857231P
Avanti
C18:1 Cyclic LPA
1-O-(9Z-octadecenyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder
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Synonym(s):
1-O-octadecenyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt); AGP 18:1
Empirical Formula (Hill Notation):
C21H44NO5P
Recommended Products
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (857231P-1mg)
manufacturer/tradename
Avanti Polar Lipids 857231P
lipid type
cardiolipins
phospholipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
CCCCCCCC/C=C\CCCCCCCCOC[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.
Packaging
5 mL Amber Glass Screw Cap Vial (857231P-1mg)
WGK
WGK 3
Certificates of Analysis (COA)
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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)
Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons.
Fujiwara Y, et al.
Journal of Neurochemistry, 87, 1272-1283 (2003)
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)
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)
Yuko Fujiwara
Biochimica et biophysica acta, 1781(9), 519-524 (2008-06-17)
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
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