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857231P

Avanti

C18:1 Cyclic LPA

1-O-(9Z-octadecenyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder

Synonyme(s) :

1-O-octadecenyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt); AGP 18:1

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About This Item

Formule empirique (notation de Hill) :
C21H44NO5P
Numéro CAS:
799268-69-2
Poids moléculaire :
421.55
Code UNSPSC :
51191904
Nomenclature NACRES :
NA.25

Essai

>99% (TLC)

Forme

powder

Conditionnement

pkg of 1 × 1 mg (857231P-1mg)

Fabricant/nom de marque

Avanti Research™ - A Croda Brand 857231P

Type de lipide

cardiolipins
phospholipids

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

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

InChI

1S/C21H41O5P.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24-19-21-20-25-27(22,23)26-21;/h9-10,21H,2-8,11-20H2,1H3,(H,22,23);1H3/b10-9-;/t21-;/m1./s1

Clé InChI

OQYRMQWRTNWOER-WBIWQBECSA-N

Description générale

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.

Conditionnement

5 mL Amber Glass Screw Cap Vial (857231P-1mg)

Informations légales

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

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Certificats d'analyse (COA)

Lot/Batch Number

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Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons.
Fujiwara Y, et al.
Journal of Neurochemistry, 87, 1272-1283 (2003)
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
Yuko Fujiwara et al.
Journal of neurochemistry, 87(5), 1272-1283 (2003-11-19)
Cyclic phosphatidic acid (cPA; 1-acyl-sn-glycerol-2,3-cyclic phosphate) is an analog of the growth factor-like phospholipid mediator lysophosphatidic acid (LPA). As brain tissue is the richest source of cPA we tested its effects on hippocampal neurons from day 16/17 embryonic rat cultured
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)
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