857328P
Avanti
18:1 Cyclic LPA
1-oleoyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder
Synonym(s):
1-(9Z-octadecenoyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt)
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C21H42NO6P
CAS Number:
Molecular Weight:
435.54
UNSPSC Code:
51191904
NACRES:
NA.25
Recommended Products
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+]
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.
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
Certificates of Analysis (COA)
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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
Naturally occurring analogs of lysophosphatidic acid elicit different cellular responses through selective activation of multiple receptor subtypes.
Fischer DL, et al.
Molecular Pharmacology, 54, 979-988 (1998)
Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA).
Mukai M, et al.
International Journal of Cancer. Journal International Du Cancer, 81, 918-922 (1999)
Inhibition of cell proliferation by a unique lysophosphatidic acid, PHYLPA, isolated from Physarum polycephalum: signaling events of antiproliferative action by PHYLPA.
Murakami-Murofushi K, et al.
Cell Structure and Function, 18, 363-370 (1993)
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