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学科主题: 药学
题名:
Trifluoromethylated cyclic-ADP-ribose mimic: synthesis of 8-trifluoromethyl-N-1-[(5 ′′-O-phosphorylethoxy)methyl]-5 ′-O-phosphorylinosine-5 ′,5 ′′-cyclic pyrophosphate (8-CF3-cIDPRE) and its calcium release activity in T cells
作者: Dong, Min2; Kirchberger, Tanja1; Huang, Xiangchen2; Yang, Zhen Jun2; Zhang, Liang Ren2; Guse, Andreas H.1; Zhang, Li He2
刊名: ORGANIC & BIOMOLECULAR CHEMISTRY
发表日期: 2010
DOI: 10.1039/c0ob00090f
卷: 8, 期:20, 页:4705-4715
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]: ADENOSINE-DIPHOSPHORIBOSE CADPR ; POTENT CA2+-MOBILIZING AGENT ; ORGANIC FLUORINE-COMPOUNDS ; CARBOCYCLIC-RIBOSE ; INOSINE DIPHOSPHORIBOSE ; 2ND-MESSENGER FUNCTION ; CRYSTAL-STRUCTURE ; N1-RIBOSE MOIETY ; DERIVATIVES ; LYMPHOCYTES
英文摘要:

A convenient trifluoromethylation method was firstly applied to the synthesis of 8-CF3-purine nucleosides. On the basis of this method, new protection and deprotection strategies were developed for the successful synthesis of the trifluoromethylated cyclic-ADP-ribose mimic, 8-CF3-cIDPRE 1. Using intact, fura-2-loaded Jurkat T cells compound 1 and 2′,3′-O-isopropylidene 8-CF3-cIDPRE 14 were characterized as membrane-permeant cADPR agonists. Contrary to the 8-substituted cADPR analogues that mainly act as antagonists of cADPR in cells, 8-substituted cIDPRE derivatives were shown to be Ca2+ mobilizing agonists. Here we report that even compound 1, the 8-substituted cIDPRE with the strong electron withdrawing CF3 group, behaves as an agonist in T cells. Interestingly, also the partially protected 2′,3′-O-isopropylidene 8-CF3-cIDPRE activated Ca2+ signaling indicating only a minor role for the hydroxyl groups of the southern ribose of cADPR for its biological activity. To our knowledge 8-CF3-cIDPRE 1 is the first reported fluoro substituted cADPR mimic and 8-CF3-cIDPRE 1 and compound 14 are promising molecular probes for elucidating the mode of action of cADPR.

语种: 英语
所属项目编号: 20332010 ; 360/13-1
项目资助者: National Natural Sciences Foundation of China ; Deutsche Forschungsgemeinschaft
WOS记录号: WOS:000282315900029
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/55440
Appears in Collections:北京大学药学院_期刊论文

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作者单位: 1.Univ Med Ctr Hamburg Eppendorf, Calcium Signaling Grp, Ctr Med Expt, Inst Biochem & Mol Biol Cellular Signal Transduct, D-20246 Hamburg, Germany
2.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

Recommended Citation:
Dong, Min,Kirchberger, Tanja,Huang, Xiangchen,et al. Trifluoromethylated cyclic-ADP-ribose mimic: synthesis of 8-trifluoromethyl-N-1-[(5 ′′-O-phosphorylethoxy)methyl]-5 ′-O-phosphorylinosine-5 ′,5 ′′-cyclic pyrophosphate (8-CF3-cIDPRE) and its calcium release activity in T cells[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2010,8(20):4705-4715.
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