. This is the first reported metabolic labelling of cyclopropene-modified sugars in vivo. Therefore, Ac(4)ManNCp is a powerful probe for efficient and rapid MOE and it may find wide applications in the labelling of glycans.

语种: 英语
所属项目编号: 2012CB822100 ; 2013CB910700 ; 91413106 ; 21232002 ; 2142015 ; YETP0063 ; BMU20140476
项目资助者: Ministry of Science and Technology of China ; National Natural Science Foundation of China ; Beijing Natural Science Foundation ; Beijing Higher Education Young Elite Teacher Project ; Center for Molecular and Translational Medicine
WOS记录号: WOS:000351597700010
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/64707
Appears in Collections:北京大学药学院_期刊论文

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作者单位: 1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
2.Peking Univ, Ctr Mol & Translat Med, Beijing 100191, Peoples R China
3.NE Normal Univ, Sch Life Sci, Changchun 130024, Peoples R China

Recommended Citation:
Xiong, De-Cai,Zhu, Jingjing,Han, Ming-Jie,et al. Rapid probing of sialylated glycoproteins in vitro and in vivo via metabolic oligosaccharide engineering of a minimal cyclopropene reporter[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2015,13(13):3911-3917.
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