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Merck
CN

524644

L-α-Phosphatidyl-D-myo-inositol-4,5-bisphosphate, Triammonium Salt, Porcine Brain

A component of membrane-bound receptors in association with phospholipase C (PLC).

别名:

L-α-Phosphatidyl-D-myo-inositol-4,5-bisphosphate, Triammonium Salt, Porcine Brain, PIP2

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关于此项目

经验公式（希尔记法）:
C47H82O19P3 · 3NH4
化学文摘社编号:
383907-42-4
分子量:
1098.18
MDL number:
MFCD02264339
UNSPSC Code:
12352211
NACRES:
NA.77
Assay:
≥98% (TLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze
desiccated (hygroscopic)
protect from light

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产品名称

L-α-Phosphatidyl-D-myo-inositol-4,5-bisphosphate, Triammonium Salt, Porcine Brain, A component of membrane-bound receptors in association with phospholipase C (PLC).

SMILES string

[P](=O)(O[C@@H]1C([C@@H](C(C(C1O)O[P](=O)(O)O)O[P](=O)(O)O)O)O)(OC[C@H](OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COC(=O)CCCCCCCCCCCCCCCCC)O.N.N.N

InChI

1S/C47H85O19P3.3H3N/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)63-39(37-61-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)38-62-69(59,60)66-45-42(50)43(51)46(64-67(53,54)55)47(44(45)52)65-68(56,57)58;;;/h11,13,17,19,22,24,28,30,39,42-47,50-52H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3,(H,59,60)(H2,53,54,55)(H2,56,57,58);3*1H3/b13-11-,19-17-,24-22-,30-28-;;;/t39-,42?,43+,44?,45-,46?,47?;;;/m1.../s1

InChI key

GAIOWTITBYPFJE-JVILRMJCSA-N

assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

white to off-white

solubility

water: 10 mg/mL
chloroform: 50 mg/mL

shipped in

wet ice

storage temp.

−70°C

Quality Level

100

相关类别

Biochem/physiol Actions

Cell permeable: no
Primary Target
Brain phospholipase D (PLD)
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Irritant (B)

General description

A component of membrane-bound receptors in association with phospholipase C. Hydrolysis of PIP2 yields IP3 and diacylglycerol, causing the release of intracellular Ca2+ and activation of protein kinase C. Potently stimulates phospholipase D activity in vitro in brain tissue. A substrate for PI 3-kinase. Antagonist of ATP inhibtion of ATP-sensitive potassium (KATP) channels when applied to inside-out membrane patches.



Note: This product is not to be used for animal treatment, in vivo research or in any other contact procedure with livestock.

Other Notes

Baukrowitz, T., et al. 1998. Science 282, 1141.
Shyng, S.-L., and Nichols, C.G. 1998. Science 282, 1138.
Mazzotti, G., et al. 1995. J. Histochem. Cytochem. 43, 181.
Liscovitch, M., et al. 1994. J. Biol. Chem. 269, 21403.
Chauhan, A., et al. 1991. Biochem. Biophys. Res. Commun. 175, 852.
Williamson, J.R. 1986. Hypertension 8, 140.
Berridge, M.J., and Irvine, R.F. 1984. Nature312, 315.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution in H₂O, store in the refrigerator (4°C). Do not freeze aqueous solutions. Following reconstitution in chloroform, aliquot and freeze (-20°C). Aqueous stock solutions are stable for up to 2 days at 4°C. Chloroform stock solutions are stable for up to 1 month at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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J R Williamson
Hypertension (Dallas, Tex. : 1979), 8(6 Pt 2), II140-II156 (1986-06-01)
Many hormones, neurotransmitters, and secretagogues act by increasing the intracellular free Ca2+ concentration in target cells. The initial event following binding of agonists to specific receptors in the plasma membrane involves a receptor-mediated activation of a guanosine nucleotide-binding protein (G
S L Shyng et al.
Science (New York, N.Y.), 282(5391), 1138-1141 (1998-11-06)
Adenosine triphosphate (ATP)-sensitive potassium (KATP) channels couple cell metabolism to electrical activity. Phosphatidylinositol phosphates (PIPs) profoundly antagonized ATP inhibition of KATP channels when applied to inside-out membrane patches. It is proposed that membrane-incorporated PIPs can bind to positive charges in
G Mazzotti et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 43(2), 181-191 (1995-02-01)
Phosphatidylinositol 4,5-bisphosphate (PIP2) is a key element of signal transduction, being the preferential substrate of specific phospholipases that produce second messengers such as inositol trisphosphate (IP3) and diacylglycerol (DG). Because PIP2 has been cytochemically identified by monoclonal antibodies not only
Natsuki Watanabe et al.
Microorganisms, 8(7) (2020-07-19)
Phosphatidylinositol phosphates (PIPs) are involved in many cellular events as important secondary messengers. In Entamoeba histolytica, a human intestinal protozoan parasite, virulence-associated mechanisms such as cell motility, vesicular traffic, trogo- and phagocytosis are regulated by PIPs. It has been well
T Baukrowitz et al.
Science (New York, N.Y.), 282(5391), 1141-1144 (1998-11-06)
Adenosine triphosphate (ATP)-sensitive potassium (KATP) channels couple electrical activity to cellular metabolism through their inhibition by intracellular ATP. ATP inhibition of KATP channels varies among tissues and is affected by the metabolic and regulatory state of individual cells, suggesting involvement
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