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857328P

Avanti

18:1 Cyclic LPA

1-oleoyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder

Synonyma:

1-(9Z-octadecenoyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt)

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About This Item

Empirický vzorec (Hillův zápis):
C21H42NO6P
Číslo CAS:
799268-72-7
Molekulová hmotnost:
435.54
UNSPSC Code:
51191904
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (857328P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 857328P

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(CCCCCCC/C=C\CCCCCCCC)OC[C@@H]1COP(O1)([O-])=O.[NH4+]

InChI

1S/C21H39O6P.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20;/h9-10,20H,2-8,11-19H2,1H3,(H,23,24);1H3/b10-9-;/t20-;/m1./s1

InChI key

BQDHONSGIYYBPK-JGSYTFBMSA-N

General description

Cyclic phosphatidic acid (cPA) is a naturally occurring analog of the growth factor-like phospholipid mediator, lysophosphatidic acid (LPA). The sn-2 hydroxy group of CPA forms a 5-membered ring with the sn-3 phosphate. cPA affects numerous cellular functions, including anti-mitogenic regulation of the cell cycle, induction of stress fiber formation, inhibition of tumor cell invasion and metastasis, and regulation of differentiation and survival of neuronal cells.
Interestingly, many of these cellular responses caused by cPA oppose those of LPA despite the activation of apparently overlapping receptor populations.

Application

18:1 Cyclic LPA has been used for the preparation of liposomes. It has also been used for the extraction recovery of cyclic phosphatidic acid (cPA) at different pH conditions using Bligh−Dyer method.

Packaging

5 mL PTFE Vial with Screw Cap (857328P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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Osvědčení o analýze (COA)

Lot/Batch Number

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Oleoyl-L-α-lysophosphatidic acid sodium salt ≥98%, solid

Sigma-Aldrich

L7260

Oleoyl-L-α-lysophosphatidic acid sodium salt

Sigma-Aldrich

Sigma-Aldrich

04482

DEAE-Dextran

Quantitative determination of cyclic phosphatidic acid in human serum by LC/ESI/MS/MS
Shan L, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 862(1-2), 161-167 (2008)
Kitti Koprivanacz et al.
Cellular signalling, 32, 66-75 (2017-01-21)
Src homology 3 or SH3 domains constitute one of the most common protein domains in signal transduction, generally characterized by their binding to proline-rich sequences on interacting signaling proteins. Caskin1, a scaffold protein regulating cortical actin filaments, enriched in neural
D J Fischer et al.
Molecular pharmacology, 54(6), 979-988 (1998-12-18)
Lysophosphatidic acid (LPA), plasmalogen-glycerophosphate (alkenyl-GP) and, cyclic-phosphatidic acid (cyclic-PA) are naturally occurring phospholipid growth factors (PLGFs). PLGFs elicit diverse biological effects via the activation of G protein-coupled receptors in a variety of cell types. In NIH3T3 fibroblasts, LPA and alkenyl-GP
K Murakami-Murofushi et al.
Cell structure and function, 18(5), 363-370 (1993-10-01)
The unique Physarum lysophosphatidic acid, PHYLPA, having a cyclopropane in the fatty acid moiety and a cyclic phosphate at C-2 and C-3 positions of the glycerol, inhibited proliferation of human fibroblast cells, TIG-3 and TIG-7, which were cultured in a
Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons.
Fujiwara Y, et al.
Journal of Neurochemistry, 87, 1272-1283 (2003)
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