3-PT-PtdIns-(3,4,5)-P3 (1,2-dioctanoyl) (sodium salt)

3-PT-PtdIns-(3,4,5)-P₃ (1,2-dioctanoyl) (sodium salt)

Cayman Chemical Item Number 10009804

3-Phosphorothioate-Phosphatidylinositol-4,5-diphosphate C-8 (sodium salt)

Description

The phosphatidylinositol (PtdIns) phosphates represent a small percentage of total membrane phospholipids. However, they play a critical role in the generation and transmission of cellular signals.^1,2 PtdIns(4,5)-P₂ can be phosphorylated by phosphoinositide (PI)-3-kinase to make PtdIns(3,4,5)-P₃ which initiates an intricate signaling cascade that has been implicated in cancer.³ 3-PT-PtdIns(3,4,5)-P₃ is an analog of PtdIns-(3,4,5)-P₃ that is resistant to hydrolysis by PTEN. It has a 5-fold reduced affinity for the specific PtdIns(3,4,5)-P₃-binding protein GRP1 and increases sodium transport in A6 cell monolayers.⁴

1 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).

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

3 Vivanco, I., and Sawyers, C.L. The phosphatidylinositol 3-kinase-AKT pathway in human cancer. Nat Rev Cancer 2 489-501 (2002).

4 Zhang, H., Markadieu, N., Beauwens, R., et al. Synthesis and biological activity of PTEN-resistant analogues of phosphatidylinositol 3,4,5-trisphosphate. J Am Chem Soc 128 16464-16465 (2006).

Synonyms

3-Phosphorothioate-Phosphatidylinositol-4,5-diphosphate C-8 (sodium salt)

Formal Name

1-(1,2-dioctanoylphosphatidyl)inositol-3-phosphorothioate-4,5-diphosphate, tetrasodium salt

Molecular Formula

C₂₅H₄₆O₂₁P₄S · 4Na

Formula Weight

930.5

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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O=C(OCC(COP(O[C@@H]1[C@H](O)[C@H](OP(O)([O-])=S)[C@@H](OP([O-])(O)=O)[C@H](OP([O-])(O)=O)[C@H]1O)([O-])=O)OC(CCCCCCC)=O)CCCCCCC

Background Reading

Zhang, H., Markadieu, N., Beauwens, R., et al. Synthesis and biological activity of PTEN-resistant analogues of phosphatidylinositol 3,4,5-trisphosphate. J Am Chem Soc 128 16464-16465 (2006).

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25 µg 
$46.00

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50 µg 
$87.00

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100 µg 
$166.00

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250 µg 
$368.00

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3-PT-PtdIns-(3,4,5)-P₃ (1,2-dioctanoyl) (sodium salt)