Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications

Article abstract of DOI:10.1016/S0040-4020(97)00714-X

Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt₃IP₃/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP₃/AM), hexakis(propionyloxymethyl) ester (IP₃/PM) and hexakis(butyryloxymethyl) ester (IP₃/BM) were therefore synthesized. Whereas extracellular application of up to 200 μM of Bt₃IP₃/AM or IP₃/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP₃/PM and IP₃/BM released internal calcium at concentrations as low os 20 μM and 2 μM, respectively.