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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
Dong, Min2; Kirchberger, Tanja1; Huang, Xiangchen2; Yang, Zhen Jun2; Zhang, Liang Ren2; Guse, Andreas H.1; Zhang, Li He2
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
2010
DOI10.1039/c0ob00090f
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
WOS记录号WOS:000282315900029
引用统计
被引频次:14[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/55440
专题北京大学药学院
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
推荐引用方式
GB/T 7714
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.
APA Dong, Min.,Kirchberger, Tanja.,Huang, Xiangchen.,Yang, Zhen Jun.,Zhang, Liang Ren.,...&Zhang, Li He.(2010).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.ORGANIC & BIOMOLECULAR CHEMISTRY,8(20),4705-4715.
MLA Dong, Min,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".ORGANIC & BIOMOLECULAR CHEMISTRY 8.20(2010):4705-4715.
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