Bt3-Ins(346)P3 / PM

Bt3-Ins(3,4,6)P3/PM is a membrane-permeant derivative of myo-inositol 3,4,6-trisphosphate (Ins(3,4,6)P3). It is the enantiomer of Bt3-Ins(1,4,6)P3/PM and can therefore be used as a stereochemical control in experiments with membrane-permeant inositol trisphosphate derivatives.

The negatively charged phosphate groups are masked by propionoxymethyl (PM) ester groups, while additional butyryl ester groups increase lipophilicity and facilitate cellular uptake. Following entry into cells, intracellular esterases cleave the ester groups to release the corresponding inositol trisphosphate.

Ins(3,4,6)P3 is also an intermediate in inositol phosphate metabolism and a substrate of inositol tris/tetrakisphosphate kinase 1 (ITPK1). Bt3-Ins(3,4,6)P3/PM is therefore suitable for stereochemical control experiments and studies of inositol phosphate metabolism and signaling.

References:

Ho M.W.Y. et al., Current Biology 2002, 12, 477–482. DOI: 10.1016/S0960-9822(02)00713-3

Whitfield H. et al., Biochemical Journal 2020, 477, 2621–2638. DOI: 10.1042/BCJ20200423