Bt3-Ins(356)P3 / PM

Bt3-Ins(3,5,6)P3/PM is a membrane-permeant derivative of myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3), the enantiomer of the intracellular second messenger Ins(1,4,5)P3.

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.

Due to its defined stereochemistry, Bt3-Ins(3,5,6)P3/PM is suitable for stereochemical control and comparative studies with membrane-permeant Ins(1,4,5)P3 derivatives. Ins(3,5,6)P3 has also been investigated as a substrate of human inositol tris/tetrakisphosphate kinase 1 (ITPK1), making the compound relevant to studies of stereospecific inositol phosphate recognition and metabolism.

References:

Xi Q. et al., Circulation Research 2008, 102, 1118–1126. DOI: 10.1161/CIRCRESAHA.108.173948

Leung L.W. et al., Carbohydrate Research 1997, 305, 171–179. DOI: 10.1016/S0008-6215(97)00267-X