From synthesis to the biological effect of isoprenoid 2′-deoxyriboside and 2′,3′-dideoxyriboside cytokinin analogues

Isoprenoid cytokinins are a class of naturally occurring plant signaling molecules. A series of prepared compounds derived from isoprenoid cytokinins (isopentenyladenine, trans-zeatin and cis-zeatin) with attached 2′-deoxy-d-ribose or 2′,3′-dideoxy-d-ribose at the N9 position of the purine were prepared and their biological activities were examined. Different synthetic approaches were employed. The final compounds were characterized with variety of physicochemical methods (TLC, HPLC-MS, and NMR) and their cytokinin activity was determined in classical bioassays such as Amaranthus, tobacco callus, detached wheat leaf senescence and Arabidopsis thaliana root elongation inhibition assay. In addition, compounds were screened for activation of the cytokinin signaling pathway (bacterial receptor, competitive ligand binding and ARR5::GUS assay) to provide a detailed assessment of CK structure-activity relationship. The prepared compounds were found to be non-toxic to human cells and the majority of assays exhibited the highest activity of free bases while 2′,3′-dideoxyribosides had very weak or no activity. In contrast to the free bases, all 2′-deoxyriboside derivatives were not toxic to tobacco callus even at the highest tested concentration (10−4 moL/l) and compound 1 (iPdR) induced betacyanin synthesis at higher concentration even stronger than iP free base in the Amaranthus bioassay. The general cytokinin activity pattern base > riboside >2′-deoxyriboside > 2′,3′-dideoxyriboside was distinguished.