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Syntheses and calcium-mobilizing evaluations of N-1-glycosyl-substituted stable mimics of cyclic ADP-ribose
Huang, LJ; Zhao, YY; Yuan, L; Min, JM; Zhang, LH
刊名JOURNAL OF MEDICINAL CHEMISTRY
2002-11-21
DOI10.1021/jm0105301
45期:24页:5340-5352
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Medicinal
研究领域[WOS]Pharmacology & Pharmacy
关键词[WOS]INDUCED CA2+ RELEASE ; ADENOSINE-DIPHOSPHATE-RIBOSE ; CARBOCYCLIC-RIBOSE ; NUCLEOSIDES ; ANALOGS ; POTENT ; DERIVATIVES ; MICROSOMES ; HYDROLYSIS ; ANTAGONIST
英文摘要

Cyclic ADP-ribose (cADPR) is not only a potent endogenous calcium modulator but also a second messenger. However, studies on the mechanism of cADPR action were limited due to its instability and lack of available structural modifications in the N-1-glyosyl unit of cADPR. In the present work, a series of N-1-glycosyl mimics with different configurational glycosyls or an ether strand were designed and synthesized mimicking the furanose ring. S(N)2 substitutions were carried out between the protected inosine and glycosyl triflates to form the N-1-glycosylinosine derivatives, accompanied with some O-6-glyeosyl-substituted as side products. The intramolecular cyclization was followed the strategy described by Matsuda et al. It was found that the 8-unsubstituted substrate could also be used to construct the intramolecular cyclic pyrophosphate. The activities of NI-glycosyl-substituted cADPR mimics were evaluated by induced Ca2+ release in rat brain microsomes and HeLa cells. It was found that the configuration of the N-1-glycosyl moiety in cADPR is not a critical structural factor for retaining the activity of mobilizing Ca2+ release. More interestingly, the N-1-acyclic analogue 6 exhibited strong activity by inducing Ca2+ release in both rat brain microsomes and HeLa cells. It constitutes a useful tool for further studies.

语种英语
WOS记录号WOS:000179344400016
引用统计
被引频次:37[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/400002259/56634
专题北京大学药学院_化学生物学系
作者单位1.Peking Univ, Natl Key Lab & Biomimet Drugs, Beijing 100083, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, Beijing 100083, Peoples R China
3.Peking Univ, Hlth & Drug Analyt Ctr, Beijing 100083, Peoples R China
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GB/T 7714
Huang, LJ,Zhao, YY,Yuan, L,et al. Syntheses and calcium-mobilizing evaluations of N-1-glycosyl-substituted stable mimics of cyclic ADP-ribose[J]. JOURNAL OF MEDICINAL CHEMISTRY,2002,45(24):5340-5352.
APA Huang, LJ,Zhao, YY,Yuan, L,Min, JM,&Zhang, LH.(2002).Syntheses and calcium-mobilizing evaluations of N-1-glycosyl-substituted stable mimics of cyclic ADP-ribose.JOURNAL OF MEDICINAL CHEMISTRY,45(24),5340-5352.
MLA Huang, LJ,et al."Syntheses and calcium-mobilizing evaluations of N-1-glycosyl-substituted stable mimics of cyclic ADP-ribose".JOURNAL OF MEDICINAL CHEMISTRY 45.24(2002):5340-5352.
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