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

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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 Wet ice 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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Pricing updated 2015-04-26. Prices are subject to change without notice.

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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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