Citation:
Ren-Min Wu, Na Qi, Yu-Wen Jia, Zhu Guan, Liang-Ren Zhang, Li-He Zhang, Zhen-Jun Yang. A novel method for the synthesis of sulfur substitutedcyclopyrophosphate of cADPR analogs[J]. Chinese Chemical Letters,
;2014, 25(12): 1583-1585.
doi:
10.1016/j.cclet.2014.07.010
-
A facile and efficient protocol for the synthesis of sulfur substituted-cyclopyrophosphate of cIDPRE (PS1-cIDPRE) was developed. The key step was the cyclization process which was completed by the sulfur substituted cyclization precursor 1b via the one-pot phosphoramidite strategy.
-
Keywords:
- cADPR,
- cIDPRE,
- Phosphoramidite strategy,
- Cyclopyrophosphate
-
-
-
[1]
[1] H.C. Lee, Physiological functions of cyclic ADP-ribose and NAADP as calcium messengers, Annu. Rev. Pharmacol. Toxicol. 41 (2001) 317-345.
-
[2]
[2] A.H. Guse, Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR), Curr. Med. Chem. 11 (2004) 847-855.
-
[3]
[3] L. Xu, T.F. Walseth, J.T. Slama, Cyclic ADP-ribose analogues containing the methylenebisphosphonate linkage: effect of pyrophosphate modifications on Ca2+ release activity, J. Med. Chem. 48 (2005) 4177-4181.
-
[4]
[4] X. Huang, M. Dong, J. Liu, et al., Concise syntheses of trifluoromethylated cyclic and acyclic analogues of cADPR, Molecules 15 (2010) 8689-8701.
-
[5]
[5] B.V.L. Potter, T.F. Walseth, Medicinal chemistry and pharmacology of cyclic ADPribose, Curr. Mol. Med. 4 (2004) 303-311.
-
[6]
[6] J. Xu, Z.J. Yang, W. Dammermann, et al., Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains, J. Med. Chem. 49 (2006) 5501-5512.
-
[7]
[7] A.H. Guse, Second messenger function and the structure-activity relationship of cyclic adenosine diphosphoribose (cADPR), FEBS. J. 272 (2005) 4590-4597.
-
[8]
[8] S. Shuto, M. Fukuoka, A. Manikowsky, et al., Total synthesis of cyclic ADPcarbocyclic-ribose, a stable mimic of Ca2+-mobilizing second messenger cyclic ADP-ribose1, J. Am. Chem. Soc. 123 (2001) 8750-8759.
-
[9]
[9] M. Dong, T. Kirchberger, X.C. Huang, et al., Trifluoromethylated cyclic-ADP-ribose mimic: synthesis of 8-trifluoro-methyl-N1-[(5''-O-phosphorylethoxy)methyl]-50-O-phosphorylinosine-50,500-cyclic-pyrophosphate (8-CF3-cIDPRE) and its calcium release activity in T cells, Org. Biomol. Chem. 8 (2010) 4705-4715.
-
[10]
[10] F.J. Zhang, S. Yamada, Q.M. Gu, C.J. Sih, Synthesis and characterization of cyclic ATP-ribose: a potent mediator of calcium release, Bioorg. Med. Chem. Lett. 6 (1996) 1203-1208.
-
[11]
[11] N. Qi, K. Jung, M. Wang, et al., A novel membrane-permeant cADPR antagonist modified in the pyrophosphate bridge, Chem. Commun. 47 (2011) 9462-9464.
-
[12]
[12] X. Gu, Z.J. Yang, L.R. Zhang, et al., Synthesis and biological evaluation of novel membrane-permeant cyclic ADP-ribose mimics: N1-[(5''-O-phosphorylethoxy) methyl]-5'-O-phosphoryl-inosine 5',5''-cyclic-pyrophosphate (cIDPRE) and 8-substituted derivatives, J. Med. Chem. 47 (2004) 5674-5682.
-
[13]
[13] R. Aarhus, K. Gee, H.C. Lee, Caged cyclic ADP-ribose synthesis and use, J. Biol. Chem. 270 (1995) 7745-7749.
-
[14]
[14] A.H. Guse, X.F. Gu, L.R. Zhang, et al., A minimal structural analogue of cyclic ADPribose synthesis and calcium release activity in mammalian cells, J. Biol. Chem. 280 (2005) 15952-15959.
-
[15]
[15] J.Wang, J. Zhou, G.P. Donaldson, et al., Conservative change to the phosphatemoiety of cyclic diguanylicmonophosphate remarkably affects its polymorphismand ability to bind DGC, PDE, and PilZ proteins, J Am. Chem. Soc. 133 (2011) 9320-9330.
-
[16]
[16] E. Krawczyk, J. Mikolajczak, A. Skowronska, J. Michalski, Reaction of tricoordinate phosphorus compounds with organophosphorus pseudohalogens: desulfurization and deoxygenation of oxophosphoranesulfenyl chlorides, scope and mechanism, J. Org. Chem. 57 (1992) 4963-4970.
-
[17]
[17] L.X. Na, X.L. Sun, M. Wang, et al., Atropisomerism of diastereomer diribonucleoside phosphotriester, Chin. Chem. Lett. 24 (2013) 13-16.
