Novel nucleobase-simplified cyclic ADP-ribose analogue: A concise synthesis and Ca2+-mobilizing activity in T-lymphocytes

被引：19

作者：

Li, Lingjun ^{[1
,2
]}

Siebrands, Cornelia C. ^{[3
]}

Yang, Zhenjun ^{[1
]}

Zhang, Liangren ^{[1
]}

Guse, Andreas H. ^{[3
]}

Zhang, Lihe ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China

[2] Henan Normal Univ, Coll Chem & Environm Sci, Xinxiang 453007, Peoples R China

[3] Univ Med Ctr Hamburg Eppendorf, Calcium Signaling Grp, Ctr Med Expt, Inst Biochem & Mol Biol Cellular Signal Transduct, D-20246 Hamburg, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 08期

关键词：

ADENOSINE 5-DIPHOSPHATE RIBOSE; CARBOCYCLIC-RIBOSE; CALCIUM-RELEASE; DIPHOSPHORIBOSE; DERIVATIVES; CHEMISTRY; POTENT; 2ND-MESSENGER; PHARMACOLOGY; CYCLIZATION;

D O I：

10.1039/b925295a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A purine nucleobase-simplified cyclic ADP ribose (cADPR) analogue 6b was synthesized, in which a 1,2,3-triazole-4-amide was constructed, instead of a purine moiety, and the northern ribose was replaced by an ether strand. Compound 6b exhibits calcium release activity in intact T-lymphocytes and indicates that it is a membrane-permeable cADPR mimic. Thus, the cADPR analogue containing 1,2,3-triazole-4-amide provides a novel template for further designing cADPR analogues and elucidating their structure-activity relationships.

引用

收藏

页码：1843 / 1848

页数：6

相关论文

共 31 条

[1] CAGED CYCLIC ADP-RIBOSE - SYNTHESIS AND USE [J].

AARHUS, R ;

GEE, K ;

LEE, HC .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (13) :7745-7749

[2] Roles for adenosine ribose hydroxyl groups in cyclic adenosine 5'-diphosphate ribose-mediated Ca2+ release [J].

Ashamu, GA ;

Sethi, JK ;

Galione, A ;

Potter, BVL .

BIOCHEMISTRY, 1997, 36 (31) :9509-9517

[3] Synthesis of 7-deaza-8-bromo cyclic adenosine 5'-diphosphate ribose: The first hydrolysis resistant antagonist at the cADPR receptor [J].

Bailey, VC ;

Sethi, JK ;

Galione, A ;

Potter, BVL .

CHEMICAL COMMUNICATIONS, 1997, (07) :695-696

[4] 7-Deaza cyclic adenosine 5'-diphosphate ribose: First example of a Ca2+-mobilizing partial agonist related to cyclic adenosine 5'-diphosphate ribose [J].

Bailey, VC ;

Sethi, JK ;

Fortt, SM ;

Galione, A ;

Potter, BVL .

CHEMISTRY & BIOLOGY, 1997, 4 (01) :51-61

[5] Cyclic aristeromycin diphosphate ribose: A potent and poorly hydrolysable Ca2+-mobilising mimic of cyclic adenosine diphosphate ribose [J].

Bailey, VC ;

Fortt, SM ;

Summerhill, RJ ;

Galione, A ;

Potter, BVL .

FEBS LETTERS, 1996, 379 (03) :227-230

[6]

CLAPPER DL, 1987, J BIOL CHEM, V262, P9561

[7] Synthesis of a novel N-1 carbocyclic, N-9 butyl analogue of cyclic ADP ribose (cADPR) [J].

Galeone, A ;

Mayol, L ;

Oliviero, G ;

Piccialli, G ;

Varra, M .

TETRAHEDRON, 2002, 58 (02) :363-368

[8] Fluorescent analogs of cyclic ADP-ribose: Synthesis, spectral characterization, and use [J].

Graeff, RM ;

Walseth, TF ;

Hill, HK ;

Lee, HC .

BIOCHEMISTRY, 1996, 35 (02) :379-386

[9] Synthesis and biological evaluation of novel membrane-permeant cyclic ADP-ribose mimics:: N1-[(5"-O-phosphorylethoxy)methyl]-5′-O-phosphorylinosine 5′,5"-cyclicpyrophosphate (cIDPRE) and 8-substituted derivatives [J].

Gu, XF ;

Yang, Z ;

Zhang, L ;

Kunerth, S ;

Fliegert, R ;

Weber, K ;

Guse, AH ;

Zhang, L .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (23) :5674-5682

[10] A minimal structural analogue of cyclic ADP-ribose -: Synthesis and calcium release activity in mammalian cells [J].

Guse, AH ;

Gu, XF ;

Zhang, LR ;

Weber, K ;

Krämer, E ;

Yang, ZJ ;

Jin, HW ;

Li, Q ;

Carrier, L ;

Zhang, LH .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (16) :15952-15959

← 1 2 3 4 →