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新型结构简化 cADPR（最初从海胆卵中分离出的钙动员第二信使）类似物的合成与生物学评价。

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

机构信息

Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via Domenico Montesano 49, 80131 Napoli, Italy.

SYSBIO, Centre of Systems Biology, University of Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, Italy.

出版信息

Mar Drugs. 2018 Mar 10;16(3):89. doi: 10.3390/md16030089.

DOI:10.3390/md16030089
PMID:29534435
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5867633/
Abstract

Herein, we reported on the synthesis of cpIPP, which is a new structurally-reduced analogue of cyclic ADP-ribose (cADPR), a potent Ca-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 Ca 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 Ca release properties.

摘要

在此，我们报告了 cpIPP 的合成，cpIPP 是环状 ADP-核糖（cADPR）的一种新型结构简化类似物，cADPR 是一种最初从海胆卵提取物中分离出的强效 Ca 释放二级信使。为了获得 cpIPP，将 cADPR 的“北”核糖用戊基链取代，焦磷酸部分用磷酸一磷酸酐取代。在 PC12 神经元细胞中，评估了新的磷酸一磷酸键的存在对 cpIPP 诱导的细胞内 Ca 释放的影响，并与结构相关的环状 N1-丁基肌苷二磷酸类似物（cbIDP）的焦磷酸桥的影响进行了比较，cbIDP 是我们实验室之前合成的，与 cpIPP 的线性前体的影响进行了比较，出乎意料的是，只有 cpIPP 的线性前体具有 Ca 释放特性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/cae74064847f/marinedrugs-16-00089-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/62665b0d72f8/marinedrugs-16-00089-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/6133f6090a10/marinedrugs-16-00089-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/daa46de3d760/marinedrugs-16-00089-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/e246a97fa1de/marinedrugs-16-00089-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/b5ec97e61b32/marinedrugs-16-00089-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/cae74064847f/marinedrugs-16-00089-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/62665b0d72f8/marinedrugs-16-00089-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/6133f6090a10/marinedrugs-16-00089-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/daa46de3d760/marinedrugs-16-00089-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/e246a97fa1de/marinedrugs-16-00089-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/b5ec97e61b32/marinedrugs-16-00089-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb68/5867633/cae74064847f/marinedrugs-16-00089-g004.jpg

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