-
[1]
-
-
-
[1]
Jie Ma , Jianxiang Wang , Jianhua Yuan , Xiao Liu , Yun Yang , Fei Yu . The regulating strategy of hierarchical structure and acidity in zeolites and application of gas adsorption: A review. Chinese Chemical Letters, 2024, 35(11): 109693-. doi: 10.1016/j.cclet.2024.109693
-
[2]
Shaoqing Du , Xinyong Liu , Xueping Hu , Peng Zhan . Targeting novel sites represents an effective strategy for combating drug resistance. Chinese Chemical Letters, 2025, 36(1): 110378-. doi: 10.1016/j.cclet.2024.110378
-
[3]
Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
-
[4]
Han Wu , Yumei Wang , Zekai Ren , Hailin Cong , Youqing Shen , Bing Yu . The nanocarrier strategy for crossing the blood-brain barrier in glioma therapy. Chinese Chemical Letters, 2025, 36(4): 109996-. doi: 10.1016/j.cclet.2024.109996
-
[5]
Dong Cheng , Youyou Feng , Bingxi Feng , Ke Wang , Guoxin Song , Gen Wang , Xiaoli Cheng , Yonghui Deng , Jing Wei . Polyphenol-mediated interfacial deposition strategy for supported manganese oxide catalysts with excellent pollutant degradation performance. Chinese Chemical Letters, 2024, 35(5): 108623-. doi: 10.1016/j.cclet.2023.108623
-
[6]
Junhua Wang , Xin Lian , Xichuan Cao , Qiao Zhao , Baiyan Li , Xian-He Bu . Dual polarization strategy to enhance CH4 uptake in covalent organic frameworks for coal-bed methane purification. Chinese Chemical Letters, 2024, 35(8): 109180-. doi: 10.1016/j.cclet.2023.109180
-
[7]
Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO2F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
-
[8]
Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
-
[9]
Zheng Zhao , Ben Zhong Tang . An efficient strategy enabling solution processable thermally activated delayed fluorescence emitter with high horizontal dipole orientation. Chinese Journal of Structural Chemistry, 2024, 43(6): 100270-100270. doi: 10.1016/j.cjsc.2024.100270
-
[10]
A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
-
[11]
Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
-
[12]
Ruixin Liu , Feng Shi , Yanping Xia , Haibing Zhu , Jiawen Cao , Kai Peng , Chuanli Ren , Juan Li , Zhanjun Yang . Universal MOF nanozyme-induced catalytic amplification strategy for label-free electrochemical immunoassay. Chinese Chemical Letters, 2024, 35(11): 109664-. doi: 10.1016/j.cclet.2024.109664
-
[13]
Zhendong Liu , Sainan Liu , Bin Liu , Qi Meng , Meng Yuan , Chunzheng Yang , Yulong Bian , Ping'an Ma , Jun Lin . Fe(Ⅲ)-juglone nanoscale coordination polymers for cascade chemodynamic therapy through synergistic ferroptosis and apoptosis strategy. Chinese Chemical Letters, 2024, 35(11): 109626-. doi: 10.1016/j.cclet.2024.109626
-
[14]
Shuheng Zhang , Yuanyuan Zhang , Wanyu Wang , Yuzhu Hu , Xinchuan Chen , Bilan Wang , Xiang Gao . A combination strategy of DOX and VEGFR-2 targeted inhibitor based on nanomicelle for enhancing lymphoma therapy. Chinese Chemical Letters, 2024, 35(12): 109658-. doi: 10.1016/j.cclet.2024.109658
-
[15]
Qiang Wu , Baofeng Wang . Exploring synthetic strategy for stabilizing nickel-rich layered oxide cathodes through structural design. Chinese Chemical Letters, 2024, 35(12): 110089-. doi: 10.1016/j.cclet.2024.110089
-
[16]
Yu-Qi Cao , Ying-Jie Lu , Li Zhang , Jing Zhang , Yin-Long Guo . Vacuum promoted on-tissue derivatization strategy: Unravelling spatial distribution of glycerides on tissue. Chinese Chemical Letters, 2024, 35(12): 109788-. doi: 10.1016/j.cclet.2024.109788
-
[17]
Yanting Yang , Guorong Wang , Kangjing Li , Wen Yang , Jing Zhang , Jian Zhang , Shili Li , Xianming Zhang . Tuning up of chromism, luminescence in cadmium-viologen complexes through polymorphism strategy: Inkless erasable printing application. Chinese Chemical Letters, 2025, 36(1): 110123-. doi: 10.1016/j.cclet.2024.110123
-
[18]
Gaojian Yang , Zhiyang Li , Rabia Usman , Zhu Chen , Yuan Liu , Song Li , Hui Chen , Yan Deng , Yile Fang , Nongyue He . DNA walker induced "signal on" fluorescence aptasensor strategy for rapid and sensitive detection of extracellular vesicles in gastric cancer. Chinese Chemical Letters, 2025, 36(2): 109930-. doi: 10.1016/j.cclet.2024.109930
-
[19]
Xilin Bai , Wei Deng , Jingjuan Wang , Ming Zhou . Enrichment-enhanced detection strategy in the optimized monitoring system of dopamine with carbon dots-based probe. Chinese Chemical Letters, 2025, 36(2): 109959-. doi: 10.1016/j.cclet.2024.109959
-
[20]
Chuyuan Lin , Hui Lin , Lingxing Zeng . Optimization strategy for rechargeable Zn metal batteries over wide-pH aqueous electrolytes. Chinese Journal of Structural Chemistry, 2025, 44(1): 100407-100407. doi: 10.1016/j.cjsc.2024.100407
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(566)
- HTML views(0)