环状ADP-4-硫代核糖作为环状ADP-核糖的稳定类似物的设计、合成及其化学和生物学性质
Design, Synthesis, and Chemical and Biological Properties of Cyclic ADP-4-Thioribose as a Stable Equivalent of Cyclic ADP-Ribose.
作者信息
Tsuzuki Takayoshi, Takano Satoshi, Sakaguchi Natsumi, Kudoh Takashi, Murayama Takashi, Sakurai Takashi, Hashii Minako, Higashida Haruhiro, Weber Karin, Guse Andreas H, Kameda Tomoshi, Hirokawa Takatsugu, Kumaki Yasuhiro, Arisawa Mitsuhiro, Potter Barry V L, Shuto Satoshi
机构信息
Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Department of Pharmacology, Juntendo University School of Medicine, 2-1-1 Hongo, Bunkyo-ku, Tokyo 113-8421, Japan.
出版信息
Messenger (Los Angel). 2014 Jun-Dec;3(1-2):35-51. doi: 10.1166/msr.2014.1035. Epub 2014 Jun 1.
Here we describe the successful synthesis of cyclic ADP-4-thioribose (cADPtR, ), designed as a stable mimic of cyclic ADP-ribose (cADPR, ), a Ca-mobilizing second messenger, in which the key N1-β-thioribosyladenosine structure was stereoselectively constructed by condensation between the imidazole nucleoside derivative and the 4-thioribosylamine via equilibrium in between the α-anomer () and the β-anomer () during the reaction course. cADPtR is, unlike cADPR, chemically and biologically stable, while it effectively mobilizes intracellular Ca like cADPR in various biological systems, such as sea urchin homogenate, NG108-15 neuronal cells, and Jurkat T-lymphocytes. Thus, cADPtR is a stable equivalent of cADPR, which can be useful as a biological tool for investigating cADPR-mediated Ca-mobilizing pathways.
在此，我们描述了环状ADP - 4 -硫代核糖（cADPtR）的成功合成，它被设计为环状ADP - 核糖（cADPR，一种钙动员第二信使）的稳定模拟物。其中，关键的N1-β-硫代核糖基腺苷结构是通过咪唑核苷衍生物与4 -硫代核糖胺在反应过程中通过α-异头物（）和β-异头物（）之间的平衡进行立体选择性缩合构建而成。与cADPR不同，cADPtR在化学和生物学上是稳定的，同时它在各种生物系统中，如海胆匀浆、NG108 - 15神经细胞和Jurkat T淋巴细胞中，能像cADPR一样有效地动员细胞内钙。因此，cADPtR是cADPR的稳定等效物，可作为研究cADPR介导的钙动员途径的生物学工具。
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