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

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

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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
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(OC[C@H]​(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.[Na+]​.[Na]​.[Na+]​.[Na+]​
InCHI Code
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​1S/C25H50O21P4S.4Na/c1-3-5-7-9-11-13-18(26)​40-15-17(42-19(27)​14-12-10-8-6-4-2)​16-41-49(36,37)​45-22-20(28)​23(43-47(30,31)​32)​25(44-48(33,34)​35)​24(21(22)​29)​46-50(38,39)​51;;;;/h17,20-25,28-29H,3-16H2,1-2H3,(H,36,37)​(H2,30,31,32)​(H2,33,34,35)​(H2,38,
InCHI Key
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VVBWSBAPPMPDDE-OHYVEFHDSA-J

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Size Price Quantity Subtotal
25 µg $48.00 $0.00
50 µg $91.00 $0.00
100 µg $173.00 $0.00
250 µg $384.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-20. Prices are subject to change without notice.

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