Molecules p. 4343 - 4356 (2012)
Update date:2022-09-26
Topics: Characterization Purification Chemical Synthesis Biological Assays Structure-Activity Relationship (SAR) Studies Further Optimization Design and Rationalization Publication and Data Sharing Biochemical Studies
Zhou, Yue
Yu, Peilin
Jin, Hongwei
Yang, Zhenjun
Yue, Jianbo
Zhang, Liangren
Zhang, Lihe
Novel cADPR mimics, which integrate nucleobase, northern and southern ribose modifications were synthesized. The key steps of the synthesis were a Cu(I)-catalyzed Hueisgen [3+2] cycloaddition and a microwave-assisted intramolecular pyrophosphorylation. Preliminary biological investigations showed that these cADPR mimics are membrane-permeating agonists of the calcium signaling pathway. The introduction of chlorine or fluorine at the 2'-position of the southern riboses led to a decrease of activity. The existence of a hydrophobic group on the 3'-OH of the southern riboses does not obviously alter the agonistic activity.
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