PtdIns-(3,5)-P2 (1,2-dioctanoyl) (sodium salt)

Cayman Chemical Item Number 10007763

DOPI-3,5-P2; Phosphatidylinositol-3,5-bisphosphate C-8

PtdIns-(3,5)-P2 (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-(3,5)-P2 (1,2-dioctanoyl) is a synthetic analog of natural PtdIns featuring C8:0 fatty acids at the sn-1 and sn-2 positions. The compound features the same inositol and diacylglycerol (DAG) stereochemistry as the natural compound. PtdIns are phosphorylated to mono- (PtdIns-P; PIP), di- (PtdIns-P2; PIP2), and triphosphates (PtdIns-P3; PIP3). Hydrolysis of PtdIns-(4,5)-P2 by phosphoinositide (PI)-specific phospholipase C generates inositol triphosphate (IP3) and DAG which are key second messengers in an intricate biochemical signal transduction cascade. PtdIns-(3,4)-P2 is resistant to hydrolysis by phospholipase C.3

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 Serunian, L.A., Haber, M.T., Fukui, T., et al. Polyphosphoinositides produced by phosphatidylinositol 3-kinase are poor substrates for phospholipases C from rat liver and bovine brain. J Biol Chem 264(30) 17809-17815 (1989).

Synonyms
  • DOPI-3,5-P2
  • Phosphatidylinositol-3,5-bisphosphate C-8
Formal Name 1-​(1,​2-​dioctanoylphosphatidyl)inositol-​3,​5-​bisphosphate,​ trisodium salt
Molecular Formula C25H46O19P3 · 3Na
Formula Weight 812.5
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)​=O)​[C@@H]​(O)​[C@H]​(OP([O]​)​(O)​=O)​[C@H]​1O)​([O-]​)​=O)​OC(CCCCCCC)​=O)​CCCCCCC.[Na+]​.[Na]​.[Na+]​
InCHI Code
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​1S/C25H49O19P3.3Na/c1-3-5-7-9-11-13-18(26)​39-15-17(41-19(27)​14-12-10-8-6-4-2)​16-40-47(37,38)​44-25-21(29)​23(42-45(31,32)​33)​20(28)​24(22(25)​30)​43-46(34,35)​36;;;/h17,20-25,28-30H,3-16H2,1-2H3,(H,37,38)​(H2,31,32,33)​(H2,34,35,36)​;;;/q;3*+1/p-3/t17-,2
InCHI Key
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YFJGBHCKHDYSQL-BHSPMXJGSA-K

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Size Price Quantity Subtotal
100 µg $40.00 $0.00
500 µg $180.00 $0.00
1 mg $320.00 $0.00
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Pricing updated 2014-04-19. Prices are subject to change without notice.

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TGX-221
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