Cyclic ADP‐Ribose Analogues with Minimal Structure: Synthesis and Calcium‐Release Activity

Zhang, Lihe; Guse, Andreas H.

doi:10.1002/9780470131862.ch8

Cited by 2 publications

(2 citation statements)

References 27 publications

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“…In other studies, the northern ribose was replaced by more flexible moieties, such as the ethoxy-alkyl or alkyl chains, both for the adenine ( 5 – 8 ) and inosine series ( 9 ). Compound 5 (cyclic adenosine 5’-diphosphate-ribose-ether, cADPRE) and its N1-alkyl congeners ( 6 – 8 ) permeate the plasma membrane and are weak agonists of cADPR in human Jurkat T cells [ 28 , 29 ]. The inosine analogue 9 (cIDPRE) [ 30 ] possesses an activity on intact human Jurkat-T-lymphocytes releasing Ca 2+ ions from intracellular stores.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs

et al. 2018

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Herein, we reported on the synthesis of cpIPP, which is a new structurally-reduced analogue of cyclic ADP-ribose (cADPR), a potent Ca2+-releasing secondary messenger that was firstly isolated from sea urchin eggs extracts. To obtain cpIPP the “northern” ribose of cADPR was replaced by a pentyl chain and the pyrophosphate moiety by a phophono-phosphate anhydride. The effect of the presence of the new phosphono-phosphate bridge on the intracellular Ca2+ release induced by cpIPP was assessed in PC12 neuronal cells in comparison with the effect of the pyrophosphate bridge of the structurally related cyclic N1-butylinosine diphosphate analogue (cbIDP), which was previously synthesized in our laboratories, and with that of the linear precursor of cpIPP, which, unexpectedly, revealed to be the only one provided with Ca2+ release properties.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs

et al. 2018

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“…It has been proved that cADPR is a signalling molecule, which regulates calcium mobilization via ryanodine receptor (RyR) in a wide variety of Ca 2+ -dependent cellular responses such as fertilization, secretion, contraction, proliferation and so on [ 2 ]. Since the discovery of cADPR, numerous works have been done on the synthesis of cADPR analogues to search for agonists or antagonists of cADPR/RyR Ca 2+ signalling system [ 3 , 4 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

Concise Syntheses of Trifluoromethylated Cyclic and Acyclic Analogues of cADPR

et al. 2010

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A novel trifluoromethylated analogue of cADPR, 8-CF3-cIDPDE (5) was designed and synthesized via construction of N1,N9-disubstituted hypoxanthine, trifluoromethylation and intramolecular condensation. A series of acyclic analogues of cADPR were also designed and synthesized. These compounds could be useful molecules for studying the structure-activity relationship of cADPR analogues and exploring the cADPR/RyR Ca2+ signalling system.

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Cyclic ADP‐Ribose Analogues with Minimal Structure: Synthesis and Calcium‐Release Activity

Cited by 2 publications

References 27 publications

Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs

Synthesis and Biological Evaluation of a New Structural Simplified Analogue of cADPR, a Calcium-Mobilizing Secondary Messenger Firstly Isolated from Sea Urchin Eggs

Concise Syntheses of Trifluoromethylated Cyclic and Acyclic Analogues of cADPR

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