D-myo-Inositol-2,5,6-triphosphate (sodium salt)

Cayman Chemical Item Number 10008424

Ins(2,5,6)P₃ (sodium salt); 2,5,6-IP₃ (sodium salt)

Description

Ins(2,5,6)P₃ (sodium salt) is a member of the inositol phosphate (InsP) family of second messengers that play a critical role in the transmission of cellular signals.^1,2 The most studied InsP, Ins(1,4,5)P₃ is a second messenger produced in cells by phospholipase C (PLC)-mediated hydrolysis of phosphatidylinositol-4,5-biphosphate.^3,4 Binding of the Ins(1,4,5)P₃ to its receptor on the endoplasmic reticulum results in opening of calcium channels and an increase in intracellular calcium.^4,5 Ins(2,5,6)P₃ is a less potent inducer of calcium release from permeabilized rat basophilic leukemia cells with an EC₅₀ value of 110 µM compared to Ins(1,4,5)P₃, which has an EC₅₀ value of 0.17 µM.⁶

1 Berridge, M.J. Inositol trisphosphate and calcium signalling. Nature 361 315-325 (1993).

2 Majerus, P.W. Inositol phosphate biochemistry. Annu Rev Biochem 61 225-250 (1992).

3 Streb, H., Irvine, R.F., Berridge, M.J., et al. Release of Ca2+ from a nonmitochondrial intracellular store in pancreatic acinar cells by inositol-1,4,5-trisphosphate. Nature 306 67-69 (1983).

4 Yoshida, Y., and Imai, S. Structure and function of inositol 1,4,5-triphosphate receptor. Jpn J Pharmacol 74 125-137 (1997).

5 Exton, J.H. Regulation of phosphoinositide phospholipases by hormones, neurotransmitters, and other agonists linked to G proteins. Annu Rev Pharmacol Toxicol 36 481-509 (1996).

6 Tegge, W., Denis, G.V., and Ballou, C.E. Synthesis and Ca2+-release activity of D- and L-myo-inositol 2,4,5-trisphosphate and D- and L-chiro-inositol 1,3,4-trisphosphate. Carbohyd Res 217 107-116 (1991).

Synonyms

Ins(2,5,6)P3 (sodium salt)
2,5,6-IP3 (sodium salt)

Formal Name

D-myo-inositol-2,5,6-tris(dihydrogen phosphate), trisodium salt

Molecular Formula

C₆H₁₂O₁₅P₃ • 3Na

Formula Weight

486.0

Formulation

A lyophilized powder

Purity

≥98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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OC1C(OP(=O)(O)O)C(OP(=O)(O)O)[C@H](O)[C@H](OP(=O)(O)O)[C@@H]1O

Background Reading

Berridge, M.J. Inositol trisphosphate and calcium signalling. Nature 361 315-325 (1993).

Majerus, P.W. Inositol phosphate biochemistry. Annu Rev Biochem 61 225-250 (1992).

Yoshida, Y., and Imai, S. Structure and function of inositol 1,4,5-triphosphate receptor. Jpn J Pharmacol 74 125-137 (1997).

Tegge, W., Denis, G.V., and Ballou, C.E. Synthesis and Ca2+-release activity of D- and L-myo-inositol 2,4,5-trisphosphate and D- and L-chiro-inositol 1,3,4-trisphosphate. Carbohyd Res 217 107-116 (1991).

Streb, H., Irvine, R.F., Berridge, M.J., et al. Release of Ca2+ from a nonmitochondrial intracellular store in pancreatic acinar cells by inositol-1,4,5-trisphosphate. Nature 306 67-69 (1983).

Exton, J.H. Regulation of phosphoinositide phospholipases by hormones, neurotransmitters, and other agonists linked to G proteins. Annu Rev Pharmacol Toxicol 36 481-509 (1996).

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100 µg 
$49.00

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500 µg 
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1 mg 
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5 mg 
$1,715.00

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D-myo-Inositol-2,5,6-triphosphate (sodium salt)