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Merck
CN

880346P

Avanti

DChemsPC

Avanti Research™ - A Croda Brand

Synonym(s):

1,2-dicholesterylhemisuccinoyl-sn-glycero-3-phosphocholine

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About This Item

Empirical Formula (Hill Notation):
C70H116NO12P
CAS Number:
1155878-69-5
Molecular Weight:
1194.64
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

DChemsPC, Avanti Research™ - A Croda Brand 880346P, powder

lipid type

cardiolipins
phospholipids

shipped in

dry ice

InChI

1S/C70H116NO12P/c1-46(2)16-14-18-48(5)57-24-26-59-55-22-20-50-42-52(32-36-67(50,7)61(55)34-38-69(57,59)9)81-64(73)29-28-63(72)78-44-54(45-80-84(76,77)79-41-40-71(11,12)13)83-66(75)31-30-65(74)82-53-33-37-68(8)51(43-53)21-23-56-60-27-25-58(49(6)19-15-17-47

InChI key

XIHPVFHVRYJTJV-DJTREBHPSA-N

SMILES string

O=P([O-])(OCC[N+](C)(C)C)OC[C@H](OC(CCC(OC1CC[C@]2(C)C(C1)=CCC3C2CC[C@]4(C)C3CC[C@H]4[C@@H](C)CCCC(C)C)=O)=O)COC(CCC(OC5CC[C@]6(C)C(C5)=CCC7C6CC[C@]8(C)C7CC[C@H]8[C@@H](C)CCCC(C)C)=O)=O

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 25 mg (880346P-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 880346P

storage temp.

−20°C

Application

DChemsPC might be used:
  • as a substitute for cholesterol in liposome formulation to study its effect on membrane stability
  • in the preparation of pH-gradient liposomes
  • to form sterol-phospholipid hybrid with palmitoyl-2-cholesterylhemisuccinoyl-sn-glycero-3-phosphocholine (PCholPC) and to study its properties and interactions

Biochem/physiol Actions

Liposome instability in blood is caused mainly due to cholesterol exchange. Sterol modified phospholipid retains the bilayer-stabilizing effect of free cholesterol, inhibiting its transfer from the bilayer. Therefore, disterolphospholipids are ideal for liposome preparation. The use of DChemsPC in liposomes prevents content leaking into the serum.

Packaging

5 mL Amber Glass Screw Cap Vial (880346P-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Vincent Forster et al.
Biomaterials, 33(13), 3578-3585 (2012-02-15)
Calcium channel blocker (CCB) overdose is potentially lethal. Verapamil and diltiazem are particularly prone to acute toxicity due to their dual effect on cardiac and vascular tissues. Unfortunately, conventional decontamination measures are ineffective in accelerating blood clearance and, to date
Aditya G Kohli et al.
Journal of controlled release : official journal of the Controlled Release Society, 176, 86-93 (2013-12-26)
We introduce a method for tracking the rate and extent of delivery of liposome contents in vivo based on encapsulation of 4-methylumbelliferyl phosphate (MU-P), a profluorophore of 4-methylumbelliferone (MU). MU-P is rapidly dephosphorylated by endogenous phosphatases in vivo to form
Michał Flasiński et al.
Langmuir : the ACS journal of surfaces and colloids, 32(16), 4095-4102 (2016-04-06)
The two synthetic sterol-phospholipid hybrids DCholPC and PCholPC were investigated in monolayers at the air/water interface. Study was based on π-A isotherm analysis complemented with application of grazing incidence X-ray diffraction. It was found that both compounds are capable of
Zhaohua Huang et al.
Journal of the American Chemical Society, 130(46), 15702-15712 (2008-10-28)
We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid
Zhaohua Huang et al.
Angewandte Chemie (International ed. in English), 48(23), 4146-4149 (2009-05-09)
Extreme makeover of cholesterol: Cholesterol exchange is a major reason for the instability of liposomes in blood. The formation of a covalent hybrid between cholesterol and glycerophosphocholine preserves the bilayer-stabilizing effect of free cholesterol but prevents its transfer from the
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